Saint Valentine's Day Massacre

• 1. Introduction

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  The Saint Valentine's Day Massacre left seven men dead in a Lincoln Park garage in Chicago on the 14th of February 1929. Between four and six gunmen walked in, and two of them were dressed as police officers. The shooters fired seventy rounds from Thompson submachine guns and one cartridge from a sawed-off shotgun. The victims were members and associates of Chicago's North Side Gang, and one of them lived long enough to be questioned. He refused to name anyone. Police, a coroner, a state attorney general and the FBI all took an interest in the crime. Who was the real target? Who gave the order? Why did a case with so many investigators never reach a verdict for the garage murders? And how did a single morning of gunfire help change American gun law?

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• 2. Prohibition Chicago

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  In 1920, the 18th Amendment banned the manufacture, distribution, importation and sale of alcoholic beverages across the United States. The Volstead Act, passed in October 1919, had already defined an alcoholic beverage as anything containing more than 0.5 percent alcohol.

  Organized crime did not begin with Prohibition. Gangs already ran brothels and gambling houses, and the new law pushed them into bootlegging. Criminologist Robert M. Lombardo described the result as "a previously unknown level of competitive violence" between rival groups. One study found that the homicide rate in Chicago rose 21 percent during Prohibition. The Chicago Crime Commission identified 729 gangland-affiliated murders in Cook County between 1919 and 1933, which made up 15 percent of all murders in the area.

  Big Jim Colosimo built the city's largest and best-organized criminal group in the early 1900s. His Chicago Outfit began with prostitution, gambling and labor racketeering. When Prohibition arrived, Colosimo hesitated to move into bootlegging. He was murdered in May 1920, probably at the order of his second-in-command, Johnny Torrio.

  Torrio did what Colosimo would not. He pushed the Outfit into liquor and made deals with smaller gangs, creating a cartel that controlled liquor trading across the city. On the 24th of January 1925, three North Side men ambushed him. Hymie Weiss and George "Bugs" Moran were two of them. Torrio survived. He spent time in the hospital, then nine months in prison on an older charge, and he was so shaken that he handed the Outfit to Al Capone and moved to New York.

  The United States Attorney General's office conservatively estimated the gang's racketeering at $105 million a year in the year Capone took over. Its weekly payroll was $300,000 for a thousand men, and bribes cost an estimated $15 million per year. By 1929, Capone's own annual income was thought to exceed $40 million.

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• 3. Moran Versus Capone

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  Historian Rose Keefe says Bugs Moran earned his nickname from an intense stare joined to a sometimes homicidal temper. He rose to lead the North Side Gang after the deaths of Hymie Weiss and Weiss's successor, Vincent Drucci. In the 1920s, only the neighboring Outfit of Torrio and Capone was more powerful.

  The North Siders ran bootlegging, speakeasies, gambling dens and labor union racketeering. They also kept up older habits such as looting warehouses, safeblowing and hijacking.

  On the 12th of January 1925, Weiss had already fired at Capone's car. He wounded the driver, and Capone escaped unharmed. The feud ran on from there.

  On the 20th of September 1926, Capone was living on two floors of the Hawthorne Hotel in Cicero, Illinois. A car drove past while a man on its running board fired blanks from a machine gun into the air. Capone wanted to see the commotion, but his bodyguard, Frank Rio, pushed him to the ground. Ten cars then rolled by and fired machine guns and shotguns into the hotel and the parked cars. Police estimated that over a thousand rounds were fired. Nobody died, but a woman in a parked car suffered glass splinters in her eye, and Capone paid her medical bills, which came to $10,000.

  The two gangs still did business together. Capone received Canadian Old Log Cabin whiskey from Detroit's Purple Gang and sold it on to Moran's speakeasies. Moran then took a cheaper supply, sold it at the same price and pocketed the difference. Customers disliked the inferior whiskey. When Moran asked to go back to the old arrangement, Capone said he had a new buyer. Moran responded by hijacking as much of the Purple Gang's shipments as he needed.

