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The Black Prince of Florence : the spectacular life and treacherous world of Alessandro de’ Medici

Ruler of Florence for seven bloody years, 1531 to 1537, Alessandro de' Medici was arguably the first person of color to serve as a head of state in the Western world. Born out of wedlock to a dark-skinned maid and Lorenzo de' Medici, he was the last legitimate heir to the line of Lorenzo the Magnificent. When Alessandro's noble father died of syphilis, the family looked to him. Groomed for power, he carved a path through the backstabbing world of Italian politics in a time when cardinals, popes, and princes vied for wealth and advantage. By the age of nineteen, he was prince of Florence, inheritor of the legacy of the grandest dynasty of the Italian Renaissance.

Alessandro faced down family rivalry and enormous resistance from Florence's oligarchs, who called him a womanizer-which he undoubtedly was--and a tyrant. Yet this real-life counterpart to Machiavelli's Prince kept his grip on power until he was assassinated at the age of 26 during a late-night tryst arranged by his scheming cousins. After his death, his brief but colorful reign was criticized by those who had murdered him in a failed attempt to restore the Florentine republic. For the first time, the true story is told in The Black Prince of Florence.

Catherine Fletcher tells the riveting tale of Alessandro's unexpected rise and spectacular fall, unraveling centuries-old mysteries, exposing forgeries, and bringing to life the epic personalities of the Medicis, Borgias, and others as they waged sordid campaigns to rise to the top. Drawing on new research and first-hand sources, this biography of a most intriguing Renaissance figure combines archival scholarship with discussions of race and class that are still relevant today.
Oxford University Press
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ISBN 13:
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the black prince of florence

b y t h e sa m e author
The Divorce of Henry VIII: The Untold Story

The Black Prince
of Florence
The Spectacular Life and Treacherous World of
Alessandro de’ Medici




Oxford University Press is a department of the University of Oxford. It furthers the
University’s objective of excellence in research, scholarship, and education by publishing
worldwide. Oxford is a registered trade mark of Oxford University Press in the UK
and certain other countries.
Published in the United States of America by Oxford University Press
198 Madison Avenue, New York, NY 10016, United States of America.
© Catherine Fletcher 2016
First published in Great Britain by The Bodley Head.
All rights reserved. No part of this publication may be reproduced, stored in a retrieval
system, or transmitted, in any form or by any means, without the prior permission in
writing of Oxford University Press, or as expressly permitted by law, by license, or under
terms agreed with the appropriate reproduction rights organization. Inquiries concerning
reproduction outside the scope of the above should be sent to the Rights Department,
Oxford University Press, at the address above.
You must not circulate this work in any other form
and you must impose this same condition on any acquirer.
Library of Congress Cataloging-in-Publication Data
Names: Fletcher, Catherine, 1975– author.
Title: The Black Prince of Florence : the spectacular life and treacherous
world of Alessandro de’ Medici / Catherine Fletcher.
Other titles: Spectacular life and treacherous world of Alessandro de’ Medici
Description: New York : Oxford University Press, [2016] | Includes
bibliographical references and index.
Identifiers: LCCN 2016004319 | ISBN 978–0–19–061272–6
Subjects: LCSH: Medici, Alessandro de’, 1510–1537. | Medici, House of. |
Florence (Italy)—Kings and rulers—Biography. | Racially mixed
people—Italy—Florence—Biography. | Florence
Classification: LCC DG737.7 .A5; 4 2016 | DDC 945/.51106092—dc23
LC record available at
Printed by Sheridan Books, Inc., United States of America

To my father


Family tree
Glossary of names






A note on money


Book One: The Bastard Son


Book Two: The Obedient Nephew


Book Three: The Prince Alone


Afterword: Alessandro’s Ethnicity










Senior branch of Medici family (selected members)
Giovanni di Bicci
m. Piccarda Bueri

Cosimo ‘the Elder’
m. Contessina de’ Bardi
Piero ‘the Gouty’
m. Lucrezia Tornabuoni


Lorenzo ‘the Elder’
m. Ginevra Cavalcanti

Carlo de’ Medici

See next page

Lorenzo ‘the Magnificent’
m. Clarice Orsini

m. Jacopo Salviati


Maria Salviati
m. Giovanni
‘delle Bande Nere’
See next page
de’ Medici
See next page


‘the Unfortunate’
m. Alfonsina Orsini


Duke of

Duke of Urbino
m. Madeleine de la
Tour d’Auvergne
of France

m. Filippo

Piero Strozzi
m. Laudomia
de’ Medici
See next page

m. Franceschetto


Luisa Strozzi
(d. 1534)

Pope Leo X

Lorenzo Cibo
m. Ricciarda

m. Piero


Duke of Nemours
m. Filiberta of Savoy


Pope Clement



Junior branch of Medici family (selected members)
Giovanni di Bicci
m. Piccarda Bueri

Cosimo ‘the Elder’
m. Contessina de’ Bardi
See previous page

Lorenzo ‘the Elder’
m. Ginevra Cavalcanti
Pierfrancesco ‘the Elder’
m. Laudomia Acciaiuoli

Lorenzo ‘il Popolano’
m. Semiramide Appiani

Giovanni ‘il Popolano’
m. Caterina Sforza

Pierfrancesco ‘the Younger’
m. Maria Soderini

Giovanni ‘delle Bande Nere’
m. Maria Salviati
See previous page


m. Piero Strozzi
See previous page

Duke of Florence;
Grand-duke of Tuscany

Glossary of names

Acciaiuoli, Roberto (1467–1547). A Florentine diplomat, active in city
service both before and after the return of the Medici in 1512.
Imprisoned during the 1527–30 republic but escaped and held high
office in Alessandro’s regime, including as one of his first four
consiglieri. One of the politicians invited by Clement VII to write an
opinion on reform of Florentine government.
Aldobrandini, Silvestro (1499–1558). A Florentine lawyer and academic,
involved in the revolt against the Medici in 1527. Held office in the
1527–30 republic; cooperated with papal officials at the end of the siege,
but was imprisoned. Freed thanks to the intervention of Bartolomeo
Valori, he was exiled. He was an advocate for the Florentine exiles
during their disputes with Alessandro in Naples and went on to a
distinguished legal career.
Aretino, Pietro (1492–1556). An author and satirist, patronised by
leading figures of sixteenth-century Italy, including Cardinal Giulio
de’ Medici (later Clement VII). Spent his early career in Rome but left
for Venice after a victim of his satire tried to have him killed and his
involvement in the production of pornography landed him in trouble.
Bandini, Giovan. A companion of Alessandro de’ Medici, involved in
a series of incidents including the attack on Cellini’s brother and the
duel for the honour of Florence.
Castiglione, Baldassarre (1478–1529). Courtier, diplomat and author, born
in Mantua but active at the courts of Urbino and Milan. Best known
for his Book of the Courtier, a dialogue on proper conduct at court.



Cellini, Benvenuto (1500–1571). A Florentine goldsmith and sculptor,
Cellini is also famed for his swashbuckling (and unreliable) autobiography. He produced works for Clement VII, for Alessandro, and for
many other patrons.
Charles V, Holy Roman Emperor (1500–1558). King of Spain from
1516; Emperor from 1519. Charles’ empire stretched from Spain and
southern Italy to the German states and Low Countries. He competed
with the king of France for dominance in central and northern Italy
but also faced challenges to his eastern dominions from the Ottoman
Cibo, Caterina (1501–1557). A niece of Pope Leo X, sister to Cardinal
Innocenzo, Lorenzo and Giovanbattista Cibo. Married Giovanni Maria
Varano, duke of Camerino, with whom she had a daughter, Giulia;
widowed in 1527 and waged a fierce fight to protect her interest in the
duchy. Lived in Florence from 1535.
Cibo, Giovanbattista (1505/08–c.1550). Bishop of Mariana in Corsica
and (from 1530) bishop of Marseilles. Brother of Cardinal Innocenzo
and related to the Medici on his mother’s side. A close companion of
Ippolito de’ Medici.
Cibo, Cardinal Innocenzo (1491–1550). A nephew of Pope Leo X, who
promoted him to the cardinalate in 1513; related on his father’s side
to another pope, Innocent VIII. Held many benefices in the Church;
became Pope Clement’s representative in Florence.
Cibo, Lorenzo (1500–1549). A military commander in papal service,
brother of Cardinal Innocenzo. Married Ricciarda Malaspina in 1520.
Clement VII, Pope (Giulio de’ Medici) (1478–1534). The illegitimate
son of Giuliano de’ Medici, the brother of Lorenzo the Magnificent.
His father was assassinated in the Pazzi conspiracy. Giulio was made
a cardinal in 1513 following his cousin Giovanni’s election as Pope Leo
X. He held a number of important offices in Leo’s administration and
was elected pope in 1523.



Della Rovere, Francesco Maria, duke of Urbino (1490–1538). Ruler
of the duchy of Urbino from 1508 to 1516, when he was supplanted
by Lorenzo de’ Medici, and again after 1521. A condottiere, he
commanded papal troops and the Venetian army at different points
in his career.
Doria, Andrea (1466–1560). A celebrated Genoese naval commander
and statesman, Doria fought for various princes but by the mid 1530s
was in the service of Charles V.
Este, Alfonso d’, duke of Ferrara (1476–1534). Came to power in 1505;
had a long-running confl ict with the popes over control of the duchies
of Ferrara, Modena and Reggio. Allied variously with France and the
Holy Roman Empire at different points during the Italian Wars.
Este Gonzaga, Isabella d’, marchioness of Mantua (1474–1539). A
member of the ruling family of Ferrara, Isabella was married to
Francesco II, marquis of Mantua, and was a distinguished political
and cultural figure of her time, known in particular for her patronage
of the arts. She was widowed in 1519.
Francis I, king of France (1494–1547). Francis came to power in 1515
following the death of his cousin and father-in-law Louis XII. He was
the first of the Angoulême branch of the Valois family to rule France.
He vied with Charles V for military supremacy in Europe.
Gheri, Goro (1470–1528). Secretary to Lorenzo de’ Medici, duke of
Urbino, for whom he carried out a variety of political and diplomatic
Giovio, Paolo (c.1486–1552). Physician, philosopher and close adviser
to Pope Clement VII, Giovio is also known for his historical writings.
Girolami, Raffaello (1472–1532). Member of a Florentine banking
family, he served in city government during the Medici exile of 1494–
1512, though was never an advocate for a very broad-based regime.
After the return of the Medici in 1512 he continued to hold office, as



he did during the republic of 1527–30, when he was one of the more
moderate voices in government. From January 1530 to the end of the
republic he served as gonfaloniere.
Gonzaga, Ercole (1505–1563). Second son of Isabella d’Este and
Francesco II Gonzaga, duke of Mantua. He was made cardinal in 1527,
following in an uncle’s footsteps. Initially preferring a princely lifestyle
of hunting and the like, he later took an important role in church
Gonzaga, Federico II, marquis (later duke) of Mantua (1500–1540).
Ruler of Mantua from 1519. Eldest son of Isabella d’Este.
Gonzaga, Ferrante (1507–1557). Third son of Isabella d’Este and
Francesco II Gonzaga, marquis of Mantua, he joined Charles V’s court
in Spain at the age of sixteen and spent his adult life in the Imperial
military service, quickly rising to high rank.
Gonzaga, Giulia (c.1513–1566). Married at thirteen and widowed at
fifteen, Giulia was a member of the Sabbioneta branch of the Gonzaga
family. She became the lover of Ippolito de’ Medici, but is better
known for the religious and spiritual activities to which she turned
after the mid 1530s.
Guicciardini, Francesco (1483–1540). Statesman and historian,
Guicciardini held senior posts in both the papal and Florentine administrations. Though he was a reluctant supporter of princely rule in
Florence, he was one of Alessandro’s most important advisers. His
History of Italy is both an important source for the events of this period
and a groundbreaking work of historical writing.
Guicciardini, Luigi (1478–1551). Florentine politician, brother of
Francesco. Held a number of offices under the Medici, including
gonfaloniere (in 1527, when the Medici were exiled) and roles as
commissar in Pisa, Arezzo, Pistoia and Castrocaro at different times.
Wrote a history of the 1527 Sack of Rome.



