Paul Castellano, known as Big Paulie, headed the powerful Gambino crime family from the mid-1970s until his assassination in December 1985. He was killed at a moment of peak legal vulnerability, facing federal racketeering charges and standing trial in a separate car theft and murder case while out on bail. Born Constantino Paul Castellano in Bensonhurst, Brooklyn, on June 26, 1915, he grew up in a family with deep ties to organized crime. His father was a butcher with connections to the Mangano crime family, which later became the Gambino family.
Castellano left formal education after the eighth grade and learned the butcher trade and the numbers game from his father. At 19, he was arrested in Hartford, Connecticut, for a robbery. He chose to serve his sentence rather than reveal his accomplices, building a reputation for loyalty under the Mafia code of silence, or omertà. Castellano’s family connections ran deep.
His sister Catherine married Carlo Gambino, who later became one of the most influential Mafia bosses in America. Castellano married his childhood sweetheart, Nina Manno, in 1937, and the couple had four children. He rose through the ranks of the Mangano family, becoming a captain under Albert Anastasia. In 1957, he attended the infamous Appalachian meeting of top Mafia figures, which was interrupted by a police raid.
Castellano was among the 61 mobsters taken into custody. He refused to cooperate with authorities, receiving a contempt citation and later a conspiracy conviction that was overturned on appeal. Castellano saw himself as a businessman more than a traditional mobster. He launched Dial Poultry, a wholesale distribution company that served 300 butchers in New York City.
He used intimidation to pressure major grocery chains like Key Food and Waldbaum’s into buying his products. His influence extended into the construction industry. His son Philip became president of Scarix Concrete Corporation, which nearly monopolized concrete supply on Staten Island. Through the “Concrete Club,” a coalition of contractors selected by the Mafia’s ruling commission, Castellano controlled high-value construction contracts ranging from $2 million to $15 million.
Contractors paid a 2 percent kickback to the commission. His oversight of a Teamsters Union local chapter of construction workers further solidified Gambino control over the city’s building sector. Despite his business-oriented facade, Castellano ordered brutal acts to maintain his authority. In 1975, he allegedly ordered the murder of his daughter’s boyfriend, Vito Borelli, after hearing the young man had compared him to Frank Perdue, the well-known poultry businessman.
The insult to Castellano’s image was seen as intolerable. In 2014, Joseph Massino, former head of the Bonanno family turned government witness, confessed that he personally arranged Borelli’s murder as a favor to Castellano. When Carlo Gambino died on October 15, 1976, he named Castellano as his successor rather than his longtime underboss, Aniello Dellacroce. Gambino favored Castellano’s preference for low-profile, lucrative white-collar operations over traditional street crime.
Dellacroce, imprisoned on tax evasion charges at the time, could not contest the appointment. Castellano allowed Dellacroce to remain underboss and oversee street-level activities like loan sharking, extortion, and robbery. The arrangement divided the family into factions, with Castellano operating from Manhattan and Dellacroce based in Brooklyn. In 1978, Castellano allegedly ordered the murder of Nicholas Scibetta, a Gambino associate and brother-in-law of Salvatore “Sammy the Bull” Gravano, whose behavior and public brawls drew unwanted attention.
Scibetta reportedly insulted the daughter of a respected family member. Gravano initially threatened retaliation but eventually accepted that Scibetta’s conduct had crossed too many lines. Later in 1978, Castellano allegedly sanctioned the murder of Gambino captain James Eppolito and his son, James Jr. Eppolito had sought permission to eliminate another captain who encroached on his territory.
Castellano, non-committal to Eppolito’s request, secretly warned the target, who preemptively murdered both Eppolito and his son. Castellano also formed strategic alliances. In February 1978, he allied with the Westies, an Irish American gang based in Hell’s Kitchen, during a meeting with their leader, James Coonan. According to Westies member Mickey Featherstone, Castellano set strict terms: “You guys got to stop acting like cowboys, acting wild.
You’re going to be with us now. If anyone is going to get killed, you have to clear it with us first. ” The alliance provided Castellano with external enforcers while keeping the Gambino family distanced from direct involvement. In September 1980, Castellano allegedly sanctioned the murder of his former son-in-law, Frank Amato, who was accused of abusing his wife, Connie, Castellano’s daughter.
According to FBI reports, Castellano assigned Roy DeMeo to handle the situation. DeMeo reportedly murdered Amato, dismembered his body, and disposed of the remains in the ocean. As his power grew, Castellano commissioned construction of a sprawling 17-room mansion on Todt Hill in Staten Island, designed to resemble the White House. It featured Carrara marble, an Olympic-size pool, and English gardens.
