Now home to a number of Italian restaurants, an antique store and several apartment complexes, North Clark Street in Chicago’s Lincoln Park section is presumably very much the same quiet, residential neighborhood as it was during the Prohibition era. But on February 14, 1929, this street would be encapsulated into history books as the site of the ‘Saint Valentine’s Day Massacre’.

At a usually inactive garage owned by the infamously active gang leader George “Bugs” Moran, seven gangsters were shot down in cold blood. The primary target, Moran, was presumably late to the meeting, which most likely saved his life. While it is speculated that the order for the hit came from Al “Scarface” Capone, neither he, nor anyone else, were ever found guilty of the crime.

According to police records and eyewitness testimony, four or five men emerged from a black Cadillac outside of the garage. Two of these men wore police uniforms as they entered through the front door of the garage. After ordering the seven men inside up against a wall, they used two tommy guns and a shot gun to spray the men with ammunition.

The men inside of the garage consisted of Johnny May, a former safecracker hired by Moran as a mechanic; Frank and Peter Gusenberg, brothers well known for their troublemaking; James Clark, convicted of robberies and murder; Adam Heyler, an embezzling accountant; Albert Weinshank and Reinhardt H. Schwimmer. All men, who were known associates of Moran, were dressed in expensive suits. They were all found with thousands of dollars in cash and their own weapons still on them and never pulled in retaliation.

Frank Gusenberg was the only one still alive when the Chicago police arrived to the scene. While gasping for air, Gusenberg told detectives that “coppers did it,” according to a number of reports.

Due to the well-known rivalry between Moran and Capone, it was suspected that Capone ordered the hit on Moran and his men, but Capone himself was being questioned in Florida at the time of the gruesome massacre.

Another theory has come to exist based on a letter sent to the F.B.I. that supports Gusenberg’s claim. This letter, filled with extraordinary detail of the events that transpired, said that the act was carried out by William “Three-Fingered Jack” White as revenge for his cousin’s death.

White had a history of working with Moran’s men and it is speculated that the men were expecting his arrival to carry out a heist. White also had a history of wearing police uniforms on the job in order to lessen any suspicion. The cousin whose murder he may have avenged was also the son of a police sergeant. Given that the massacre was hardly ever investigated, police involvement with White’s revenge seems plausible.

The case remains open nearly 90 years after the events on North Clark Street. Historians suggest that the publicity of this case is what eventually led to Capone’s demise.

Editor’s Note: The information within this article is largely based on the book, “Get Capone,” by Jonathan Eig.