“Old Blue Eyes” and the Mob: Investigating Frank Sinatra’s Organized Crime Ties

For years, rumors have persisted that iconic American singer and actor Frank Sinatra was connected to underworld figures. In fact, the FBI kept a file on him for more than 40 years

This article originally appeared on the true crime newsletter Tales From the Underworld. Subscribe for new and exclusive historical true crime content.

Depiction of Frank Sinatra (Image generated via Midjourney)

Background

In the opening of the iconic film The Godfather, the audience is introduced to the characters as they celebrate the marriage of family patriarch Vito Corleone’s daughter, Connie.

The atmosphere is festive, with children running and playing while adults sip their drinks and mingle.

The audience is then introduced to a character named Johhny Fontane. Fontane, a handsome Italian crooner, is performing for the bride and groom and all of their guests.