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Digital Subscriptions > History Revealed > June 2016 > JFK, Sinatra and the Mob

JFK, Sinatra and the Mob

How did the leader of the Rat Pack, a man with rumoured Mafia connections, help JFK reach the White House? Nige Tassell tells a story of corruption, greed and perhaps even murder…
THICK AS THIEVES Frank Sinatra and his pal John F Kennedy are all smiles at the Sands Hotel in Las Vegas in February 1960. But how long will the good times last?
GETTY X2

Frank Sinatra was angry. Livid. Livid enough to take an axe to the fixtures and fittings of his Palm Springs home. Livid enough to storm out of the house, brandishing a sledgehammer. Livid enough to rain blows down upon the heli-pad he had recently had modified, shards of concrete flying off in all directions.

John F Kennedy was the reason for his anger. The President – his close friend – had just cancelled a March 1962 visit to Sinatra’s California residence, the desert retreat that the singer had recently upgraded, at no small cost, in advance of the presidential arrival. But this was no casual change of plans.This was a snub to Sinatra, to his standing, to his reputation. It was a loss of face that signalled the end of both their friendship and their political allegiance.

The fracture was terminal because Kennedy’s trip still went ahead. He flew out to Palm Springs as planned, but stayed with a musical rival of Sinatra’s instead – his near-neighbour Bing Crosby. What made things even worse for the lifelong, dyed-in-the-wool Democrat was that Crosby was a staunch Republican. The official explanation offered was that Crosby’s house provided a more secure base for the most powerful man on the planet. But Sinatra knew that was baloney.The real reason was that the White House didn’t want to be tainted by the singer’s close connections to some of organised crime’s biggest players.

A third party was used to deliver the message to Sinatra – Peter Lawford, one of his partners in the showbiz gang the Rat Pack who just happened to also be JFK’s brother-in-law. And, with that, the President severed all ties with Ol’ Blue Eyes – a man who may have been key to JFK’s ascendancy less than two years earlier. But the sidestepping of such potentially negative publicity was deemed to be worth the loss of friendship. Besides, the switch of venues had another advantage. Marilyn Monroe was allegedly keeping Kennedy’s bed warm round at Bing’s place.

It had all been so different. In the election year of 1960, Sinatra and the then-Senator had partied together, whether in the finest Las Vegas hotels or on the set of the Rat Pack film Ocean’s 11. The pair had stood shoulder-to-shoulder on campaign platforms. Sinatra had recorded a campaign song for the Democrat candidate. And, on the eve of JFK’s inauguration, the singer had organised and hosted a star-studded celebratory gala.

The pair made an irresistible combination – the politician and the entertainer, both with voter-friendly, matinee-idol looks. The bromance continued once Kennedy took office. “JFK was his friend,” Sinatra’s daughter Nancy later wrote. “For the patriotic American dreamer, this was the ultimate compliment: the President of the United States was his friend.”

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