The Washington PostDemocracy Dies in Darkness

How a Valentine’s Day massacre tied to Al Capone became mob legend

Chicago gangster Al Capone is photographed in custody in Philadelphia in May 1929 on charges of carrying concealed weapons. (AP)
5 min

On the day seven men were executed in a Chicago garage, a lone lightbulb hung from the ceiling.

Cars and trucks sat parked in oversize spaces. Sunlight peeked in through a dirty window. Members of George “Bugs” Moran’s bootlegging gang were gathered in the garage they had rented for storage and repairs, the author Jonathan Eig chronicled in the book “Get Capone.”

It was Feb. 14, 1929 — a day meant to be about love — when a handful of men pulled up in a black Cadillac, stepped out armed with machine guns and shot the gangsters dead.

The St. Valentine’s Day Massacre, as it became known, cemented Chicago’s place in the history of organized crime and put a target on the back of the famed mobster Al Capone, who was widely believed to be behind the killings. Outraged Americans pressured officials to crack down on the rampant gang violence fueled by Prohibition era bootlegging. Eventually, prosecutors arrested Capone for tax evasion and won a conviction.

“That probably takes him out of Chicago gangland,” said John Binder, the author of “Al Capone’s Beer Wars.” “So the Capone problem is in many ways — probably in the eyes of many people — solved.”

Nobody was charged in the killings, which began when several men strode through the door of the SMC Cartage Company garage on North Clark Street around 10:30 a.m. Two of them were dressed as police officers.

The assailants told the gangsters and their associates that they were under arrest. They forced the men to line up against a wall, raised their machine guns and other firearms, and fired at least 70 shots.

Responding police officers — real ones — found one gang member, Frank Gusenberg, alive by the skin of his teeth. Pressed to identify his killers, Gusenberg was tight-lipped.

“Cops did it,” he told a sergeant, according to Eig’s book. He refused to reveal more before he died hours later.

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Among the other six victims, according to Eig: An auto mechanic, a convicted armed robber, an accountant and embezzler, a nightclub owner, and an optometrist who hung around Moran’s gang mostly for bragging rights. The mechanic’s dog, Highball, was tied to a truck by a leash and was howling when police arrived.

Although Americans were used to mob violence, the carnage was a bridge too far for many. In the growing anger, President-elect Herbert Hoover saw an opportunity: He had run on a platform of being tough on crime. Now he had a chance to attach actions to his words.

Tabloids, newly popular, helped Hoover argue that the gangs were out of control. The newspapers put the crime squarely in the public’s sights, running gruesome photos of the victims strewn about with the blood that had poured from their bodies pooled on the cement floor.

“Suddenly, people were looking at these things with their coffee and eggs in the mornings,” Eig said in an interview.

Suspicions turned immediately to Capone, whose associates had a long-standing rivalry with Moran’s North Side Gang. Moran, who was running late on his way to the garage the day of the massacre and missed being slain, later told reporters, “Only Capone kills like that.”

Capone was in Florida at the time, but that didn’t stop public opinion from settling on the idea that he must have ordered the hit. One of his associates, Fred “Killer” Burke, was found to have two weapons with bullets matching those used in the massacre. Three people told police they had seen Burke enter the garage that day. And the gangster Byron Bolton claimed to law enforcement that he was involved in the killings and that Capone had planned them.

An affair. The mob. A murder.

Eig, the author of “Get Capone,” doubts that Capone was the mastermind. He posits that the perpetrator probably was William “Three-Fingered Jack” White, whose cousin was allegedly shot by Gusenberg or his brother Peter Gusenberg, who also was killed in the massacre. The Valentine’s Day attack may have been an act of revenge, Eig argues.

“The police and feds couldn’t believe that Capone had anything to do with this crime, nor did they ever solve it,” Eig said. “But it nevertheless gave them more incentive to turn the screws on Capone and try to get him off the streets by any means necessary.”

The killings also had broader impact. In the aftermath, a group of Chicago civic leaders traveled to Washington to beg Hoover to get Capone under control, said Binder, the author of “Al Capone’s Beer Wars.” The U.S. Bureau of Prohibition created a special squad, called the Untouchables, meant to aggressively shut down Capone’s operations. Capone and the leaders of several other prominent gangs made a peace treaty, which held for about a year.

In 1967, the garage where the massacre took place was razed. More than half a century later, just a grassy yard remains.