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Why Frank Sinatra Was Banned From The White House, Despite Being Close Friends With The President

Frank Sinatra; John F. Kennedy: have there ever been bigger icons of American culture? Though these two powerful men came from very different backgrounds, the pair maintained a close friendship and working relationship. That is until the F.B.I. got involved, however – and the agency’s shocking discovery meant the two would never be on speaking terms again.

Like any great story involving Ol’ Blue Eyes, Sinatra and Kennedy’s story could only have started in one place: Las Vegas. It was here while performing with the Rat Pack that the “My Way” singer met the politician’s sister, Pat Kennedy Lawford, in the 1950s. And it was through her that the two began an – almost – inseparable friendship.

At this point in his political career, Kennedy was at a kind of slump. Having been elected to the Senate in 1952, the politician was growing fatigued with only being able to oversee events in his native Massachusetts. What he wanted was a bigger platform: a presidential platform. But to get there, he needed all the help he could get.

Befriending Sinatra, then, was a godsend for Kennedy’s career. In the 1950s, the crooner was hitting a new high and finding a new audience beyond the bobby soxers of his early days. Besides recording some of his most acclaimed music this decade, the singer had also gained a new fanbase through a successful film career.

Plus there was the fact the crooner was on Kennedy’s side politically. Born to a mother who served as a Democratic Party committeewoman, Sinatra learned about politics at an early age. As quoted by Sinatra.com’s Steve Pond in 2011, Sinatra once said, “I just think it is the duty of every American citizen to take part in political races and vote.”