Frank Sinatra was a fan of many Mobster’s like Johnny Roselli, and Mafia Don, Carlo Gambino. According to entertainer ,Jerry Lewis, Frank Sinatra once served as a Mafia courier and narrowly escaped arrest with a briefcase containing $3.5 million in cash. Mafia fink , Jimmy “the weasel” Fratianno always maintained that Sinatra was an associate of Chicago Mobster, Sam Giancana. Tina Sinatra says her father told her that Kennedy patriarch Joseph P. Kennedy wanted the Mafia’s help in delivering the union vote in the 1960 West Virginia primary, in which John Kennedy, then a U.S. senator, faced Sen. Hubert Humphrey of Minnesota. The elder Kennedy asked Frank Sinatra to make a request to then-Chicago crime boss Sam Giancana.