In this article:
- Frank Sinatra was a famous singer known for his deep, mellow voice that put him on par with the likes of Elvis Presley and the Beatles in terms of popularity.
- The singer’s cultural impact can be felt in movies featuring his songs, but what most people don’t know about him is that he may have been affiliated with the Italian mafia.
- Born to Italian immigrant parents in Hoboken, New Jersey, Sinatra grew up around Hell’s Kitchen and was no stranger to the mob’s influence.
- Sinatra has been photographed hanging out with known mafia members, but he also sometimes pissed them off leading to him having to play eight nights in a row to appease a mob boss who shared a mistress with John F. Kennedy.
Even if you don’t know Frank Sinatra (but honestly, how?) or have never actively listened to his songs, you’ve definitely heard at least one of them. Fly Me to the Moon, New York, New York, and Chicago are common staples in films set in the aforementioned cities.
The singer’s warm, mellow, and deep voice together with his killer looks made him one of the biggest heartthrobs of his time and a major influence on the artists that came after him. Despite his romantic songs, no amount of just the way you look tonight can erase how temperamental Frank Sinatra actually was.
Rumors about Sinatra having mob ties made people even more eager to avoid his wrath.
Frank Sinatra’s Roots in Hell’s Kitchen
Frank Sinatra reached the height of stardom during the 1940s to 1950s when he became known for jazzy numbers that romanced the ears of men and women alike.
Before he became famous enough to tour the country, though, he was singing in his childhood home in Hoboken, New Jersey. He also became known for his piercing blue eyes which is how he got the nickname Ol’ Blue Eyes.
Sinatra, whose full name is Francis Albert Sinatra, was born in 1915 to Italian immigrants Natalina Garaventa and Antonio Martino Sinatra. Garaventa’s family was from the Liguria region of Italy.
It was Antonio Sinatra who came from Sicily. Even back then, Sicilian Italians were already known for the rampant organized crime in their region, which may have been why Garaventa’s parents didn’t approve of Antonio Sinatra.
The two later eloped and married before having only one child: Frank Sinatra.
And boy did they win the child lottery.
Frank Sinatra saw Bing Crosby sing in the ’30s and decided he would become a singer. Though only a teenager, the young Sinatra was clearly the type of person to follow his plans through to the end. He joined the glee club at his school and started singing at local nightclubs.
It was at these local nightclubs that led Frank Sinatra to be heard on the radio. Radio brought him to Harry James and that lead him to being invited to join the band of Tommy Dorsey, a jazz trombonist who was, in a way, the Frank Sinatra of Sinatra’s time.
But rumors say Frank Sinatra developed his connections with the mob during his local dive signing days.
Frank Sinatra Wasn’t in the Mob — But He Was With the Mob
Many bars and restaurants during Frank Sinatra’s time were owned by the Italian mafia. Crime families would often use these bars as a means of laundering money and as meeting places for gang members to do business at. You read between the lines.
Frank Sinatra first became acquainted with the mob at the very places he used to sing at. Rumors about the connection between his fame and his friendships with mafia members culminated in a little film you may have heard of, The Godfather. We’ll get to that later.
One famous restaurant owned by Mafiosi, albeit in Chicago, is an Italian restaurant called Piero’s which counted Frank Sinatra among its regulars. Okay, so he ate at a mafia-owned restaurant, that doesn’t make him a mafia member, right?
Of course not, but Frank Sinatra had a public friendship with the owner, Joseph Pignatello. Pignatello had worked with Al Capone’s mother and as a personal chef to Chicago Outfit boss Sam Giancana before starting his own restaurant.
Sinatra’s own parents had shady ties for the time. Antonio Sinatra ran a bar during the prohibition while his mother, a midwife, was said to have performed illegal abortions.
You would have had to know people who knew people not to get caught or given up to the authorities at the time. Plus, his uncle, Bob Garavante, was a member of a Genovese crime family.
Going back to Frank Sinatra, he had tons of mob buddies with whom he was photographed in public. Among these mob friends was John “Sonny” Franzese who was also known for hanging out with none other than Marilyn Monroe.
And remember Sam Giancana? Here’s him all buddy-buddy with Ol’ Blue Eyes.
Sinatra is also known to have been acquainted with Neil Dellacroe, an underboss of the Gambino crime family as well as Michael Spilotro.
Spilotro was a Chicago Outfit enforcer and the brother of Anthony Spilotro, a gangster known as “Tony the Ant” who led a crew in Las Vegas before being murdered by, ahem, upper management for disagreements with his manner of managing the Chicago Outfit’s affairs in Las Vegas
Despite Sinatra’s seeming friendship with Mafia members, he would often vehemently deny that he was a mobster or that he had connections to the mob.
Sinatra once told his manager Tony Oppedisano that just because he hung out at nightclubs owned by mob bosses doesn’t mean he’s a mobster himself.
“He would say to me, ‘Tony, I don’t get it. If the nightclubs were all owned by cardinals and monsignors, I guess I would have been spending time with cardinals and monsignors, but that doesn’t make me a cardinal or a monsignor, nor does working in a club that was owned by wiseguys make me a wiseguy.’” Oppedisano said in an interview with Page Six.
