Dean O’Banion The North Side Gangster

Dean O’Banion was born in Maroa, Illinois in 1892, where he spent his early childhood before moving to Chicago in 1901 with his father, brother, and sister. O’Banion’s mother, Emma Brophy, who was first generation Irish her parents were from Ireland, died of the dreaded Tuberculosis, one of the biggest killers in the late 19th and early 20th centuries. His father married again and Dean O’Banion would refer to his stepmother as mother throughout the rest his life.

They settled in Kilgubbin on the North Side of Chicago which was a notorious neighborhood known for its high crime rate, it also had the name “Little Hell”, an area of the Northside that is now Cabrini Green & Goose Island. It was named “Little Hell” in the 1850s and known for its toughness and violence.

Michael Cassius McDonald or “King Mike” lived there for a while and organized his gambling empire, Big Jim Colosimo also began his life in “Little Hell”.

As a young man, O’Banion sang in the church choir at the Holy Name Cathedral but music or religion was not for him. Dean would become intrigued with the life of crime on the streets of the North Side. Along with his some of friends, Hymie Weiss, Vincent Drucci, and George “Bugs” Moran, they joined one of many of Chicago’s street gangs, whose main specialty was theft and robbery.

In 1908, a 16-year-old Dean O’Bannion was employed in McGovern’s Tavern as a singing waiter, serving drinks, mopping the floors, and allegedly tipping off his friends as to which patrons were drunk so they could be robbed when they left. Today McGovern’s Tavern is The Kerryman Inn and Restaurant

The gang would later start working in the newspaper circulation wars for the Chicago Tribune as “sluggers” who would be sent out to beat, intimidate, and harass newsstand owners who wouldn’t sell the paper they were pushing. After they got a more attractive offer they switched to the rival Chicago Examiner

Reiser taught them how to crack safes with nitroglycerine and a range of other tools, but safe-cracking was not Dean’s strong point. O’Banion was seen as reckless and careless with the explosives though Weiss was proficient with them.

O’Banion, along with Hymie Weiss, Charles Reiser, and “Bugs” Moran were all caught in the act and arrested for safe-cracking. The floor was covered in wet blankets to try to deaden the sound, however, just as the explosion went off, a policeman who was alerted by suspicious behavior entered the room, O’Banion went for his gun but was overpowered by Ryan who brought them all in for questioning, without much trouble

All four gave false names, O’Banion gave the name Edward Sterling, Moran gave George Morrissey, Weiss used Oscar Nelson and Reiser used the name John Sibly. The arresting officer, patrol sergeant John Ryan got a $300 per year pay raise and also won the Chicago Tribune’s “Hero’s Prize” for the month of May, along with a $100 cash prize.

Through contacts in the newspaper industry the gang was introduced to the political bosses of the 42nd and 43rd wards, their new job was to help achieve the desired outcome of elections through voter intimidation, violence, and other means of getting the result that was asked for.

The gang began liquor hijacking, performing Chicago’s first hijacking on 19 December 1921

According to the Chicago Tribune Dean O’Banion’s and some of his gang’s names regularly appeared in investigations into the “big time” booze, jewelry, and gambling crimes throughout Chicago between 1921 & 1924.

They soon eliminated the rest of the competition by muscling in on them or by providing higher-quality alcohol than them so that the O’Banion mob ruled the North Side and the Gold Coast. The Gold Coast was a wealthy and lucrative area of Chicago situated on the northern lakefront.

Dean O’Banion was a popular figure and known to be quite generous, he would offer tipsters 10% of the total take, which resulted in the gang receiving the best tips on booze shipments or other high-value targets. It seemed that everything O’Banion touched between 1920 to 1924 turned to gold.

Being a florist or undertaker etc. during the 1920’s would have been seen as a great return on the investment. One way mobsters showed their respects was at the infamous mob funerals during the 1920’s. In the 1920s, Chicago mob funerals often attracted politicians, judges, etc., and thousands of curious onlookers, a floral arrangement would be a highly visible way to show respect.

Mobsters would often go to Schofield’s flower shop and spend large amounts of money on floral arrangements. Mike Merlo’s, President of Unione Siciliana, floral arrangement for his funeral cost well over $30,000, while Al Capone’s brother Frank Capone’s funeral cost as much as $20,000, a lot of it spent at Schofield’s flower shop.

Al Brown the used furniture dealer better known as Al Capone once spent $5,000 on flowers alone for a funeral.