He rarely left the residence, relying on captains to visit and report. Clad in satin and silk dressing gowns, he issued orders from the mansion. He also conducted an affair with his Colombian maid, Gloria Olarte. Unrest was brewing within the family.
John Gotti, a protégé of Dellacroce, grew frustrated with Castellano’s leadership. Gotti felt Castellano was disconnected from street operations and too controlling over financial matters, including profits from hijacking operations at JFK International Airport. Gotti was also allegedly involved in drug dealing, a venture Castellano had strictly prohibited within the family. In January 1983, Castellano allegedly ordered the murder of Roy DeMeo, who was found dead in the trunk of his Cadillac.
That year, the FBI made a breakthrough that began Castellano’s downfall. While he vacationed in Florida, federal agents disabled the security system at his Staten Island mansion, drugged his guard dogs, and installed hidden listening devices. The bugs provided investigators with evidence implicating Castellano in numerous crimes. In August 1983, Gambino family members Angelo Ruggiero and Gene Gotti were arrested on heroin distribution charges.
Evidence used against them came from recorded conversations in Ruggiero’s home. Castellano demanded access to the transcripts, sparking tension with Ruggiero, who refused to hand them over. Castellano threatened Gotti over the recordings. In March 1984, Castellano was indicted on federal racketeering charges, including drug trafficking, extortion, theft, and murder.
He was released on $2 million bail. In February 1985, he was arrested again as part of the Mafia Commission trial, a massive racketeering case against the leadership of New York’s five Mafia families. He posted bail of $3 million. By July, he was indicted on additional charges, including loan sharking and tax evasion.
During this period, car thief Vito Arena testified that Castellano was the head of a stolen car ring and linked him to several murders. When Aniello Dellacroce died of cancer on December 2, 1985, Castellano chose not to attend the wake, a decision many family members saw as a disrespectful slight. He appointed Thomas Bilotti, a close ally with limited diplomatic experience, as his new underboss. Rumors circulated that Castellano intended to dismantle John Gotti’s crew, further inciting Gotti’s resentment.
Sammy Gravano suggested taking drastic measures, proposing that Castellano and Bilotti be killed. Plans for the hit took shape when Gotti learned from Frank DeCicco that Castellano planned a meeting at Sparks Steakhouse on December 16, 1985. On that evening, as Castellano and Bilotti arrived at the restaurant at approximately 5:26 p. m.
, a team of gunmen ambushed them. Shooters, reportedly including Salvatore Scala, Edward Lino, and John Carneglia, closed in quickly. Across the street, Gotti and Gravano watched from a parked car. Castellano was struck multiple times, with rumors that Carneglia delivered the fatal shot to the head.
Bilotti, the loyal driver and bodyguard, was also shot as he attempted to exit the car. Gotti reportedly drove past the scene to survey the aftermath. Castellano was interred at Moravian Cemetery on Staten Island. The Archdiocese of New York denied him a traditional Catholic funeral, a rare decision that underscored the notoriety of his lifestyle.
Just two weeks after the assassination, Gotti claimed the title of boss within the Gambino family. Vincent Gigante, head of the Genovese family, was furious at the breach of Mafia protocol. Gigante enlisted Anthony Corallo, the Lucchese family boss, in a plan to eliminate Gotti. On April 13, 1986, a car bomb intended for Gotti detonated outside a social club in Bensonhurst, but it claimed the life of Frank DeCicco instead, leaving Gotti unharmed.
In late 1990, Gotti was arrested by the FBI on racketeering charges. Following a lengthy legal battle, with Gravano turning government witness, Gotti was convicted on April 2, 1992, for a string of criminal activities including Castellano’s murder. He received a life sentence in federal prison on June 23. Gotti remained incarcerated until his death from throat cancer in 2002.
Gotti was the only person convicted for the killing. Castellano’s legacy in the American Mafia is complex. Known for his lavish lifestyle and interest in legitimate-looking businesses, he helped bring a more corporate approach to organized crime. He aimed to move the Gambino family away from street-level crime, focusing on sophisticated rackets that kept the family wealthy and less visible.
His leadership was controversial among underlings who saw him as out of touch and overly concerned with appearances. The Staten Island mansion, dubbed “The White House,” became a symbol of his detachment from rank-and-file members. His assassination marked a significant turning point in organized crime, illustrating internal divisions within the Mafia and foreshadowing the decline of its traditional hierarchical structure in America.