THE MOB'S CROONER
Kennedy, Sinatra and the Mafia, review: a compelling tale of a very glitzy bromance

Anita Singh
Sat, 4 November 2023 

John F Kennedy and Frank Sinatra attend a Democratic Committee dinner in Los Angeles in 1960 - Benjamin E 'Gene' Forte/Getty Images/CNP

“The Rat Pack was the Mount Rushmore of men having fun,” someone said at the beginning of Kennedy, Sinatra and the Mafia (Channel 4), which is the sort of quote that gets my attention. Mind you, it’s not difficult to be seduced by this story, which takes us from the tenements of Hoboken to the glamour of Las Vegas and Palm Springs.

Despite the title, it is more Frank Sinatra’s story, with John F Kennedy playing second fiddle. It wasn’t that way in real life. “Sinatra, all his life, could never totally glory in his own genius because he always saw himself as lesser than, and Jack Kennedy was class incarnate. Sinatra was helplessly and hopelessly and pitifully drawn towards what he considered ‘class’ because he didn’t think he had any, and Jack Kennedy was the whole package.” That’s the opinion of James Kaplan, a Sinatra biographer and one of many engaging contributors to this lively history.

To understand Sinatra’s mindset, the film documented his humble roots and a rise aided at almost every step by the mobsters whom he idolised from childhood. When he suffered a career slump in the early 1950s, it was the Mafia who stepped in, offering him gigs at their clubs. On the up again, he was introduced to Kennedy, then a rising political star. A friendship developed which benefited both men – proximity to power for Sinatra, access to showbusiness and beautiful women for Kennedy – but Sinatra felt genuine affection, it was suggested here, whereas for Kennedy it was a means to an end.

Sinatra and the Mob helped to get Kennedy into the White House, but there the relationship cooled. Told that he had to call off a planned stay at Sinatra’s compound in Palm Springs – FBI director J Edgar Hoover had caught wind of a love triangle involving the president, his mistress and Mob boss Sam Giancana – Kennedy went to stay at Bing Crosby’s house instead. Sinatra, who had gone to great lengths to ready his home for the presidential visit, felt so humiliated that he smashed up the newly installed helicopter pad with a sledgehammer.

Sometimes the commentary strayed from fact to what feels like fiction – did Sinatra and Kennedy really experience their first meeting as a “thunderbolt”, as Kaplan suggests? Does the Mob focus skew the emphasis, as when biographer Robbyn Swan claimed that the star’s career came to a halt “because the world began to notice that he was associated with organised crime” and no other reasons? It’s difficult to know the answer to these questions without doing more research. But it’s the sign of a decent documentary that it leaves you wanting to go and find out more.