When Carlo Gambino died of natural causes at home on October 15, 1976, he chose Paul Castellano to succeed him over his underboss, Aniello “Neil” Dellacroce. However, when Dellacroce died of cancer on December 2, 1985, a chain of events would start that did not end well for the new crime boss. On Monday, December 16, 1985, Castellano was headed to a pre-arranged early evening meeting at Sparks Steakhouse in Midtown Manhattan. As Castellano was exiting the car at the front of the restaurant at around 5:26 PM, gunmen ran up and shot him several times, ultimately ending his life.
Castellano, who hated his first name Giuseppe, was a butcher and an early member of the Mangano crime family, the forerunner of the Gambino family. He dropped out of school in the eighth grade to learn butchering from his father and collecting numbers game receipts from him. He was arrested for the first time in July 1934 in Hartford, Connecticut, for robbing a haberdasher. The 19-year-old Castellano was sentenced to three months in prison after refusing to identify his two accomplices to police.
His reputation for Mob loyalty grew as a result of his refusal to cooperate with authorities. Castellano became a member of the Mangano family in the 1940s when Albert Anastasia, the successor to boss Vince Mangano, promoted him to capo. After Anastasia’s murder and Carlo Gambino’s promotion to boss, Castellano attended the ill-fated Appalachian meeting in Apalachin, New York, in 1957. He was one of 61 high-ranking mobsters arrested when New York State Police raided the meeting.
He spent a year in prison on contempt charges after refusing to answer grand jury questions about the meeting. Castellano was sentenced to five years, but the charges were later dismissed. Despite his criminal activities, Castellano was identified as a businessman rather than a hoodlum. He took over illegal businesses and converted them into legal ones.
However, Castellano and his son’s businesses benefited from their mob connections. Castellano used his butcher connections to dominate the construction concrete business on Staten Island. Castellano was also in charge of the Gambino interests in the Concrete Club, a group of contractors chosen by the Commission to handle contracts ranging from two million dollars to fifteen million dollars. In exchange, the contractors gave the Commission a two percent kickback on the contract value.
Castellano also oversaw Gambino’s control of Teamsters Union Local chapter 282, which provided workers to pour concrete at all major New York and Long Island construction projects. In 1975, Castellano allegedly murdered Vito Borelli, the boyfriend of his daughter Constance, after hearing Borelli compare him to Frank Perdue, the owner and commercial spokesman for Perdue Farms, according to court documents. In 2004, Joseph Massino, a government witness and former Bonanno crime family boss, admitted to murdering Borelli as a favor to Castellano. When Carlo Gambino died, he chose Castellano as his successor, and Dellacroce was unable to challenge Castellano’s succession.
Castellano’s succession was confirmed at a meeting on November 24, which included Dellacroce. He arranged for Dellacroce to keep his position as underboss while directly carrying out traditional Cosa Nostra activities like extortion, robbery, and loan sharking. While Dellacroce accepted Castellano’s succession, the agreement effectively divided the Gambino family into two opposing factions. Castellano is accused of ordering the murder of a cocaine and alcohol user who was involved in several public fights and insulted George DeCicco’s daughter.
Because the man, Shibetta, was Salvatore “Sammy the Bull” Gravano’s brother-in-law, Castellano requested that Frank DeCicco notify Gravano of the impending hit first. When told of his brother-in-law’s fate, Gravano became enraged and declared that he would kill Castellano first. Gravano was eventually calmed down by DeCicco and accepted Shibetta’s death as punishment for his actions. A Gambino soldier had complained to Castellano that Anthony Gaggi was invading his territory and had requested permission to kill him.
The soldier received a non-committal response from Castellano, who later warned Gaggi about the soldier’s intentions. Gaggi and soldier Roy DeMeo retaliated by murdering both father and son. Castellano arranged a deal between the Gambino family and the Westies, an Irish-American gang from Hell’s Kitchen, Manhattan, in February 1978. He wanted hitmen who could not be directly linked to the Gambino family, and the Westies wanted Gambino protection from the other Cosa Nostra families.
A meeting between Westies leader James Coonan and Castellano established the Gambino-Westies alliance. Castellano also formed an alliance with the Cherry Hill Gambinos, a New Jersey-based group of Sicilian heroin importers and distributors, to use as gunmen. He now commanded a small army of capable killers with the Westies and the Cherry Hill Gambinos. Gambino soldier Roy DeMeo, a hijacker and minor criminal, had physically abused his wife, Connie, Castellano’s daughter, during their marriage according to FBI documents.
Castellano allegedly ordered the murder of DeMeo, who was found shot to death. The FBI obtained a warrant in March 1983 to install secret listening devices in Castellano’s home. Agents drugged Castellano’s watchdogs, disabled his security system, and planted devices in his dining and living rooms while he was on vacation in Florida. These devices gave authorities a tremendous amount of incriminating information about Castellano.
Angelo Ruggiero and Gene Gotti were arrested for heroin dealing in August 1983 based primarily on recordings from a bug in Ruggiero’s house. Castellano, who had prohibited made men from his family from dealing drugs under threat of death, demanded transcripts of the tapes and threatened to demote Gotti if Ruggiero refused. On March 30, 1984, Castellano was indicted on federal racketeering charges in the Gambino case, which included the Eppolito and DeMaio murders. Extortion, narcotics trafficking, theft, and prostitution were among the other charges.
He was released on two million dollars bail on February 18, 1985. A series of events contributed to the plot to assassinate Castellano. His failure to attend Dellacroce’s wake was an insult to the Dellacroce family and followers. Second, Castellano appointed his bodyguard, Thomas Bilotti, as acting underboss, replacing the ailing Dellacroce.
This infuriated Gotti, who began to plot the hit on Castellano. On December 16, 1985, the new boss was gunned down outside Sparks Steakhouse, and John Gotti took over as the head of the Gambino family.