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• 4. The Garage on Clark Street

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  Accounts of the build-up to the killings do not agree. Writer Troy Allen and historian Paul R. Kavieff say that on the 13th of February 1929, Moran got a phone call offering a truckload of hijacked Purple Gang whiskey. He told the caller to deliver it to the garage at 2122 North Clark Street at 10:30 am.

  William J. Helmer and Arthur J. Bilek doubt this. Most of the men in the garage were Moran's trusted inner circle and best killers, and all wore expensive suits, which makes unloading a truck unlikely. Rose Keefe interviewed one of Moran's relatives, who said there was no meeting with out-of-town gangsters and no plan to unload bootleg. In that account, the men came to meet Moran because he had been shot and the gang was losing territory to Capone.

  Moran and two fellow gang members, Willie Marks and Ted Newberry, were running late. Waiting inside were Albert Kachellek, who used the alias James Clark and was Moran's brother-in-law and second in command, and Adam Heyer, the gang's bookkeeper and business manager. Albert Weinshank managed several cleaning and dyeing operations for Moran. Frank Gusenberg and his brother Peter were enforcers. Two outsiders were there as well. Reinhardt H. Schwimmer was a former optician turned gambler who liked to hang around the gang. John May was an occasional mechanic, fixing a truck wheel with his dog Highball beside him.

  Between 10:30 and 10:35 am, a black Cadillac stopped outside. The driver and front-seat passenger wore police uniforms, and the three men in back wore ordinary clothes. Moran drove past soon afterward, saw what looked like a police car and went around the corner for coffee, assuming a raid was under way.

  Inside, the men were forced to face the wall. The gunmen shot them in the back, sweeping the line three times at head, chest and stomach height. They finished Clark and May with the shotgun. Then they walked out the front door. Two in civilian clothes raised their hands, and the two in uniform followed holding the Thompsons as if making an arrest.

  Highball's barking alerted the neighbors, who called the police. Officers found six men dead and Frank Gusenberg alive, despite multiple wounds. He had crawled 20 feet from where he fell. At the Alexian Brothers Hospital in Elk Grove, Sergeant Clarence Sweeney of the Chicago Police Department asked, "Who shot you?" Gusenberg answered, "No one.... No one shot me." Sweeney pressed him, saying, "Frank, Pete's dead and you're in a bad way." Gusenberg repeated, "No one," and died shortly afterward.

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• 5. Shock and Fallout

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  Historian Laurence Bergreen notes that newspapers gave the killings an unprecedented amount of space and sold millions of copies. Capone's biographer Jonathan Eig wrote that people from coast to coast seemed to conclude "that a line had been crossed, that the violence had become too much to bear." He added that many felt Prohibition itself had "blown up once and for all."

  Moran checked into St. Francis Hospital in Evanston, Illinois, under an alias and claimed to have the flu. He stayed four days. He sent a message to John Egan, head of detectives at the Chicago Police Department, saying "We don't know what brought it on. We're facing an enemy in the dark." When a reporter found him, Moran said "Only Capone kills like that."

  A federal grand jury met in Chicago on the 12th of March to hear evidence about bootlegging, and Capone was subpoenaed. He sent a note from a Miami doctor saying he had bronchopneumonia since January and that leaving southern Florida could risk his death. The FBI gathered affidavits from several people who had seen Capone at public events. On that evidence, a judge refused his request for a forty-day postponement and ordered him to appear on the 19th of March. His testimony slipped one day, and on the 20th of March he was questioned for an hour.

  Capone admitted he had not paid income tax. He had once said "The government can't collect legal taxes from illegal money." Now he suggested he might split any difference with the government. George Johnson, the United States Attorney for the Northern District of Illinois, then said no more testimony was needed and let him go.

