13 Mafia Bosses Who Defined The History Of The Mob

Published December 20, 2023
Updated June 7, 2024

John Gotti, The “Teflon Don” Who Ruled Late 1980s And Early ’90s New York

Mob Boss John Gotti

NYPDJohn Gotti pulled off one of the most infamous assassinations in Mafia history.

Infamous as the mastermind of Paul Castellano’s murder, John Gotti was also known as the “Dapper Don” for his flashy suits and the “Teflon Don” for his seemingly endless ability to avoid prison. To this day, he remains one of the most famous Mafia bosses in history.

Born on Oct. 27, 1940, John Gotti started working for the Gambino Family at the age of 12. He rose through the ranks due to his ruthless nature and his close relationship with Aniello Dellacroce, who became the Gambino Family’s underboss after the death of Carlo Gambino in 1976.

By the 1980s, however, the relationship between Gotti and the new Gambino Family boss, Paul Castellano, had grown tense. Castellano didn’t approve of Gotti’s gambling habit, heroin dealing, or erratic behavior, and Gotti was furious when Castellano, fearing attention from the FBI, failed to attend Dellacroce’s funeral after he died of cancer in December 1985.

Castellano was also facing legal trouble and had irritated some of his capos and soldiers with his reclusive nature. Gotti decided that Castellano had to go. He quietly elicited support from both inside and outside the Gambino Family, reaching out to some of his peers in the Lucchese, Colombo, and Bonanno Families.

John Gotti Mugshot

FBIThough John Gotti became the boss of the Gambino Family, he eventually died in prison.

Then, on Dec. 16, Gotti made his move. After he gave the order via walkie-talkie from a car nearby, several hitmen took out Castellano and his underboss, Thomas Bilotti, as they arrived at Sparks Steak House in Midtown Manhattan.

This officially made John Gotti a Mafia boss and the new head of the Gambino Family — but it also put him in hot water. Mob bosses like Vincent Gigante were furious that Gotti hadn’t consulted the Five Families first, which led to a failed attempt on Gotti’s life, and Gotti meanwhile faced legal woes in the form of racketeering charges.

In 1990, he was arrested and charged with a number of crimes, including Paul Castellano’s murder. And though Gotti had famously beaten all charges brought against him in the past, this time, his own underboss, Sammy Gravano, testified against him. Gotti was convicted in 1992 and spent the rest of his life in prison, eventually dying there of cancer on June 10, 2002.

author
Kaleena Fraga
author
A staff writer for All That's Interesting, Kaleena Fraga has also had her work featured in The Washington Post and Gastro Obscura, and she published a book on the Seattle food scene for the Eat Like A Local series. She graduated from Oberlin College, where she earned a dual degree in American History and French.
editor
Cara Johnson
editor
A writer and editor based in Charleston, South Carolina and an assistant editor at All That's Interesting, 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 and has written for various publications in her six-year career.
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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 June 27, 2024.