"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

Depiction of Frank Sinatra

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.

Photo of actor Al Martino as Johnny Fontane in The Godfather (Historica Wiki)

Michael Corleone’s fiancée Kay is astonished that someone as famous as Fontane would be performing at a wedding, not yet fully realizing the depth of the Corleone’s power and influence.

Then Michael, in a rare display of honesty and candor, explains to Kay how his father had a big role in Fontane’s success and career.

He goes on to explain that Fontane is Vito’s godson, and when Johnny was first starting out, he signed a bad contract, and as he became more successful, he wanted to be released from his contract.

So Vito went to see the band leader who held Fontane’s contract and offered to buy out Fontane’s contract for $10,000. The band leader refused.

The following day, Vito returned with his henchman Luca Brasi, and within an hour, the man had signed away Fontane’s contract for a thousand dollars.

A stunned Kay asked, “Well, how’d he do that?”

Michael: “My father made him an offer he couldn’t refuse.”

Kay: “What was that?”

Michael: Luca Brasi held a gun to his head and assured him that either his brains or his signature would be on that contract.” “That’s a true story.”

Photo of actors Al Martino and Marlon Brando in The Godfather (Paramount Pictures)

The Real Johnny Fontane

Johhny Fontane is famously based on singer and actor Frank Sinatra. Sinatra’s legendary career spanned decades. From his chart-topping hits to leading man status in major Hollywood films to his wild escapades with the Rat Pack, Frank Sinatra was one of the most notable American entertainers ever.

Photo of Frank Sinatra (Stacker)

However, like his on-screen counterpart Johhny Fontane, Sinatra was rumored to be friendly with some very powerful figures in the world of organized crime.

In fact, the story that Michael tells Kay about Fontane’s contract was based on a story in which powerful Genovese mobster Willie Moretti held a gun to big band leader Tommy Dorsey’s head to get Sinatra released from his contract.

This event is perhaps eluded to in the film when Michael ends with, “That’s a true story.”

It should be noted that Frank Sinatra was Willie Moretti’s godson.

Photo of Frank Sinatra (second from L) and members of the Rat Pack (Las Vegas Weekly)

Beginnings

Frank Sinatra’s story began in Hoboken, New Jersey, on December 12, 1915. The son of Italian immigrants. His father was a boxer who later joined the Hoboken Fire Department, becoming a captain.

Frank’s mother Dolly’s strong-willed and driven personality was said to have had an influence on young Frank’s personality.

Sinatra became interested in music at a young age, and though it was his father’s desire for Frank to obtain an education, Sinatra found himself expelled from high school for “general rowdiness.”

Mugshot of a young Frank Sinatra (Reddit)

He then enrolled at Drake Business School but dropped out less than a year later. Sinatra found himself working odd jobs, while at the same time beginning to sing and perform in local clubs in New York and New Jersey.

Though unable to read music, Sinatra learned by ear and, by the mid-1930s, was singing in local groups.

Frank eventually caught on with the Tommy Dorsey band. Dorsey became like a father figure to Sinatra and had a big influence on his career and even his style and mannerisms.

Ironically, Sinatra even asked Dorsey to be godfather to his daughter Nancy.

Sinatra began to see success with a string of hits in the early 1940s. It was shortly after this that Willie Moretti allegedly intervened on Sinatra’s behalf and threatened Dorsey into releasing Sinatra from his contract.