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The story of Kennedy, Sinatra and the Mafia is one of corruption and betrayal that is difficult to believe.


There is a significant overlap between politics, showbiz, and organized crime, which is concerning. The similarities between these fields are undeniable. Both involve acquiring and utilizing at least two of the three highly coveted aspects: fame, wealth, and influence.

The story of Kennedy, Sinatra, and the Mafia delves into the incredible narrative of how these three unlikely allies navigated the tumultuous landscape of post-World War II America. Despite their initial successes, their collaboration ultimately ends in tragedy for multiple parties. While JFK is infamously assassinated, Sinatra’s fame and fortune cannot protect him when he becomes entangled with powerful and dangerous individuals.

The show does not utilize its format in a significant or intelligent manner, switching between interviews and historical footage (although the use of basic film featuring New York and Las Vegas from the 1940s to the early 1960s is a rarity). However, this is unnecessary as the plot, which becomes increasingly complex, is exceptional.

The starting point is the upbringing of Kennedy and Sinatra. Kennedy was prepared for a prestigious political career since birth, being the son of a man who had gained his wealth through manipulating the stock market and engaging in bootlegging. The latter activity had led to connections with the mafia.

Sinatra came from the tough immigrant community of Hoboken, New Jersey, where his parents owned a bar known as Marty O’Brien’s, or MOB for short. He used his singing abilities as a means of escape and gained recognition by performing in mafia-owned clubs. When he landed his big break singing with bandleader Tommy Dorsey, he didn’t worry about being tied into a restrictive contract because he had connections who could convince Dorsey to change his mind.

During the early 1950s, Kennedy rose to the Senate through elections, while Sinatra struggled to revive his career. His public association with organized crime hindered his success. To make a comeback, he relied on the mafia’s assistance and performed half-empty shows in their clubs. Was Sinatra’s surprising role in 1953’s From Here to Eternity due to the mob’s influence in Hollywood? This lively documentary avoids dull explanations and explores the possibility. The mafia showed a great interest in Las Vegas, which only became a bustling city with the necessary influx of gamblers after Sinatra took up residence and formed the Rat Pack.

Certain information, like the impact of Kennedy’s Catholic faith on his popularity in elections, is briefly touched upon before being disregarded as the program rushes towards the more enticing content: the direct interaction between the singer and politician. Sinatra introduced Kennedy, who was known for his constant infidelity, to a glamorous lifestyle filled with lavish parties and attractive women. It’s almost scandalous to see photos of these two incredibly famous men from seemingly different worlds, lounging on club couches, surrounded by alcohol and smoke, appearing untouchable.

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Sinatra, overwhelmed by the close proximity to authority, enthusiastically supported Kennedy’s bid for presidency in 1960. He not only released a clumsy reworking of his popular song High Hopes (“K-E-double-N-E-D-Y, Jack’s the most beloved man in the nation”), but also actively made phone calls, raised campaign funds, and secured the backing of the mafia, particularly from the notoriously unstable leader of the Chicago Outfit, Sam Giancana. The mafia held influence over unions, whose members typically voted together, and were promised leniency by the new administration in exchange for their help in Kennedy’s victory.

However, once Kennedy emerged victorious, it became evident which level of power the mafia occupied. With Bobby Kennedy as attorney general, the mafia’s downfall was imminent as he shattered their perceived agreement. Sinatra, who had assumed he was a lifelong gangster, realized he was only valued as long as he served their purposes.

Could you tell me about Jack, his former friend who had previously joined him in partying in Las Vegas and is now the current president? Kennedy no longer required Sinatra’s companionship. In 1962, with the FBI director, J Edgar Hoover, closely monitoring the president, Kennedy’s planned visit to Sinatra’s California mansion – for which the singer had eagerly spent a significant amount of time and money preparing – was ultimately called off.

Sinatra, feeling humiliated, harbored intense resentment and insecurity which led him to become a Republican. Sadly, Kennedy was assassinated just a year later. The movie implies that it was a mafia-orchestrated murder. This is a fitting conclusion to a thrillingly gritty tale.

Source: theguardian.com