Capone and Company's botched plan

The St. Valentine's Day massacre—the most spectacular gangland slaying in mob history—was actually somewhat of a failure.

Al Capone had arranged for Chicago mobster George "Bugs" Moran and most of his North Side Gang to be eliminated on February 14, 1929. The plan, probably devised by Capone's henchman "Machine Gun" Jack McGurn, was simple and deviously clever, but Capone's primary target escaped.

The Plan

A bootlegger loyal to Capone would draw Moran and his gang to a warehouse under the pretense that they would be receiving a shipment of smuggled whiskey for a price that proved too good to be true. The delivery was set for a red brick warehouse at 2122 North Clark Street in Chicago at 10:30 a.m. on Valentine's Day.

Capone arranged to distance himself from the assassinations by spending time at his home in Miami while the heinous act was committed.

The Morning of February 14, 1929

That snowy morning, a group of Moran's men waited for Bugs Moran at the warehouse. Among them were Jon May, an auto mechanic hired by Moran; Frank and Pete Gusenburg, who had previously tried to murder Machine Gun Jack McGurn; James Clark, Moran's brother-in-law; and Reinhardt Schwimmer, a young optometrist who often hung around for the thrill of sharing company with gangsters. Moran happened to be running a bit late.

When Moran's car turned the corner onto North Clarke, he and his lackeys, Willy Marks and Ted Newbury, spotted a police wagon rolling up to the warehouse. Figuring it was a bust he watched as five men—including three dressed in police uniforms—entered the warehouse. With the arrival of the "cops," Moran and Co. scrammed.

The Massacre

Inside the warehouse, Moran's men were confronted by the hit men disguised as policemen. Assuming it was a routine bust, they followed instructions as they were ordered to line up against the wall. The hit men then opened fire with Thompson submachine guns, killing six of the seven men immediately. Despite 22 bullet wounds, Frank Gusenberg survived the attack but died after arriving at Alexian Brothers Hospital.

After the attack, the uniformed perpetrators marched their plain-clothed accomplices out the front door with their hands raised, just in case anyone was watching. Capone's hit men piled into the police wagon and drove away.

The Aftermath

The newspapers instantly picked up on the crime, dubbing it the "St. Valentine's Day Massacre." The story appeared on front pages around the country, making Capone a nationwide celebrity. While Capone seemed to revel in his new fame, he also had to deal with the new level of attention from federal law enforcement officials.

George "Bugs" Moran knew Capone wanted him killed and pegged the crime on him right away. "Only Capone kills like that," he said, though authorities had no concrete evidence. Capone was in Florida and his henchman McGurn had an alibi of his own. No one was ever tried for this most spectacular slaying in mob history.