Henri, duke of Orléans (1519–1559). Second son of the king of France,
Henri was married to Catherine de’ Medici in 1533. He unexpectedly
became heir to the throne in 1536 after the death of his elder brother,
and reigned as Henri II from 1547.
Leo X, Pope (Giovanni de’ Medici) (1475–1521). Second son of Lorenzo
‘the Magnificent’, Giovanni was made a cardinal before his seventeenth
birthday. He was elected pope in 1513 but became notorious for his
nepotism and worldly lifestyle.
Machiavelli, Niccolò (1469–1527). Political theorist, administrator
and writer, Machiavelli was a leading civil servant in the Florentine
Republic from 1498 until the return of the Medici in 1512. Although
he advised Leo X on the government of Florence, his relations
with the Medici family were never comfortable. Best known as the
author of The Prince, he also wrote a discussion of republics (the
Discourses on Livy), comedies, poetry and a number of political
Malaspina Cibo, Ricciarda (1497–1553). Daughter of the marquis of Massa,
Ricciarda became the effective ruler of Massa and Carrara following her
father’s death in 1519. She married Lorenzo Cibo in 1520, and was also
the lover of her husband’s brother, Cardinal Innocenzo Cibo.
Malaspina, Taddea (1505–1559). Daughter of the marquis of Massa
and younger sister of Ricciarda, Taddea was married to Count
Giambattista Boiardo da Scandiano but was widowed in her early
twenties. In the 1530s she became the mistress of Alessandro de’
Margaret of Austria (1522–1586). Illegitimate daughter of Charles V
and Johanna ( Jeanne) van der Gheynst, Margaret is better known as
‘Margaret of Parma’ after the title of her second husband. Married
to Alessandro de’ Medici in 1536, she was quickly widowed and married
Ottavio Farnese in 1538. She served as governor of the Netherlands
from 1559–1567 and from 1578–1582.



Marzi de’ Medici, Angelo (1477–1546). Given the name de’ Medici
through the favour of a minor branch of the family, Angelo Marzi
worked in the Florentine chancellery and performed many services
for the Medici family. From 1529 he held the position of bishop of
Ser Maurizio da Milano. Chancellor to the Otto di Guardia (‘Eight of
Watch’, responsible for internal security) during Alessandro’s rule of
Florence, Ser Maurizio (whose title suggests he was a notary) was a
senior civil servant. He gained a reputation for brutality in his enforcement of laws such as the ban on weapons.
Medici, Alfonsina Orsini de’ (1472–1520). Mother of Lorenzo, duke
of Urbino; grandmother of Alessandro and Catherine. A member of
a wealthy and infl uential Neapolitan family, Alfonsina exercised considerable power in Florence in the years 1515–19, particularly during her
son’s absences from the city.
Medici, Catherine de’ (1519–1589). Daughter of Lorenzo, duke of
Urbino and half-sister of Alessandro, Catherine married Henri, duke
of Orléans, in 1533. Henri became heir to the throne of France following
his elder brother’s death in 1536, and king in 1547. Catherine survived
him and saw three of her sons rule the kingdom as well as acting as
regent of France herself.
Medici, Cosimo de’ ‘the Elder’ (1389–1464). Used his father’s banking
fortune to establish the Medici in Florentine politics, though not
without a brief period of exile in 1433–34 when he was accused of
tyranny. Noted cultural and artistic patron. Father of Piero ‘the gouty’;
grandfather of Lorenzo ‘the Magnificent’.
Medici, Cosimo de’ (1519–1574). The son of Giovanni de’ Medici and
Maria Salviati, Cosimo was a member of the junior branch of the
Medici family, sometimes known as the ‘popolano’ branch. He became
duke of Florence on the death of his distant cousin Alessandro in 1537,
and from 1569 was grand duke of Tuscany.



Medici, Giovanni de’ see Leo X
Medici, Giuliano de’, duke of Nemours (1479–1516). Third son of
Lorenzo the Magnificent and younger brother of Pope Leo X, Giuliano
married Filiberta of Savoy in 1515 and was granted his title by the king
of France in the same year. He was the Medici family figurehead in
Florence from their return in 1512 until his death. He had one illegitimate son, Ippolito.
Medici, Giulio de’ see Clement VII
Medici, Cardinal Ippolito de’ (1511–1535). Illegitimate son of Giuliano
de’ Medici, Ippolito was the Medici family representative in Florence
from 1524 until their expulsion in 1527. He was made a cardinal in 1529
by Pope Clement VII, his cousin once removed.
Medici, Lorenzino de’ (1514–1548). A member of the junior ‘popolano’
branch of the Medici family, Lorenzino joined Alessandro’s court in
the 1530s. He gained some reputation as a man of letters but is most
famous as the Duke’s assassin. He was killed in revenge in 1548.
Medici, Lorenzo de’, ‘the Magnificent’ (1449–1492). Effective ruler of
Florence from 1469, after his father’s untimely death. Survived the Pazzi
conspiracy of 1478 in which his brother was murdered; consolidated
Medici power in Florence but saw the family bank suffer serious problems.
Medici, Lorenzo de’, duke of Urbino (1492–1519). Eldest son of Piero
di Lorenzo de’ Medici (who was in turn the eldest son of Lorenzo
the Magnificent) and Alfonsina Orsini. Made duke of Urbino in 1516,
thanks to the patronage of his uncle Pope Leo X; acted for a time as
family representative in Florence. Married Madeleine de la Tour
d’Auvergne in 1518: they had a daughter, Catherine. Generally acknowledged as the father of Alessandro de’ Medici.
Medici, Ottaviano de’ (1482–1546). Member of a junior branch of
the Medici and husband of Francesca Salviati (daughter of Jacopo



Salviati and Lucrezia de’ Medici). Managed Alessandro’s household
affairs in Florence as well as holding a number of important city
Medici Strozzi, Clarice de’ (1493–1528). Niece of Pope Leo X and
sister of Lorenzo, duke of Urbino. She married Filippo Strozzi in 1508
and stoutly defended the interests of their children against the illegitimate Medici offspring Alessandro and Ippolito.
Nardi, Jacopo (1476–1563). A politician and historian, Nardi served
in Florentine government both before and after the 1512 return of
the Medici, but threw his lot in with their opponents after 1527.
He was exiled in 1530 and subsequently took a leading role in
republican politics, liaising between the oligarchs and the more
radical exiles.
Passerini, Silvio, cardinal of Cortona (1469–1529). Brought up with
the future Pope Leo X, Passerini was promoted to the cardinalate
along with many other Medici friends in 1517. He held a number of
lucrative church offices and acted as a guardian to Ippolito de’ Medici
during his period in Florence in the 1520s.
Paul III, Pope (Alessandro Farnese) (1468–1549). A long-serving
cardinal, elected pope on the death of Clement VII in 1534. Paul sought
to advance the interests of his Farnese nephews, and successfully
established them as dukes of Parma and Piacenza. Responsible for
initiating the Council of Trent that oversaw a process of reform within
the Roman Catholic Church.
Ridolfi, Cardinal Niccolò (1501–1550). Son of Contessina de’ Medici
and a nephew of Pope Leo X, Niccolò Ridolfi became a cardinal in
1517 and archbishop of Florence in 1524. He resigned that post in 1532
and supported Ippolito’s challenge to Alessandro’s rule.
Salviati, Cardinal Giovanni (1490–1553). A nephew of Pope Leo X,
son of Jacopo Salviati and Leo’s sister Lucrezia de’ Medici. Appointed
cardinal by his uncle in 1517.



Salviati, Giuliano (d. c.1562). A distant cousin of Cardinal Giovanni
Salviati; a companion of Alessandro, who played a central role in the
Luisa Strozzi affair.
Salviati, Jacopo (1461–1533). Married to Lucrezia de’ Medici (sister of
Leo X). Secretary to Pope Clement VII and senior figure at the papal
court. Father of Cardinal Giovanni Salviati and of Maria Salviati
(mother of the future Duke Cosimo de’ Medici).
Schömberg, Cardinal Nicolas (1472–1537). Originally from Meissen in
what is now Germany, Schömberg was a Dominican priest who carried
out various diplomatic missions for German princes and the Holy
Roman Emperor. He was appointed archbishop of Capua by Pope
Leo X and made cardinal by Paul III in 1535.
Simunetta. Name commonly given to Alessandro de’ Medici’s mother,
a servant or slave in a Medici household, most likely that of Alfonsina
Orsini de’ Medici. Also referred to as Anna.
Sforza, Francesco II, duke of Milan (1495–1535). Held the duchy from
1521 until his death, though it was effectively under the control of Spanish
troops. Married Christina of Denmark, niece of Charles V, in 1534.
Soderini de’ Medici, Maria (1487–1525). A member of the Soderini
family, which had been prominent in Florentine government during
the exile of the Medici from 1494–1512, Maria married Pierfrancesco
the Younger, a member of the cadet branch of the Medici. One of
their four children was Lorenzino.
Strozzi, Filippo (1489–1538). A prominent papal banker, married to
Clarice de’ Medici (sister of Lorenzo, duke of Urbino).
Strozzi, Luisa (d. 1534). Daughter of Filippo Strozzi; her premature
death prompted rumours of poisoning.
Strozzi, Piero (c.1510–1558). Son of Filippo Strozzi and cousin to
Alessandro and Catherine. Married Lorenzino’s sister Laudomia de’



Medici and became a prominent opponent of the Medici regime in
Florence. Had a distinguished career in French military service and
was a confidant of Catherine de’ Medici.
Valori, Bartolomeo (d. 1537). Initially a Medici ally, he supported
the family’s restoration to power in 1512. Papal commissioner with the
Imperial army during the siege of Florence, he served in Florentine
government and held the office of governor of the Romagna (in
the gift of the papacy). After the death of Clement VII he lost infl uence in the papal bureaucracy and eventually left Florence. Executed
in 1537 after fighting with the rebels at the Battle of Montemurlo.
Varano, Giulia (1523–1547). Heiress to the duchy of Camerino and
related to the Medici via her mother (Caterina Cibo). Considered as
a possible bride for both Alessandro and Ippolito, Giulia married
Guidobaldo II, future duke of Urbino, in 1534.
Vasari, Giorgio (1511–1574). Artist, architect and historian, Vasari
studied alongside Alessandro and Ippolito de’ Medici, and later worked
for both of them. His Lives of the Artists is a key source for Renaissance
art history.
Vettori, Francesco (1474–1539). Florentine statesman; served in city
government both before and after the 1512 return of the Medici in
posts including gonfaloniere and ambassador. Best known for his correspondence with Niccolò Machiavelli.
Vitelli, Alessandro (d. 1556). Military commander in the service of
Charles V. After participating in the siege of Florence, he was appointed
as head of Alessandro de’ Medici’s Florentine guard. Later enjoyed
military success in service of Duke Cosimo de’ Medici.



