What is now a parking lot adjacent to a senior living center on Clark Street in Lincoln Park was once the location of a shocking, violent event at the height of Chicago’s gangland wars of the 1920s.
The St. Valentine’s Day Massacre marked a critical point in the Beer Wars, a years-long conflict between Chicago’s gangs who were battling for control of the bootlegging market and organized crime during Prohibition.
On February 14, 1929, six men associated with George “Bugs” Moran’s North Side gang were in a garage on Clark Street, likely awaiting an illegal liquor shipment. They were Peter Gusenberg, his brother Frank Gusenberg, James Clark, Reinhardt Schwimmer, Adam Heyer, and Albert Weinshank – all men associated with the North Side gang. Another man, John May, had some ties to the gang and was also present.
Four other men, two of whom were dressed like police officers, showed up. Thinking their operation had been busted – a familiar occurrence for bootleggers – the North Siders gave up their weapons and lined up against the wall.
But the men disguised as police officers took out Thompson machine guns and other weapons, and they sprayed a hail of bullets into the North Siders. Six of the men died on the scene, and a seventh would die hours later. The imposters escaped before the real police showed up and discovered the grisly scene.
Bugs Moran had narrowly escaped the hit when he saw what he thought were authorities entering the garage to bust the crew, according to John J. Binder in Al Capone’s Beer Wars, so the gang’s leader avoided the hit.
While many gangland battles saw two or three gangsters killed at a time, there had never been gang violence with this kind of death toll. “It jumps all the way up to seven in very spectacular fashion using machine guns,” Binder told Chicago Stories.
“The crime really shocks America,” Jonathan Eig, author of Get Capone, told Chicago Stories. “There are seven people dead in a parking garage, and not only that, the newspaper photos are gruesome.”

Newly elected President Herbert Hoover made fighting crime a priority of his campaign and his administration, and Al Capone was his primary target. But was Capone behind the St. Valentine’s Day Massacre?
At the time, Capone had a solid alibi: He was in Miami at the time of the murders, not Chicago. “I don’t think Capone had anything to do with the Valentine's Day Massacre. We know for a fact that he wasn’t there,” Eig said. “The feds were after him. He was in Miami when it occurred. He knew that the FBI and the IRS were breathing down his neck. There’s just no reason to think that he would’ve ordered this hit. There’s just no logic to it.”
But Binder argued that Capone likely hired outsiders to do the job, and Capone’s name has long been associated with the massacre.
“I think it is quite erroneous to claim that Capone had nothing to do with the St. Valentine’s Day Massacre,” Binder said. “He didn’t go in there and shoot those guys himself. He made sure he was out of town, and he didn’t use…men from his gang whose faces would be recognized by the North Side gangsters. But it was definitely a Capone operation.”

The shooters were never conclusively identified, either. Fred Burke, a member of the St. Louis gang Egan’s Rats (which was allied with the Capone gang) has widely been suspected of being one of the killers. One of the most compelling pieces of evidence for this was a confession from a man named Byron Bolton. Bolton served as one of the lookouts for the massacre and told the FBI a few years later some of the details of the crime. Byron’s confession, upon which the FBI never acted, implicated the gangsters Burke, Fred Goetz, Gus Winkler, Raymond Nugent, and Bob Carey as the killers.
“We’ll never know for sure because the crime,” said Eig, “almost a hundred years later remains unsolved.”