How Paul Castellano Became The ‘Boss Of Bosses’ — Before He Was Brazenly Murdered By John Gotti

Published September 26, 2021
Updated July 14, 2022

On December 16, 1985, John Gotti oversaw the assassination of Gambino family boss Paul Castellano outside Sparks Steak House in Manhattan — a hit that would change the Mafia forever.

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

Paul Castellano

Bettmann/Getty ImagesGambino boss Paul Castellano on February 26, 1985, after he posted a $2 million bail following an indictment on racketeering charges.

The man responsible for organizing Paul Castellano’s death had been none other than the Dapper Don himself, John Gotti.

The Public Death Of Paul Castellano

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

According to The New York Times, Gravano told the court that he sat next to Gotti waiting for the murder to unfold as they watched from across the street.

By 5 PM, he testified, several hitmen were waiting outside the entrance to Sparks Steak House on 46th Street near Third Avenue in Midtown Manhattan. When Castellano’s car pulled up alongside them at a red light, Gotti gave the order over a walkie-talkie.

Paul Castellano Death

Bettmann/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 gunmen shot Castellano six times and Bilotti four times as they exited the car. Gotti then drove slowly past the bodies, looking to make sure his targets were dead, before making their exit onto Second Avenue and turning south 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 Rises 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.

Carlo Gambino

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

According to Mitchel P. Roth’s 2017 book Global Organized Crime, 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 the 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 routinely delivered 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.

Yet Castellano had good reason to be wary of unwanted attention. In 1957, he was one of more than 60 mobsters who police arrested at what was supposed to be a secret conclave of international representatives to crown a new “boss of the bosses” in Upstate New York. Instead, the presence of dozens of luxury cars in the tiny hamlet of Apalachin made the local police suspicious. They raided the meeting before it even began, and the subsequent congressional hearings exposed the global network and power of the Mafia for the first time in history.

Still, over time Castellano had developed a reputation for being a greedy miser 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 significant blow for Gambino mobsters as drug trafficking was arguably the biggest earner for the Mafia during the 1970s and 1980s.

Paul Castellano’s decisions infuriated John Gotti, then a mid-level capo, especially since he was dealing heroin on the side. At the time, underboss Aniello Dellacroce kept Gotti in line. Even though Dellacroce had been passed over for the head of the family after Gambino died, he still expected absolute loyalty to Castellano from everyone below him.

Cracks In The Gambino Don’s Armor

But Paul Castellano was fast losing respect. When word got out that the boss had had a penile implant to help his impotence, Castellano’s hold on the family became shaky at best. Then in March 1984, 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.”

Paul Costellano Apalachin Meeting

Bettmann/Getty ImagesPaul Castellano (center) along with Gambino associates Joseph Riccobondo (left) and Carmine Lombardozzi (right) following their 1959 congressional testimony about the infamous Apalachin meeting where some 60 mobsters were arrested. Castellano said he went because he thought it was to be a “party.”

Castellano wasn’t a fan of Gotti to begin with. But when he heard that Ruggiero and Gotti’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 civil war within the family.

Castellano wanted the transcripts from the wiretapped conversations. But Ruggiero refused, knowing what it would mean for him and Gotti. Instead, Aniello Dellacroce 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 to 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.

Paul Castellano’s Arrest And Murder

DeMeo’s death did not prevent Castellano from being tied to the car theft ring. Under the 1970 Racketeer Influenced and Corrupt Organizations (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 Commission on Staten Island. Castellano made the $2 million bond and was released the next day.

Death Of Paul Castellano

Bettmann/Getty ImagesFor years before Paul Castellano’s death, he tried to turn some of the Gambino family’s illicit operations into legitimate businesses and banned associates from the drug trade, drawing the ire of young mobsters like John Gotti.

By this time, Ruggiero’s wiretap tapes had been released to defense attorneys, and Castellano demanded Dellacroce give them to him. But 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 at a mobster’s funeral would not help his case. But in a rude twist of fate, this act of seeming self-preservation led directly to Paul Castellano’s death just two weeks later.

Gotti was extremely loyal to Dellacroce and was offended by Castellano’s absence. To add further injury to insult, Castellano passed over Gotti for underboss. Instead, Castellano tapped his personal bodyguard, Thomas Bilotti, to become Dellacroce’s replacement.

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

So, with nominal 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 after the hit, Gotti was formally confirmed as head of the Gambino crime family.

How John Gotti Became The New Mafia King

John Gotti And Sammy Gravano

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

John Gotti’s bold takedown of Paul Castellano came at a price.

According to The New York Daily News, Castellano was already fighting a racketeering case. And according to one 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, Castellano would get him.

Ironically, Gotti’s murder of Paul Castellano made him an even bigger target for a time. Genovese boss Vincent Gigante was so enraged that Gotti didn’t consult the heads of the Five Families that he personally ordered Gotti killed for his brazen breach of protocol. Only after Gotti survived the assassination attempt did Gigante relent.

Soon, John Gotti became a household name. But just five years after becoming the Gambino boss, he too was arrested for racketeering. Two years later, in 1992, he was found guilty of a litany of charges, including five murders, one of which was Paul Castellano’s. No one else was ever charged.

After learning about Paul Castellano’s death at the hands of John Gotti, read about Richard Kuklinski, the most prolific hitman in Mafia history. Then, discover how the 1931 murder of the first “boss of the bosses” Joe Masseria gave rise to the Mafia’s golden age.

Daniel Rennie
Daniel Rennie is a freelance writer residing in Melbourne, Australia.
Adam Farley
Adam Farley is an Assistant Editor at All That's Interesting. He was previously content director of and deputy editor of Irish America magazine. He holds an M.A. from New York University and a B.A. from the University of Washington.