Was Ol' Blue Eyes simply well connected… or something more?

Frank Sinatra sold more than 150 million records, won an Academy Award, helped define Las Vegas, and became one of the most recognisable entertainers in history.

But alongside the music was another story.

One involving Mafia bosses, FBI surveillance, politicians, casinos, Hollywood, and a 2,300-page FBI file.

Did Sinatra simply move in circles where organised crime figures were impossible to avoid? Or were his relationships with some of America's most powerful mobsters closer than he ever admitted?

Dee separates fact from fiction, exploring Sinatra's early arrest, his friendship with notorious gangster Willie Moretti, the famous Tommy Dorsey contract rumours, the Cal-Neva Lodge scandal, his connections to John F. Kennedy, and why the FBI spent decades watching one of America's favourite singers.

Despite years of surveillance, one fact remains clear: Frank Sinatra was never convicted of any organised crime offence.

So how much was evidence…

…and how much became legend?

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Sources

• FBI Records: The Vault – Frank Sinatra

• Smithsonian Magazine website

• History.com