Bugs Moran — Al Capone’s Greatest Enemy

Who Was Bugs Moran?

George Clarence Moran was born on August 21, 1891, in St Paul, Minnesota, to Irish-Polish parents. He moved to Chicago as a teenager and quickly fell into a life of crime, racking up three arrests before his 21st birthday. His volatile temper earned him the nickname “Bugs” — slang for crazy — and it stuck.

Moran came up through Chicago’s criminal underworld during the early years of Prohibition, joining the North Side Gang under Dean O’Banion — the Irish-American gangster who controlled Chicago’s north side bootlegging territory from a flower shop on North State Street. When O’Banion was murdered in November 1924 on the orders of Johnny Torrio, Moran became one of the gang’s most powerful figures alongside Hymie Weiss.

After Weiss was killed in 1926, Moran became the undisputed boss of the North Side Gang — and the last major obstacle standing between Al Capone and complete dominance of Chicago organised crime.

He is best known for his ferocious and sustained war against Capone’s Chicago Outfit, for surviving the St Valentine’s Day Massacre by sheer luck, and for the extraordinary decline that followed — from the most feared gangster in Chicago to a broken old man dying penniless in federal prison.

The North Side vs South Side War

During Prohibition, Chicago was divided between two major criminal organisations. The South Side was controlled by Johnny Torrio and, increasingly, Al Capone — together forming what would become the Chicago Outfit. The North Side was controlled by Dean O’Banion’s gang, who ran bootlegging operations across the north of the city with characteristic Irish aggression and limited regard for diplomatic niceties.

The war began when O’Banion started hijacking alcohol trucks belonging to the South Side, selling their contents on his own territory. Torrio attempted to keep the peace for years but O’Banion pushed too far — he sold Torrio his share of a brewery for $500,000, knowing federal agents were about to raid it. Torrio was arrested in the raid. The vote for O’Banion’s murder was unanimous.

O’Banion was killed in his flower shop in November 1924 by Frankie Yale, John Scalise and Albert Anselmi. He thought they had come to collect a floral arrangement. He was wrong.

For Bugs Moran, his boss’s murder was personal. He spent the next five years trying to kill Al Capone.

Moran vs Capone

Moran’s hatred of Capone was absolute and undisguised. He publicly called Capone a low-life and despised his involvement in prostitution. He made multiple attempts on Capone’s life — drive-by shootings, targeted assassinations of bodyguards, attacks on Capone’s establishments. He burnt down Capone’s nightclubs, hijacked his liquor supplies and murdered anyone who worked too closely alongside him.

One assassination attempt nearly succeeded when Moran’s men sprayed bullets through the windows of a hotel lobby where Capone was drinking. Capone escaped unharmed but was shaken enough to have an armoured car built — a car so heavily fortified it would later be used by President Roosevelt.

Capone briefly called a truce. It didn’t last. The war between the two men was destroying both organisations — costing Capone friends, money and men on an almost weekly basis.

By early 1929, Capone had decided the only solution was to eliminate Moran entirely.

The St Valentine’s Day Massacre

On February 14, 1929, seven members of Moran’s North Side Gang were lured to a garage at 2122 North Clark Street on the pretext of receiving a delivery of hijacked whiskey. When they arrived, four of Capone’s men — two dressed as police officers — entered the garage, lined the seven men against the wall as if conducting a raid, and executed them with Thompson submachine guns and shotguns.

Moran himself was supposed to be among the dead. Capone had been told he would be there. But Moran arrived late, saw a police car outside and assumed it was a genuine raid. He kept walking. One of Capone’s lookouts mistook another man for Moran and gave the signal anyway.

The St Valentine’s Day Massacre shocked the nation and triggered an unprecedented law enforcement response directed at Capone. It did not destroy Moran — but it effectively ended the North Side Gang as a meaningful force. Moran could no longer field the men, the money or the organisation to seriously threaten Capone.

When asked later that day if he knew who was responsible, Moran reportedly said: “Only Capone kills like that.” Capone, who had been in Florida, claimed the same: “The only man who kills like that is Bugs Moran.”

Decline and Fall

After the Massacre, Moran’s power evaporated rapidly. Prohibition ended in 1933, removing the bootlegging income that had sustained his operation. Without the money, he couldn’t hold men or territory. By the mid-1930s, the North Side Gang that had once rivalled Capone’s empire existed in name only.

Moran drifted from Chicago, running petty rackets in the Midwest through the 1940s. In 1946, at the age of 54, he was arrested for robbing a bank messenger in Dayton, Ohio, and sentenced to ten years at Ohio State Penitentiary.

On his release, rather than retiring, he robbed another bank. He was arrested again in 1956 and sent to Leavenworth Federal Penitentiary. He had been there only a few months when he was diagnosed with lung cancer.

George “Bugs” Moran died on February 25, 1957, aged 65, in the prison hospital at Leavenworth. He was buried in the prison cemetery. His entire estate amounted to $100.

Frequently Asked Questions — Bugs Moran