Alessandro born


Giovanni de’ Medici elected Pope Leo X


Birth of Alessandro’s half-sister, Catherine de’


Death of Alessandro’s father, Lorenzo, duke
of Urbino


Death of Pope Leo X; succeeded by Adrian VI


Alessandro made duke of Penne


Birth of Margaret of Austria, illegitimate
daughter of Holy Roman Emperor Charles V


Death of Adrian VI; Giulio de’ Medici elected
Pope Clement VII


Alessandro’s cousin Ippolito made family
figurehead in Florence


Alessandro and Catherine sent to Florence;
Alessandro lives at Poggio a Caiano villa, just
outside city




Sack of Rome; Medici family expelled from
Florence and city government taken over by



Ippolito de’ Medici made a cardinal
Treaty of Barcelona between Clement VII and
Charles V; Alessandro betrothed to Margaret
of Austria



Coronation of Charles V as Holy Roman
Emperor in Bologna
Florentine regime falls after months of siege;
pro-Medici faction takes over with Imperial




Alessandro travels around German states and
Low Countries with court of Charles V



Alessandro makes entry to Florence



Ducal authority granted to Alessandro in
constitutional reform of Florence



Margaret of Austria visits Florence before
going on to Naples



Foundation stone of Fortezza da Basso laid
Death of Clement VII



Delegation of Florentine exiles, Alessandro’s
opponents, meets Charles in Barcelona
Ippolito de’ Medici implicated in plot to assassinate Alessandro
Ippolito de’ Medici poisoned
First garrison installed in Fortezza da Basso








In Naples, Charles V hears cases of Alessandro
and the exiled republicans on the government
of Florence
Ring ceremony of Alessandro and Margaret
Marriage of Alessandro and Margaret


Alessandro assassinated by cousin Lorenzino

A note on money

A range of coins and currencies circulated in Italy in the sixteenth
century. The various city-states on the peninsula issued their own
coinage, and exchange rates were not stable, particularly not during
periods of war. Most day-to-day transactions were made in silver coins,
known in Florence as grossi (groats); these were later replaced by the
giulio. Major (and international) payments were denominated in gold
coins such as ducats (the generic term for money of this type) and
florins (the Florentine version). These were gradually superseded by
the scudo, worth about 6 per cent less. A parallel system of lire, soldi
and denari (pounds, shillings and pence) was often used for accounting
purposes, though lire and soldi did not exist as coins. In the period
covered by this book, a florin was worth somewhere between seven
and eight lire.
Many people were not paid in cash alone, and reliable price indexes
are lacking, so it is hard to estimate the purchasing power of particular
sums of money. However, as a rough guide, unskilled labourers could
expect to earn 20–22 scudi in a year; skilled workers might make twice
that. In 1504–5, Michelangelo had a stipend of 120 florins. Soldiers’ pay
ranged from around thirty ducats a year to over 100 if they had to
cover the cost of a horse and followers. Cardinals’ annual incomes,
on the other hand, ranged in 1521 from 2,000 to 50,000 gold ducats.
In 1528, it was estimated that around eighty Florentines had estates
worth more than 50,000 florins: Jacopo Salviati, whose estate in Rome
was valued at 350,000 florins in 1532, was one of the super-rich. Grain,
a staple commodity, was considered expensive when in the 1530s the
price of 200 kg reached five ducats, which gives some indication of
how extraordinary the incomes of the wealthy were.1

the black prince of florence


It was the eve of Epiphany, 1537, a night of the most dazzling moonlight. Alessandro de’ Medici, duke of Florence, had an assignation.
His cousin Lorenzino, little Lorenzo, had promised him the favours
of Caterina de’ Ginori.
Alessandro’s enemies called Lorenzino his pimp.
Caterina, it was said, was beautiful and virtuous. She was married,
but tonight her husband was many miles to the south in Naples on
business. Lorenzino had assured Alessandro, lord of the city, that
Caterina could be persuaded.
After dinner that night, Lorenzino had explained his plan. Caterina
lived on the narrow street just behind the Palazzo Medici. Alessandro
should make excuses to his friends and head for the privacy of
Lorenzino’s palace apartment rather than his own. Lorenzino would
bring Caterina in discreetly, by the back door, to protect her reputation.
Clad in a cloak of fine Neapolitan silk, lined with sable, the Duke
headed out with four friends. In public he usually wore a doublet lined
with fine chain mail to protect himself from any enemy quick with
a knife. But there was no need for such precautions on a short walk
to meet the pretty Caterina. Arriving in the Piazza di San Marco, just
a few minutes away from his home, Alessandro dismissed all his
companions except one. His servant l’Unghero was to keep watch
on the comings and goings at Lorenzino’s from the Sostegni house
across the road. L’Unghero, lazy and familiar with the Duke’s womanising, expected a long wait. He decided not to watch but to take
himself off to sleep.
There was a warm fire burning in Lorenzino’s chamber. Alessandro
took off his sword and threw himself down on the bed. He too had
decided to take a nap.



When Lorenzino came into the room and found his cousin asleep
he took Alessandro’s sword and quickly wound the belt around its
hilt, so that it could not easily be drawn from its sheath. He placed it
carefully by the bolster, crept out of the chamber and closed the door
behind him.
Lorenzino’s companion that night was one Piero di Gioannabbate,
known by the curious nickname Scoronconcolo, a man of low rank whose
ears he had filled with his grievances against a certain unnamed courtier.
This courtier, Lorenzino told Scoronconcolo, had cheated him and interfered in his business. Scoronconcolo, who owed Lorenzino favours, had
promised to deal with Lorenzino’s tormentor, even to kill him. Even if
he were a favourite of the Duke’s. Even if he were Christ himself.
‘My brother,’ said Lorenzino, ‘now is the time; I have shut that
enemy of mine in my chamber, and he is asleep.’
‘Let’s go,’ said Scoronconcolo.
When they reached the landing, Lorenzino turned to Scoronconcolo
and said: ‘Don’t worry that he’s a friend of the Duke, just make sure
you get his hands.’
‘That I’ll do,’ replied his friend, ‘even if he’s the Duke himself.’
‘Are you ready?’ asked Lorenzino cheerfully. ‘He can’t slip through
our fingers now. Let’s go.’
‘Let’s go,’ said Scoronconcolo.
Lorenzino tried the latch. The door did not open.
He tried again. This second time, he entered.
‘My lord, are you asleep?’ he asked, and plunged his sword into
Alessandro’s stomach.
Alessandro lurched up from the bed and made a dash for the door,
seizing a stool to use as a shield, but Scoronconcolo pulled a knife.
Slashing down from the left temple, he sliced open the Duke’s left
Lorenzino pushed Alessandro onto the bed. He used the weight of
his own body to force the Duke down. He tried to cover Alessandro’s
mouth so he couldn’t scream, but the Duke bit so angrily into his
thumb that Lorenzino collapsed beside him.
As the pair grappled, Scoronconcolo drew his sword. Fearful of
cutting Lorenzino, he managed only to slash the mattress. Finally he
pulled a knife and plunged it into Alessandro’s throat.



It was said that for all the time that Alessandro waited, held down
by Lorenzino, for Scoronconcolo to strike, he never wept or pleaded
for his life. Nor once did he let go of his cousin’s thumb.
Lorenzino and Scoronconcolo lifted Alessandro’s body from the
blood-covered floor, and placed it on the bed. They left it hidden
beneath the canopy and went on their way.
The first duke of Florence was dead.1

It was the misfortune of Alessandro de’ Medici to be assassinated twice:
first with a sword, then with a pen. Thanks to Lorenzino, and to the
many enemies of the Medici family, Alessandro has gone down in
history as a tyrant. Not only did Lorenzino murder the Duke, he wrote
an eloquent justification of his actions. He found, too, a sympathetic
interviewer in Benedetto Varchi, the historian who later prepared an
account of Alessandro’s years on the commission of Cosimo I,
Alessandro’s successor as duke. ‘I will recount this death (about which
there are various tales and reports) with greater truth,’ wrote Varchi,
‘having heard it from Lorenzo himself . . . and from Scoronconcolo.’2
Although the first reports of Alessandro’s death were matter-of-fact
Varchi’s story of Lorenzino’s dramatic tyrannicide grips the imagination.
For centuries after Alessandro’s assassination, it suited both former
allies and enemies to make a villain of him. The enemies were mostly
sincere in their dislike. And it was convenient for the Medici family
that Alessandro could take the blame for the brutal first years of their
rule as princes of Florence. Even the friendlier historians of his rule
tell a bloody tale, and it is hard to challenge their version of events
because the bulk of Alessandro’s papers have disappeared. Perhaps
they were lost in the chaos that followed his murder, or perhaps
someone decided to destroy the evidence of Alessandro’s crimes. We
are left with the partisan commentary of the contemporary historians.
Alessandro de’ Medici has unreliable narrators by the dozen. Writing
this book, I have sometimes felt that I have been making a compendium of stories, each told by someone with his (and it is usually his)
own reasons for telling. In many cases I have only a single source, and
cannot check the facts. In general, I have given a little more weight
to the contemporary letters of secretaries and diplomats than to the



historians writing with hindsight. I have trusted the keeper of the
wardrobe a little more again. (A box of masks is either in its place or
not, and if cloth of gold went missing there’d be trouble.) Still, I have
more doubts and questions than I would like. Even when a writer is
sincere, memory can be faulty. To make this book readable I have
avoided interrupting the narrative too often with caveats and qualifications, and I encourage readers who are interested in the detail of
the historical sources to consult the notes.
The most famous accounts of Alessandro begin with the tales of
his wickedness, in all its bloody glory. His murder, wrote his assassin,
was ‘a deed incumbent on any good citizen’. He was a tyrant like
Nero, Caligula or Phalaris. He was a monster, driven by his ‘innate
cruelty and savagery’. What do those words allude to? It has long
been said that Alessandro was the son of a Moorish slave, or a ‘halfNegro’ woman.3 Were Lorenzino’s words a racial insult? The answer
is not straightforward. Sixteenth-century people thought about the
things we now call ‘race’ and ‘class’ in very different ways than we
do today. Moors – Muslims from North Africa and Spain – were part
of the ethnic-religious picture in sixteenth-century Europe, as were
Jews, but other racial categories were only just emerging. The Ottoman
Empire, which stretched from eastern Hungary through Turkey and
along the coast of North Africa, was an ethnically diverse place. Its
rulers had themselves portrayed with pale skin, but there were black
Turks too, who sometimes appear in the European depictions of the
time. In parts of Europe black saints and the black Magus were a
feature of sixteenth-century art, where they pointed to the global
reach of Christendom. As European slave-trading in West Africa
expanded, black Africans were brought to Italy in increasing numbers:
they were stereotyped as uncivilised and inferior.
Yet the modern idea of ‘race’, which emerged with the Atlantic
slave trade, is very different from anything that existed in the 1530s. It
may be disconcerting to readers who have grown up with today’s
labels and categories that we do not find them in Alessandro’s world.
Blood and descent were certainly important; positive qualities were
associated with the colour white and negative ones with black.4 Yet
while in Spanish and Portuguese, the European languages most associated at the time with slave-trading, the word negro had been used