In April 1922, “Dapper Dan” McCarthy and Dean O’Banion were having breakfast together in the Hotel Sherman cafe when they received a tip-off from a speakeasy owner, Hymie Levin, he had overheard a truck driver say that he was delivering liquor to the West Side.

In 1923 Samuel “Nails” Morton died in a horse riding accident, this was perhaps the single biggest blow to O’Banion’s dominance, the death of his friend and mentor. Morton would often keep O’Banion in check, making sure he focused on the business and avoiding making bad decisions in anger. O’Banion had been known to be a hothead but also a bit of a joker and could lose focus easily.

The death of “Nails” Morton was said to have taken a toll on the rest of the gang, reportedly Louis Alterie, Schemer Drucci, Bugs Moran and Hymie Weiss brought the horse to a field where they all got drunk and each shot the horse dead in revenge for their friend’s death, however, there is no proof to back up that claim but it does make for some shock value to the legend.

In January 1924 John Duffy sometimes known as John Dougherty, a mobster from Philadelphia who moved to Chicago and did some work for O’Banion’s Northside Gang killed his newlywed wife Maybelle Exeley Duffy. Some reports say he smothered her, while other reports say he shot her in a drunken rage.

Duffy, who was in a panic began to reach out to people in the hopes of getting out of town, reportedly, O’Banion agreed to help Duffy and arranged to meet at The Four Deuce’s, Al Capone’s place on South Wabash Avenue. John Duffy was last seen alive at 8 PM outside the Four Deuce’s getting into a car by eyewitnesses, who said they had seen him getting into a Studebaker with two men. John Duffy’s body was found the following morning on a snowbank in Chicago.

Police began their investigation naturally by focusing on Al Capone, as The Four Deuces was his headquarters and Duffy was last seen outside it. Soon though, the suspicion turned to O’Banion’s gang.

Police could never gather enough evidence to pin Duffy’s murder on O’Banion. The police worked on the theory that O’Banion and two accomplices drove Duffy away from the Four Deuces. Stopping at a remote area, they believe that Duffy and O’Banion got out of the car to relieve themselves. At that point, O’Banion stood behind Duffy and shot him in the back of the head, Duffy was shot twice more before his body was dumped in the snow.

Louis “Two-Gun” Alterie and “Dapper Dan” McCarthy both cleared themselves and removed themselves from the investigation, while fellow mobster, Julian “Potatoes” Kaufman, was believed to have been the last person seen with Duffy. Dean O’Banion was sought for a few days before being questioned, Chief of Police Collins said “We are not worrying about locating O’Banion. He is never a hard man to find”. Police think that Duffy was killed because Dean O’Banion wanted to avoid a highly publicized investigation into Duffy’s wife’s murder.

1924 seemed to be a busy year for Dean O’Banion, apart from the Duffy murders, O’Banion along with Hymie Weiss and “Dapper Dan” McCarthy were also indicted and stood trial for a $30,000 beer hijacking in broad daylight. The jury in the trial couldn’t reach an agreement on a verdict after the star witness, Charles Levin, got a sudden case of “Chicago Amnesia” on the stand.

On the day of the booze robbery, O’Banion had been wanted in connection to shooting Davie Miller at the La Salle Theater five days previous.

Davie Miller was a boxer and brother of Hershie Miller, a Jewish bootlegger. According to reports Davie Miller met Dean O’Banion and Hymie Weiss in the lobby, they shook hands and exchanged pleasantries, and went their ways on good terms.

Hirschie, Maxie and Davy Miller

An associate of the Northside Gang “Yankee” Schwarts, met Davie Miller shortly after, and some words were exchanged between Schwarts and Miller. Schwarts made up a lie that Miller had spoken badly of both O’Bannion and Weiss too. After the performance O’Bannion, Weiss, and Schwarts were waiting for Davie Miller, O’Bannion asked him what he meant by the insult, things got heated between the parties and Davie Miller challenged all three to a fight and without warning O’Banion shot Miller. O’Banion, Weiss, and Schwarts all escaped.

It was inevitable that they would soon clash with enemies who turned to friends, who were now turning to enemies again, some of these enemies were Johnny “The Fox” Torrio and his protege, Al Capone, who went under the alias Al brown, they were from the Italian South Side gang and the “Terrible” Genna Brothers from Little Italy, near O’Banion’s territory on the North Side.

John “The Fox” Torrio & Al Capone

Torrio coveted the Gold Coast territory but had come to a compromise with O’Banion’s gang, agreeing to a sharing of profits in breweries and casinos. O’Banion accepted but continued hijacking shipments, angering Torrio and Capone as some of the booze that was being hijacked belonged to them. Al Capone was incensed by what he saw as an insult and asked Torrio to care of it but to keep the peace with O’Banion, Torrio refused to deal with it.

