Castellano joined the Mangano family in the 1940s and eventually became a
caporegime (
capo, or captain) under
Carlo Gambino. In 1957, after Anastasia's murder and Gambino's elevation to boss, Castellano attended the abortive
Apalachin meeting in
Apalachin, New York. When the
New York State Police raided the meeting, Castellano was one of 61 high-ranking mobsters arrested. Refusing to answer
grand jury questions about the meeting, Castellano spent a year in prison on
contempt charges. On January 13, 1960, Castellano was sentenced to five years in prison for
conspiracy to withhold information. However, in November 1960, Castellano's conviction was reversed on appeal. Castellano identified more as a businessman than a criminal, taking over non-legitimate businesses and converting them to legitimate enterprises. However, his businesses, and those of his sons, still benefitted from their mob ties. In his early years, Castellano used his butcher's training to launch Dial Poultry, a poultry distribution business that once supplied 300 butchers in
New York City. Castellano used intimidation tactics to force his customers, which included supermarket chains
Key Food and
Waldbaum's, to buy Dial's products. Castellano handled Gambino interests in the "Concrete Club," a club of contractors selected by
The Commission, the mob's ruling body, to handle contracts between $2 million and $15 million. In return, the contractors gave a two-percent
kickback of the contract value to The Commission. Castellano also supervised Gambino control of
Teamsters Union Local Chapter 282, which provided workers to pour concrete at all major building projects in New York and
Long Island. In 1975, Castellano allegedly had Vito Borelli, his daughter's boyfriend, murdered because he heard Borelli had compared him to
Frank Perdue, the owner and commercial spokesman for
Perdue Farms. In 2004, court documents revealed that
Joseph Massino, a government witness and former boss of the
Bonanno crime family, admitted to murdering Borelli as a favor to Castellano.
Succession On October 15, 1976, Gambino died at his home of
natural causes. Against expectations, he appointed Castellano to succeed him over his
underboss,
Aniello "Neil" Dellacroce. Gambino appeared to believe that his crime family would benefit from Castellano's focus on
white collar businesses. Dellacroce, at the time, was imprisoned for
tax evasion and was unable to contest Castellano's succession. Castellano's succession was confirmed at a meeting on November 24, with Dellacroce present. Castellano arranged for Dellacroce to remain as underboss while directly running traditional mob activities such as
extortion,
robbery and
loansharking. While Dellacroce accepted Castellano's succession, the deal effectively split the Gambino family into two rival factionsDellacroce's faction in
Manhattan, and Castellano's faction in
Brooklyn. That same year, Castellano allegedly ordered the murders of Gambino
capo James Eppolito and his son, James Eppolito Jr. Eppolito Sr. had complained to Castellano that
Anthony Gaggi, another Gambino
capo, was infringing on his territory and asked permission to kill him. Castellano gave Eppolito a noncommittal answer, but later warned Gaggi about Eppolito's intentions. In response, Gaggi and
soldier Roy DeMeo murdered Eppolito and his son. In February 1978, Castellano made an agreement between the Gambino family and the
Westies, an
Irish-American gang from
Hell's Kitchen. Castellano wanted
hitmen that law enforcement could not tie directly to the family. The Westies wanted Gambino protection from the other mob families. The Gambino–Westie alliance was set in a meeting between Castellano and Westies leader
James Coonan. According to Westies gangster
Mickey Featherstone, Castellano gave them the following directive: 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. Castellano also forged an alliance with the Cherry Hill Gambinos, a group of Sicilian
heroin importers and distributors in
New Jersey, also for use as gunmen. With the Westies and the Cherry Hill Gambinos, Castellano commanded a small army of capable killers. In September 1980, Castellano allegedly ordered the murder of his former son-in-law,
Frank Amato, for physically abusing his wife, Castellano's daughter Connie, when they were married. At the height of his power, Castellano built a lavish 17-room mansion on a ridgeline in
Todt Hill on Staten Island. Designed to resemble the in the mansion featured
Carrara marble, an
Olympic-size swimming pool and an
English garden. Castellano engaged in an affair with his Colombian maid, Gloria Olarte. Castellano became a recluse and rarely ventured outside the mansion, requiring his
capos to visit the residence to give information and receive orders. When not entertaining guests, Castellano wore satin and silk
dressing gowns and velvet slippers around
John Gotti, a former protégé of Dellacroce, became deeply dissatisfied with Castellano's leadership, regarding the boss as being too isolated and greedy. Like other members of the family he disliked Castellano on a personal level, feeling he lacked
street credibility. Gotti also had an economic interest: he had a long-running dispute with Castellano on the split Gotti took from hijackings at
John F. Kennedy International Airport. Furthermore, Gotti was rumored to be expanding into
drug dealing, a lucrative trade Castellano had banned under threat of death.
Legal problems In January 1983, Castellano allegedly ordered the murder of DeMeo, who was found shot to death in the trunk of his
Cadillac. In August 1983, Gambino members
Angelo Ruggiero and
Gene Gotti were arrested for dealing heroin, based primarily on recordings from a device in Ruggiero's house. Castellano demanded transcripts of the tapes, and when Ruggiero refused he threatened to demote Gotti. On March 30, 1984, Castellano was
indicted on federal
racketeering charges, as well as
extortion,
drug trafficking,
theft,
prostitution and the murders of Eppolito and DeMeo. He was released on $2 million
bail. Castellano's legal challenges mounted in 1985. On February 25 he was one of many mob bosses arrested on charges of racketeering, which was to result in the
Mafia Commission Trial; he was released on $3 million bail. On July 1 he was indicted on loansharking charges and with tax evasion for not reporting the profits from an illegal racket, and pleaded not guilty. On November 4, in a testimony from car thief Vito Arena, Castellano was named the head of the stolen-car ring that employed him, as well as having been connected to five murders.
Conspiracy Dellacroce died of cancer on starting a chain of events that led to Castellano's murder two weeks Castellano's failure to attend Dellacroce's
wake was taken as an insult by members of the Manhattan faction. Then, Castellano named
Thomas Bilotti, a loyalist with little diplomatic skill, as the new underboss. Castellano also hinted that he planned to break up John Gotti's crew. Gravano suggested killing both Castellano and Bilotti while they were eating breakfast at a diner. However, when DeCicco tipped Gotti off that he would be having a meeting with Castellano and several other mobsters at Manhattan's
Sparks Steak House on December 16, Gotti and the other conspirators decided to kill him then. entrance at 210 East 46th Street, the scene of Castellano's murder == Murder ==