Up until his death, Sinatra denied having connections to the mob, likely because his Sicilian friends were members of competing factions. Besides, Sinatra drew crowds. If they could get him to sing for them, they’d be making bank.
Sinatra’s paradoxical behavior toward the mob led to several legends about the true depths of his connections to Italian Mafiosi which is how he came to berate Mario Puzo, the author of The Godfather.
Frank Sinatra, The Godfather‘s Johnny Fontane, and the Urban Legends About How Close Frank Was to the Italian Mafia
Frank Sinatra had a temper. A real temper with a mean streak a mile wide. While stars today get flak for so much as looking at a paparazzi wrong, Ol’ Blue Eyes wasn’t afraid to publicly go after anyone who wrote negatively about him.
His reputation was so well known that comedians avoided joking about Frank Sinatra out of fear of pissing him off.
After all, this was a guy known for shaking hands with gang members. Even back then, no one was sure exactly how close Frank Sinatra was to the mafia. Don Rickles, a comedian who was close friends with Sinatra, was the only one who dared to poke fun at him in public.
Mario Puzo, author of The Godfather, apparently didn’t get the memo that you couldn’t talk about the Chairman of the Board, another nickname of Sinatra’s, without his permission.
If you haven’t read The Godfather, the book contains a reference to Sinatra in the form of the character Johnny Fontane. Fontane is depicted as a friend to the Corleone children and a singer who performed for Vito Corleone.
The book later shows Fontane getting several favors from Vito Corleone such as helping him get out of his old contract. But what likely got Sinatra truly angry was the part of the film that showed Fontane getting a film role by asking Corleone to “help” him “convince” the producer to cast him in a role.
At the time, there were rumors about Sinatra having worked his mob connections to land a role in From Here to Eternity, a film that everybody thought would go to a different, more experienced actor since Frank Sinatra had had no acting roles before.
The prevailing rumor at the time was that Sinatra’s mafia friends had put the severed head of a horse under the bed of the owner of Columbia Studios.
A much older rumor involved Sinatra and Tommy Dorsey. Though Dorsey had helped Sinatra get his start, it wasn’t entirely out of the goodness of heart. When Sinatra later asked to be released from his contract with Dorsey, Dorsey demanded a third of Sinatra’s earnings for life and an additional ten percent to be paid to his agent who was, as you can guess, Dorsey himself.
Willie Moretti, an underboss of the Genovese crime family, privately bragged about convincing Dorsey by shoving the barrel of a gun into his trombone-tooting mouth. Years later, Sinatra performed at Moretti’s daughter’s wedding and brought other big names such as Dean Martin, Jerry Lewis, and Milton Berle to join him.
Sinatra had already caught wind of Johnny Fontane before the book was released and sent an army of lawyers to demand a copy of the manuscript from the publisher.
When Sinatra and Puzo met personally at a dinner party at Chasen’s, Sinatra took offense to Puzo daring to come to his table. Puzo was dragged out of the restaurant by two other men while Sinatra shouted after him, “Choke! Go ahead and choke!“
Al Martino, who played the role of Fontane in The Godfather, shared in an interview with Seal that people would tell him, “If you take the role, Sinatra will bar you from Las Vegas.”
Sometimes, Frank Sinatra Also Pissed-off Gang Leaders
Sinatra brushed elbows and held palms with major wiseguys to the point that when the U.S. senate made a committee to investigate the organized crime scene in the country, Sinatra’s name always kept coming up.
Likely knowing better than to sing, Sinatra vehemently denied that he was ever more than acquaintances with the likes of Lucky Luciano, Bugsy Siegel, Willie Moretti, and The Fischetti Brothers.
Sammy Davis Jr., another singer friend of Sinatra’s, only had this to say to the Feds, “Baby, let me say this. I got one eye and that one sees a lot of things that my brain tells me I shouldn’t talk about. Because, my brain says that if I do, my one eye might not be seeing anything after a while.”
Regardless of what Davis Jr. knew, it was clear not even Sinatra could escape the rage of the mob.
Ol’ Blue Eyes once made the mistake of standing up John Gotti Sr., boss of the Gambino crime family, after sending him tickets to see Sinatra perform at Carnegie Hall. Sinatra canceled at the last minute claiming to be ill but was later seen at Savoy Grill hanging out with a friend. Gotti Sr. ordered Joe Watts, a henchmen of his, to “tear Sinatra a new asshole.”
Sinatra’s many friendships also got him in hot water.
Sam Giancana did John F. Kennedy a favor by helping him solve a dispute with Frank Costello, another mob boss. When Kennedy reneged on his promise to give Giancana “the president’s ear”, Giancana was furious. It also didn’t help that the two men were sleeping with the same woman, Judith Campbell.
Sinatra, together with Sammy Davis Jr. and the rest of the Rat Pack, were forced to play for eight nights in a row at Villa Venice, a club that Giancana owned. The reason? Sinatra was a mutual friend of Giancana and Kennedy.