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Dark Details About Frank Sinatra That Everyone Ignores

When people think about Frank Sinatra they will no doubt remember him as a singer who changed the face of music in the twentieth century. He was an inspiration to so many other musicians who would try their best to capture his sparkle.

But the Chairman of the Board who was the singer of such classics as “My Way” “New York, New York” and “I’ve Got You Under My Skin” had a dark history too. Let’s take a look at some of those dark details about Frank Sinatra that everyone ignores.

Frank Sinatra Nearly Didn’t Come to Be

Let’s start at the beginning of Frank’s life. Francis Albert Sinatra was born in the kitchen of his parents’ apartment in Hoboken, New Jersey. But he nearly declared dead on arrival.

Born at a staggering 13.5 pounds Frank needed to pulled from the womb using forceps.

Frank thought to be dead because he was blue and wasn’t breathing, however, while the doctor was treating Frank’s mother, his grandmother ran him under cold water and slapped him on the back which revived him.

His birth would leave a scar on Frank for the rest of his life. The forceps that used during Frank’s birth would leave him facial scarring on the left-hand side of his face, neck, and jaw. This would earn him the nickname “Scarface.” During his career, Frank would hide his facial scars with heavy makeup.

Frank not actually supposed to called Frank. He meant to be named “Martin” after his father, but a misunderstanding at his christening meant that he was baptized after his godfather, Frank Garrick. The name stuck, and the rest, as they say, is history.

Frank was the only child of Italian immigrants. His father “Marty” owned a tavern and was a part-time prizefighter while his mother, Dolly was a midwife who used to help women have illegal abortions. Dolly also involved in local politics.

But with his parents leading such busy lives, they often not at home and young Frank often left on his own or with his grandmother. Frank longed for a sister or brother. All the other kids in Frank’s mostly Italian neighborhood would come from large families.

Frank Was a Man Who Driven By Ambition

Success didn’t come easy to Frank, and his parents weren’t all that supportive of his becoming a professional singer. Marty Sinatra wanted his son to get a steady job. Dolly, on the other hand, eventually came around to the idea and would help him out by buying him sheet music and sound equipment as well as using her political sway to hook Frank up with some gigs. It was Dolly that would get Frank a spot in a local singing group, the Hoboken Four, which would put him on the path to stardom.

It didn’t take long for it to become obvious that Frank was the only one with real ambition in the Hoboken Four. Once the group broke up, Frank would wait tables between gigs with local dance bands. His biggest break would come in 1940 when famous bandleader Tommy Dorsey offered him a contract. By 1942, Sinatra’s fame would eclipse Dorsey’s and Frank would look to go solo.

Sinatra’s biggest inspiration was Bing Crosby. Crosby’s style would be a huge influence on the laid-back singing style that Frank would become famous for. Frank met Bing briefly in 1935 at a club, but they wouldn’t meet again for ten years- by which time Sinatra was a huge star.

Sinatra’s fame was on the rise, but Bing was still a hit in the 40s. But while bing had fans, they weren’t the shrieking teenage girls that made up Frank’s fanbase. Crosby would take Sinatra’s rise in popularity in his stride, joking that Sinatra was the kind of singer that would come around once in a lifetime, “but what did it have to be my lifetime?”

Following this quip, a rivalry was born. The two signers would often trade verbal blows with each other. Of course, the rivalry played up to get more exposure. Later in their careers, the crooners would duet and star in movies like High Society.

Sinatra Had Strong Mob Connections

Although it was always denied, Sinatra did have mob links. Sinatra said to be friendly with Chicago mob boss Sam Giancana. He would regularly seen socializing with the Fischetti Brothers who ran illegal gambling rings, and he would party with Detroit mobsters Anthony and Vito Giacalone. If Frank ever needed out of a contract or had insulted, someone somewhere would get a visit from some of Frank’s friends.

The FBI certainly kept an eye on Sinatra’s friendships. Although he never charged with anything, his associations laid bare when Frank Sinatra’s full FBI record released after his death.

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Frank Sinatra Was a Friend of JFK

Sinatra was a keen supporter of the Democrats. Especially JFK. It isn’t known how the two men actually met, however, Kennedy’s sister Pat married to Rat Pack member Peter Lawford.

When Kennedy announced that he was standing for president, Sinatra used his fame to endorse JFK. He lent JFK’s aides his private jet, allowed the song “High Hopes” to become the theme song for Kennedy’s campaign, held donor dinners, and appeared on political radio ads. It also speculated that Joseph Kennedy wanted Sinatra to use his sway with the mob and unions to help bring his son extra votes.