Despite their animosity, O’Banion did work together by getting some of his gang to work with Torrio and Capone in trying to influence the results of the mayoral election in 1924. During that election cycle, Al Capone’s brother Frank was shot and killed in outbreaks of violence throughout the city.

In return for his help, Torrio gave Dean a piece of Cicero’s beer rights and a quarter-interest in a casino called The Ship. O’Banion accepted but cheated Torrio by moving some Cicero speakeasies into his North Side and not sharing the profit. When Capone protested, Torrio tried to reason with O’Banion to abandon this course of action in exchange for some South Side brothel proceeds. O’Banion flatly refused, as he hated prostitution.

Left to right  Sam, Angelo, Peter, Tony and James. Mike Genna is not in the picture, presumably taking the photo  

Meanwhile, there was trouble on the horizon coming from the Genna brothers, who controlled Little Italy in Chicago’s downtown area and had begun encroaching into North Side territory, selling their lower-quality alcohol in the North Side, which raised tensions between the gangs.

O’Banion had complained to Torrio and asked him to call the Gennas off and stop cutting into his territory. John Torrio told O’Banion he would try but they wouldn’t listen to him, so O’Banion took matters into his own hands, he decided that the gang would meet every encroachment into their territory aggressively, and they also began hijacking Genna Brothers beer trucks.

Angelo Genna

O’Banion made matters between himself and the Gennas worse one night at The Ship casino, as they were counting the night’s takings and dividing the profits, it was brought to attention that one of the Genna brothers, Angelo, had an I.O.U for $30,000. O’Banion made an issue of it and John Torrio suggested they let it go in order to keep the peace. Angered, O’Banion refused and demanded a telephone and got Angelo Genna on the phone to pay in full the $30,000 debt he owed to The Ship.

Famous last words, not quite, there are differing views on what O’Banion said exactly but it was some combination of the quote above, maybe with some racial slurs perhaps. Nonetheless, the words were taken as they were meant, at this point the Genna’s wanted to get rid of Dean O’Banion immediately but John Torrio wouldn’t allow it, Torrio knew that Mike Merlo, President of Unione Siciliana wouldn’t allow such a thing to happen, Merlo was powerful and influential in the Sicilian American community and preferred peace and profit over violence.

In what became the final straw and insult Dean O’Banion tried to trick Torrio, by telling him that he was leaving the rackets and bootlegging, and he wanted to sell his stake in Sieben’s brewery on North Larabee Street.

Siebens Brewery North Larrabee Street 1956 (photo taverntrove)

In reality, it’s believed that Dean O’Banion had gotten a tip-off that the brewery was to be raided by the police and federal agents. O’Banion knew that John Torrio already had a charge for violating the Prohibition Laws and another violation would land Torrio a mandatory prison sentence.

So, O’Banion concluded, that setting Torrio up for the police / federal raid on the Sieben Brewery would put Torrio out of action for a while.

On the 19th May 1924 while John “The Fox” Torrio was attempting to buy alcohol and the brewery from O’Banion for $500,000 when Captain Matthew Zimmer and Chief Morgan Collins led thirty policemen to raid Sieben’s. Inside they found loaded beer trucks, drivers, employees of the brewery, and many gangsters, police found John Torrio, Dean O’Banion, and Louis Alterie overseeing the proceedings.

Interestingly Al Capone was not present, he had gone into hiding since “Ragtime” Joe Howard had been murdered. All of them gave aliases, were arrested, and brought to a federal building, John Torrio didn’t remain in custody for long, he could pay his bail money and went free.

Dean O’Banion, Louis Alterie, and others couldn’t pay the bail money at that time and so remained in custody until some bondsmen arrived to bail them out. Curiously though John Torrio could have easily posted bail for them but didn’t, what had taken place must have slowly sunk in for Torrio, he was humiliated, out of pocket to the tune of $500,000, and facing a mandatory jail term with a fine.

In total 38 people were indicted as a result of the raid in Sieben’s from brewery workers to truck drivers to mobsters and corrupt cops. John Torrio was sentenced to nine months and a $5,000 fine, while Dean O’Banion’s case never made it to court.

Although O’Banion saw it as a prank, Torrio didn’t see it that way and it was enough to finally put an end to O’Banion. But as long as Mike Merlo was alive nothing would happen, but Mike Merlo’s life was shorter than he thought.

