Valentine's Day Massacre
The Valentine's Day Massacre, which occurred on February 14, 1929, in Chicago, is one of the most infamous events in American organized crime history. Set against the backdrop of Prohibition and the fierce rivalry between rival gangs, the massacre involved the brutal killing of seven members of Bugs Moran's North Side gang. Allegedly orchestrated by Al Capone's South Side gang, the attack was executed by men disguised as police officers who lined the victims up and shot them in a garage.
The event was fueled by ongoing battles for control over illegal alcohol distribution and marked a significant escalation in gang violence in the city. Although Capone was widely suspected of orchestrating the hit, there was never enough evidence to convict him. The massacre not only highlighted the rampant lawlessness of the era but also contributed to Capone's eventual downfall, leading to his imprisonment for tax evasion in 1934. It remains a pivotal moment in the history of organized crime, reflecting both the brutality of gang warfare and the complex interplay of power within the criminal underworld. The Valentine's Day Massacre continues to captivate public interest, illustrating the dark legacy of this turbulent period in American history.
Valentine's Day Massacre
Date February 14, 1929
When George “Bugs” Moran’s gang was executed by a group of men dressed as police officers in a garage in North Chicago, Al Capone was believed to be behind the hit, and the event marked the beginning of the end of Capone’s reign as Chicago crime czar. The massacre sparked a wave of reforms that helped to dismantle Capone’s empire.
Also known as St. Valentine’s Day Massacre
Locale Chicago, Illinois
Key Figures
Al Capone (1899-1947), leader of Chicago’s South Side gangGeorge Moran (1893-1957), leader of Chicago’s North Side gangJack McGurn (1905-1936), Chicago gangster and lieutenant to MoranFrank Gusenberg (1893-1929), Chicago gangster and lieutenant to MoranPete Gusenberg (1889-1929), Chicago gangster and lieutenant to MoranAdam Heyer (1889-1929), Chicago gangster and lieutenant to MoranJohn May (1894-1929), Chicago gangster and lieutenant to MoranAl Weinshank (1893-1929), Chicago gangster and lieutenant to MoranAlbert Kachellek (1890-1929), Chicago gangster and Moran’s brother-in-lawDean O’Banion (1892-1924), leader of Chicago’s North Side gangAbe Bernstein (d. 1968), leader of Detroit’s Purple Gang
Summary of Event
During Prohibition, Chicago’s Beer Wars were at the forefront of the national imagination. For years the city had been turned into a battleground. Dean O’Banion ruled the North Side, and Al “Scarface” Capone and Johnny Torrio had the South Side. O’Banion was killed in 1924 by Frankie Yale, John Scalise, and Albert Anselmi, gunners for Capone, and Torrio was killed the following year by North Siders Earl “Hymie” Weiss, Vincent “The Schemer” Drucci, and George “Bugs” Moran. Soon after, Weiss, Drucci, and Moran made an attempt on Capone’s life. They failed, and Weiss later died at the hands of two Capone gunmen; Drucci was killed by a young cop. Eventually, Moran was the only one of O’Banion’s men left, and he took over the North Side operation. Moran swore an eternal vendetta against Capone, who had long been desperate to have control of the North Side as well as the South Side. While on vacation at his home in Palm Island, Florida, in early 1929, Capone received word that Moran’s gunners had killed several of his top lieutenants.

What happened next would become the source of a great deal of speculation. Capone was the logical person on whom to pin any attack against the North Siders, and many believed that he had ordered a hit on Moran’s entire gang. According to this theory, Capone made contact from Florida with Abe Bernstein, leader of Detroit’s Purple Gang. Capone and Bernstein concocted an elaborate scheme that involved placing a call to Bugs Moran. Bernstein probably placed the call—according to reports, he had somehow worked his way into Moran’s good graces—and reported that a recently hijacked shipment of bonded whiskey was being sold at a cheap price. Moran jumped at the chance to get hold of the whiskey and told the caller to have the shipment delivered to his headquarters—a garage on Chicago’s North Side—the next day.
On the morning of February 14, 1929, the day after the alleged call was placed to Moran, Moran’s gangsters assembled at his headquarters. The garage, which was located at 2122 North Clark Street and owned by Moran stooge Adam “Frank” Heyer, was a front and had a phony sign in the window that said “S.M.C. Cartage Company.” There were seven men present at the garage: Heyer; Frank and Pete Gusenberg, Moran’s top gunners; safe blower John May; speakeasy owner Albert Weinshank; bank robber Albert Kachellek (also known as James Clarke); and Dr. Reinhardt Schwimmer, an optometrist who liked to hang around with gangsters for excitement and probably used his business as a cover for criminal activities. The men were anxiously awaiting the arrival of Bugs Moran, who was traveling with two other members of the gang, Willie Marks and Ted Newbury, and was late. When Moran, Marks, and Newbury arrived at the garage, they saw a black Cadillac—the type that detectives used at the time—pulled up to the curb. Figuring that the cops had been tipped to the shipment of whiskey, Moran, Marks, and Newbury retreated to a nearby coffee shop.
