Hymie Weiss — October 11, 1926

Hymie Weiss was the most dangerous enemy Al Capone ever faced. Relentless, fearless and driven by a fury that even Capone respected, Weiss came closer to killing Capone than anyone else in Chicago’s gangland wars. He was 28 years old when Capone finally got him — shot down on the steps of Holy Name Cathedral with so many bullets that the church itself still bore the scars.

Who Was Hymie Weiss?

Hymie Weiss was born Earl Wojciechowski in Poland in 1898 and grew up on the North Side of Chicago, where he fell into the criminal world at a young age. His adopted name — Hymie Weiss — stuck despite the fact that he was a devout Catholic who attended Mass regularly and wore a religious medal around his neck. The contradiction between his faith and his profession apparently caused him no difficulty.

He became one of the founding members of the North Side Gang under Dean O’Banion — the Irish-Polish gang that controlled the North Side of Chicago during Prohibition and was the chief rival of Johnny Torrio and later Al Capone’s organisation. Weiss was O’Banion’s closest friend and most trusted associate. When O’Banion was murdered in his own flower shop on November 10, 1924, Weiss took it personally in a way that transformed the already vicious Chicago gang wars into something approaching a vendetta.

Weiss is widely credited with inventing the one-way ride — the practice of luring a victim into a car under some pretext, then murdering them while driving and dumping the body. Whether or not he actually invented the technique, he certainly used it and his name became synonymous with it.

The War with Capone

After O’Banion’s murder, Weiss became the driving force behind North Side Gang retaliation. In January 1925, he organised the attempted assassination of Johnny Torrio — Capone’s mentor and the man who had ordered O’Banion’s killing. Torrio was shot multiple times outside his own apartment building and barely survived. The experience so shook him that he handed control of the entire Chicago Outfit to the 26-year-old Capone and retired to Italy. Weiss had effectively handed Capone his empire.

That irony was lost on Weiss, who continued his campaign against the Outfit with the same intensity. Multiple attempts were made on Capone’s life throughout 1925 and 1926. Capone survived them all — on one occasion reportedly by diving under a table at the first sound of gunfire.

The most audacious attack came on September 20, 1926. Weiss organised a convoy of vehicles that drove slowly through Cicero, Illinois — where Capone maintained his headquarters at the Hawthorne Inn — with gunmen firing continuously from the windows. Over 1,000 rounds were fired into and around Capone’s hotel. Capone survived only because he had hit the floor at the very start of the attack. Several of his associates were wounded. The sheer scale and brazenness of the assault shocked even the most hardened Chicago observers.

Capone later said of Weiss: “I paid my respect to O’Banion’s memory. I wanted to forget the whole thing. But Hymie Weiss was like a crazy man. He wouldn’t stop.”

Three weeks after the Hawthorne Inn attack, Capone stopped him permanently.

October 11, 1926 — The Shooting

Capone’s men had identified Weiss’s routine. His headquarters were at Schofield’s flower shop on North State Street — the same shop where O’Banion had been murdered two years earlier, which Weiss had taken over almost as an act of tribute. He passed the shop constantly and was known to use it as a base when attending hearings at the nearby courthouse.

Two Capone gunmen rented a room in a boarding house directly across the street from the flower shop at 740 North State Street. They set up a submachine gun and a shotgun at the window and waited.

On the morning of October 11, 1926, Weiss returned from a court hearing with four associates — bodyguard Sam Pellar, investigator Benny Jacobs, lawyer W.W. O’Brien and Patrick Murray. As they approached the flower shop the gunmen opened fire.

The attack was intense. Weiss was hit multiple times and began to collapse onto the pavement. What happened next has become one of the stranger footnotes of the Chicago gang wars. His bodyguard Sam Pellar — panicking, firing blind — drew his .38 and fired into the chaos. In the confusion he accidentally shot the already dying Weiss as he fell to the ground.

The gunmen had fired so many rounds that bullets struck the cornerstone of Holy Name Cathedral directly across the street. The bullet holes remained visible for years. Patrick Murray was also killed in the attack. The other three associates were wounded but survived. Hymie Weiss died on the pavement outside his mentor’s old flower shop. He was 28 years old.

No one was ever charged with the murder. Capone, when asked about the killing, offered his condolences and expressed his regret that it had come to this. Nobody believed him.

What Happened Next

With Weiss gone, Bugs Moran took over the North Side Gang. The feud continued — but without Weiss’s focused fury it was a different kind of conflict. Capone, now unchallenged as the dominant power in Chicago, sought a peace conference with the remaining gang leaders. A temporary truce was established.

It didn’t last. On February 14, 1929 — the St Valentine’s Day Massacre — seven members of the Moran gang were shot dead in a garage on North Clark Street by Capone’s gunmen. Moran himself survived only because he arrived late. The massacre ended the North Side Gang as a serious force in Chicago, and marked the beginning of the end of Capone’s own reign — the public outrage it generated accelerated the law enforcement pressure that would eventually send him to prison.

Frequently Asked Questions — Hymie Weiss

How was Hymie Weiss killed?

Weiss was shot dead on October 11, 1926, on State Street in Chicago. Two Capone gunmen firing from a rented room across the street hit him multiple times as he returned from a court hearing. In a grim footnote, his own panicking bodyguard accidentally shot him again as he fell. Bullets from the attack chipped the cornerstone of Holy Name Cathedral across the street.

Who was Hymie Weiss?

Born Earl Wojciechowski in Poland in 1898, Weiss was leader of the North Side Gang after Dean O’Banion’s murder in 1924. He is credited with inventing the one-way ride and was Al Capone’s most persistent and dangerous enemy, coming closer to killing Capone than anyone else. He was 28 when he died.

Did Hymie Weiss try to kill Al Capone?

Yes — multiple times. Most notably in the Hawthorne Inn attack of September 1926, when a convoy of cars fired over 1,000 rounds into Capone’s Cicero headquarters. Capone survived by hitting the floor. Weiss also organised the near-fatal shooting of Capone’s mentor Johnny Torrio in 1925. Capone had Weiss killed just three weeks after the Hawthorne attack.

Who took over after Hymie Weiss was killed?

Bugs Moran took over the North Side Gang. The feud with Capone continued until the St Valentine’s Day Massacre of February 1929, when seven Moran gang members were shot dead in a Chicago garage. Moran survived only because he arrived late. The massacre ended the North Side Gang as a serious force.

Why were bullet holes found in Holy Name Cathedral?

Capone’s gunmen fired so many rounds during the Weiss shooting that bullets struck the cornerstone of Holy Name Cathedral directly across the street. The bullet holes remained visible for years — a permanent reminder of one of the most violent incidents in Chicago’s Prohibition-era gang wars.