Many prohibition era criminals have become folk heroes and topics of popular movies such as Pretty Boy Floyd and Al Capone. But the rule of organized crime particularly in large urban cities like Chicago is well known.
And the viciousness of the battles between warring factions of prohibition gangs was just as real and bloody as they are depicted to be in the movies.
There may be no event that became more well known because it illustrated how brutal the war between the north side and south side Chicago crime lords had become than the St. Valentine’s Day Massacre on February 14, 1929.
The lead up to the massacre started when the leader of Chicago’s north side crime organization, Dion O’Banion was gunned down by the south side crime bosses lead by Johnny Torrio and Al Capone.
As often happens in these kinds of exchanges, that murder lead to an open war between the two crime organizations. As a result, an attempt was made on Torrio’s life that was unsuccessful. But the outcome was that Torrio left Chicago and turned over the south side crime organization to Al Capone.
The attacks back and forth continued over the years. Capone almost lost his life in September 1926. In retaliation, Capone had O’Bannion’s successor, Hymie Weiss murdered.
With the top spot of the north side organized crime business in need of leadership, the notorious “Bugs” Moran took over. Early in 1929, Moran struck the Capone south side crime syndicate when they gunned down one of Al Capone’s men, Pasquillano Lolordo.
This murder so infuriated Capone that he vowed to get even on Valentine’s Day. This was a vow he would carry out with a vengeance. An ambush was arranged through a contact in Detroit who contacted Bugs Moran to arrange a shipment of bootleg whiskey.
That contact was made on February 13, 1929 and the meeting was made to receive the shipment at a garage at 2122 North Clark Street on the next day, February 14, 1929, Valentine’s Day.
On that infamous morning, a gathering of Moran’s men arrived at the predestinated spot to receive the whiskey.
Those men included a safecracker named Johnny May, Frank and Pete Gusenberg, James Clark, Al Weinshank, Reinhardt Schwimmer, and Moran’s brother-in-law Adam Heyer. Bugs Moran himself was late to the meeting and as he approached, he saw a police car pull up to the garage.
Moran skipped into a nearby building fearing a bust. But the two uniformed men and three men in civilian clothes that got out of that police car and went into the building were gunmen working for Al Capone.
Within moments, the sounds of the machine gun execution of Moran’s men and the cries of the dying were heard all around the neighborhood.
The massacre was so brutal that it became one of the most notorious gangland murders in the history of 20th century crime. Capone arranged to be in Philadelphia during the hit. Ironically, it was there that he was arrested for having concealed weapons and it was that charge that sent Capone to prison.
In prison, Capone began to be “haunted” by the ghost of James Clark and the prison night was often broken by Capone’s cries begging Clark to leave him alone.
Those hauntings continued to trouble Capone until his death. Even the site on 2122 North Clark Street became a haunted location with many reports of sounds of screams or gunfire coming from the abandoned building.
Small wonder that the St. Valentine’s Day massacre has become one of the most well known incidents in 20th century crime history.