Inside the garage, men dressed as police officers lined the seven members of Moran’s gang up against the wall and shot them to death. Neighbors heard the racket, but minutes later those who had come outside to see what was happening witnessed two cops putting two men in plainclothes into the back of the Cadillac. Relieved because they believed the police were already there, none of the neighbors called the police. What they did not realize, of course, was that the men they had seen were not real cops.
John May’s dog had been left howling in the garage, and a landlady from a nearby building, annoyed by the dog’s whining, sent one of her boarders to investigate. The boarder found the dead men and called the police, who were surprised to find the dead men’s large rolls of cash intact. The motive, then, was clearly slaughter. All but one of the men—Frank Gusenberg—died on the spot. Gusenberg was taken to a nearby hospital, where he obeyed the gangster’s code of silence and refused to say who had shot him. Different reports indicate that his dying words were either “Nobody shot me” or “I’m not gonna talk.”
It was assumed that Capone had ordered the hit in retaliation for Moran’s strike against his gang. Moran, disobeying the same code of silence that Frank Gusenberg had upheld, openly pinned the massacre on Capone. Out-of-town gunman Fred “Killer” Burke and John Scalise, Albert Anselmi, and Jack “Machine Gun” McGurn, top Capone hit men, were popularly regarded as part of the extermination posse but were never convicted of the crime. Capone denied any involvement in the hit and played on Moran’s comments, suggesting that only Moran himself would commit those types of murders.
Reports varied widely, but certain versions of the story recount that two of the killers were identified by a teenager walking past Moran’s headquarters on the morning of the shooting. Supposedly, the teen identified McGurn and Burke, but no one was convicted. In any case, after all the attention that the slaughter had drawn to Capone and his gang, McGurn faded from the public eye. Capone insisted that he stay out of sight, and McGurn was killed in 1936, on the eve of the anniversary of the Valentine’s Day Massacre. He was shot to death with machine guns in a bowling alley by two men who, legend has it, were all that was left of Bugs Moran’s gang.
Of course, much of the information surrounding the Valentine’s Day Massacre was speculative, and conjecture about the issues often became legend. Later information, however, suggested that Capone’s gang may not have committed the carnage. In their 2004 book titled The St. Valentine’s Day Massacre: The Untold Story of the Gangland Bloodbath That Brought Down Al Capone, William J. Helmer and Arthur J. Bilek assert that much of the evidence points to a crew from St. Louis, known to Capone’s Italian mob as the American Boys, as the perpetrators of the massacre.
Significance
It is believed that Al Capone ordered the death of five hundred men in Chicago and that more than a thousand people died in his bootleg wars, but there was never enough evidence to convince authorities that he was behind the Valentine’s Day Massacre. In 1934, Capone went to prison for tax evasion; the public, convinced that he had been responsible for the massacre, had long called for his imprisonment. Paroled in 1939, Capone lived out his final years at his Palm Island estate off the coast of Miami, although by this time he was a mental and physical wreck. His body was ravaged by syphilis, which he had contracted years before, and he died in 1947 at the age of forty-eight.
No matter who was behind it, the Valentine’s Day Massacre certainly signaled the beginning of the end of Capone’s reign as Chicago’s crime czar. The event also ushered in a wave of violence in the Midwest that carried on well into the years of the Great Depression. Ultimately, the popular image of the public enemy was largely drawn from Capone, and the massacre at Moran’s North Side headquarters clearly showed how gangsters dealt with one another. Like so many gangster stories, the tale of what happened at the garage on Clark Street continued to capture the public imagination.
Bibliography
Helmer, William J., and Arthur J. Bilek. The St. Valentine’s Day Massacre: The Untold Story of the Gangland Bloodbath That Brought Down Al Capone. Nashville: Cumberland House, 2004. Challenges the assumption that Al Capone ordered the annihilation of Moran’s gang.
Keefe, Rose. The Man Who Got Away: The Bugs Moran Story—A Biography. Nashville: Cumberland House, 2005. In-depth look at the life of North Side gang leader Moran. Tells about the decline of Moran’s gangland power after his top men were killed in the Valentine’s Day Massacre.
Ruth, David E. Inventing the Public Enemy: The Gangster in American Culture, 1918-1934. Chicago: University of Chicago Press, 1996. Looks at Al Capone and other “invented” gangsters of the 1920’s and 1930’s and explores the role that they play in the American imagination.
Schoenberg, Robert J. Mr. Capone. New York: HarperCollins, 1992. Biography of Al Capone that traces his life from his boyhood in Brooklyn, New York, through his years as leader of the Chicago underworld, his imprisonment on charges of tax evasion, and his early death from syphilis.