Be My Valentine? Maybe Not.
In the late 1920s, the rivalry between Chicago's two main bootleg gangs — Al Capone's and George "Bugs" Moran's — had reached a boiling point. Both bootleggers wanted revenge for past killings and control of Chicago's illicit liquor market. There being no real law enforcement in Chicago, none of Moran's boys blinked when three men in police uniforms showed up at one of their secret locations on February 14, 1929. Assuming the cops just wanted a payoff, the Moran gang members dutifully lined up against one of the garage's walls waiting to be told what the bribe would be. The "cops" were actually henchmen sent by Capone. They shot the Moran boys in cold blood and clipped an innocent bystander in the process. When it was all over, seven were dead. Moran's lateness that day saved his life.
The incident broke Moran's will, however, and he never again challenged Capone. Sent to Leavenworth prison on burglary charges, he died there in 1957.