Today in History—February 14: The Day Chicago’s Bootlegging War Spiraled Out of Control

At 10:30 am on this day in 1929, light snow was falling in Chicago. A black Cadillac—the kind favored by police—pulled up outside the North Side garage of mobster George “Bugs” Moran. Four men got out, two of them in police uniforms.

The men entered the small, one-story garage that housed the cars used in Moran’s operations. Inside, seven men were surprised by the interlopers. When ordered to line up against the wall, Moran’s men complied, believing they were being raided by police.

They weren’t. They were executed with Thompson submachine guns—Tommy guns—by associates of South Side rival Al Capone. It marked one of the deadliest and most infamous escalations of violence in Chicago’s gang wars.

Moran was supposed to be there too, but he was late. When he arrived and saw the Cadillac, he and two associates kept walking—and lived to bootleg another day.

The seven men inside were killed: Peter Gusenberg (mob enforcer), Frank Gusenberg (mob enforcer—talent runs in the family), Albert Kachellek (mob enforcer), Adam Heyer (mob business manager), Albert Weinshank (mob business operator), Reinhardt Schwimmer (optician with questionable taste in friends), and John May (mechanic for the mob).

Prohibition had been in effect since 1920, and Chicago had become the bootlegging capital of the country. What the government took away, the gangs supplied: Alcohol flowed in from Canada or from hidden stills. Speakeasies and illicit sales flourished.

But on this day, the city’s gang rivalry spiraled out of control. Public reaction was understandably intense. Until then, Capone had enjoyed a reputation as a kind of folk hero, a rough-edged neighborhood guy who gave to the poor. But the wanton violence ended that.

No one was ever convicted. Capone was in Florida at the time. Authorities brought charges against a few of his associates, but none stuck. (One suspect quickly married his alibi—er, girlfriend—so she couldn’t be compelled to testify.)

The murder weapons were later recovered from a house in Michigan. One of the men believed to have used them, Capone associate Fred “Killer” Burke, was arrested there and sentenced for an unrelated killing. He was never charged for his alleged role in the massacre.

The outrage ran straight up to the White House, where newly elected Pres. Herbert Hoover authorized federal help to bring down Capone. It took two years. The charge that finally toppled the untouchable gangster? Tax evasion. It landed him in prison long enough to lose control of his empire.

In the end, Capone wasn’t brought down by bullets—but by his books.