How John Gotti Assassinated Paul Castellano, “The Boss Of Bosses”

Published May 22, 2018
Updated May 24, 2018

On December 16, 1985, John Gotti organized a ruthless assassination on Gambino crime boss Paul Castellano outside Sparks Steak House in New York City. It was a murder that would change the New York Mafia forever.

Paul Castellano

Getty ImagesPaul Castellano

On Dec. 16, 1985, Gambino crime family boss Paul Castellano and his underboss Thomas Bilotti were brazenly gunned down outside Sparks Steak House in Midtown Manhattan.

The man responsible for organizing the hit had been none other than the Dapper Don himself, John Gotti.

Killing A King

At Gotti’s 1992 trial, Salvatore “Sammy the Bull” Gravano described the planning and execution of Castellano. Gravano, who was Gotti’s former underboss in the Gambino family and trusted co-conspirator in Castellano’s demise, had four months earlier turned informant. After the trial, he would be known as the man who helped bring down John Gotti.

Gravano told the court he sat next to Gotti waiting for the murder to unfold as they watched close by. At 5 p.m., Gotti’s four hitmen were waiting outside the entrance to Sparks Steak House. When Castellano’s car pulled up alongside them at a red light, Gotti gave the order over a walkie-talkie.

Paul Castellano Murder Scene

Getty ImagesPolice remove the blood-covered body of Paul Castellano from the scene of his murder after he and his driver were gunned down outside Sparks Steak House by three gunmen who fled on foot.

Gravano and Gotti watched from behind the tinted windows of a Lincoln sedan as the four gunmen shot Castellano six times and Bilotti four times as they exited the car. Gotti then drove slowly past the bodies before making their exit onto Second Avenue and back to Brooklyn.

While Gotti became the new boss of the Gambino crime family following the hit, the situation surrounding Castellano’s murder was more complex than a simple power grab.

Tension Between Paul Castellano And John Gotti

Paul Castellano made a lot of enemies since he took over as boss of the Gambino crime family in 1976. He was known as the “Howard Hughes of the Mafia,” because like Hughes, he was somewhat of a recluse. Castellano saw himself as a businessman who distanced himself from the guys who were the bread-and-butter of his business: the Gambino’s capos, soldiers, and associates.

Instead, he met only with top brass in his sprawling 17-room Staten Island mansion, nicknamed “the White House.” Not only did he repeatedly insult his men with his continual snubs but he was also out of touch. Capos would routinely deliver envelopes stuffed with cash to his doorstep without being invited in.

“This guy’s sitting there in his silk robe, and his velvet slippers in his big white house and he’s taking every dollar we got,” said Ernest Volkman, author of Gangbusters.

Castellano developed a reputation for being a greedy fool among his underlings. He had amassed millions through legitimate business and criminal enterprises starting in the 1970s but that didn’t stop him from wanting more. By the early 1980s, he put the squeeze on his men by increasing his take of their earnings from 10 percent to 15 percent.

With his men’s earnings already taking a hit, Castellano also kept in place a cardinal rule of predecessor Carlo Gambino: Gambino family members were prohibited from drug dealing. Any individuals dealing drugs could not become made men and any implicated in drug trafficking would be killed. It was a major blow for Gambino mobsters as drug trafficking was arguably the biggest earner for the Mafia during the 1970s and 1980s.

Castellano’s decisions infuriated Gotti, especially since he was dealing heroin. At the time it was underboss Aniello Dellacroce who kept Gotti in line, who despite the boss’ greed, expected absolute loyalty to Castellano.

Cracks In Paul Castellano’s Armor

Carlo Gambino

New York Police Department/Wikimedia CommonsCarlo Gambino, former head of the Gambino crime family.

But Castellano was fast losing respect. When word got out that the boss had had a penal implant to help his impotence, Castellano’s hold on the family was becoming shaky at best. Then in March 1992, wiretaps caught loudmouth Gambino soldier Angelo Ruggiero and John Gotti talking about how much they hated Castellano. This became a potential death sentence for “The Dapper Don.”

Castellano wasn’t a fan of Ruggiero’s capo, Gotti. When he heard that Ruggiero and John’s brother Gene were arrested for dealing heroin and that the feds had wiretapped their conversations, the mobster in him wanted to demote Gotti and disband his crew. But the business side of Castellano knew he had to avoid a Gambino civil war.

Castellano wanted the transcripts from the wiretapped conversations but Ruggiero refused, knowing what it would mean for him and Gotti. Instead, Gambino underboss Delacroce convinced Castellano to wait for the prosecutors to release the tapes.

On the strength of the information on the tapes, a judge approved the bugging of Castellano’s home which resulted in over 600 hours of tape connecting the Five Families in a garment industry racket.

Meanwhile, the FBI also looked into a Gambino car theft ring, particularly the dealings of its ringleader Roy DeMeo. Because DeMeo took envelopes of cash to Castellano, the Gambino crime boss was implicated as a co-conspirator. Castellano tried to get Gotti to kill DeMeo. But Gotti feared DeMeo and the job was handed to another hitman.

Arrest And Murder

John Gotti And Sammy Gravano

Getty ImagesJohn Gotti, center, enters the Brooklyn Federal courthouse with Sammy “The Bull” Gravano in May 1986.

DeMeo’s death did not prevent Castellano from being tied to the car theft ring. Under the RICO Act, crime bosses could be implicated in the criminal activities of their underlings. Castellano was arrested in 1984 but was released the next day.

However, he received a second indictment a year later after surveillance photographs showed the bosses of the Five Families leaving a meeting of the Mafia Commision on Staten Island. Castellano made the $4 million bond and was released the next day.

By this time Ruggiero’s wiretap tapes had been released to defense attorneys and Castellano demanded Dellacroce give them to him. Dellacroce never did. He stalled until he died from cancer in December 1985.

The noose was tightening around Castellano. He did not want to give the FBI any more ammunition against him. So he did not attend the funeral of his loyal underboss, Dellacroce, believing that being seen a mobster’s funeral would not help his case.

Gotti was extremely loyal to Dellacroce and was offended by Castellano’s absence. To add further injury to insult, Gotti was passed over as underboss. Instead, Bilotti became Dellacroce’s replacement.

Gotti wanted the Gambino boss dead. Gotti managed to solicit support from a number of peers in the Lucchese, Colombo, and Bonanno families. But Castellano had a close relationship with Genovese family boss Vincent “Chin” Gigante, so Gotti did not dare approach an important figure inside the Genovese family.

With mid-level support from three out of the other four families, Gotti, with the help of Ruggiero, chose Gambino soldiers to carry out the hit.

A month later after the hit, Gotti was formally confirmed as head of the Gambino crime family.

A New King Crowned

John Gotti Mugshot

Wikimedia CommonsJohn Gotti

Gotti’s bold takedown of Paul Castellano came at a price. Castellano was already fighting a racketeering case and according to a former Gambino mafioso, “Paul was going to jail anyway, he didn’t have to die.” But Gotti believed that if he did not get Castellano, that Castellano would get him.

John Gotti became a household name, but in just five years after becoming Gambino boss, he was arrested. Two years later in 1992, he was found guilty of a litany of charges including five murders, one of which was Castellano’s.

Despite imprisonment, Gotti remained Gambino boss, at least in his eyes, until he died from throat cancer in 2002.


Enjoy this look at John Gotti and Paul Castellano? Next learn, about Richard Kuklinski, the most prolific hitman in Mafia history. The discover how Joe Masseria’s murder gave rise to the Mafia’s golden age.

Daniel Rennie
Daniel Rennie is a freelance writer residing in Melbourne, Australia.
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