Old Blues Eyes is well known for his silver tongue and long-running acting gigs, but he may be the most mob-connected celebrity to ever set foot in Hollywood. His ties to the Mafia began at birth, as his uncle Bob Garavante was a part of Willie Moretti’s gang.
Throughout his life, his close association with the mob would continue, from playing mob-owned clubs to a long-running friendship with West Coast boss Benny “Bugsy” Siegel.
His flirtation with the mob culminated in a trip to Havana, Cuba in February of 1947 where Sinatra was photographed leaving a plane carrying a large square case.
During that trip he spent time with deported mobster Lucky Luciana, sang and entertain visting mafia members, and was amply rewarded with women and money.
However, the trip was reported in American news and culminated in a 4 AM hearing with a Senate comittee in which a visibly nervous Sinatra testifying that he didn’t know what business those men were in.