to mean a black person since the fifteenth century, elsewhere in
sixteenth-century Europe the equivalent words were only just coming
into existence. The French noun nègre, meaning a black person, was
first recorded in 1516; negro, the Italian equivalent, dates to 1532. When
Giulio Landi, an Italian author, discussed the Portuguese colony of
Madeira in the 1530s, he made a point of explaining the racial categories
used there – Moors, Ethiopians, blacks and mulattoes – to his readers.5
He did not assume they would be familiar. If you went back in time
to early sixteenth-century Florence and asked whether any given individual was black or white you would probably get a puzzled look.
Adjectives like moro, nero, and negro, variations on ‘black’, were used
to refer to dark- or darker-skinned people but did not define a specific
ethnicity.6 In the sixteenth century ‘Moor’ was a nickname given to
all sorts of people. Among them was Ludovico il Moro – ruler of
Milan from 1494 to 1499 – who is not thought to have had African
ancestry at all. For mixed-race people the picture is more complex
still. The categorisation of people of mixed African and European
descent as black – through the ‘one-drop rule’ – was a phenomenon
of early twentieth-century America.7 We should not expect to find it
in Renaissance Italy. In the Florentine piazza, if you used the word
mulatto (which was used to describe Alessandro) a person would
understand you but not in straightforwardly racial terms. Mulatto –
meaning ‘little mule’ – was a term applied to bastards. It had a connotation of species-mixing: a mule is a cross between a horse and a
donkey. But it was not necessarily associated with race. (A more
detailed discussion of this issue can be found in the Afterword.)
It was not until the nineteenth and early twentieth centuries that
discussion of Alessandro’s ‘race’ came into its own – and then not in
a good way. Scientific racism provided the intellectual backdrop against
which historians of the Medici judged Alessandro’s rule. But Alessandro
also attracted the attention of scholars seeking to challenge racism.
In 1931, in the United States, Arturo Alfonso Schomburg, co-founder
of the Negro Society for Historical Research and creator of one of
the most important collections of sources for African history, wrote
an article about him for The Crisis, the magazine of the US-based
National Association for the Advancement of Colored People. Still,
while the story may have been known in the USA, it was far from



visible to me as a traveller to Florence, which I had visited three times
before I heard it. When I did, I found it not in the city’s galleries, but
in an academic book chapter in the University of London library.8 In
the museums of Florence itself there was scanty evidence even for
Alessandro’s existence. A few years ago, when I visited the Uffizi
Gallery, his portrait was not on display. To prove to friends that he
was real, I was reduced to apologetic leafing through old exhibition
catalogues in the gallery bookshop. A friend who had spent a decade
studying sociology at the University of Florence knew nothing of the
tales of Alessandro’s ethnicity. Nor did my Florentine landlady, who
had lived in the city for years. She smelt a conspiracy. In the past ten
years or so, there has been greater acknowledgement – both in
academic literature and in the art world – of the likelihood that
Alessandro was mixed-race.9 Yet he is still very far from a well-known
historical figure.
Probably the only black person in the western popular imagination
to exist before the seventeenth century is fictional. Shakespeare’s
Othello is a timeless character, often transplanted out of the sixteenthcentury context, but the text gives us important clues to how
Europeans saw Africans in this period, not least the ambiguity of their
language. Shakespeare calls Othello ‘the Moor of Venice’, but we
cannot tell from the text whether Othello is meant to be from North
Africa, or further south. The insults directed at Othello sometimes
point in the direction of Arab ancestry (‘Barbary horse’), and sometimes to sub-Saharan origins (‘old black ram’, ‘thick lips’, ‘sooty bosom’
and simply ‘black Othello’). Different productions make different
choices. Othello is a former slave, captured by his enemies then
redeemed. When Brabantio says angrily that if Othello gets away with
marrying Desdemona ‘bondslaves and pagans shall our statesmen be’
his concern is with Othello’s status and (supposed) lack of Christian
religion. Othello himself emphasises his ‘free condition’. The writers
who insult Alessandro do so by saying that his mother was a peasant
and a former slave. Yet, as we will discover, perhaps a more telling
parallel between Othello and the story of the Medici lies in Shakespeare’s
portrayal of a man – Iago – who like Alessandro’s cousin and rival for
the dukedom of Florence Ippolito de’ Medici believes he has been
passed over for a promotion he deserves.



For a very long time, the city of Florence has been mythologised
as the symbolic heart of European culture, the cradle of western
civilisation. It abounds with the images and stories of great men:
Dante, Botticelli, Lorenzo de’ Medici, Michelangelo, Galileo. The
Renaissance was the first period – so the traditional history went – in
which we could truly speak of the great individual, of the ‘Renaissance
man’. Alessandro’s story reminds us that Renaissance men may not
always have been white. Alongside the art and poetry, the scheming,
intriguing, bloody side of Renaissance politics is well known too. As
Orson Welles famously riffed, ‘In Italy for 30 years under the Borgias
they had warfare, terror, murder, and bloodshed, but they produced
Michelangelo, Leonardo da Vinci, and the Renaissance.’ To terror,
murder, and bloodshed, Alessandro’s story adds slavery and the seeds
of racism. That said, I have tried to tell it on its own terms, and
to avoid imposing a modern mentality of ‘race’ that he and his contemporaries did not share.
Alessandro’s story is a challenge to the way we think of the
Renaissance and Florence. His is an exceptional life, and that is why
we know so much about it. It is not always a heroic life. Alessandro
de’ Medici is not a fine example of princely virtue. He may well have
been responsible for murder. But you could say much the same of
many contemporaries in European politics. For centuries, Alessandro’s
story has been distorted and overlooked. There is good reason to
rediscover it. It would be no bad thing to hang his portrait a little
more prominently on Florence’s gallery walls.

The Bastard Son


It was February 1518, and Lorenzo de’ Medici, duke of Urbino and de
facto ruler of Florence, had another boil on his leg. It caused him
some discomfort, but not enough to prevent his travel to France a
few months later for his wedding. Lorenzo, the last legitimate heir in
the main line of the Medici family, was to marry Madeleine de la Tour
d’Auvergne, an heiress and a distant relative of the French royal family.
Within a couple of months, Madeleine was pregnant. She made her
entry to Florence on 7 September. ‘May God grant long life to the
Duke and to her,’ wrote Goro Gheri, Lorenzo’s secretary, ‘and many
By November, Lorenzo’s health had begun to waver. He had a little
tertian fever, ‘a small thing,’ his secretary insisted. A month later,
though he appeared better, he still could not deal with business. His
health deteriorated. In February, seeing no improvement, he rode out
to his country villa but the journey did him more harm than good.
He was now suffering fever and joint pains, and had trouble with his
voice. By April he was struggling to sleep and eat.2
The duchess’ pregnancy, in contrast, went well. On 13 April, she
gave birth to a daughter, Catherine. She had a little fever afterwards,
but that was normal, said her ladies. Ten days later, the fever had
worsened. On 26 April, the physicians turned to holy oil. They held
out little hope. On 28 April 1519, the duchess died. The news did little
for the Duke’s health. ‘Every hour [his condition] seems more serious
and more dangerous,’ wrote Gheri to Cardinal Giulio de’ Medici,
Lorenzo’s cousin. Not only was the Duke’s life now at risk: Gheri
feared a rising against the Medici in Florence. He sent for Vitello
Vitelli, one of the family’s favoured commanders, and a squadron of



On 4 May, Lorenzo died of syphilis. He was twenty-six. The troops
were not needed, in the end. The city stayed quiet. But with Madeleine’s
child a girl, and Lorenzo gone, the Medici had no legitimate male
heir. The dynasty’s future lay with two small boys: eight-year-old
Ippolito, illegitimate son of a noblewoman, and his seven-year-old
cousin Alessandro, dark-skinned and said to be the illegitimate son of
a slave. As one historian has put it: ‘The gods were briefly standing
up for bastards.’4

In 1519, no one imagined that Alessandro de’ Medici would become
duke of Florence. That he did so, observed one sixteenth-century
historian, was ‘indeed a great and singular prodigy of Fortune’.5 On
his childhood before Lorenzo’s death, the vast Medici archives are
silent. Perhaps somewhere in Rome there is a record of his baptism,
but the absence is telling. The son of a slave is a non-person. Only
after Lorenzo was gone, when the Medici desperately needed any
heirs they could get, did Alessandro come to be one of the family.
He had been born in 1511 or 1512, the son of Lorenzo de’ Medici
and a woman referred to as either Anna or Simunetta. Lorenzo later
became the duke of Urbino, a small, beautiful cultural centre in the
Marche, towards the Adriatic coast, but he is most famous as a dedicatee of Niccolò Machiavelli’s The Prince. At the time of Alessandro’s
birth, the Medici family were in exile from their native city of Florence
in north-central Italy. They had been expelled in 1494. As a French
army had marched down through Italy, their opponents had taken the
chance to seize power and had forced Lorenzo’s father Piero, nicknamed ‘The Unfortunate’, into exile. Piero died in 1503, leaving the
family reliant for its fortune and social status on his brother, Cardinal
Giovanni de’ Medici (later Pope Leo X), and his power base in the
A few writers of Alessandro’s own time claimed his real father was
Giulio de’ Medici, Lorenzo’s illegitimate cousin and the future Pope
Clement VII. Others, more malicious, said that since his mother had
slept with not only Lorenzo but Giulio and her own husband, a
coachman, too, it was impossible to be certain. But most accepted
him as Lorenzo’s son.6 It was also widely agreed that Alessandro’s

the bastard son


mother was a servant or slave in a Medici household – either Lorenzo’s
own house or that of his mother, Alfonsina. (It is often hard to distinguish servants from slaves in records of this period: the same words
could be used for both.)7
Other commentators focused not on her position in the household
but on the lowness of her birth. Jacopo Nardi, an opponent of the
Medici, and Benedetto Varchi (Cosimo de’ Medici’s official historian
and likewise no friend of Alessandro) referred to her viltà, a word best
translated as ‘baseness’ (as in the Shakespearean ‘base-born’). As we
will see, Varchi describes her as a ‘poor peasant woman’ of Collevecchio.
(The location probably comes from Lorenzino, whom he interviewed.)
Another of Varchi’s informants said she was a housekeeper. There
was a castle belonging to Alfonsina’s family, the Orsini, in Collevecchio:
perhaps she worked there, or in a family property nearby. It is likely
that rather few people knew the full facts. Of those who probably
did, Lorenzo and his mother Alfonsina were dead by 1520, while Leo
X died the following year. When his enemies taunted Alessandro for
his low birth, he joked that he appreciated them telling him where
he was born, because he didn’t know himself.8 There may have been
some truth in that retort.
Since the 1880s it has been assumed that Alessandro’s mother was
the woman who wrote the following letter to the ‘Magnificent Lord
Alessandro’ in 1528 or 1529, when he would have been around seventeen years old:
Magnificent Lord Alessandro, dearest son
Extremity leads me to write to you, and forces me with
this visit to beg you and, as far as I can, prevail upon you,
that for the love of God you should not abandon me in the
necessity in which I now find myself. I have two little children, and I don’t have the means to feed them. Even if I
make economies, I still can’t even relieve their hunger with
bread once a month. My own [hunger] means nothing to
me. . . . Less than nothing, if I should have to sell such
little holdings as I have, so as to sustain myself and not die
of hunger. Even if I could sell them, there is no grain to
buy. On account of this, my son, were it not for this last



