Paul Castellano and The Westies: An Unlikely Alliance

Paul Castellano: The Gambino Kingpin

Paul Castellano, known as “Big Paul,” was the epitome of Mafia sophistication. As the head of the Gambino crime family, one of New York’s Five Families, he controlled a vast empire of racketeering, drug trafficking, and extortion. Unlike the street-level brawlers of Hell’s Kitchen, Castellano operated from luxurious offices, maintaining a polished image while orchestrating the city’s underworld.

Castellano’s power stemmed from his ability to delegate. He preferred to keep his hands clean, outsourcing violent tasks to trusted allies. This strategy led him to Jimmy Coonan and The Westies, whose raw aggression complemented the Mafia’s structured operations.

The Westies: Hell’s Kitchen’s Irish Enforcers

The Westies, led by Jimmy Coonan, were the antithesis of the Gambino family’s polished hierarchy. Rooted in Hell’s Kitchen’s Irish-American community, The Westies were known for their brutal tactics—extortion, loan-sharking, and gruesome dismemberments that sent chills through New York’s underworld. Their small size belied their ferocity, making them ideal partners for the Mafia’s dirtier jobs.

Coonan’s ambition drove him to seek legitimacy beyond Hell’s Kitchen. Aligning with Castellano offered The Westies protection and access to the Mafia’s resources, elevating their status in the criminal world.

The Alliance: A Marriage of Convenience

In the mid-1970s, Coonan and Castellano struck a deal that would define Hell’s Kitchen’s criminal era. The Westies became the Gambino family’s enforcers, handling contract killings, debt collection, and street-level intimidation. In return, Castellano provided The Westies with a share of profits and a degree of autonomy, allowing them to operate under the Mafia’s umbrella.

This partnership was a win-win: the Gambinos outsourced their most violent tasks, while The Westies gained power and legitimacy. However, the alliance was not without friction. The Irish Mob’s chaotic style often clashed with the Mafia’s rigid structure, and Coonan’s ambition occasionally tested Castellano’s patience.

For more on the broader context of this rivalry, read our article on the Irish Mob vs. Italian Mafia.

Tensions and Betrayals

The alliance thrived for years, but cracks began to appear. The Westies’ expansion into drug trafficking—a domain the Mafia fiercely controlled—sparked tensions. Castellano, wary of Coonan’s growing influence, kept a close eye on his Irish allies. Meanwhile, internal betrayals within The Westies, particularly Mickey Featherstone’s decision to become an FBI informant, threatened the entire operation.

By 1986, the FBI’s crackdown dismantled The Westies, with Coonan convicted of racketeering and murder. Castellano’s own fate was sealed in 1985, when he was assassinated by John Gotti, ending the Gambino-Westies partnership in a hail of bullets.

Legacy of the Castellano-Westies Alliance

The alliance between Paul Castellano and The Westies was a fleeting but pivotal chapter in New York’s criminal history. It showcased the power of unlikely partnerships, where Irish grit and Italian strategy briefly aligned. Hell’s Kitchen, the backdrop for this saga, remains a symbol of the era’s violence and ambition, even as it transforms into a modern neighborhood.

The story of Castellano and Coonan is a testament to the complexities of power, loyalty, and betrayal in the underworld. Their alliance, though short-lived, left a lasting mark on the Irish-American and Italian-American criminal legacies.

About the Author: Seamus is dedicated to uncovering the untold stories of Irish heritage and crime. Follow Secret Ireland for more gripping tales of the underworld.