  Capone also dealt with problems inside his own camp. He heard that his men John Scalise and Albert Anselmi had met with his long-time rival Joe Aiello, with another Capone man, Joe Giunta, also present. He believed they were plotting to assassinate him and take his territory. He invited the three to a dinner in their honor at The Planation, a roadhouse he owned. There he killed all three with a cut-down baseball bat, and he and his men shot the bodies. They were found on the 8th of May.

  On the 13th of May, crime bosses met in Atlantic City, New Jersey. Many worried about the publicity from the massacre and the new official interest in their business, and some were angry about the three Sicilian hitmen. They pressed Capone to lower his profile by spending a short time in prison. On the way home, Capone and his bodyguard were arrested in Philadelphia by two police officers he knew, James Malone and John Creedon. Within sixteen hours he had been charged, tried and sentenced to a year in prison.

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• 6. Detectives and Ballistics

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  Within hours, Chicago's district police, the city's detective bureau, the Illinois Attorney General's office and the coroner's office under Herman Bundesen each opened their own investigation. They worked largely apart. Major Frederick D. Silloway, the deputy Prohibition administrator, added confusion by announcing that the police had done the killings. He retracted it that day, yet several newspapers had already run headlines saying police were involved.

  The day after the massacre, Bundesen ordered a reenactment at the garage, with Highball the dog present. Instead of a coroner's jury, he assembled a panel of Chicagoans headed by Burt Massee, president of the Colgate Palmolive Peet Company. Massee contacted Calvin Goddard, a pioneer in forensic ballistics, and paid for him to set up a laboratory in Chicago with his team and equipment. Goddard examined shell casings and bullets from the scene. He also tested the Chicago police's own Thompson machine guns and stated that they had not been used.

  House-to-house questioning turned up two landladies. Minnie Arvidson, who kept the rooming house at 2051 North Clark opposite the garage, described two men posing as taxi drivers who had rented a front room. These were later identified as the lookouts Byron Bolton and James "Jimmy the Swede" Morand, or possibly Jimmy McCrussen. Mrs. Michael Doody at 2119 North Clark described another suspected lookout, who also claimed to be a taxi driver. She picked out Purple Gang member Harry Keywell from photographs, but he gave a solid alibi. Police also raided many speakeasies, costing the Outfit considerable income.

  On the 22nd of February, a garage fire on Wood Street revealed a partly dismantled, burnt 1927 Cadillac sedan. Saws, an ax and an acetylene torch had been used on it. Inside were a police siren, a Thompson drum magazine and a Luger pistol. The car had been bought second-hand on the 15th of December 1928 for $350 by a James Morton of Los Angeles, whom the Los Angeles police could not identify. The garage had been rented by a man calling himself Frank Rogers, at an address linked to Claude Maddox, a gangster with ties to Capone.

  St. Louis police told Chicago that criminals there had worn police uniforms before. The best known was Fred Burke of Egan's Rats, who was missing a front tooth. His partner used the alias "James Ray," which belonged to Gus Winkler. The chauffeur of H. Wallace Caldwell, president of the Chicago Board of Education, had seen the fake police driver outside the garage and noticed a missing front tooth. Police named Burke a suspect.

  On the 27th of February, a 1926 Peerless touring car was blown up in Maywood. It held another siren, matching shotgun shells, license plates with the prefix used by the detective squad and a notebook belonging to the victim Weinshank. Police thought it was a plant to disrupt their work. Keefe thinks it supports the idea that two cars were used.

  Police Commissioner William Russell ordered an investigation of the Outfit, since Capone had been in Florida. Police arrested Jack McGurn at Chicago's Stevens Hotel, where he stayed under the name Mr. D'Oro with his girlfriend. She provided his alibi. His biographer Amanda Parr called him "one of mob history's most prolific and notorious hit men." Scalise, Anselmi and Rocco Fanelli were also arrested. McGurn, Anselmi and Scalise were charged, but the charges were dropped for lack of evidence.

