He was born Constantino Paul Castellano, in Brooklyn, on June 20, 1915.
Paul was the youngest of three and was the only boy. As most children did, Paul dropped out of school in the eighth grade
and learned to be a meat cutter and was running numbers for his father.
His father was a butcher but he also ran numbers for bookies.
Paul grew up in a middle class, Italian neighborhood where the crime was not that evident.
At the age of 19, Paul was involved in an armed robbery. His two friends escaped, but Paul was convicted and spent 3 months in jail. He was sentenced to a year in Hartford County jail but would only serve 3 months and 4 days. When he returned home, he was hailed a hero for never ratting out the other boys that got away from the police. This would be the beginning of Paul's reputation for being a "stand up guy".
This was Paul's first run in with the law and would be his last one for almost twenty three years.
At age 22, in 1937 he married his childhood sweetheart Nina Manno,
Nino Manno was the sister in law of Carlo Gambino.
They had 3 sons and a daughter. But while the marriage appeared to be good on the outside, it soured quickly in private. Castellano suffered from diabetes, and it was said that one of the side effects was sexual impotency.
He separated from his wife, and had an affair with his Colombian house keeper, Gloria Olarte.
It was rumored that he had a penile implant. Whether it was true or not, his underlings believed it and ridiculed him. They lost respect for him. And the more they lost respect for Castellano, the weaker he became as a boss.
After Paul's marriage he set himself up in the meat business and by the early 1950's, Paul was running an extremely successful wholesale operation known as Blue Ribbon Meats. While running his legitimate meat business, Castellano continued to do jobs to consolidate his position within the Brooklyn boys.
Paul became close to his cousin Carlo, and developed the so called "White Rackets," construction bids, union affairs and political ties, while another Carlo Gambino friend, Aniello "Neil" Dellacroce, managed the "blue collar" side of the family that was head quartered at the Ravenite Social Club in Little Italy.
The key to Paul's rise to stardom was his cousin Carlo. Carlo Gambino became boss of his own family and ruled masterfully for many years. When Carlo was at his death bed he declared that his cousin Paul would take over as boss.
Dellacroce, was a man's man, he was from the old school who followed the tradition of unquestioned loyalty, accepting the death bed decision of Carlo Gambino to anoint Castellano as the new Gambino family head.
While Dellacroce used respect and loyalty to keep his turf in line, Castellano preferred dealings. He negotiated a truce with the leaders of the Irish New York Mafia; the Westies, offering their leaders, Jimmy Coonan and Nicky Featherstone, to use the Gambino family name in their business in exchange for 10 percent of their earnings out of Hell's Kitchen on the West Side of Manhattan. However, they could not kill anyone unless they had permission from Big Pauly. The Westies abused the privilege and in an ironic twist, forced the police to confront Castellano in a private meeting concerning Westies committed murders. The police wanted Castellano to cut his ties with the Westies, which he did.
Castellano, although adverse to using violence, did not shy from it. It is alleged he turned to one of his guys Roy DeMeo, to murder his son in law, Frank Amato, whom he had heard was beating his pregnant daughter, Connie, and was having affairs. When Connie had a miscarriage, Amato's body disappeared on Sept. 20, 1980.
A federal probe of DeMeo in 1982 prompted Castellano to meet with DeMeo. When DeMeo refused to meet with Castellano to discuss the federal probe. DeMeo's body was found in the trunk of his car Jan. 10, 1983.
Castellano lived in a mansion on a 3.5 acre estate on Staten Island at the top of Todd Hill, valued at $3.5 million and built as a copy of the White House. In fact, he called it his "White House." It sharply contrasted the humbled, middle class home of Carlo Gambino and most of his Gambino family underlings. The mansion was protected by a rottweiler named "Duke."
Castellano did not mingle with his family underlings, and instead spent most of his time with his lover, Gloria Olarte
and big money private industry friends, dining frequently at Sparks Steak House in New York.
Ironically it was his lover and maid that betrayed him.
The FBI planted bugs in Castellano's "White House" in late 1983 with the help of his maid and lover, Gloria Olarte.
She had been upset with they way her affair was going with Paul. It was Gloria Olarte who told the FBI that Paul Castellano often sat at his kitchen table where he discussed business with family members.
While Castellano and his trusted aide and driver Tom Bilotti were out dining,
Gloria Olarte let an FBI agent posing as a repairman, into Big Paul's house. He planted a bug in the kitchen near the table.
The bug recorded 600 hours of conversations detailing Gambino family business.
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