How Vito Genovese Fought His Way To The Top Of The Mob — Twice

Public DomainVito Genovese reigned as one of the most powerful Mafia bosses of his era, but ended his life in prison.
Over the course of his life, Vito Genovese desired one thing above all else: power. And he’d go to great lengths to get it.
Born in Naples on Nov. 21, 1897, Genovese arrived in New York City with his family as a teenager. Before long, Genovese drifted toward a life of crime and began a fateful friendship with Lucky Luciano. Though they were initially aligned with Joe Masseria, Luciano and Genovese eventually helped take him out. The New York Times reports that Genovese is believed to be one of the men who shot Masseria to death as he dined in a Coney Island restaurant in 1931.
As Luciano’s power grew following the assassinations of Masseria and mob boss Salvatore Maranzano, so did Genovese’s. Genovese even became the acting boss of the Luciano Family (which would eventually bear Genovese’s name) after Luciano was convicted of several charges in 1936. But Genovese himself was forced to flee a murder charge the next year. He went to Italy, and handed power to Frank Costello.
But as soon as he was able to come back to the United States, Genovese did so. When he found that Costello refused to relinquish power, he turned to Luciano — then living in Cuba — and tried to convince his old friend to let him become the “boss of all bosses.” But Luciano refused.

Public DomainVito Genovese after his arrest in 1958.
“There is no Boss of Bosses,” Luciano told Genovese. “I turned it down in front of everybody. If I ever change my mind, I will take the title. But it won’t be up to you. Right now you work for me and I ain’t in the mood to retire. Don’t you ever let me hear this again, or I’ll lose my temper.”
Undeterred, Genovese used violent means to consolidate power. In 1957, he backed Carlo Gambino when he wanted to assassinate Albert Anastasia, and ordered a hit on Frank Costello. Though Costello survived, he agreed to hand over power of the family to Genovese.
But Vito Genovese didn’t have much time to savor his victory. In 1959, he was convicted on federal narcotics charges and sent to prison. Though Genovese continued to conduct business as a Mafia boss from behind bars, he’d never taste freedom again. He died of a heart attack on Feb. 14, 1969 at age 71.
Paul Castellano, The Mafia Boss Who Was Assassinated By John Gotti

Bettmann/Getty ImagesPaul Castellano is best known for his shocking 1985 assassination organized by John Gotti.
Though Gambino Family kingpin Paul Castellano did plenty in his time as a mob boss, he remains best known for his shocking 1985 murder at the hands of his soon-to-be-famous underling John Gotti.
Born on June 26, 1915, in Brooklyn, New York, Castellano seemed destined to be a Mafia boss. His cousin, Carlo Gambino, became the head of the Gambino Family (formerly the Mangano Family) after the assassination of its boss Albert Anastasia in 1957, and Castellano’s sister was Gambino’s wife. When Gambino died in 1976, he chose Castellano to succeed him.
At the time, Castellano was seen as the “Godfather” or the “boss of bosses” because the Gambino Family was the most powerful organization in New York. However, some also called him the “Howard Hughes of the Mafia” because of his reclusive nature, which could rub capos and soldiers in the Gambino Family the wrong way.

Bettmann/Getty ImagesPaul Castellano was assassinated by John Gotti on December 16, 1985.
By 1985, Castellano had trouble on several fronts.
He and other mobsters had been indicted under the Racketeer Influenced and Corrupt Organizations Act, and the mob boss and other Gambino Family members also faced a looming trial related to a car theft ring. What’s more, some family members were frustrated that Castellano had followed Gambino’s example in forbidding them from engaging in the lucrative drug trade.
This, along with several other internal issues, led Gambino Family member John Gotti to plot Castellano’s murder. On Dec. 16, 1985, Castellano and his underboss Thomas Bilotti were killed in a hail of bullets as they arrived at Sparks Steak House in Midtown Manhattan. To this day, it remains one of the most infamous mob hits of all time.
This brazen takedown of a Mafia boss would elevate Gotti to the head of the Gambino Family. But it would also put a target on his back.