Dean O’Banion and Louis Alterie wanted to get out of town till the heat died off, they both headed west to Colorado, where Alterie had a ranch. Louis Alterie is an extremely eccentric character and while he was in Colorado he lived his life as his alter ego, “Diamond Jack” Alterie a rancher and cowboy.

This trip would have dramatic consequences in mob history, the introduction of a terrifying new weapon.

On this trip to Colorado O’Banion, Alterie, and others went out hunting, while they were hunting the party was given a demonstration of the Thompson Machine Gun. Ranchers had been using the Thompson or Tommy Gun to shoot coyotes on their land. Through Alterie they set up a meeting where O’Banion bought at least one Tommy Gun, but possibly up to four. Either way, at least one Tommy Gun made it back to Chicago with Dean O’Banion and into mob history.

The Tommy Gun became the weapon of choice for gangsters, it became such a popular tool in the criminal world that the media called it the “Chicago Piano” or the more popular name the “Chicago Typewriter”.

One of these Chicago Typewriters made it into the hands of a friend of O’Banion, the notorious Frank McErlane leader of the McErlane / Soltis gang from the South Side of Chicago, who worked with O’Banion in the early days as newspaper sluggers. Whether O’Banion gave or sold one of these to McErlane or maybe had even shown or told McErlane about the Tommy Gun is unknown. What is known is that Frank McErlane was the first person to use one in gangland, in an attempt on the life of Edward “Spike” O’Donnell.

Edward “Spike” O’Donnell (left) Frank McErlane (right)

The following month after Dean O’Banion returned to Chicago another shift in Chicago’s gangland was about to happen. On the 8th of November, Mike Merlo President of Unione Siciliana died of cancer. Now with Merlo out of the way, a greenlight for a hit on O’Banion was just made easier for both John Torrio and the “Terrible” Genna Brothers.

With a major funeral happening in the city that was sure to attract every gangster, politician, and official, along with many curious on-lookers, florists were working flat out to keep up with the demand for floral arrangements, making thousands of dollars in the process.

On 10 November 1924, O’Banion was working in Schofield’s flower shop when three men entered O’Banion approached them saying “Hello boys, you here for Merlo’s flowers, O’Banion extended his hand for a handshake.

An employee in the store and best witness as to what happened, William Crutchfield, saw the three men enter and described them as two Italian men “who were short, stocky and looked rough” and the third man, who walked in between the two others, as “tall, well built, well dressed, smooth-shaven, wore a brown overcoat and brown hat. He might have been a Jew or a Greek”. The employee, assuming O’Banion knew the men went into the backroom, and moments later he heard shots fired.

Outside the flower shop three boys who were going home from school for lunch had stopped outside when the door burst open and three men ran out, one boy was pushed onto the ground by the first man to leave the shop, who he described as wearing a blue suit and blue hat and another of the boys was also pushed over by the third man who was wearing a brown overcoat and brown hat who looked older than the other two men.

The boys got on their feet and ran back to the school to get help, while the other boy followed the men who were running away and turning onto Superior Street, the boy said “When I got to the corner, I saw them get into an automobile that was parked at an alley on State Street. A woman was at the wheel of the car, with the doors open for the men” He described the woman as wearing a black veil with a brown coat and fur collar, although some others would say a man was the getaway driver.

Back in Schofields Father O’Brien and Father Morrison had arrived, having been alerted by the two boys who had run back to the school. However Dean O’Banion was dead having been shot in the head, neck, and chest, the priests gave Dean O’Banion his last rites, although he wouldn’t be buried in consecrated ground as the Catholic Church had a policy of not allowing mobsters to be buried consecrated ground. No one was ever held responsible for The Murder of Dean O’Banion but as always in mob history there were plenty of suspects.

The long-believed story of what happened is, that the evening before, Vincenzo Genna dropped by Schofield’s, paid for $750 worth of flowers, and scouted out the layout of the inside of Schofield’s. Later a phone call order for $2,000 was placed for Mike Merlo’s funeral, to be picked up the following day.

Police believe this is what may have caught the usually cautious O’Banion completely off-guard, it’s believed O’Banion came from a back-room with a shears in one hand and his hand ready for a handshake with the other. Police Captain Shoemaker said Dean O’Banion would have usually had one hand near one of his specially tailored pockets that held a gun.

O’Banion greeted Frankie Yale with a handshake, although some say it could have been Mike Genna and not Frankie Yale at all, people point to the fact that out of all the reprisals carried out against the Genna brothers, John Torrio and Al Capone, the North Side Gang didn’t make an attempt on Frankie Yale. But for argument’s sake, we will continue with Frankie Yale as the third man.

