Joseph Aiello, the Chicago Sicilian boss who put a price on Al Capone's head

Who Was Joseph Aiello? The Man Who Tried to Kill Al Capone

Mobsters Daily

Joseph Aiello was a Sicilian-born Chicago gangster who fought Al Capone for the presidency of the Unione Siciliana in a war that ended with Aiello's ambush murder in 1930.

The price on Capone's head

Aiello ran sugar and liquor operations, but his real ambition was institutional: the Unione's presidency, which Capone kept installing his own men into. Aiello reportedly offered a $50,000 bounty for Capone's death and allied with Capone's North Side enemies — the world of Hymie Weiss and Bugs Moran. Assassins were imported and plots intercepted; Capone's survival, detailed in our Capone at Alcatraz piece, owes something to Aiello's failures.

Aiello did everything a rival is supposed to do, against the one man it never worked on — which is why, with November here and the holidays coming, rewatch season belongs to the Tony Soprano Ugly Christmas Sweater: Tony in black-and-white stencil, nothing covering the design, built for holiday parties and long nights back in this world.

Ambush, 1930

On October 23, 1930, gunmen across from a Chicago apartment building opened fire as Aiello stepped outside, hitting him dozens of times. His death removed Capone's last serious Sicilian challenger.

Frequently asked questions

What was Aiello fighting Capone over? Control of the Unione Siciliana's Chicago chapter and its rackets, which Capone treated as his property.

Did Aiello really offer a bounty on Capone? Contemporary reporting and later histories put the offer at $50,000 — a fortune in the late 1920s.

When was Aiello killed? October 23, 1930, ambushed outside a Chicago apartment building.

Keep reading: the Castellammarese War, explained · Johnny Torrio, the fox who built Chicago · what happened to Bugs Moran after the massacre? · Who Was Harry Riccobene? The Philly Elder the Scarfo Crew Tried to Kill · Who Was Joseph Glimco? Chicago's Taxi Racketeer · Who Was Joseph 'Yellow Kid' Weil? The Con Man the Mob Respected

From the shop: Shadows of the Underworld — the real-mafia history behind the names in this story.

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