On the night of Feb. 13, 1929, Chicago's North Side Gang leader, George "Bugs" Moran, received a phone call from an unknown bootlegger, offering him a shipment of Old Log Cabin whiskey at the phenomenal price of $57 per case. To make the deal even sweeter, the bootlegger claimed he stole the shipment from Moran's nemesis, Al Capone. Moran agreed to have the booze delivered to his warehouse headquarters at 2122 North Clark St. the next day. What followed would be the infamous Saint Valentine's Day Massacre.
Since the enactment of Prohibition in 1920, the black market sale of alcohol had become an immensely lucrative business, and organized criminals violently competed for turf and profits. Chicago became the symbol of this bloodshed. The two most powerful factions were the largely Irish- and Polish-American North Side Gang and the predominantly Italian-American South Side Gang, also known as the Chicago Outfit.
Full-scale war broke out in 1924 when Chicago Outfit leader Alphonse Capone decided to have his North Side rival, Dion O'Banion, "whacked" in O'Banion's florist shop headquarters.
The North Side's new leader, Hymie Weiss, and his lieutenants (including Moran) forced Capone's partner into hiding and killed several prominent South Side allies. Capone retaliated by ordering a hit on Weiss in 1926, which eventually left Moran in charge.
Moran continued to obstruct Capone's plans to move operations into the more upscale northern parts of the city. The Irish mobster also opposed the Chicago Outfit's involvement in prostitution.
In late 1928, after further escalation of the warfare, Capone decided Moran's gang needed to be destroyed in one fell swoop. To ensure that none of the killers would be recognized, Capone hired men from outside Chicago to do the dirty work. As an alibi, Capone would be in sunny Florida while the killings took place.
On a chilly Saint Valentine's Day morning in 1929, seven North Side men waited for the shipment Moran had agreed to accept. They included five actual gang members, Moran's mechanic, and an optician, who enjoyed the company of mobsters.
Moran himself was running late, and when he saw a Cadillac in front of his warehouse garage, he decided to continue walking, believing the Cadillac to be a police car. Four men, two dressed as police officers and two as civilians, exited the car and entered the garage. Believing this was a police raid, the North Siders lined up. The intruders mowed them down with Thompson sub-machine guns, firing more than a hundred bullets per minute. The gang members masquerading as policemen then escorted the two "civilians" out to give the appearance of a simple arrest.
The Saint Valentine's Day Massacre left a grisly scene. Some of the bodies had nearly been cut in half by the spray of bullets. Although there had been dozens of individual murders during the long feud, the mass slaughter was unprecedented. The subsequent police investigation was unable to result in any convictions, and the identity of the shooters is still the subject of debate.
Though Moran had survived, his organization never recovered. He became a petty criminal after Prohibition and died in prison in 1957.
Although Capone had won the gang war, Chicago's citizens were disgusted by the massacre. In 1932, Capone was imprisoned - not for murder, racketeering, or the bootlegging of alcohol, but for failure to pay taxes on his illegal income. After spending over seven years in prison, including a few in the newly opened Alcatraz Federal Penitentiary, Capone was paroled for health reasons. He died from syphilis in 1947 at his Florida mansion.