hope remaining to me only in Your Magnificence, I should
have nowhere to turn, no recourse. So I beseech you, for
such love as you bear for God, not to forget me in such
necessity and extremity. The bearer of this letter is my
husband, who I recommend to you, as I do myself, and
these two poor children.
In Collevecchio on the 12 February 1529
Your dear mother
Taking it at face value, the letter confirms that Simunetta came from
Collevecchio – as reported by Lorenzino and Varchi. It confirms that
she was married – as Lorenzino wrote in his justification of Alessandro’s
murder. It confirms what we would expect to hear about food shortages in war-torn Italy. It places her as a small property-holder, with
two other children. If she had been a servant or slave in the Medici
household, this letter suggests that by the 1520s she had left (or been
freed) and granted a settlement. Given what we know about Simunetta,
the chances she wrote it herself are slim. Few lower-class women
were literate, but she may have found someone to dictate it to. But
her letter also raises many questions. Most of Alessandro’s papers
were known by his first biographer, the eighteenth-century writer
Modesto Rastrelli. This letter was not. There have long been doubts
about its authenticity, and the only copy has gone missing from the
archive, so it cannot be checked.10
If Alessandro’s mother did work for Alfonsina, there might be
some reference to her in household documents. Most of these records
do not survive, but Alfonsina’s will, made shortly before her death
in February 1520, listed a series of women servants who were
to receive legacies. To the house-girl went 100 florins, according to
Florentine custom. The wet-nurse was to be given a dowry and
married off; Madonna Fioraliza, who looked after the little girl
(presumably Alessandro’s half-sister Catherine), was given 150 gold
ducats; to Senoera went fifty gold ducats, so that she could buy land
at the ‘Castello’.11 Might this Senoera – whose position in the household is not explained – be Alessandro’s mother? The castle mentioned
here is probably the Castello Santo Angelo in Tivoli, part of Alfonsina’s

the bastard son


dowry and a property that Alessandro would eventually claim as his
own. A later reference to Alessandro’s mother, from 1535, describes
her as ‘poor, currently living near certain castles of Rome, and she
begs, leading a miserable life’.12 That is certainly compatible with the
story of a woman who in 1520 received a legacy allowing her to buy
land near the Castello Santo Angelo but subsequently struggled
through periods of war and difficult harvests. The absence of any
detail about Senoera’s role in the household is also intriguing. It
would fit with a desire for discretion. Senoera is not a standard Italian
name, which, in light of the questions about Alessandro’s ethnicity,
makes her more interesting still. (It is tempting to read the name as
a corruption of the Spanish Señora or Portuguese Senhora.) But this
single document is all we have and it is not enough to draw firm
Whether servant, slave or poor countrywoman, Simunetta fits the
typical pattern of the mother of an illegitimate child. Women from
all three categories were easy prey for wealthy men. In a mid fifteenthcentury survey of Florence over one-third of the bastard children
whose mother was named were children of slaves. Another 20 per
cent had a servant mother. Sexual violence against lower-status
women was very common in this society, to the point that many
probably saw it as ‘normal’.13 Whether or not there was violence in
this case (and there was always a continuous threat of violence against
runaway slaves) there was an enormous imbalance of power between
Simunetta and the man whose child she bore. At any rate, she was
far from the first woman to find herself in such a situation. There
were precedents for slave mistresses in the Medici family. Cosimo the
Elder, Alessandro’s great-great-great-grandfather, had a son with an
enslaved Circassian woman named Maddalena. (Circassia is a region
on the north-east coast of the Black Sea, now part of Russia.) Born
around 1428, the child was christened Carlo. He was brought up with
Cosimo’s legitimate heirs and had a career in the Church. He held
important papal offices in Tuscany, and helped pave the way for later
Medici sons to become cardinals. Cosimo’s son, Giovanni, also had
an enslaved Circassian mistress,14 while Giulio de’ Medici – who became
Clement VII – was himself illegitimate, son of a woman known as
Fioretta from a family of modest means. In cases like these, where



paternity was acknowledged, there was presumably enough exclusivity
in the arrangement for the master to be relatively sure that the child
was his.
Between about 1 and 1½ per cent of the eleven million people in
sixteenth- to seventeenth-century Italy were enslaved.15 As the
Circassian cases show, slaves were of varying ethnicities but by the
beginning of the sixteenth century slave-trading with these eastern
territories was in decline. The Atlantic trade, in contrast, was growing.
Unlike the Spanish and Portuguese, Italians were never central to the
trade in slaves from West Africa to the Americas, though some
Genoese merchants were involved, and Sicily (for its proximity to
Spanish trading posts in the Mediterranean) had a high percentage
of black African slaves. During the first half of the sixteenth century
the ethnic composition of the slave population in Italy was very mixed.
Wars in the Mediterranean had increased demand for galley slaves.
The majority now came from Ottoman territories: Turkey, the
Balkans, the Middle East and North Africa. Most were Muslims but
some were Jews. Black Africans were a ‘modest percentage’ of the
total. Enslaving people from Western Christendom, members of the
Roman Catholic communion, was forbidden, though some unscrupulous traders tried it. Once enslaved, though, conversion to
Christianity did not mean automatic freedom for the person concerned.
That said, slavery in Renaissance Italy had a different character to the
Atlantic slave trade. It was normal for slaves to be freed after a period
of service, or on the death of their master.16 Simunetta may have
been the daughter of a free African.
The Medici family is not associated with the purchase of enslaved
Africans to the same extent as some other Renaissance rulers. Still,
an African archer is depicted in the mid fifteenth-century fresco of
their family chapel in the Palazzo Medici-Riccardi. Piero di Cosimo’s
painting of The Liberation of Andromeda, commissioned in 1513 as an
allegory of Duke Lorenzo’s return to Florence, shows at least two
black Africans, albeit in a fantastic mythological scene. (Andromeda,
though shown as white in the painting, was supposed to have been
an Ethiopian princess.)17 Alfonsina Orsini de’ Medici came from the
Neapolitan branch of the Orsini family, and black Africans formed the
majority of the slave population of late fifteenth-century Naples.18 It

the bastard son


is well within the bounds of possibility that Alfonsina’s household
included enslaved African women.

The second bastard child in the Medici family in 1519, Ippolito de’
Medici, was the son of Giuliano, duke of Nemours (the brother of
Cardinal Giovanni/Pope Leo), and Pacifica Brandani, a gentlewoman
of Urbino. Baptised on 19 April 1511 in Urbino, he was probably born
earlier that year. He was older than Alessandro and his mother was
of higher social status. Of the two illegitimate Medici offspring, he
was the senior.19
Shortly after the birth of both boys, the fortunes of the Medici had
changed for the better. Exiled from Florence since 1494, they had built
their power in Rome and the Church. In 1512 they fought their way
back, led by the brothers Cardinal Giovanni de’ Medici and Duke
Giuliano. Unsure of their forces against the city militia, with the help
of Spanish troops they instead attacked the smaller town of Prato,
north-west of Florence. Perhaps two thousand people died; there was
mass rape; citizens were tortured. It was a terrible and effective piece
of psychological warfare. The Florentines panicked and came to terms.
The following year, there was more good news for the Medici. Cardinal
Giovanni was elected Pope Leo X. Sometime in the autumn of 1513,
Ippolito was taken to Rome.20
The popes of the early sixteenth century were very different to
their modern counterparts. As heads of the Western Church they
were – until religious division took hold with the Reformation –
considered to be the representative of Christ on earth. European
monarchs would seek the pope’s approval for seizures of power, for
conquests of new territory, for marriage and (less often) divorce. But
the popes were also rulers of a large part of Italy, stretching from
Rome north to Bologna and across to Ravenna on the Adriatic coast,
with all the usual responsibilities of government (and confl icts with
neighbouring states) that entailed. Their incomes came from landowning, from taxes on church office-holders, from the sale of church
offices (controversially), and from more surprising sources such as a
monopoly on alum, a chemical compound vital to the textile industry.
It was sometimes hard to distinguish them from any other European



monarch. Pope Leo X, for example, took every opportunity to celebrate
his family. In September 1513, he honoured his brother Giuliano, duke
of Nemours, and nephew Lorenzo, duke of Urbino, with the citizenship of Rome. He had a temporary theatre seating over a thousand
constructed on the Capitoline Hill, and held a twenty-course banquet
for the assembled dignitaries. They watched a performance of Plautus’
comedy, Poenulus or The Puny Punic, a moderately racy tale of a young
man in love with a prostitute who has to rescue her from her pimp.
It was performed in Latin but had sufficient slapstick to keep the less
scholarly entertained. Giuliano, meanwhile, used his relationship with
the Pope to bolster Ippolito’s prospects: he hoped to secure a rich
property in papal territory near the northern Italian city of Parma for
the three-year-old.21
Giuliano was now the chief representative of the Medici in
Florence, responsible for maintaining their party’s grip on government, and his life looked promising indeed. In February 1515 he
married the duke of Savoy’s daughter Filiberta, the first of his family
to enjoy such an international aristocratic match. Later that year, on
30 November, Leo X made a spectacular ceremonial entrance to
Florence. His entrata was an opportunity to celebrate his family’s
power in the city. Seven great triumphal arches, each depicting one
of the Virtues, and an eighth showing all seven Virtues together, were
set up along his route. Prudence, constancy, honesty, sobriety, chastity,
modesty and abstinence were not, perhaps, qualities associated with
the reality of Leo’s rule – his was a fleshy, worldly papacy – but they
were certainly part of his rhetoric.22 The crowds greeting Leo are
portrayed in a fresco in the Palazzo Vecchio, Florence (then known
as the Palazzo della Signoria). In Vasari’s image a group of women,
kneeling with their children, beg absolution from the pope for their
sins. One of them, an indistinct figure, holds the hand of a small,
dark-skinned child. Vasari gives no name to this figure, but it is easy
for a viewer to imagine it is the future Duke Alessandro, still outside
the family, his mother seeking to atone for having borne an illegitimate son.
A year later, aged just thirty-seven, and without a legitimate heir,
Giuliano died. Lorenzo de’ Medici had been made duke of Urbino in
1516 in a manoeuvre that saw Pope Leo X oust a nephew of his

the bastard son


predecessor, Pope Julius II, from the tiny state in favour of one of his
own. Now, as the sole heir to the family fortune and with his mother
Alfonsina in tow, Lorenzo took over the Florentine government.23 That
left Ippolito as the second-ranking layman in the family. His prospects
continued to improve. In 1517 he was created archbishop of the rich
diocese of Avignon, with a dispensation for his tender age. It was
usually expected that a bishop should be thirty.24 The acquisition of
church benefices – bishoprics, legateships, abbacies and the like – was
a route to a substantial income. At another point Pope Leo planned
for a marriage between Ippolito and a daughter of the Colonna family,
Roman barons allied to Spain. He obtained a lordship in the realm of
Naples – a part of Italy then under Spanish control – for Ippolito,
giving his nephew an income of 6,300 ducats a year. (That was, in
fact, a bribe from the king of Spain, Charles, to ensure Leo’s support
for his efforts to be elected Holy Roman Emperor.)25
Whether Alessandro grew up alongside his cousin Ippolito is not
clear, but it was not unusual for rich parents to find a slave or servant
child to act as their own child’s companion, so it is possible that he
did. The Strozzi family of Florence discussed buying a slave girl or
Moorish boy to be a friend for their own toddler son. The Medici,
like other noble parents of this period, took a great deal of interest
in the proper rearing of their children. Like little Catherine de’ Medici,
Lorenzo’s daughter, very young children would have had a wet-nurse.
Country girls were preferred. Once a little older, they were placed in
the care of tutors and nursemaids. Some religious training of children
was entrusted to women, but for the most part education was the
responsibility of fathers. Education was preparation for the masculine
sphere of political life. In the case of orphans, it fell to uncles or
in-laws to make decisions on schooling. Study began early. Even twoyear-olds might be taught their alphabet. One family memoir records
how parents would carve letters out of fruit: if a child guessed correctly,
he could eat the fruit as a reward. From the age of five, boys would
have a tutor, charged with beginning their formal education. Yet while
three-year-old ‘Ippolitino’ – little Ippolito – was numbered among the
guests at a 1514 wedding in Rome, his status as Giuliano’s son acknowledged in the list, Alessandro was not. If he was living in the household
at the time, it was not as a child of nobility.26



