13 Mafia Bosses Who Defined The History Of The Mob

Published December 20, 2023
Updated January 6, 2025

Paul Castellano, The Mafia Boss Who Was Assassinated By John Gotti

Mafia Boss Paul Castellano

Bettmann/Getty ImagesPaul Castellano is best known for his shocking 1985 assassination organized by John Gotti.

Though Gambino Family kingpin Paul Castellano did plenty in his time as a mob boss, he remains best known for his shocking 1985 murder at the hands of his soon-to-be-famous underling John Gotti.

Born on June 26, 1915, in Brooklyn, New York, Castellano seemed destined to be a Mafia boss. His cousin, Carlo Gambino, became the head of the Gambino Family (formerly the Mangano Family) after the assassination of its boss Albert Anastasia in 1957, and Castellano’s sister was Gambino’s wife. When Gambino died in 1976, he chose Castellano to succeed him.

At the time, Castellano was seen as the “Godfather” or the “boss of bosses” because the Gambino Family was the most powerful organization in New York. However, some also called him the “Howard Hughes of the Mafia” because of his reclusive nature, which could rub capos and soldiers in the Gambino Family the wrong way.

Murder Of Paul Castellano

Bettmann/Getty ImagesPaul Castellano was assassinated by John Gotti on December 16, 1985.

By 1985, Castellano had trouble on several fronts. He and other mobsters had been indicted under the Racketeer Influenced and Corrupt Organizations Act, and the mob boss and other Gambino Family members also faced a looming trial related to a car theft ring. What’s more, some family members were frustrated that Castellano had followed Gambino’s example in forbidding them from engaging in the lucrative drug trade.

This, along with several other internal issues, led Gambino Family member John Gotti to plot Castellano’s murder. On Dec. 16, 1985, Castellano and his underboss Thomas Bilotti were killed in a hail of bullets as they arrived at Sparks Steak House in Midtown Manhattan. To this day, it remains one of the most infamous mob hits of all time.

This brazen takedown of a Mafia boss would elevate Gotti to the head of the Gambino Family. But it would also put a target on his back.

author
Kaleena Fraga
author
A senior staff writer for All That's Interesting since 2021 and co-host of the History Uncovered Podcast, Kaleena Fraga graduated with a dual degree in American History and French Language and Literature from Oberlin College. She previously ran the presidential history blog History First, and has had work published in The Washington Post, Gastro Obscura, and elsewhere. She has published more than 1,200 pieces on topics including history and archaeology. She is based in Brooklyn, New York.
editor
Cara Johnson
editor
A writer and editor based in Charleston, South Carolina and an editor at All That's Interesting since 2022, Cara Johnson holds a B.A. in English and Creative Writing from Washington & Lee University and an M.A. in English from College of Charleston. She has worked for various publications ranging from wedding magazines to Shakespearean literary journals in her nine-year career, including work with Arbordale Publishing and Gulfstream Communications.
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Fraga, Kaleena. "13 Mafia Bosses Who Defined The History Of The Mob." AllThatsInteresting.com, December 20, 2023, https://allthatsinteresting.com/mafia-bosses. Accessed August 6, 2025.