Soon after the election, the Kennedy-Sinatra love-in would turn sour. Wiretaps revealed that Sinatra having an affair with Kennedy’s married sister Pat. The recordings made it clear that Frank was using Pat to sway her brothers and steer the government away from his mob friend’s activities.

Sinatra Known For His Bad Temper

He may have been the master of the romantic song, but Frank Sinatra had a violent temper. It is said that during a show in Hong King a missed lighting cue led to him trashing his dressing room and his hotel suite, smashing antiques in the process. Another rage attack saw Sinatra driving a golf cart through the window of a shopping mall.

Sinatra also had a habit of bullying venue employees and less famous entertainers. Anyone he didn’t like would beaten up by his mob friends. Stand-up comedians seemed to get it worse than anyone else. Shecky Greene, a comic, once angered Sinatra and mobbed by some of Frank’s friends. Jackie Mason joked about the age gap between Frank and his 21-year-old wife Mia Farrow. Mason refused to stop telling jokes and shots fired in his hotel room. Later, he had his nose and cheekbone broken.

Frank Sinatra Was Married Four Times

Married four times, numerous accounts reveal that Sinatra was unfaithful and controlling. His first wife was Nancy Barbato. They had three children: Nancy, Frank, Jr, and Tina. Sinatra’s infidelity caused the marriage to end. Shortly after the divorce was finalized, Sinatra remarried. This time to the actress Ava Gardner. The couple would have explosive fights in public, both had affairs, and both drank heavily. They’d eventually divorce after six years.

With a thirty-year age gap, Sinatra would go on to marry Mia Farrow. Sinatra would demand that Farrow give up acting to which Farrow would agree. Eventually, she would get fed up of the life of a housewife and took the lead role in Rosemary’s Baby. Sinatra gave in and arranged a small role in his latest movie for after she was done. Filming of Rosemary’s Baby ran over schedule and Sinatra demanded she quit. She wouldn’t, so Sinantra filed for divorce.

Finally, Sinatra would marry Barbara Marx with whom he had a “Jekyll and Hyde” relationship, showering her with affection and gifts one minute and screaming at her and threatening her the next. The couple remained marriage until Sinatra’s death.

Sinatra Had Depression

Sinatra was plagued by the black dog on his shoulder. Throughout his career he would have depressive bouts and may have even had bipolar disorder. On several occasions Frank tried to commit suicide, once turning the gas on and putting his head in the oven, and another time with a gun.

There is a story that Ava Gardner tried to wrestle the gun away from him and the gun went off. Luckily the bullet missed the both of them.

Sinatra had a deep longing for love and companionship but didn’t seem to be able to maintain a health relationship and so was always searching for something.

Frank Jr. Got Kidnapped

Frank Sinatra Jr. followed in his father’s footsteps and wanted to become a singer. His career was on the rise when, in 1963, at the age of 19, he was performing a gig in Lake Tahoe. He was in his dressing room with a friend when someone claiming to have a delivery knocked on the door. Opening the door, Frank Jr was tied up and blindfolded and forced out into a waiting car.

The friend got away and notified the police. The three kidnappers, John Irwin, Joe Amsler, and Barry Keenan demanded a ransom of $240,000 from Frank senior. Frank paid the ransom with the help of the FBI. Keenan and Amsler took the suitcase, but Irwin got nervous and freed Frank Jr. The FBI caught the three kidnappers and recovered the money. The kidnapper’s defense was that they had been put up to it by Frank Jr, claiming that it was all a publicity stunt. The FBI evidence went against this point and the three kidnappers were found guilty.

Frank Sinatra’s Died Aged 82

Frank Sinatra died aged 82, on May 14th 1998. His wife Barbara and three children were all at his bedside.

Frank’s final few years had been filled with health problems, such as heart and breathing problems, pneumonia, bladder cancer, and dementia. His final words were “I’m losing.” He was buried with a pack of Camel cigarettes, a bottle of Jack Daniels, a lighter, and a dollar in dimes.

So, was Frank Sinatra a musical genius who should be looked on favorably, or was he a problematic and complicated character? Let us know what you think of him in the comments. And, i you’ve enjoyed this video, please like it and share it.

Written by Alex Carson

Alex Carson is a seasoned writer and cultural historian with a passion for the vibrant and transformative decades of the 1960s and 1970s. With a background in journalism and a deep love for music, film, and politics, Alex brings a unique perspective to the ever-evolving landscape of entertainment.

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