When booze was banned in the United States in the 1920s, it was supposed to inaugurate a brave new era of health and morality. Instead, Prohibition unleashed a crime wave that made parts of the nation into urban war zones. One of the front lines was Chicago, the domain of flashy, flamboyant kingpin Al Capone, whose name has always been linked with the most notorious gangland crime of all time: the St Valentine’s Day Massacre of 1929. All these years later, the case has never been officially solved, and the question remains: was Capone really behind it?
A major reason Capone’s always been considered suspect number one is that the victims were part of the North Side Gang, led by Capone’s bitter nemesis Bugs Moran. The two mobsters loathed each other, and fought savagely for control of Chicago’s streets. If anyone stood to gain from the blood-splattered events of that infamous day, it was Al Capone.
On St Valentine’s Day morning in 1929, a group of Moran’s men were huddled in a garage used to repair the gang’s vehicles. It was quite a cross-section of characters, ranging from hard-bitten gangsters like Frank and Peter Gusenberg – two brothers who were among Moran’s most violent and notorious trigger-men – to criminal accountant Adam Heyer, to the relatively blameless John May, a mechanic for the Moran organisation who had the bad luck to be working on a vehicle that day.
At around 10.30am, men in police uniforms entered the garage. The mobsters and the mechanic, assuming it was just another mundane raid, calmly lined up for inspection. Then, according to the usual version of events, more men entered – this time in plain clothes – and mowed the group down with Tommy guns. Cleverly, the plain-clothed assassins were led out at gunpoint by their uniformed accomplices, so witnesses thought a police raid was underway.
When the actual police arrived, they were met by a scene of slaughter that was gruesome even by Chicago standards. The victims’ bodies had been all but obliterated by shower of bullets, but one man was still just about breathing. It was Frank Gusenberg, himself a veteran hitman, now the one dying in a pool of blood. Recognizing Frank, one of the cops bent down and asked who’d shot him. According to different accounts, Gusenberg either blamed the cops themselves, or simply said “Nobody shot me”, obeying the Mob’s code of silence to the very end.
Nobody shot me
The St Valentine’s Day Massacre shocked the nation, and brought new police and media scrutiny on the operations of mobsters everywhere. This is one of the reasons some are sceptical about the theory Capone ordered the hit. Some historians point out that Capone’s rivalry with Moran simply wasn’t enough of a reason to orchestrate a shocking massacre that would attract so much unwelcome attention. Besides, if he’d wanted to assassinate key players in Moran’s gang, it would surely have made more sense to pick them off separately, in low-key hits, rather than a sensational orgy of blood-letting.
It doesn’t help that there’s still so much ambiguity over the basic details of the massacre. For example, why were Moran’s men even gathered in the garage that morning? The conventional version of events has it that they were lured by a mysterious bootlegger who’d promised to sell them a consignment of cut-rate whisky, but there are other theories. Some have even suggested that Moran himself ordered the men there to purge them from his ranks and pin the blame on Capone.
Unlikely? Perhaps. And certainly, the single best lead in the case seems to connect the massacre to Al Capone. This lead was Fred Burke, bluntly nicknamed “Killer”, who was identified by an eyewitness on St Valentine’s Day. Later that year, Burke was implicated in the senseless killing of a young patrolman who’d intervened when Burke got into a minor car collision. Burke shot the cop in cold blood, and was eventually jailed for the crime, but here’s the interesting thing for Mob historians: Burke’s home was found to contain guns which forensics tests proved had been used in the St Valentine’s Day Massacre.
This bombshell didn’t lead to any further revelations. It seems that Burke’s status as a cop-killer trumped the messy events in Chicago. But Burke’s known association with Capone means that – if he was indeed one of the killers that day – then it’s very likely Capone was indeed the mastermind.
Some still dispute it, though. One of them is Jonathan Eig, author of Get Capone, who argues that Capone had little to gain but a lot to lose from such an audaciously bloody operation. Eig subscribes to the so-called “Farrell Theory”, named after a Chicago citizen called Frank Farrell, who’d sent a letter to the FBI claiming that the massacre had nothing to do with mob rivalries at all.
According to this theory, it was a simple act of revenge, enacted by William White, aka “Three-Fingered Jack”, a veteran thug who held the Gusenberg brothers responsible for the shooting of his firefighter cousin. “Just about any time you see seven men dead, there's a reason that somebody was angry,” Eig says. “In this case, I suspect that it was the family of a young firefighter who was killed by some members of the Moran gang.”
Absolving Al Capone, Eig argues the personal nature of this motive would account for the savagery of the attack. But you could argue that this theory is based purely on hearsay, and doesn’t explain why some of the guns wound up in the possession of known Capone minion Fred Burke. On balance, it seems more likely than not that Chicago’s most mythologised mobster really was behind the events of that bloody Valentine’s Day, but it’s a mark of that crime’s impact that it’s still arousing intrigue almost a century later.