Chicago, IL

The Worst Massacre in Mob History

Ryan Fan

From the Chicago Bureau at the Federal Bureau of Investigation — Public Domain

Don’t mistake my kindness for weakness. I am kind to everyone, but when someone is unkind to me, weak is not what you are going to remember about me.” — Al Capone

It was Al Capone’s last step before conquering Chicago’s bootlegging business.

The target during the Prohibition era was George “Bugs” Moran, one of the long-time enemies of Capone. According to History, Capone wanted to eliminate his rivals in bootlegging, gambling, and prostitution, and on February 14, 1929, seven men associated with Moran were killed by men dressed as policemen.

The crime was never linked to Capone, but he is thought to be responsible since most of the victims were part of Chicago’s Irish North Siders. But it would raise Capone’s profile, with the media blaming him for the killings, and the federal government devoting itself to taking Capone down.

This is the story of the 1929 Valentine’s Day Massacre, the worst massacre in mob history.

The incident

According to John O’Brien at the Chicago Tribune, seven men were lined up against a wall and shot with 90 bullets from different guns, including submachine guns, shotguns, and a revolver.

“It was the most infamous of all gangland slayings in America, and it savagely achieved its purpose — the elimination of the last challenge to Al Capone for the mantle of crime boss in Chicago,” O’Brien writes.

However, the problem was that Moran wasn’t there — he’d overslept that morning. The massacre happened at about 10:30 a.m., in the SMC Cartage Co. garage Moran used for illegal business. Two men dressed as police officers and two others announced a raid, and they made seven men in the garage line up against the wall. And then they shot them all.

The shooters then fled in a black Cadillac that looked like a police vehicle. The victims killed included Frank Gusenberg, a Moran enforcer, and Peter Gusenberg, his brother. The others were also members of Chicago’s Irish North Siders, but one man was an optician who just associated with the Moran gangsters, named Dr. Reinhardy Schwimmer.

When real police officers showed up at the scene, Frank, even close to death, said that nobody shot him, upholding his oath of silence. One member, Albert Weinshank, had a very similar appearance to Moran, so Capone’s enforcers thought they killed Moran.

Al Capone was in Florida, a fact he used to escape any culpability. He was vacationing in Palm Springs, Florida, and claimed to have no knowledge of the killings. However, there was never any evidence he was associated with the crimes either, and according to O’Brien, no one would ever be held accountable for the St. Valentine’s Day Massacre.

The rivalry between Moran and Capone

Moran and Capone, before the massacre, had been feuding for a long time. According to Joe Sommerlad at The Independent, Moran and Capone had a turf war over control of Chicago’s illegal liquor black market. In 1920, the 18th amendment banned the production, import, or sale of alcohol.

The beef that started the feud was the murder of Dean O’Banion, a North Side boss, at a flower shop in 1924. He was a rival of Capone and his predecessor, Johnny Torrio. Sommerlad notes that Torrio and Capone had an agreement with O’Banion, ceding territory on the North Side of Chicago to O’Banion. However, the South Side started making a significant income, and O’Banion schemed to convince speakeasies on the South Side to move to his part of town.

According to Gus Russo in The Outfit, the Chicago Outfit, another name for the South Side Gang, was the subject of multiple assassination attempts as well. Capone and Torrio both survived assassination attempts. After one attempt, Torrio handed over control of the Chicago Outfit to Capone. Torrio returned to Italy to live a peaceful life.

Capone had a looser trigger than Torrio. He was known as a drinker and a trouble-maker, and was more obsessed with his reputation than Torrio ever was. Capone refused to take a low profile. According to History, his headquarters was in a fancy suite at the Metropole Hotel in downtown Chicago. Capone spent his money very liberally, and always used cash. Local newspapers estimated with a net worth at $100 million.

During the Prohibition era, the ban on alcohol was not popular with everyone. Despite the violence of his operation, Capone would earn a reputation as a Robin Hood, who fed the hungry and provided alcohol. But his reputation would wane as it increasingly became tied to the violence in Chicago.

The man who would take over for O’Banion was Hymie Weiss. Weiss would later be killed shortly after O’Banion, as would another Weiss associate. The next man in charge of the North Side Gang was Moran.

According to the National Crime Syndicate, Moran wanted revenge against the Chicago Outfit. Moran regularly gossiped and ran his mouth about Capone’s integrity and his involvement in the prostitution business. For protection, Capone got himself an armor plated car, while Moran attempted multiple assassinations on Capone.

Multiple bodyguards and friends of Capone would be killed by Moran’s men. Capone’s nightclubs and liquor supplies would regularly be robbed.


The St. Valentine’s Day Massacre would be the beginning of the end for Capone. While it gave him control over Chicago’s bootlegging business over Moran, President Herbert Hoover personally intervened to catch Capone and stop the violence in Chicago. As Hoover recalls in his 1952 memoir that a friend told him:

“Chicago was in the hands of the gangsters, that the police and magistrates were completely under their control, …that the Federal government was the only force by which the city’s ability to govern itself could be restored. At once I directed that all the Federal agencies concentrate upon Mr. Capone and his allies.”

The federal government would then launch a multi-pronged attack on Capone and organized crime in Chicago. Particularly, they wanted to catch Capone for income tax prosecutions, according to historian James Calder. One of the detectives involved in the investigation was Eliot Ness, who was the leader of a team known as The Untouchables. The team earned the name for being incorruptible detectives in a city tainted with corruption. Above all, they refused to take bribes.

Capone was arrested numerous times for non-tax related reasons. In April 1930, he was arrested in Miami and charged with perjury, but no conviction would stick long — there wasn’t enough evidence to put Capone away for a long time.

However, since mob figures never filed tax returns and touted their luxurious lifestyles, many realized figures like Capone could be indicted for tax evasion. On June 5, 1931, this is exactly what happened — Capone was indicted on 22 counts of income tax evasion. Capone would later be found guilty and sent to prison for 11 years.

In his first two years in prison, Capone was incarcerated in a federal prison in Atlanta. In 1934, however, Capone was sent to Alcatraz, where he would serve the rest of his sentence. In 1939, he was released after serving six and a half years but would suffer from neurosyphilis, leading him to stay in a psychiatric hospital while his health declined. Capone died on January 25, 1947, of a stroke.

The worst massacre in mob history would be memorialized in several classic movies, including Scarface: Shame of the Nation, Some Like It Hot, The Untouchables, and Capone. Prohibition would end in 1933 with the passage of the 21st amendment. But it would be the St. Valentine’s Day Massacre that would involve the FBI and other branches of the federal government in investigating Capone. Due to the brutality of the massacre, government agencies had no choice besides holding Capone accountable by whatever means necessary.

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