  The case stalled until December 1929, when a drunk Fred Burke drove into another car in St. Joseph, Michigan. Patrolman Charles Skelly intervened, and Burke shot him three times and fled. Skelly died three hours later. In Burke's bungalow, police found $310,000 in stolen bonds, two Thompsons with nine ammunition drums, six tear gas bombs, two rifles, a sawed-off shotgun and about 5,000 rounds. Forensic examination tied the weapons to the massacre, and one had also killed New York mobster Frankie Yale eighteen months earlier. Burke was captured in March 1931, tried in Michigan for Skelly's murder, and sentenced to life. He died in prison in 1940.

  On the 17th of November 1931, Bundesen closed his inquest. All the suspects were dead, he said, except Burke, who had a life sentence. His final report concluded that "The killings were by persons unknown."

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• 7. Competing Theories

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  Police and historians have long speculated that Moran was the intended victim, and much of the speculation has asked whether Capone was behind it. In January 1935, Byron Bolton, the suspected lookout, was arrested on an unrelated matter. Questioned by the FBI, he gave full details of the killings. FBI director J. Edgar Hoover passed them to Assistant Attorney General Joseph B. Keenan in a memorandum.

  Bolton named Fred Goetz, Gus Winkler, Fred Burke, Ray Nugent and Bob Carey as the killers. He said he bought the Cadillac touring car himself, with money from Louis Lipschultz. He denied taking part in the murders. According to Bolton, Capone ordered Moran killed to take over his territory. None of the killers knew what Moran looked like, so they killed everyone in the garage rather than risk missing him. The same names appear in the 1934 memoirs of Gus Winkler's widow, Georgette.

  Jonathan Eig disputes Bolton's account. He says two of the people named had alibis. He also argues that so large a plot to kill one man makes little sense, since a single gunman could have waited outside Moran's house. Eig favors "Three Fingered Jack" White, a vicious killer who had earlier disguised himself as a police officer to commit murder. White's motive, in this theory, was that the Gusenberg brothers had murdered his cousin. Frank T. Farrell, a Chicago resident, raised White's name in a letter to Hoover.

  Criminologists Arthur J. Lurigio and John J. Binder call Farrell's letter problematic. Many of its names and dates are wrong, including the probable identity of the cousin's murderer. The biggest weakness is that White sat in Cook County Jail between March 1926 and July 1929.

  Criminologist Arthur J. Bilek reaches a third conclusion. He believes Tony Accardo of the Chicago Outfit was one of the gunmen, in a team assembled by Jack McGurn with Burke, Winkler, Goetz and Carey. Bilek sees the massacre as the start of Accardo's rise to eventually lead the Outfit.

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• 8. Guns and Memory

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  The fight between the North Side Gang and the Chicago Outfit continued until 1930-1931, when Capone's gang took over its neighbor's territory. In June 1931, Capone was indicted on 22 counts of income tax fraud. His trial came in October 1931, and he was found guilty and sentenced to eleven years in prison.

  The Thompson machine gun became a symbol of the era. Its violence in the massacre, in John Dillinger's crimes and in the death of Chicago mayor Anton Cermak during an assassination attempt on President-elect Franklin D. Roosevelt pushed Roosevelt to act. After his inauguration he proposed a bill to regulate the sale of handguns and machine guns. The National Firearms Act of 1934 was not passed in its first form. Congress eventually removed the handgun restrictions, and the bill became law. It taxed every machine gun at $200, doubling the weapons' cost. It also created a licensing system for dealers with an annual $200 fee.

  The garage at 2122 North Clark Street was demolished in 1967, and the site later became a lawn. A Canadian businessman bought the bricks of the north wall where the victims had been shot. For many years they appeared in crime-related novelty displays, and many were later sold individually. As of 2025, the remaining bricks belong to the Mob Museum in Las Vegas. The massacre also lives on in histories and on screen.

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