At Giancana’s suggestion, Sinatra introduced Kennedy to an ex of his, a lady named Judith Campbell, sparking an affair between the two which would go down in history. At the same time Giancana started dating Campbell, not because he desired Campbell but because he had a habit of wooing the wives and girlfriends of men he wanted to control to gain inside information and show that he could have anything his target held dear.

As for the business relationship between Sinatra and Giancana, nothing was ever clearly proven, apart from the scandal surrounding the Cal-Neva Lodge (that was situated on both Nevada and California soil) and Giancana’s ownership in the casino that led to Sinatra’s gambling license being revoked even though he claimed that he stayed on the California side of the casino, not the Nevada side that he was forbidden to cross, according to Nevada law.

It was due to Giancana’s relationship with Frank that he lost any hopes of gaining access to the White House, as JFK dumped Frank due to his mob connections and friendship with Giancana even though Giancana had played a key role in ensuring JFK became President.

With Sinatra out of Kennedy’s good books, wiretaps revealed Giancana’s disappointment and his low regard for the singer. When it became clear that Sinatra wasn’t going to get him what he wanted, the mobster had no use for him and the friendship soured. In an FBI taped conversation, Giancana expresses his anger at Sinatra, who had chosen the Kennedy’s over him, that he was going to make a hit on not only Frank but the entire Rat Pack for their treatment of the mobster.