Frank Sinatra and Frank Costello
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Frank Costello was acting boss of what later became known as the Genovese family during Luciano’s incarceration and exile. In 1947 he became the boss, but spent the next 10 years feuding with Vito Genovese for control of Luciano’s empire. In 1957 he was shot and wounded by Vincent "Chin" Gigante. Costello subsequently retired in favour of Genovese.

Many rumors and reports of Sinatra’s connection with Costello exist, but there is very little evidence to back them up. Sinatra and his sycophant group, The Varsity, spent a great deal of time at boxing matches at Madison Square Garden in the early 1940s. Frank Costello was known to hang out there as well, so it is very likely that they met.

Costello was known to be the padrino of Willie Moretti so it is possible that he also took an interest in Sinatra’s career. Costello owned the Copacabana nightclub in New York and always attended Sinatra’s engagements there. Costello was believed to be the true owner of the Sands Hotel in Las Vegas, in which Sinatra also had a part ownership. The San Francisco police also believed Costello to be the true owner of Hollywood Nite Life.

Sinatra and Frank were great friends. Whenever Sinatra had a problem he went to Frank to solve it, and even secured the role of Maggio in "From Here to Eternity" for Sinatra. While it is highly likely that Sinatra asked for Costello’s help in this, and Harry Cohn, of Columbia Pictures, had as many mob ties as Sinatra, it is also clear that it was Sinatra's own efforts, with an assist from Ava Gardner, that got him that role.

There are several rumours in Sinatra’s FBI file that Sinatra was "brought up" by Costello and that Costello put pressure on Willie Moretti to help Sinatra. Again there is no proof behind these rumors and, knowing Sinatra’s connection to Moretti, it is more likely that Moretti gave Sinatra an "in" with Costello, than the other way around.