In tales of the Chicago Outfit, the widowed Annette Nitti mostly stayed in the shadows – Chicago Tribune Skip to content
  • The .32-caliber Colt revolver and slug used by Frank "The...

    H.C. Lyon / Chicago Herald American

    The .32-caliber Colt revolver and slug used by Frank "The Enforcer" Nitti to kill himself March 19, 1943, shown at the county morgue.

  • Frank Nitti at the criminal courts building after surrendering on...

    Chicago Tribune historical photo

    Frank Nitti at the criminal courts building after surrendering on Oct. 9, 1940, on a conspiracy indictment.

  • Frank "The Enforcer" Nitti at the criminal courts building after...

    Chicago Tribune historical photo

    Frank "The Enforcer" Nitti at the criminal courts building after surrendering on a conspiracy indictment in 1940.

  • The scene on March 19, 1943, as police gathered around...

    Ray Gora / Chicago Tribune

    The scene on March 19, 1943, as police gathered around Frank Nitti's body along a railroad embankment in North Riverside after Nitti committed suicide. This photo was taken looking north along the Illinois Central Railroad tracks, south of Cermak Road.

  • Frank "The Enforcer" Nitti, left, with Louis "Little New York"...

    Chicago Tribune historical photo

    Frank "The Enforcer" Nitti, left, with Louis "Little New York" Campagna in 1936, was considered the man who organized hits for Chicago mob boss Al Capone and then took over the crime syndicate after Capone's conviction on tax evasion.

  • Mrs. Annette Nitti, circa 1946, during the time that she...

    Chicago Herald-American

    Mrs. Annette Nitti, circa 1946, during the time that she was testifying about her husbands estate. Editors note: this historic print has some hand painting on it.

  • Frank Nitti had a knack for staying out of jail...

    Chicago Tribune historical photo

    Frank Nitti had a knack for staying out of jail for most of his career and was even said to be claustrophobic. Rather than face trial and possible prison time on extortion charges, Nitti took his own life on March 19, 1943. After his wife left for church, Nitti walked along railroad tracks near Harlem Avenue and shot himself.

  • Mrs. Annette Nitti, widow of Frank Nitti, walks in to...

    William Yates / Chicago Tribune

    Mrs. Annette Nitti, widow of Frank Nitti, walks in to the Federal Building on April 10, 1957, after her appearance before a grand jury investigating the income tax returns of Paul Ricca.

  • The body of Frank "The Enforcer" Nitti is carried away...

    Associated Press

    The body of Frank "The Enforcer" Nitti is carried away from the scene after it was found on March 19, 1943, near a railroad embankment in North Riverside, a Chicago suburb. Police Sgt. William Rowe said the chief of the Capone syndicate killed himself. Nitti was facing extortion charges when he took his life.

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The name Annette Caravetta Nitti does not echo in the alleyways of local infamy.

Perhaps that is understandable. The gangster history of Chicago — glorified in movies, television, themed restaurants, touristy tours — is dominated by men and you know many by their names and nicknames: Al Capone (Scarface), George Moran (Bugs), Tony Accardo (Big Tuna), Paul Ricca (The Waiter), Joseph Lombardo (The Clown), and on and on.

As I have written before, “Old mobsters never die. They won’t even fade away. Instead, they wind up … tucked firmly in our consciousness. This is especially, perhaps even uniquely, true of Chicago, this hotbed of gangster-dom where many people could today tell you more about (bygone mobsters) than they could about candidates running for local office.”

Ever hear of Louise Rolfe?

She is a woman who has a role in an ancient (1945) book “Chicago Murders” by Sewell Peaslee. He tells of the day, shortly after the St. Valentine’s Day Massacre, that in trying to tracking down the killers, police detectives “broke into the Stevens Hotel suite occupied by Jack McGurn, well-known in machine-gun circles (and) found him very comfortably ensconced with a very attractive blond named Louise Rolfe.”

She told the police that she and McGurn had occupied the suite for a month, never leaving. The detectives asked if she was married. As Peaslee relates: ” ‘Not yet,’ said Louise shyly.”

Peaslee nicknamed Rolfe “The Blond Alibi.”

Mrs. Annette Nitti, circa 1946, during the time that she was testifying about her husbands estate. Editors note: this historic print has some hand painting on it.
Mrs. Annette Nitti, circa 1946, during the time that she was testifying about her husbands estate. Editors note: this historic print has some hand painting on it.

