Generations of Americans assume that Al Capone was responsible for the St. Valentine’s Day Massacre, the murder of seven associates of rival mobster George “Bugs” Moran in a Chicago garage on February 14, 1928. In fact, Capone, the flamboyant Chicago crime boss, was never even questioned in the murders. No one was ever brought to trial in the case, making the St. Valentine’s Day Massacre the most spectacular unsolved crime in gang history.
What is not disputed is that a black Cadillac pulled up to the SMC Cartage Company garage on North Clark Street around 10:30 a.m. and disgorged four – possibly five – men, two of whom were carrying police uniforms. They ordered the seven men inside the garage to line up facing the wall and opened fire with two Thompson submachine guns, strafing the victims with over 70 bullets. Moments later, the gunmen came out with their hands up, shoved by the alleged cops, and left. Six of the victims died at the scene. Before succumbing, the seventh spat “The cops did it” or “Nobody shot me”, according to various accounts.
As newspapers splashed the gruesome photos across the country, dozens of theories emerged. Most were as riddled with holes as the blood-splattered garage wall. Several key questions remain unanswered:
Why were Bugs Moran’s men in the garage that morning?
Early theories held that the seven victims – mob accountant Adam Heyer, second-in-command Albert Kachellek; nightclub owner Albert Weinshank, enforcers Peter and Frank Gusenberg, mechanic John May and Reinhardt Schwimmer, an optometrist who enjoyed spending time with them, were there to split a hijacked shipment of whiskey or headed to Detroit to collect some others. But most were dressed in expensive suits, not the typical booze-unloading attire. They may have been called into a business meeting, real or fake, and may have lined up in a compliant fashion, assuming corrupt cops were just putting on a show. The victims still had thousands of dollars in their pockets, so the theft apparently had no motive.
Bugs Moran was not among them. A spotter for the shooters apparently mistook one of the other men for Moran, who was still a block away, and reported that the shot was starting too soon.
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Who killed them and why?
Capone had an airtight alibi. He was in a Dade County, Florida courthouse that morning being questioned by prosecutors about another murder. Of course, Capone could have ordered the hit from Florida. He had motives: his men and Moran’s had been exchanging fire for years and vying for control of bootlegging, cleanup operations, and dog racing in and around Chicago. Police arrested several Capone soldiers, but released them for lack of evidence.
Mafia historians offer conflicting theories. In their 2004 book, The St. Valentine’s Day Massacre, William J. Helmer Jr. and Arthur J. Bilek claim that Capone called in a secret St. Louis crew dubbed the “American Boys” to take out Moran. Not knowing what he looked like, the gunmen shot everyone in the garage to be sure. But Jonathan Eig, in his 2010 biography Get Capone, argues that if Capone wanted Moran dead, he would have posted a lone hitman outside the rival’s house. “Killing seven guys out in a carefully planned way doesn’t make sense,” Eig told HISTORY.com.
A possible rift in the case came in late 1929, when Fred “Killer” Burke, a former Capone associate, fatally shot a policeman in Michigan. A huge weapons cache found at Burke’s home included two Tommy pistols that matched bullets from the Valentine’s Day shot. Burke was sentenced to life for the murder of cops, but was apparently never questioned about the guns in the massacre.
READ MORE: How the Prohibition Era Boosted Organized Crime
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In January 1935, the chicago american The newspaper declared the matter “solved”, reporting that Bryon Bolton, a member of another gang, had confessed to taking part in the massacre. Local and federal officials vehemently denied the story, which died down amid the confusion. Behind the scenes, however, federal authorities questioned Bolton, according to a 1936 summary in FBI files. Bolton claimed he bought the Cadillac and was present at a Wisconsin resort where Capone planned the hit. He also named five triggers, including Burke and other “American boys,” all of whom were dead, missing, or in jail on other charges at the time. The FBI apparently never shared this information with Chicago police, and Bolton’s allegations were not investigated.
Was it a case of revenge?
Yet another massacre theory surfaced years later in unsealed FBI files. In a 1935 letter, Frank Farrell, a state highway employee, urged FBI Director J. Edgar Hoover to investigate the fatal 1928 shooting of William Davern, Jr., the son of a Chicago Police Sgt. According to Farrell, Davern told his rogue cousin, William “Three-Fingered Jack” White, that Moran’s henchmen had shot him. White then staged the massacre in revenge, Farrell wrote, luring Moran’s men to the garage under the guise of implicating them in a factory heist.
Eig says Farrell’s account resolves many details, including why the men were in the garage and why the Chicago police might have looked in the direction or even participated, avenging the loss of one of their own. Doubters note that White was in prison from 1926 to July 1929. But Eig says he could have bribed his way for brief periods. White, who also worked as an FBI informant, was shot in his home in 1934.
Why were the Chicago cops so ineffective?
According to Helmer and Bilek, organized crime was rampant in Prohibition-era Chicago, which had 10,000 speakeasy and 500 unsolved gang murders. “The whole system was corrupt – they had been bought off at every level,” Eig said. Capone was arrested frequently, but never detained for long. Bolton told federal authorities the Chicago detective chief was on Capone’s payroll, receiving $5,000 a week at the time of the massacre.
In contrast, when the Philadelphia police arrested Capone and a bodyguard later in 1929 for carrying illegal weapons, they were charged, convicted, and sentenced to a year in prison within 16 hours.
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Where was the FBI?
Although J. Edgar Hoover later turned the FBI into a crime-fighting powerhouse, he was unwilling to participate in the St. Valentine’s Day Massacre, insisting it was a local affair. He rejected Justice Department requests to investigate the case and denied that organized crime even existed until the 1950s. Several authors have suggested that mob bosses had blackmail material on the head of the FBI; others argue that he was simply more concerned with bank robbers and suspected subversives.
Determined to arrest Capone, President Herbert Hoover (no relation) ordered his Treasury Department to investigate the mobster’s finances instead. The man nicknamed “Public Enemy No. 1” was sentenced to 11 years in prison for federal tax evasion in 1931.
Could Capone have been charged with the massacre after his release, as some newspapers have speculated? In theory, but by then Capone’s brain was so plagued with syphilis that he was no longer considered a threat to society. He died in 1947.
Furthermore, Eig suggests that letting the cloud of suspicion hover over Capone was more helpful to feds than trying to prove it in court and risk having him beat the rap again. Meanwhile, Capone’s legend grew increasingly in books, movies, and TV series as a mobster who got away with the St. Valentine’s Day Massacre.
