Politics overlaps with showbiz and organised crime much more than it ought to, but the similarities are undeniable. Each profession involves gaining and wielding at least two of the holy triptych of fame, money and power.
Kennedy, Sinatra and the Mafia rattles through the scarcely believable tale of how the US president, the world’s favourite singer and some particularly nasty gangsters helped each other to succeed in the rotten chaos of the US after the second world war. Of course, it ends tragically for more than one of the players. John F Kennedy is assassinated, but Frank Sinatra doesn’t get off scot-free. He had fame and money, but when he mixed it with people who had power, they crushed him.
The programme does nothing big or clever with its format, alternating between talking heads and archive footage (although even bog-standard celluloid showing New York and Las Vegas in the 40s, 50s and early 60s is something you can’t see too often). And it needn’t: the twisting, steadily intensifying story is a corker.
It begins with Kennedy and Sinatra’s upbringings. Kennedy was groomed for high office from birth, the son of a man who had made his fortune from stock market manipulation and bootlegging. The second exploit had brought the family into contact with the mafia.
Sinatra emerged from the scrappy immigrant enclave of Hoboken, New Jersey, where his parents ran a bar called Marty O’Brien’s, or MOB for short. Latching on to his singing talent as his ticket out, the young Sinatra established himself by singing in clubs owned by the mafia. By the time he broke through by singing with the bandleader Tommy Dorsey, discovering that Dorsey had tied him into an extortionate long-term contract was not a problem; Sinatra knew a guy who was happy to visit Dorsey to persuade him to reconsider.
In the early 50s, Kennedy was continuing his ascent via election to the Senate, but Sinatra was struggling to revive a career that had stalled in part because the public had got wind of his association with organised crime. He leaned on the mafia to help him back up and was allowed to play half-empty gigs in their clubs. Was the shady influence of the mob in Hollywood the reason for Sinatra landing a surprising comeback role in 1953’s From Here to Eternity? This documentary is having far too much fun to countenance any more prosaic explanations. Certainly, the mafia took a great interest in Las Vegas, with the city as we know it – with the churn of punters necessary to make a mob-financed expansion viable – emerging only after Sinatra had taken residence there and formed the Rat Pack.
Some details, such as how Kennedy’s Roman Catholicism affected his electoral appeal, are mentioned briefly then tossed aside as the programme gallops shamelessly towards the good stuff: the singer and the politician interacting directly. Sinatra welcomed Kennedy, a pathological philanderer, into an intoxicatingly cool world of exclusive parties and beautiful women. There is a sinful thrill in looking at the photographs of these two impossibly famous men from two supposedly separate worlds, palling around on club banquettes, in a whiskey-and-cigarettes fug, apparently invincible.
Sinatra, dizzied by this proximity to power, was fully on board with Kennedy’s presidential run in 1960, not just releasing an awkward new version of his hit High Hopes (“K-E-double-N-E-D-Y, Jack’s the nation’s favourite guy”), but working the phones, raising campaign funds and helping to secure the support of the mafia, chiefly the notoriously unstable Chicago Outfit boss Sam Giancana. The mafia controlled the unions, whose members tended to vote as a bloc; in return for helping Kennedy to win, mobsters were led to believe that the new administration would go easy on them.
But when Kennedy prevailed, it soon became clear exactly where in the food chain the mafia sat. Bobby Kennedy was appointed attorney general and set about bringing down the mob, shattering the informal agreement it believed it had brokered. Sinatra, who had thought he was a gangster for life, discovered that he was one of them only for as long as he was useful.
What about his old pal Jack, the guy who had partied with him in Vegas and was now the president? Kennedy didn’t need Sinatra’s friendship any more. In 1962, with the FBI chief, J Edgar Hoover, on the president’s tail, Kennedy’s scheduled stay at Sinatra’s mansion in California – a visit for which the singer had proudly spent much time and money preparing – was cancelled.
The humiliated Sinatra was left with such deep-seated resentment and insecurity that he became a Republican. Kennedy, meanwhile, was shot dead a year later. The film is happy to let us assume that it was a mafia hit. It is an apposite end to an exhilaratingly grubby fable.
• Kennedy, Sinatra and the Mafia was on Channel 4 and is available to stream
