The St. Valentine’s Day Massacre: What Happened Before That Caused This Infamous Crime?

Marcy Kennedy Knight is an award-winning writer who has written for television, theater, publications and the web. 

The brutal murder of seven men in that cold Chicago garage on February 14, 1929, was the beginning of the end of Al Capone. Never could he have imagined that this one particular crime put the target mark on his back – not just from the Federal government but also from the syndicate.

Many people know what happened after the Massacre, but most people are sketchy as to what led up to this crime and the players involved. This article will give a quick synopsis to help bring the pieces to the Massacre puzzle together.

“Big Jim” Colosimo, owner of more than 100 brothels in Chicago, refused to even consider bootlegging at the start of Prohibition as suggested by his business partner Johnny Torrio. Rebuffed by Colosimo, Torrio reached out to Colosimo’s allies, the Genna Brothers and Joe Aiello and then called a New York friend and associate Frankie Yale (who had just sent him one of his employees who was running from a New York murder charge, Al Capone.) Torrio was also furious at “Big Jim” on a personal level; Colosimo had just divorced his wife (who happened to be Torrio’s aunt), and married an actress and singer. On May 11, 1920, Yale came to Chicago to visit. Colosimo was murdered. Torrio was now in charge of the gang with Al Capone as second-in-command.

The main Mob organization in Chicago at that time was run by Dean O’Banion of the “North Siders.” He and Torrio together owned a number of gambling and drinking establishments, but their business partnership eroded when Torrio forgave a $30,000 gambling debt incurred by one of the Genna brothers, the same Gennas that were encroaching on O’Banion’s territory.

O’Banion, in turn, sold Torrio the Siben Brewery, which just happened to be raided the day of the sale. (Torrio was sentenced to nine months in jail.) Before serving his sentence, Torrio asked Frankie Yale to come back to Chicago to visit. On the morning of November 10, 1924, O’Banion was murdered inside his flower shop business. Hymie Weiss took over the North Side Gang.

January 12, 1925 – North Siders riddled Capone’s car with bullets. Capone was not hit.

January 24, 1925 – North Siders Weiss, Vincent “The Schemer” Drucci and George “Bugs’ Moran, tried to kill Torrio before he went to prison; the gun failed, and they ran.

March 13, 1925 – Capone was trying to control the Unione Siciliana. His handpicked president Sam “Samoots” Amatuna, leading member of the Genna gang, was gunned down. It was believed the shooter was Drucci.

March 26, 1925 – The new Unione Siciliana president, “Bloody” Angelo Genna, was gunned down.

Mid April 1925 – Angelo Genna’s brother Mike was gunned down.

September 20, 1926 – Capone was shot at while having lunch at an Italian restaurant; he survived.

October 11, 1926 – “Little Hymie” Weiss was gunned down outside the same flower shop where O’Banion had been murdered almost two years before. Vincent Drucci now headed the North Side Gang.

April 4, 1927 – Drucci was gunned down by a police officer as they exchanged verbal assaults. Moran now headed up the North Side Gang.

Sometime in between – North Sider brothers Frank Gusenberg and Peter “Goosey” tried to knock off one of Capone’s top gunmen, “Machine Gun” Jack McGurn. They failed.

November 27, 1927 – Joe Aiello felt he earned the presidency of the Unione Siciliana; Capone had other ideas and made that perfectly clear when Aiello brothers Robert and Frank were gunned down.

July 1, 1928 – Frankie Yale, who had formed an alliance with Aiello, was visited by several of Capone’s men in New York. Yale didn’t survive.

January 8, 1929 – Joe Aiello and Bugs Moran paid a visit to the new Unione Siciliana President Antonio “The Scourge” Lombardo. A few shots later, the office of the President was again vacant.

February 14, 1929 – The key members of the North Side Gang were scheduled to meet at the SMC Cartage Company Garage. There was a traitor in the ranks and Moran wanted to discuss strategies with his men. Moran was running late due to a haircut; that haircut saved his life. While approaching the garage that morning, he saw a “police” car out front and retreated. Moran had no way of knowing that his men were being massacred in the very moments that he walked away.

Who actually shot the seven men that frigid February morning? No one will ever know for sure. The Saint Valentine’s Day Massacre is one of the most notorious unsolved mysteries – a mystery that continue to fascinate people almost 100 years later.