Frank Sinatra ‘facilitated' John F Kennedy's other life, but couldn't outrun his mafia connections: The rise and ruin of their unlikely friendship

Indian Express

16-05-2025

The month of May marks the 27th death anniversary of the legendary Italian-American crooner Frank Sinatra who passed away on May 14, 1998, due to a heart attack in Los Angeles. Apart from his stellar career as a singer and the fact that his music still finds space in big-budget movies and also your dad's playlist titled 'This Is Real Music', Sinatra had a colourful personal life, to say the least. He had FBI files dedicated to his relationship with the mob, that one character from The Godfather which was 'definitely not based on him', and, of course, his confusing relationship with the former US president John F. Kennedy.
Sinatra and Kennedy had very different upbringings; one broke through the proverbial glass ceiling, while for the other that limit did not necessarily exist. Singing in mafia-controlled bars and venues, the 'Fly Me to the Moon' singer made a lot of friends on his way to fame, friends who weren't exactly on the right side of the law and helped Fontane, scratch that, Sinatra break through contracts, land roles and flourish in a whirlwind of an industry. After Sinatra rose through the fulminations of his beguiling life and stalling career with the film From Here to Eternity (1953), he made friends with an upcoming politician from Massachusetts named Kennedy. It almost feels perverse and impossible when you look at their pictures together from the early years of their association. Two men smiling through cigarette smoke, mixed with an air of nonchalance and greatness, while the world around them tried to chisel their way into the truth behind this relationship. Along with Sinatra, Kennedy was chummy with the entire 'Rat Pack', which consisted of singer Dean Martin and Sammy Davis Jr, along with actors Angie Dickinson and Peter Lawford.
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Sinatra was almost the facilitator of Kennedy's 'other life', as he introduced him to a different world, which was filled with vices in expensive glasses and escape routes dressed as beautiful women. He was allegedly the man who was responsible for Kennedy's association with Marilyn Monroe, and he did it presumably during the time when the actor was renting the guest house of Sinatra's home in Los Angeles. Apart from the booze and the philandering, Sinatra incorporated himself into the politician's professional front as well; he fully supported him in his campaign for presidency, writing songs, raising funds and even convincing mob bosses to influence the vote of the workers' union. Everyone was aware that the union voted as one unit, and them going over to Kennedy's side would go a long way in his battle against Richard Nixon. Sinatra seemed to cut a deal with the Chicago boss, Sam 'Mooney' Giancana, who probably helped with the union in the hopes that the Kennedy administration would take things easy on them.
As Kennedy emerged victorious over Nixon, Sinatra grew in confidence just by association. He had always been boastful about his connections, and in Kennedy he saw legitimacy, invincibility. But Sinatra's dreams of being in cahoots with the highest office in the country were soon shattered as John's brother Robert F Kennedy (also known as Bobby) took over the office of Attorney General and began his onslaught on organised crime. Amidst all this, Sinatra offered to host John during his visit to Los Angeles, but now with Kennedy's new office and credentials, some arrangements had to be made. The singer got in touch with the Secret Service and made several modifications to his infamous house, including adding a helicopter pad. But just like a Bollywood wedding gone wrong, Kennedy's first visit back would be the last verse in the glorious and controversial friendship. While the president was in transit to Los Angeles, Kennedy was informed by his brother that the FBI had just released documents regarding Sinatra's ties with the mob, and the evidence in those files was damning enough for the Attorney General. More than that, the then FBI director J. Edgar Hoover was perched up on Kennedy's head and had more files on their parties than Sinatra's entire discography.
Ultimately the trip was cancelled, and Kennedy chose to go to singer Bing Crosby's estate instead. An enraged Sinatra felt betrayed and ransacked his newly refurbished home. His hopes of outrunning his mafia connections and changing the people's perception about him went down the drain as the citizens of America seemed to forget everything their Roman Catholic golden boy did before entering the White House on a rather questionable steed. The close friends did not maintain any contact with each other, and just a year later, Kennedy was assassinated.
Their rise to the top was meteoric, and the duo lived like rockstars before it was even a thing, including every single mistake the upcoming generation of rockstars would make. Intoxicated dreams, dilapidated morals and fractured relationships – maybe Sinatra got back exactly what he sold at those lavish parties at his house. Even though we will never know the extent of what all transpired between the two personalities, it can be argued that both of them were never actually friends. It was a relationship built on favours and promises, and one decided to step off before the other could cash in, and that, people, was the straw that broke the singing camel's back.