Unlike Giuliano, Lorenzo does not seem to have taken much of an
interest in his son. Lorenzo acknowledged Ippolito. He even gave him
a horse with a black velvet saddle and cover in 1517. In contrast, the
records say nothing to indicate a relationship with his own son,
Alessandro. A 1518 letter from his secretary noted that ‘His Holiness
has another nephew, that is, Ippolitino.’ It made no reference to
Alessandro, whose absence from the records in these years is striking.
Later observers noted Alessandro’s ‘lack of learning’ (whereas Ippolito
was widely praised on this account). That story would fit with a late
start to his education.27 At the beginning of 1519, Alessandro de’ Medici
was still nowhere near the rank of duke. Probably he was not even
acknowledged by his father.
Lorenzo was now the principal Medici representative in Florence,
though he was not the most popular of leaders. He teetered too close
to ruling like an absolute lord. Criticism was greeted with draconian
punishment. In one incident, a local who described him not as ‘Lorenzo
the Magnificent’ but as ‘Lorenzo the Shit’ was sentenced to exile for
eight years. Heavy taxes and a lack of consultation with other leading
families caused tension. His decision to leave his Neapolitan mother
Alfonsina in charge of the city while he went off on campaign
prompted great disquiet. The Florentines disapproved of a woman,
and worse a foreigner, taking charge of city business.28
(That hostility towards female rule also explains why Catherine de’
Medici was not a potential ruler for Florence. Though she would
become one of the most powerful women of her age as queen and
queen mother of France, in Florence women were almost entirely
excluded from public life. Even by the standards of the time this was
a notably male-dominated society.)29
When Lorenzo, duke of Urbino, died in May 1519, Leo and his
ministers moved fast. On the very day of the Duke’s death, they
legitimised Ippolito de’ Medici. He was now the main hope for securing
the dynasty.30
It is possible that Alessandro was legitimised at the same time, but
there is no firm evidence for the date of this process, and it may have
happened somewhat later; his name does, however, appear in a late
seventeenth-century record of legitimised Florentine bastards, now in
the city’s state archive. His mother’s social status mattered here. In

the bastard son


fifteenth-century Florence children of slaves were less likely to be
legitimised than those of higher-ranking mothers. While legitimisation
allowed a child to inherit, it could not remove the ‘stain’ of dishonour
that came from conception outside marriage. Nor could it change
what one historian has called ‘the quality of blood that flowed in the
child’s veins’. In Venice the children of servants and slaves were
excluded from entering the nobility.31 Indeed, a Venetian ambassador,
writing from Rome about the death of Duke Lorenzo, did not even
seem to know of Alessandro’s existence. ‘There’s not a single legitimate son left in the house of Medici, say the Pope’s men,’ he wrote,
‘except a natural son of the late Magnifico Giuliano.’ That was
The ambassador’s apparent ignorance of Lorenzo’s bastard confirms
that Alessandro’s profile had been low. Diplomats were expected to
know such details. But Alessandro was rapidly discovered. A few days
earlier, a better-informed private correspondent to Venice had written
that ‘there are two little bastards, one of this Duke Lorenzo and one
of the Magnifico Giuliano.’ And by the end of the month the ambassadors had more information on Leo’s plans: ‘the Pope will raise up,
it’s said, a natural son of Giuliano, and will put Lorenzo’s son into
the Church.’33 As with Carlo de’ Medici the century before, a clerical
role was a likely option for the illegitimate son of a serving-woman.
No direct comment from Alessandro on his illegitimacy survives, but
a later story about his life, written for his own bastard daughter, hints
at how he may have felt. As duke of Florence, hearing the case of a
man who claimed an illegitimate nephew could not inherit, Alessandro
asked: ‘For all that he’s a bastard, is he not made of flesh, and born
of man and woman, like you? . . . And for all that he’s a bastard, does
he not have soul and body like all those legitimately born?’34

Leo also looked to political solutions for the problems that now faced
the Medici. In the early sixteenth century, the Italian peninsula was
divided into numerous different states. There were five large ones:
the Papal States, Naples, Florence, Venice and Milan. There were many
smaller polities: for example Siena, Lucca, Urbino, Mantua and Ferrara.
Some of the Italian states were ruled by a prince – in the terminology



of the period the word ‘prince’ was applied to a range of aristocratic
title-holders including dukes, marquises and lords. Other states,
including Florence, Venice and Genoa, had an elected head of government, though generally on a very limited franchise of elite citizens.
Florence, therefore, was formally a republic, though the Medici had
become more and more princely in their style of government. Leo
now commissioned Niccolò Machiavelli to write a report on the best
options for Medici rule of Florence.
Machiavelli’s relationship with the Medici was difficult. He had held
office in Florence during their exile and had been removed from his
positions when the Medici returned in 1512. His rehabilitation had
been slow. Now, for Leo, he explained that the Medici needed to
choose between a republic (his preference) and a principality. Either
would be more stable than a hybrid solution. He proposed that
the Medici and their allies in Florence institute a radical reform of the
city’s political institutions, in which power would be shared between
the aristocracy, the middle ranks and the people, but ensured that the
Medici would be able to control appointments.35
However, the political complexities facing them extended well
beyond Florence itself. Since 1494 the larger European powers had
been fighting sporadic wars on the peninsula in alliance with various
Italian states. This was essentially a struggle for power between the
kings of France and the Holy Roman Emperor (ruler of various
German states, not yet united into a single country, Austria, the
Netherlands and after an accident of inheritance Spain too). In this
context of confl ict, states could be lost as easily as won. Even before
the deaths of Lorenzo and Madeleine, the Medici had struggled to
hold the duchy of Urbino. A year before, the city had been attacked
by its former rulers, the della Rovere relatives of Pope Julius II. With
Lorenzo gone, the ousted Duke Francesco Maria della Rovere saw his
chance. His troops advanced; Lorenzo’s infant daughter and bastard
son were hardly serious rivals. The Medici had lost Urbino. Would
they lose Florence too?
With Giuliano and Lorenzo dead, and with no heir of sufficient
age to govern, responsibility for the city now fell to Leo’s cousin,
Cardinal Giulio de’ Medici. He was its third ruler in seven years.

the bastard son


Adopted into the family as a last resort, to ‘reinforce a family line
that was disappearing’, as Paolo Giovio (a well-established adviser to
Pope Leo) put it, there were now significant changes in Alessandro’s
life. For a start, he was afforded a ‘refined education’ in the household
of his grandmother Alfonsina in Rome.36 Here, as the ‘spare’ to the
heir, Ippolito, Alessandro de’ Medici had ample time to observe and
absorb the spectacle of the splendid, decadent world of the Leonine


The court of Leo X was one of glitter, colour, glamour and spectacle.
Leo went hunting most days. He kept a menagerie in the grounds of
the Vatican. Foreign envoys competed to provide him with the next, most
exotic gift. He had an elephant, Hanno, a gift from the king of Portugal;
the king tried to send him a rhinoceros, but it drowned en route. Perhaps
its story made an impression on the young Alessandro. Later he made
the rhinoceros his emblem. Behind the scenes, Leo had a household staff
of almost seven hundred people, not including the artists and poets, or
the military officials (though an astrologer and a jester were accounted
for). Many of Leo’s cardinals openly favoured mistresses. Cardinal Dovizi
da Bibbiena, one of his closest lieutenants, commissioned Raphael to
design erotic frescoes for his Vatican bathroom. Attitudes towards papal
and indeed clerical celibacy were relaxed. The point of the celibacy rule
was that priests’ children should not inherit – and that the Church could
thereby keep control of its property. But if Leo’s court looked brilliant
to his admirers, to his critics it was worldly and licentious. Amid deepening wars on the Italian peninsula and calls for reform further north,
Leo’s government was little short of irresponsible.1
Like many wealthy families, the Medici had decided that dispatching
a second son into the Church would be a useful means of advancement. The best bishoprics brought with them substantial landholdings
and rich incomes through taxation and rents. Senior Church positions
also brought political clout. Leo’s election in 1513 had been the culmination of long efforts by the Medici to expand their infl uence in Rome.
He continued the efforts of his predecessors to assert the personal
power of the pope in the Church against those clerics who advocated
a less authoritarian system. Yet power and money also drove conspiracy.
In the summer of 1517 it had been announced that a plan to assassinate

the bastard son


Leo had been uncovered. No fewer than five cardinals were implicated,
chief among them the Sienese Cardinal Petrucci, accused with two
henchmen of scheming to poison Leo. Arrested along with Petrucci
were cardinals Riario, Sauli, Castellesi and Soderini. The evidence for
the plot was shaky at best. Careless conversation could be proven, but
little more. Some supposed that Leo had framed his enemies: the plot
was suspiciously convenient for the Pope.2
In the autumn of 1517, prompted by nervousness at Giuliano’s death
the previous year, concern to secure the Medici succession and fear
(perhaps justified) of further conspiracy, Leo had diluted the power
of the old guard in the College of Cardinals, promoting a staggering
thirty-one new men. Among them were nephews and relatives by
marriage: Giovanni Salviati, son of his sister Lucrezia; Niccolò Ridolfi,
son of his sister Contessina; Luigi de’ Rossi, a cousin. Leo’s approach
in the College of Cardinals mirrored his family’s long-time practice in
Florence of governing with a party of allies, their relationships consolidated by intermarriage. But the promotions made Leo enemies among
the cardinals who remained. Before, they had shared Church income
among barely half that number. Now, the best benefices had to be
divided between many more people. And Leo decided who got what.
That said, while nepotism aroused the ire of both jealous rivals and
Church reformers, not everyone in the sixteenth century saw it so
negatively. Within limits, the desire to do well for one’s family was
praiseworthy. Leo was hardly the first pope to promote his relatives.
In the past sixty years, Pius II had enriched his Sienese clan, the
Piccolomini; Alexander VI had done the same for the Borgias; Sixtus
IV and Julius II for the della Rovere family. Cesare Borgia, the son of
a pope, had featured at length in The Prince, Machiavelli’s famous,
though often ironic, guide to taking and holding power. Cesare had
died too young to hold his state in the Romagna, and Machiavelli
hinted that his was not an example to follow, but plenty of papal
nephews would try. From early in Leo’s reign drafts and extracts of
The Prince were being exchanged in select circles, although it would
not be published until 1532, after its author’s death.3
It was the measure of Leo’s papacy that he focused his efforts on
favouring friends and tackling enemies in Rome: his priorities were
family, legacy and power on the Italian peninsula. But further north



