Was Frank Sinatra affiliated with the mob? This is a question that has been tossed around since Old Blue Eyes himself was still a young man. In her unauthorized Sinatra biography “His Way,” author Kitty Kelley details numerous meetings and relationships with some of America's most powerful mafia figures. And while there is no evidence that Frank was ever a “made man,” there is some convincing evidence that he indeed had friends in low places.

Sinatra certainly didn't have a wealthy or powerful upbringing. In fact, he grew up in a relatively poor neighborhood, surrounded by other working class Italians in Hoboken, New Jersey. His father Marty was a firefighter and his mother Dolly worked as a back alley abortionist. But as Frank began singing professionally, first with the Hoboken Four and then with various nightclub gigs, a lot of people began to take an interest in the young man's talent.

But in his memoir “Dean and Me,” actor Jerry Lewis explains that in the heyday of clubs like the Copa Cabana and the 500 Club, a performer could not run the nightclub circuit without making friends in the mob. Quite simply, the mafia controlled the club scene, so as a performer, you learned how to deal with the wise guys. Lewis also points out in his memoir that while he and his partner (Dean Martin) never got too close to the mob, Sinatra may have been seduced by their influence and power.

There are a couple of common stories that circulate about Sinatra and the mob. One of these stories involves the famous band leader Tommy Dorsey, who gave Sinatra his first professional singing job, and subsequently made Sinatra sign a contract that entitled Dorsey to a cut of the young singer's earnings...for a lifetime. Eager to get out of his contract, Sinatra employed the help of some mob friends, and (as the legend goes), Tommy released Frank from his contract for one dollar, with a mobster's gun barrel sticking in his mouth.

This story appears to be at least partially based in fact. The mobster in question is Willie Moretti, then underboss of the Genovese crime family. He has reportedly boasted about paying Tommy Dorsey a visit, although Sinatra vehemently denied that the mob had anything to do with his contract release. Still, it is true that Dorsey abruptly relieved Sinatra of his contract in 1943, despite having a reputation as somewhat of a tyrant. In 1951, Dorsey even admitted to having been approached by three men who told him to “sign or else.”

Another common legend involves Sinatra and Harry Cohn, the former head (and co-founder) of Columbia Pictures. Sinatra's career was tanking in the early '50s, and he desperately sought to reinvent himself with a role in Columbia Pictures' “From Here to Eternity.” He ultimately got the role, but the legend proposes that Harry Cohn was coerced by the mob, and given an offer he couldn't refuse, so to speak. In fact, this legend was even the basis for the famous dead horse scene in “The Godfather.” This legend, though, appears to be entirely fictitious. Cohn and Sinatra both denied the legend, and in fact Sinatra lobbied for the role of Maggio in “From Here to Eternity” and was ultimately granted the role because of his thin, lanky build (which the role called for).

Throughout his life, Sinatra kept many friends and acquaintances who were “connected,” but Sinatra himself was far too stubborn and independent to ever officially join the ranks of any organization that demanded absolute loyalty. He was very much his own man. In the words of one of his beloved songs, penned by Paul Anka (which has its own specious mob legend behind it), “I did it my way.”