Yale clasped O’Banion’s hand in a death grip while John (Giovanni) Scalise and Alberto Anselmi fired two bullets into O’Banion’s chest, one in his cheek, and two in his throat. Finally, one of the gunmen stood over O’Banion’s body and fired a bullet close range into his other cheek.

Dean O’Banion’s funeral was lavish by all accounts, in fact, one of the biggest funerals ever held for a mobster in Chicago. The funeral was attended by up to 20,000 thousand mourners, elected officials, mobsters, and a mile-long procession of cars and trucks. 

O’Banion’s casket, which was made of silver and bronze cost $10,000 alone. His body lay in state for 3 days surrounded by many thousands of dollars of flowers, which needed 26 flower cars and trucks to carry them to the cemetery, where 5,000 curious onlookers had already gathered. The route in which the funeral procession traveled to the cemetery was lined by thousands of mourners and on-lookers,

A simple basket of roses near his casket which had a condolence card attached that was sent from Al Brown, Used Furniture Dealer. Al Brown was an alias for Al Capone who was John Torrio’s Second in Command. Capone was known for sending flowers to rival mobsters’ funerals. It’s not clear if John Torrio or the Genna Brothers sent flowers or attended the funeral, presumably they did, as is customary in gangland.

Over 200 policemen were brought in to try and control the traffic and crowds of people who thronged the route to catch a glimpse of Dean O’Banion’s funeral cortege, while the cortege itself had a police escort. People packed the rooftops along the route but the Chief of Detectives Hughes ordered the rooftops to be cleared. Mayor Dever ordered the police to search and disarm any gunman, no one was disarmed though.

Incensed by O’Banion’s murder, Louis Alterie gave a statement to reporters saying “The killers who got Dean will not catch Louis Alterie napping. I will not shake hands with anyone outside of my own family. If I can make an appointment with the killers I will shoot it out with them. One of them will never shake hands with me while two others pump me full of lead”

Alterie also publicly challenged his killers to a shootout, saying “I challenge the murderers of Dean O’Banion to a shootout with me at State and Madison!”.

Alterie’s buffoonery upset other members of the gang, they were focused on getting revenge, they were worried that Alterie would bring unwanted attention, so Weiss and Moran convinced Alterie to leave Chicago until it was safe to return.

Mrs. Viola O’Banion (4), Mrs. Margaret O’Banion (5), Dean’s stepmother, Rev. Patrick Malloy (6), William Schofield (9) owner of Schofield’s flower shop (where O’Banion was murdered, Sergeant Thomas O’Neill (14).

Other mourners included current and former State Senator’s, State Representative’s, Aldermen, Union officials

No one was ever charged for the murder but there was a who’s who rogue’s gallery of suspects

O’Banion’s murder sparked a brutal gang war in Chicago between the North and South Sides that would last until the St. Valentine’s Day Massacre in 1929. There were reprisals and spectacular shoot-outs between rivals looking for revenge and to prevail in the bootlegging wars.

In this series we will take a look at the aftermath, the individual members of the North Side gang, the enemies, suspects, and killers in connection to the Murder of Dean O’Banion

Stay tuned for more tales of gangsters, gunmen, murder, mayhem, and riots!

Sources:
http://tonsoffacts.com/
http://www.historicmoderndenver.com/
http://www.myalcaponemuseum.com/
https://www.nationalcrimesyndicate.com/
https://en-academic.com/dic.nsf/enwiki/3686945
https://chicagology.com/notorious-chicago/chalesdeanobanion/
https://www.chicagomag.com/arts-culture/june-2017/beer-wars/
https://homicide.northwestern.edu/docs_fk/homicide/ICS/ICS.20.pdf
https://chicagoandcookcountycemeteries.com/2020/01/06/a-basket-of-roses-from-al-brown/
Chicago Tribune (Chicago, Illinois) · 7 Mar 1924, Fri · Page 3
Chicago Tribune (Chicago, Illinois) · 26 Apr 1924, Sat · Page 3
Chicago Tribune (Chicago, Illinois)  Wed, Jun 1, 1921 Page 3
https://www.newspapers.com/article/chicago-tribune-duffy-murder-suspects/130546359/
https://www.amazon.com/Guns-Roses-Untold-OBanion-Chicagos
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https://www.taverntrove.com/siebens-brewery-of-chicago-illinois-usa-br-5830.html?pID=17619