20. The Mob’s Most Notorious Payback Massacre

Prohibition fueled organized crime by pouring unimaginable riches into its coffers. It also fueled a cycle of escalating violence and payback between gangsters competing for a slice of the increasingly lucrative illegal alcohol. In Chicago, that competition reached a crescendo on February 14th, 1929. Seven members of George “Bugs” Moran’s North Side Gang were stood up against a wall, then cut down by automatic weapons gunfire, in what came to be known as the Valentine’s Day Massacre.

Capone had hatched a plan to lure Moran to a warehouse, with the promise of delivery of cut-rate stolen whiskey, then kill him along with his chief lieutenants. However, just before reaching the warehouse, Moran spotted a police car nearing the warehouse, and turned around. Four men in police uniforms exited the vehicle, entered the warehouse, and ordered its occupants to line up against a wall for a pat-down. The cops were fake, and soon as the men turned around to face the wall, the “policemen” opened fire with shotguns and Thompson submachine guns. Six died on the scene. A seventh, despite taking 14 bullets, refused to ID the shooters, telling investigators “nobody shot me”, before expiring.