Mrs. Nitti is one of the principal characters in the story I began recently about the checkered past of the 33 W. Kinzie St. building that now houses the centerpiece of the seven-restaurant Harry Caray gastronomic empire. It is richly tied to the city’s history and has connections with the city’s early pioneers and recent sports stars and celebrities. During this pandemic, Grant DePorter, the CEO of the Harry Caray’s Restaurant Group, has been devoting considerable time to historical research of the building.

He will tell you that few of those he has encountered were as remarkable as Annette.

“She has to rank as the toughest and smartest female of the Al Capone era and beyond,” he says.

There are photos of Annette on his restaurant’s walls and they show a formidable looking person.

She came to prominence as a secretary for a man named Edward “Easy Eddie” O’Hare, who was a racetrack owner and Capone’s attorney/crony. He was also, as they say in the mob biz, a “rat,” testifying as a prime witness against Capone in the tax evasion trial that landed Capone in prison from 1931 to 1939.

The week of Capone’s release, Annette is said to have helped arrange the murder of O’Hare, who was shotgunned to death while driving his car near the intersection of Ogden Avenue and Rockwell Street. His two killers were never found.

In the wake of that murder, Annette, who had been given power of attorney over O’Hare’s assets, began to sell, trade and otherwise exercise those considerable holdings.

In 1942, she married Frank Nitti (nee Nitto), who had been serving as either mob boss or puppet for others — there will ever be some debate about his status — during Capone’s imprisonment. As a nuptial gift, Nitti he gave his new bride $75,000. DePorter, among many others, believes this could been payment for helping arrange the hit on O’Hare. She used that money to purchase the building that is now Harry Caray’s.

Unfortunately, her marriage did not last long. On March 19, 1943, Nitti, facing trial and possible imprisonment for his role in a Hollywood movie studio extortion scheme, drank himself into a semi-stupor and fatally shot himself three times as he wandered in the railroad yard only blocks from his Riverside home.

Frank Nitti at the criminal courts building after surrendering on Oct. 9, 1940, on a conspiracy indictment.
Frank Nitti at the criminal courts building after surrendering on Oct. 9, 1940, on a conspiracy indictment.

As she battled grief (I assume), Annette also began lengthy battles on legal-financial fronts. But she and the 10-year-old Joseph, the son Frank Nitti had adopted during a previous marriage, had always kept in close contact with O’Hare’s son, Butch. Raised mostly in St. Louis, he became a World War II hero when, on Feb. 20, 1942, he singlehandedly downed a number of Japanese bombers attacking his aircraft carrier. This would make him the first naval aviator recipient of the Congressional Medal of Honor. In presenting the award, President Franklin D. Roosevelt referring to O’Hare’s skill as “the most daring single action in aviation history.”

O’Hare would die on Nov. 26, 1943 while leading the U.S. Navy’s first nighttime fighter attack launched from an aircraft carrier. His plane and his body were never recovered. But in 1949, with the enthusiastic support of Robert R. McCormick, the publisher of the Tribune, the name of the city’s Orchard Depot Airport was changed as a tribute to O’Hare. (Annette and Joseph were among the “dignitaries” at the formal and lavish renaming ceremony in March 1963, when President John Kennedy spoke of O’Hare’s bravery).

Annette was ever doing battle with the ferocious forces of the IRS and others. One of those was Alex Greenberg, a mob accountant. She demanded that he give her the $2 million that she claimed Nitti had entrusted to him for her. He refused and in December 1955 he was fatally shot and stabbed along with his wife Pearl after they had dined at a restaurant named the Glass Dome Hickory Pit on the South Side.

She tried keep a low profile, though she and son Joseph would help run Caravetta Foods, a wholesale business that was started by her father, Louis. It was an Italian food import business, one of its main product was Parmesan cheese and it was for a few years headquartered in the Kinzie Street building. She sold that building in 1969 and lived a quiet life until her death in 1981. She is buried in Mt. Carmel Cemetery in west suburban Hillside. There are a lot of other gangsters buried there. Some you might have heard of, some not. Nitti’s grave is not far from those of her husband and Capone.

DePorter tells me that he is in contact with members of the Nitti and Caravetta families and that they continue to provide him with memorabilia and stories, feeding his passion for the past and his attempts to bring in into the present.

He has carved from a recently discovered second floor space in the restaurant a handsome private party room that he has named Nitti’s Speakeasy. It has its own menu and few special cocktails. One is “The Black Widow,” a nickname given to Annette by a writer. It is a concoction made of gin, lemon juice, honey, blackberry preserves and a lemon twist.

“It is a just a nod to this fascinating woman,” he says. “She seems to deserve that.”

Not exactly my kind of drink but I might be tempted.

rkogan@chicagotribune.com