Frank Sinatra and John F. Kennedy admired each other greatly. So much so, Sinatra produced a JFK song
John F. Kennedy lived a gilded life, replete with celebrities, but his friendship with Frank Sinatra was perhaps the most curious of them all.
Kennedy had a deep respect for the singer, and Sinatra venerated him in return.
“There was a joke at the time that ended up having a lot of truth to it, that in a way, Kennedy wanted to be Sinatra and Sinatra wanted to be Kennedy,” said Steven Watts, who wrote the book, “JFK and the Masculine Mystique: Sex and Power on the New Frontier.”
Frank Sinatra introduces JFK to Marilyn Monroe
The pair were both womanizers and, whilst Sinatra naturally respected Kennedy due to the power he exuded as Commander-in-Chief, the President was also drawn to the singer who epitomized more than anyone else (except Marilyn Monroe) the glamour of Hollywood.
“Kennedy was everything the Rat Pack envisioned themselves to be, and vice versa,” Watts writes in his book.
“Sinatra took the bait hard. Helping Kennedy succeed would provide a kind of legitimacy that even Hollywood could never bestow.” Naturally, it was Sinatra who first introduced Kennedy to Monroe, one night after a concert in Las Vegas whilst JFK was still a candidate.
After Kennedy stopped by his home, he had a sign that read “JFK Slept Here” hung in the bedroom and when Kennedy clinched the nomination at the Los Angeles Convention the Rat Pack temporarily transformed into the “Jack Pack.”
JFK's campaign song produced by Frank Sinatra
Such was the extent of which Sinatra and the newly-dubbed "Jack Pack" supported Kennedy for president, they even reworked the song "High Hopes" into a JFK campaign song.
Mafia links causes friction in Kennedy/Sinatra friendship
And yet, after Kennedy reached the pinnacle of power relations between the storied pair cooled.
Sinatra was unable to shake off rumors of a connection to the mob and JFK was loathe to do anything that could taint him politically with that toxic stench.
RFK, as Attorney-General, was particularly wary of the singer and advised his older brother to keep his distance.
For his part, Sinatra was left bitterly disappointed after Kennedy opted not to stay with him on a trip to California in 1962. He’d spent a small fortune installing a helipad for Marine One but, despite that the President decided to stay with Bing Crosby instead.
But the grief caused by Kennedy’s premature death was profound. Like many Americans, Sinatra wept for days for his slain Commander-in-Chief.
A guiding light for America had been cut down and so, too, had a once deep and meaningful friendship.