in Europe his policies were about to provoke a revolutionary reaction.
The Church had long supplemented its finances by selling ‘indulgences’.
In return for a donation to the Church, purchasers could redeem some
sins and spend less time in Purgatory before ascending to Heaven.
Cardinal Albrecht von Brandenburg, appointed in 1514, had borrowed
heavily from German bankers to pay his ‘annates’, the year’s income
that was the effective price of a cardinal’s hat, and to make a large
donation to the restoration of St Peter’s Basilica. Leo authorised the
sale of indulgences to pay off the Cardinal’s debts. But when one of
the Cardinal’s salesmen went too far, he found himself in confrontation
with a man about to become the most famous theologian in Europe:
Martin Luther. From 1517, when Luther’s challenge to church doctrine
became public, Leo became the target of Protestant propaganda,
contrasting his lavish lifestyle with the poverty of Christ. His decadent
doings were written up in lurid terms and illustrated in cutting detail
by reformers who had decided that the Pope was the Devil on earth.
Leo was slow to grasp the political dimensions of the threat. Indeed,
many of those who saw Leo’s court would have considered his magnificence to be a virtue. It was quite proper for rulers to display their wealth
through costly building projects, art commissions and the like. Pennypinching was not commendable in a prince. The social hierarchy
depended on the rich being seen to be rich, and being seen to be generous,
with gifts to charity, public festivals and entertainments, endowments
for churches and hospitals. Leo’s lavish rule continued unabated. The
Roman satirists were generally vicious about the Florentines, of which
Pope Leo was one. This poem, written after his death, sums it up:
Contrarians, rebels,
Sodomites, tyrants,
Sad little people,
Usurers, enemies of Christ in Heaven.
When did we ever see
The seat of Peter so despoiled
If not when Florence got its hands on the Church.4

the bastard son


It was entirely in keeping with Leo’s regime, therefore, that Alfonsina
Orsini de’ Medici, his sister-in-law, presided over a magnificent household in Rome, and it was here that Alessandro now found himself.
The Medici residence was the grand house now known as Palazzo
Madama. Leo’s three sisters, Lucrezia, Maddalena and Contessina,
stayed there during visits. Alfonsina was a wealthy woman, whose
property holdings ranged from this Roman palace to dairy farms in
Tuscany.5 Her daughter Clarice was married to Filippo Strozzi, a banker
and close ally of the Medici; they had a son, Piero, who was of an
age with Alessandro and Ippolito. Here Alessandro spent the formative
years of his childhood.
Renaissance boys were expected to acquire an impressive standard
of education, encompassing good manners and sporting prowess as
well as academic knowledge. Leo himself had been tutored by the
celebrated poet Angelo Poliziano. But, as Baldassarre Castiglione wrote
in his advice for the courtier, ‘good masters not only teach children
their letters but also polite manners and correct bearing in eating,
drinking, speaking and walking.’ To that could be added hunting,
hawking and the other sporting pursuits befitting a young prince. The
education of the young Medici boys was entrusted to Pierio Valeriano,
one of the star scholars of Leo’s court.6 Here in Rome, Alessandro
could watch Leo’s conduct of politics, and learn from that too.

On 1 December 1521, Pope Leo X died. In the conclave that followed,
Leo’s cousin Giulio de’ Medici, he who had inherited the late Lorenzo’s
mantle in Florence, had significant support, but the cardinals were
reluctant to follow one Medici pope with another. To avoid the election of a serious rival, Giulio and his fellow cardinal Alessandro Farnese
(scion of an old Roman family who owed his promotion to his sister’s
affair with Pope Alexander VI) manoeuvred an outsider into place.
Their dealings were reported to include plans for a marriage between
Ippolito and one of Farnese’s bastard daughters.7 Their compromise
candidate was a 62-year-old Dutch cardinal, Adriaan Florenszoon
Boeyens, head of the Spanish Inquisition and former tutor of the
Emperor Charles V. (Charles, king of Spain, had won his election to
become Holy Roman Emperor and now ruled the States of Germany



and the Netherlands too.) Adriaan was not even present at the conclave.
On 9 January 1522, after much wrangling, he was elected. He finally
arrived for his coronation in August that year. His serious and impartial approach to papal government sat uneasily with the men who had
elected him. His asceticism did not suit the courtiers accustomed to
Leo’s more worldly style.
Giulio de’ Medici still held the important vice-chancellorship of the
Church, making him the leading administrator of the Papal States.
But his family no longer wielded the same power in Rome, and Giulio
now had to operate a little differently. He made a settlement with the
rival della Rovere claimants to the duchy of Urbino, effectively
acknowledging that the Medici were in no position to revive their
claim on the city. He worked to cultivate the support of Charles V,
who had already promised him a pension of 10,000 ducats a year from
the archbishopric of Toledo. He commissioned another report on the
government of Florence, this time from Francesco de’ Pazzi. Pazzi
took a very different line from Machiavelli, arguing that the Medici
could best win support by satisfying the material self-interests of the
By 1522, although his family’s powers were somewhat diminished,
Alessandro’s personal stock was rising. Having been acknowledged as
one of the Medici, he needed the accoutrements of rank, and that
year Charles granted him the duchy of Penne, a fief in the realm of
Naples, along with the town of Campli, a little way to the north.
Penne lies in the eastern foothills of the Apennines, not far from the
coastal city of Pescara. This tiny medieval hill town of around seven
hundred hearths had been inhabited since long before the Romans
and was well fortified. Though Penne was not nearly as grand as
Urbino, its grant compensated the Medici a little for the loss of that
duchy. Moreover, the towns provided Alessandro with a substantial
income: at least 3,000 ducats a year. Most importantly for Alessandro,
though, the grant of a duchy ‘gave him more reputation’. Dukes, even
of minor Imperial fiefs, outranked every other sort of nobleman.
Before, he had been a mere ‘natural nephew’ in the Medici family.
Now, Alessandro was styled ‘Illustrious Duke of the City of Penne’,
and as the only duke in the Medici family he was often referred to
simply by that title.9

the bastard son


Nor were the Medici out of power for long. To the relief of the
more worldly cardinals, Adrian was a short-lived pope. He survived
barely a year, dying on 14 September 1523. The cardinals quickly
reverted to a devil they knew. Cardinal Giulio de’ Medici was elected
pope. He took the name Clement VII. In control of the Church once
again, the Medici were able to contemplate greater projects than ever
before. The Pope’s nieces and nephews became pawns for dynastic
alliances. Early in 1524 they were on show at the papal court. Alessandro
was by now twelve or so, his cousin Ippolito a little older, his sister
Catherine not quite five. It was Carnival and an observer described
the spectacle:
Plenty of masquerades here. Yesterday there was horseracing. The Cardinal of Lorraine had a livery made up,
with outfits of velvet and gold, and there were four of
them, viz. the little nephews and niece of the Pope and
their master, all very gallant, and they were praised. The
aforesaid cardinal of Lorraine paid for the lot: he spends
plenty and quickly throws his money away; he’s rich, he
can do it. There was another show, of Noah’s ark, in which
there was some music and they sang about the passing of
the flood and they threw birds out of the ark, quite a nice
invention from Cardinal Cesarino, but rather cheap.10
Giulio’s election as pope left a vacancy – again – for the rulership of
Florence. Since Lorenzo’s death, Giulio had done his best to oversee
the city’s government, but that was no longer possible. In December 1523
it had been reported that Ippolito might be appointed bishop of
Florence, but the benefice went instead to Cardinal Niccolò Ridolfi,
a cousin. In April 1524 Silvio Passerini, cardinal of Cortona and another
Medici ally, joined Ridolfi in Florence. Later that summer Ippolito,
now about thirteen years old, went too. Like Alessandro’s appointment
to Penne, this was a means of ‘giving him reputation’.11 It put him in
line to take on the role of chief family representative and de facto
lord of Florence that his father had enjoyed before him.
On 30 August Ippolito arrived in the city on a bay jennet, a small
Spanish saddle horse. He was clad in black. His entourage of ten



grooms wore red silk and white leather corselets. That this could be
described by Varchi as ‘without any ceremony’ indicates just how
extravagant normal life could be. Ahead of their procession rode a
ten-year-old black page, on a dappled jennet.12 Black pages were rather
fashionable among the nobility of Renaissance Italy. Although, as we
have seen, Europeans did not yet have a fully worked out theory of
race, they stereotyped and objectified black Africans in various ways.
These children, for example, were treated as exotic objects, through
whom a master (or owner) could demonstrate good taste and refinement. Titian had painted Laura Dianti, mistress of the duke of Ferrara,
with a black page the year before. Isabella d’Este, marchioness of
Mantua, sought to purchase black child slaves, on one occasion sending
instructions to her agent to find a girl who was ‘as black as possible’,
most likely in order to provide an aesthetic contrast to the Marchioness’
fashionably fair skin.13
Ippolito took up residence in the Medici palace in Florence, the
long-standing family home commissioned from Michelozzo in the
1450s, located between the Duomo and the Dominican convent of
San Marco. Within a year there were rumours that he might be created
cardinal. Clement, however, had much grander schemes for his
nephew. Charles V, Holy Roman Emperor, had an illegitimate daughter,
Margaret. In December 1525, a Venetian ambassador, reporting directly
on a conversation with the Pope, wrote: ‘As for the alliance that it’s
said His Holiness will make with the Emperor, viz. to give a natural
daughter of the Emperor to Signor Ippolito de’ Medici, he says it’s
not an idle rumour, but he wants to sort out public affairs before
private ones.’ Margaret was, in any case, only three years old, so
marriage was necessarily a long-term plan.14 For the moment, Ippolito
had to establish himself in the political circles of Florence.
On 19 June 1525, Alessandro and his six-year-old half-sister Catherine
were sent to join him. Although it was not yet clear whether either
of them would take any substantial role in the city government, they
needed to become accustomed to Florentine affairs and manners.
Their father Lorenzo’s regime had suffered as a result of his lack of
familiarity with the city’s customs; Lorenzo’s secretary had emphasised
the importance of sending Ippolito to Florence ‘as a citizen’ (that is,
not in too lordly a fashion).15 Alessandro, however, did not join Ippolito

the bastard son


in town. He lived about twelve miles outside the city, at the Medici
villa in Poggio a Caiano that had been his father’s last retreat. It was
a suitably discreet home for a young man of secondary status in the
family. Throughout Alessandro’s life, Poggio, with its rich hunting
grounds, would be his favoured residence. Also in Florence in 1525
was the eleven-year-old Lorenzino de’ Medici, scion of a separate,
junior branch of the family; the following year he was placed into the
care of Cardinal Passerini, along with his cousins.16
The illegitimacy of the Medici nephews occasionally prompted
comment, not least because Clement VII had been illegitimate too,
his parents’ secret marriage conveniently discovered long after the
supposed event. Michelangelo – no admirer of the Medici – joked that
the family holdings should be turned into a Piazza dei Muli, a piazza
for mules, playing on the word’s use as slang for ‘bastard’.17
At any rate, despite their differences in rank, to some observers
Alessandro and Ippolito were close enough to seem like brothers.18 A
few letters from these teenage years survive. Alessandro wrote from
Poggio asking to be recommended to ‘the Magnificent Lord’ – Ippolito
had borrowed the soubriquet used by his father and by Lorenzo the
Magnificent before him. He corresponded about silverware, and he
began collecting guns. Small matchlock firearms, a relatively new
technology, had come into their own in the Italian Wars, proving
decisive for the Spanish in more than one battle.19 Perhaps the young
Alessandro had his eye on a military career. That was a likely ambition
for an illegitimate son in Renaissance Italy. In terms of government,
Alessandro had little to do, as his affairs in his duchy of Penne had
been placed in the hands of an experienced governor, Roberto
Alessandro’s guardian at Poggio was Giovanni di Bardo Corsi,
formerly a member of Giuliano de’ Medici’s circle. A politician,
diplomat and man of letters, Corsi was well-placed to guide the education of the Pope’s nephew. In the city, Silvio Passerini, cardinal of
Cortona, was Ippolito’s political guide, a bad choice, some thought,
for his grasp of Florentine politics was poor. Ottaviano de’ Medici,
member of a junior branch of the family and husband of Leo’s niece
Francesca Salviati, took responsibility for the households of both



Alessandro was joined in the schoolroom by Giorgio Vasari. The
future author of the Lives of the Artists was of an age with the young
Duke, and spent two hours a day with him and Ippolito. Pierio
Valeriano, their tutor, boasted that under his guidance Ippolito acquired
‘perfect’ knowledge of Latin and Greek. Jacopo da Pontormo, an
up-and-coming artist who had already worked on the decoration of
the Poggio villa, painted them on Ottaviano’s commission. He showed
Ippolito with his favourite dog, Rodon. The dog, said Vasari, was done
‘so well and naturally, that he seemed alive’.22

Rumours about Clement’s plans for his nephews and niece continued
to circulate. In May 1526 there was speculation that Ippolito and
Catherine might marry as a means of preserving her inheritance for
the family. Alessandro was slated to become a cardinal.23
Ippolito, now about sixteen, was beginning to take a role in political life. In early 1527 he was to be found greeting a visiting Venetian
ambassador and attending meetings of the Otto di Pratica, the eightstrong city magistracy that dealt with external and military affairs.
When the Viceroy of Naples visited in April of that year, Ippolito led
the welcome party.24 It must have been a tense visit. Florence and
Naples were at war. The victories of Charles V against the French
had left Clement wary of growing Imperial power on the Italian
peninsula. He had established the League of Cognac – an alliance of
France, the Papacy, Florence, Venice, England and Milan – to challenge
There were challenges too within his home city. Since their return
in 1512, the Medici had run through four different figureheads: Dukes
Giuliano and Lorenzo, Cardinal Giulio and now Ippolito. Over the
years, their regime had crept closer to lordship, and that had
compounded many small resentments. Now that Ippolito was sixteen,
the prospect that he might personally come to dominate government
like his precedessors in the family grew closer. Within days of the
Viceroy’s visit, rebellion broke out.


