Today, people have the option to celebrate Valentine’s Day with loved ones, or to celebrate not having a significant other, or even to protest against the garish commercialism that has come to represent the holiday. But in 1929, Valentine’s Day was the bloody climax of Chicago’s notorious gang war between George “Bugs” Moran and the infamous Al Capone.
Both gang leaders ran their bootlegging operations out of Chicago. Illegal liquor was big money, and the rivals fought for control of the booze business — and therefore millions of dollars in profits — in the Windy City.
On February 14, 1929, five of Moran’s men, an optometrist friend of Moran’s crew named Reinhardt Schwimmer, and a mechanic were waiting for an arranged shipment of booze in a garage on the North Side of Chicago. Moran himself was scheduled to be there, but as he was pulling up, he saw men dressed as police officers entering the garage and, thinking it was an alcohol raid, left. It turned out that being fashionably late would save his life.
Inside of the garage, four men, two dressed as police officers, had the seven men in the garage line up facing against the wall. The men dressed as police were not police, but rather Capone’s hitmen, who were likely trying to target Moran himself. They fired more than 160 machine gun rounds, executing the men on the spot.
When the actual police arrived, Frank Gusenberg, one of the gang members who was shot, was still clinging to life. He refused to talk, allegedly responding to the question of who shot him with, “No one, nobody shot me.”
The bloody event marked the beginning of the end for organized crime’s unchallenged romp through Chicago as law enforcement began cracking down on gang activity. No one, however, went to trial for the seven murders of the St. Valentine’s Day Massacre.