In 1920’s Chicago, during the era of Prohibition, two rival organized crime gangs, led by George “Bugs” Moran and Al “Scarface” Capone, fought each other in the streets for control of the lucrative rackets in the north side of the city. On February 14, 1929, that battle was ended by a hail of machine gun bullets in one of the most famous crimes in US history, the St Valentine’s Day Massacre.
Al Capone in a 1929 mugshot
In 1920, the US ratified the Eighteenth Amendment to the Constitution, which outlawed the manufacture or sale of alcohol. Prohibition was the work of religious reformers who hoped to improve the moral character of America. Instead, it made illegal bootlegging one of the most lucrative businesses in the US, and made the criminal gangs who controlled the booze business insanely rich and powerful.
In 1919, a year before Prohibition, a smalltime hood from New York had arrived in Chicago. Alphonse Capone had worked as a bouncer in a nightclub run by mobster Frankie Yale (during a fight in the club over a woman, Capone had been slashed on the cheek with a knife, giving him the nickname “Scarface”). In Chicago, Capone worked for local gangster Johnny Torrio, who ran a huge gambling and prostitution empire under Chicago’s crime boss, “Big Jim” Colosimo. There was tension between Colosimo and Torrio, however. Colosimo was opposed to entering the new bootlegging business, fearing it would bring increased law enforcement pressure from the Federal government, while Torrio saw bootlegging as a way to make enormous sums of money and thought Colosimo’s reluctance was holding the entire organization back. The business dispute was resolved when Colosimo was shot to death in May 1920, allowing Johnny Torrio to take over as boss. Capone was suspected by police of being the gunman, presumably on Torrio’s orders. He became Torrio’s second-in-command, and the two set up a city-wide network of illegal breweries, distilleries, and liquor clubs known as “speakeasies”.
Torrio’s largest rival in the Chicago bootlegging business was the North Side Gang, an Irish/Jewish group run by Dion O’Banion. The commercial rivalry soon turned to open conflict, as each side began to encroach onto the other’s territory. Torrio tried to keep things peaceable, but when the North Side Gang cheated him in a deal (which led to Torrio’s brief arrest), matters turned violent. In November 1924, O’Banion was shot and killed by Torrio gunmen, and Hymie Weiss took over leadership of the North Side Gang. In January 1925, Weiss, accompanied by North Side gunmen Vincent “Schemer” Drucci and George “Bugs” Moran, in turn ambushed Torrio outside his apartment and shot him. Torrio survived, but decided that gangster life was no longer for him. He retired to Italy, and left his Chicago criminal empire to Al Capone.
For the next several years, Capone expanded “The Outfit” and soon controlled virtually all of the bootlegging, gambling and prostitution in Chicago. With an income of over $100 million a year, Capone bribed police and politicians alike, including Chicago’s corrupt Mayor “Big Bill” Thomson. Unlike most gangsters, who shunned publicity and tried to avoid attracting attention, Capone loved the spotlight, lived a lavish lifestyle, and cultivated his contacts with the press, telling reporters that he was just a businessman who was providing Americans with the booze that they wanted.
The war with the North Side Gang also continued. Capone’s driver was kidnapped and killed, then in 1926 the restaurant where Capone was staying was sprayed with machine gun bullets. In retaliation, Hymie Weiss was ambushed and shot in October 1926. That left Vincent “Schemer” Drucci in charge of the North Side Gang, until he was himself killed in a fight with police in April 1927. “Bugs” Moran took over leadership. He soon began hijacking Capone’s beer trucks.
By 1929, Capone decided to end the conflict with the North Side Gang once and for all. Moran ran his gang operations from a building at 2122 North Clark Street that housed the “SMC Cartage Company” as a front. Capone had his henchmen rent an apartment in a building across the street to keep an eye on Moran and his lieutenants. In February 1929, a local bootlegger, acting on Capone’s instructions, told Moran that he had a load of whiskey illegally smuggled from Canada at a good price, and they agreed to meet on Valentine’s Day to make the deal.
On the appointed day, Capone’s lookouts watched as Moran’s men entered the building for the meeting. At about 10:30 am, they saw a person they took to be Moran go inside, and gave the signal. A car pulled up in front of the Cartage Company, and three men in police uniforms got out. At the same time, another car stopped at the rear entrance to the building, with two more men. Inside Moran’s headquarters, there were seven people: James Clark was Moran’s second-in-command, brothers Peter and Frank Gusenberg were enforcers for the North Side Gang, Adam Heyer and Albert Weinshank were minor gang members, Reinhardt Schwimmer was an optician who hung around with the gang, and John May was a car mechanic who occasionally repaired the gang’s autos. Investigators later concluded that the three “policemen” ordered the seven men to line up against a wall, and thinking this was a routine police raid, the gang members complied. Then the two other men entered the building, pulled out Tommy guns, and emptied 70 submachine gun rounds and 2 shotgun shells into them. The only survivor of the shooting was John May’s German shepherd “Highball”, who was tied to one of the cars. The “policemen” then took the two plainclothes men out of the building with their hands raised, to convince any eyewitnesses that they had been arrested.
The massacre had missed its primary target. The lookouts had apparently mistaken Weinshank for Moran: Moran himself was a few minutes late, and was walking down the block towards the building with a fellow gang member when they saw the “police” arrive, turned around, and walked quickly away.
When the real police arrived at the scene, they found one of the victims, Frank Gusenberg, remarkably still alive after having been hit 14 times. Gusenberg was taken to the hospital where he refused to talk to police, and died three hours later.
The “St Valentine’s Day Massacre”, as it was immediately dubbed by the press, created a sensation, taking Chicago gang violence to a new level. Bugs Moran, whose organization had now been completely destroyed, bitterly told reporters, “Only Capone kills like that.” Capone himself had conveniently been in Florida on the day of the shootings, but police soon tied his associates to the crime. The lookouts in the apartment across the street were identified as members of Detroit’s “Purple Gang”, who were working with Capone. In February 1930, police arrived at a garage that had been set on fire and found a car inside with two Thompson submachine guns. The car belonged to Capone enforcer Fred “Killer” Burke, and ballistics tests showed that these were the two weapons used in the massacre. Police also suspected Capone gunmen “Machine Gun” Jack McGurn, John Scalise, and Albert Anselmi. Charges were filed against McGurn and Scalise, but Scalise was killed by gunmen before the trial (along with Anselmi–they had been caught plotting to overthrow Capone), and the charges against McGurn were dropped for lack of evidence.
Ultimately, the massacre led to Capone’s downfall. Appalled by the level of violence, the Federal government took an interest in him, and targeted him for investigation. In November 1931, Capone was convicted of tax evasion and sentenced to 11 years, first in Atlanta and then in Alcatraz. While in prison, he began to suffer from previously-undiagnosed syphilis, and by the time he got out of jail in 1939, his mental abilities had been destroyed. Capone died, delusional and broken, in his home in Florida in January 1947.
The brick building where the St valentine’s Day Massacre took place was demolished in 1967. Today it is a parking lot for a nursing home.
The site of the St Valentine’s Massacre today. The tree stands at around the spot where Bugs Moran’s men died.