Florence was a city of merchants. ‘They most excel in trade,’ Pope
Pius II had written, ‘which philosophers think sordid.’ (Pius was
from the rival city of Siena, and some hostility was only to be
expected.) The wealth of the Medici family was based on the wool
trade but most importantly on banking. By the beginning of the
fifteenth century they were one of the leading families in Florentine
government. In 1421 Giovanni di Bicci de’ Medici became gonfaloniere – literally, the standard-bearer of the republic, one of the most
prestigious offices in the city. He was also a banker to the popes in
Rome, and his bank has been called ‘the most successful commercial
enterprise in Italy’.1 It was the basis for his son Cosimo the Elder’s
rise to power.
These fifteenth-century Medici did not rule Florence by dynastic
right, but exercised considerable authority as the city’s leading
oligarchs. In fact, Florence excluded its old noble families, the grandi,
from government (some even changed their names in order to gain
access to power). Instead, the city was controlled by a series of elected
committees. Any member of the city’s twenty-one guilds who was
aged thirty or over was eligible to hold office. Office-holders typically
served for very short terms, a couple of months at a time. As well
as the nobility, this system of election excluded ordinary people such as
day-labourers, who were not eligible for guild membership. Threequarters of the population had no political rights at all. A handful of
families, linked through ties of friendship and marriage, could effectively manipulate the elections. In political or military emergencies,
and increasingly under the Medici’s sixty-year ‘rule’, a system of preselection of candidates allowed them further control. And with access
to city offices came access to power, infl uence and wealth.



Officially, then, Florence was a republic – and the Medici made
good use of the rhetoric of republicanism. But as Pius II put it, Cosimo
the Elder was ‘king in everything but name,’ although (in a backhanded
dig at Florentine commerce) ‘more cultured than merchants usually
Because the power of the Medici in Florence hovered on the
boundary between oligarchy and tyranny, there had been many
attempts by their competitors to move against them. The great rivals
of the Medici in Florence were the Albizzi family. Their confl ict came
to a head when in 1433 the Albizzi contrived to have Cosimo arrested.
They called a parliament, excluding Medici supporters. But infl uential
customers of the Medici bank – the Republic of Venice, the marquis
of Ferrara – came to Cosimo’s aid. The Albizzi had hoped for his
execution but had to settle instead for his banishment to Padua. The
following year, as Florence faltered in a war with Milan, Cosimo’s
supporters won the city elections. The Medici were back.
Cosimo was succeeded by his son, Piero ‘the Gouty’. Piero survived
an attempted coup but died in 1469, leaving his twenty-year-old son
Lorenzo as head of the family. This Lorenzo – ‘the Magnificent’ – was
the target of the most infamous attack on the Medici, the Pazzi
conspiracy of 1478, when assassins succeeded in killing his brother
Giuliano. Thanks to Lorenzo’s brilliant personal diplomacy, however,
the Medici held on to power. In March 1480 Lorenzo returned to
Florence, his regime secure. ‘If Florence was to have a tyrant,’ observed
Francesco Guicciardini, ‘she could never have found a better or more
delightful one.’3
The Medici had always ruled a ‘rhetorical republic’. Their opponents
had constantly accused them of exceeding their power. Back and forth
went the power play, the accusations. Lorenzo helped himself to
money held in trust for his cousins, the cadet branch of the family,
descendants of Cosimo the Elder’s brother (another Lorenzo). He
took money from the public treasury too. (It was an allegation that
would later be repeated against Pope Clement VII, following his spell
as the chief Medici representative in Florence: in November 1527 he
was deemed to owe the city 212,658 florins.)4 Lorenzo was a great
patron of art – the man who patronised Botticelli and the young
Michelangelo – but his grip on the family bank was far less secure

the bastard son


than his ancestor’s. When King Edward IV of England failed to repay
loans owed to the Medici bank, its London branch collapsed. Branches
in Milan and Bruges followed: those in Lyons, Rome and Naples were
in trouble too. As the bank faltered, the Medici became ever more
reliant on the state of Florence for their wealth and position.
Lorenzo died in 1492 and his son Piero proved a weaker ruler. He
quarrelled with the cadet branch of the family. In 1494, when French
troops marched down through Italy, his rivals in the cadet branch
backed the French. Piero surrendered. The city authorities had had
enough. The priors slammed the gates of Florence in Piero’s face,
tolled the great bell, called a parliament and threw the Medici out.
For a while, Girolamo Savonarola, a Dominican monk, ruled a virtual
theocratic state. Offending books were burnt, and art, but his populist
regime did not last. He was excommunicated and burnt at the stake
in 1498. Florence returned to a more conventional republican government, but the Medici stayed in exile. Piero de’ Medici died in 1503 while
serving with the French army. His successor as head of the family was
Cardinal Giovanni de’ Medici, the future Pope Leo X. For the next
three decades, the fortunes of the Medici would be tied to papal politics. It was thanks to the Cardinal that in 1512 the Medici made their
way back to power in Florence. But it should have come as no surprise
that their enemies would try to move against them again.

On 26 April 1525, Ippolito de’ Medici was out of town at the family
villa in Castello. A couple of miles to the north of the city, this elegant
country residence with its imposing white front and red-tiled roof
belonged to the junior branch of the Medici. Along with three cardinals – Passerini, Ridolfi and Innocenzo Cibo – Ippolito had gone to
dine with the duke of Urbino, Francesco Maria della Rovere. Two
armies were encamped nearby. The Duke led the army of the League
of Cognac but his old rivalry with the Medici over Urbino made him
an uneasy ally. His troops faced those of the Holy Roman Empire. A
rumour spread in Florence that Ippolito and the Medici had fled the
city, fearful of the Emperor’s army, fearful that the city would rebel.
Giovanni Agnello, an eyewitness to events, explained what happened
next. Having dined, he had joined the cardinals and some Florentine



gentlemen on their way back to Florence. ‘A stone’s throw away from
the city, we heard news that the whole place was up in arms, and that
the citizens had seized the main square.’ Sceptical of the rumours, they
went on to the Medici palace. It was ‘full of armed men’. As they tried
to find out what was happening, Cardinal Cibo’s brother Lorenzo and
Federico Gonzaga da Bozzolo, one of the mercenary commanders,
tried to get closer to the city centre. They were detained and taken
prisoner in the Palazzo della Signoria, Florence’s seat of government.5
The whole city, wrote Marco Foscari, a Venetian ambassador,
‘seemed to have turned upside down’. With a band of infantry, the
duke of Urbino led the way to the Palazzo, securing the streets against
the insurgents as he went. The rebels – mainly disgruntled young men
from local families – had not had much time to raise support. The
people had barred their doors and stayed inside. The rebels retreated
to the Palazzo, sniping from the windows with their arquebuses. They
killed seven or eight men, and injured many more, including one of
Cardinal Cibo’s entourage, Luciano Pallavicino. Michelangelo’s statue
of David, which stood in the piazza, nearly lost an arm.6
Supporters of the Medici brought three pieces of artillery into the
piazza ‘to clear out the palace and cut everyone inside to pieces’. The
Duke, Francesco Maria della Rovere, persuaded them not to fire,
though, and instead talked the rebels out. Realising they lacked
support, they freed Federico Gonzaga. The Duke secured written
agreement from the city authorities that the rebels would not be
penalised either personally or by confiscation of property, and they
quickly cleared out of the palace. Francesco Guicciardini, a key Medici
ally, took a hand in settling things.7 But, as Agnello explained, the
whole affair boded badly for the Medici:
The real basis for all this, as far as I’ve been able to gather,
is that many gentlemen from the most noble houses of the
city, among them the Strozzi, the Salviati, the Martelli,
unhappy with the government of their fatherland, feeling
that they were being tyrannised and mistreated, took the
opportunity of the absence of the three cardinals and
Ippolito. Thinking that they could exclude them and take
over the city government, they took up arms and began to

the bastard son


shout ‘Liberty, liberty, people, people,’ to which cry around
two hundred armed men quickly gathered, and these were
the ones who took over the palazzo. And if the lord duke
[of Urbino] hadn’t got there so quickly, and made the good
provisions I’ve described, or if they had begun an hour
earlier, they could have achieved their plan, because the
people had begun to take up arms and go in their favour,
and they would have had the backing of the greater part
of the territory.8
In fact, rumour had it that an uprising had been planned for
the following day, only to be scuppered by the spontaneous action
of the 26th.9 Foscari was more sceptical than Agnello about the
extent of popular support for the rebels; the source of their grievance,
he said, was frustration at not being permitted to carry arms in the
city (a privilege important to wealthy youths but not the most obvious
issue to rouse the people more widely). But Foscari also knew that a
city rebellion would have been especially dangerous if the Emperor’s
forces had been encamped nearby. ‘It was a good thing that the enemy
[troops] were far away; because, if they’d been near, things would
have gone badly.’10
The Medici could take heart, however, because Agnello’s report in
fact exaggerated the number of their allies involved. Most had stayed
loyal, including the main branches of the Strozzi and Salviati, traditional allies with whom they were intermarried: Clarice de’ Medici to
Filippo Strozzi; Lucrezia de’ Medici to Jacopo Salviati; their daughter
Francesca to Ottaviano de’ Medici.11 The Medici had always ruled with
a coalition of families behind them. The loss of their support would
be damaging indeed, but for now it was only rumour. Back in the
Palazzo Medici, surrounded by armed guards, Ippolito and Passerini
waited to see what might happen now.12
On 6 May 1527, Giovanni Guiducci, an agent of Cardinal Innocenzo
Cibo, arrived in Florence. He dropped in on Cibo’s fellow cardinals
Passerini and Ridolfi, advisers to the young Ippolito, hoping for news.
He found Passerini in bed, with some eye trouble and a fever. Ridolfi
was reading in the study, with its blue-and-white-tiled ceiling that
depicted the twelve months. Good-natured, quiet and virtuous, the