The two had a relationship that went far beyond the White House
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This undated file photo shows actor and singer Fra
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John F. Kennedy hobnobbed with plenty of superstars during his presidency, but perhaps one of his most famous friendships was with Frank Sinatra and the Rat Pack. In the new book JFK and the Masculine Mystique: Sex and Power on the New Frontier, author Steven Watts takes a closer look at this relationship, and how the two men influenced ideas of masculinity in the Camelot era.

On the night before his inauguration, Kennedy took a moment to thank Sinatra for his work on his campaign, particularly for spearheading the night’s concert that featured big names like Ella Fitzgerald, Gene Kelly and Nat King Cole. Sinatra was said to have organized the show and even bought out Broadway theaters that night so performers could make their way to the stage in D.C. He performed himself — renditions of “That Old Black Magic” and “You Make Me Feel So Young” — and when he was in the audience, he sat in the presidential box, right next to Kennedy’s wife, Jacqueline.

“We’re indebted to a great friend — Frank Sinatra,” Kennedy said. “You cannot imagine the work he has done to make this show a success.”

Clearly, the incoming president had a great deal of respect for Ol’ Blue Eyes — and that adoration went both ways.

For starters, both had tons of power in their own rights, but lusted after the sort of influence the other held.

“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,” Watts says.

According to Watts, for Sinatra, that was the public approval and respect that Kennedy had earned in Washington, while Kennedy longed for the glitz and glamour of Sinatra’s life in Hollywood. The two also bonded over the pursuit of women, Watts wrote.

It was Sinatra who introduced Kennedy to Marilyn Monroe, among other celebrities, after Kennedy attended the Sands shows in Las Vegas in 1960 on a campaign break. According to Watts, it was after this introduction that Kennedy and Monroe began their relationship, even spending a night together during the Democratic National Convention. The morning after said night, Monroe was “making knowing comments about the time she had just spent with the nominee of the party,” Watts shares, adding, “Kennedy was everything the Rat Pack envisioned themselves to be, and vice versa.”

Sinatra would invite Kennedy to his shows in Las Vegas, bringing him on stage and then back to their hotel suites for post-concert parties. On the campaign trail, Kennedy extended a stop in California so he could spend two nights at Sinatra’s Palm Springs home. For Sinatra especially, the respect an association with Kennedy could provide was unmatched.

“Sinatra took the bait hard,” the book reads. “Helping Kennedy succeed would provide a kind of legitimacy that even Hollywood could never bestow.”

He also liked to boast about his association with Kennedy, Watts says, even going as far to label the room in his house where Kennedy had slept with a sign that read “JFK Slept Here.”

At the 1960 Democratic Convention, fittingly held in Los Angeles, the Rat Pack morphed into the “Jack Pack.” The night Kennedy was nominated, Sinatra was watching nearby at the Marion Davies mansion in Beverly Hills, alongside Joe and Bobby Kennedy and brother-in-law Peter Lawford.

When Kennedy’s nomination was announced, Watts writes that Sinatra was “exuberant.” He said: “We’re on our way to the White House!”

However, their friendship wasn’t built to last. After Kennedy had been in the White House for about a year-and-a-half, their warm relations started to fizzle. Sinatra’s rumored connections to the mob led those in the White House to start to view him as a “political liability,” Watts says. Bobby Kennedy, in particular, started to discourage the relationship. Kennedy began to distance himself from Sinatra, and things came to a head after Kennedy decided to stay with Bing Crosby, rather than Sinatra, during a visit to Palm Springs in 1962. This last-minute change came after Sinatra had spent a significant sum in preparation for Kennedy’s visit, creating a helicopter landing pad and accommodations for the Secret Service, according to Watts.

Though things turned sour between the two, that didn’t stop Sinatra’s heartbreak at Kennedy’s assassination: He reportedly cried for days after his death, according to his daughter Nancy.

By 1970, Sinatra had swung to the right and was endorsing Ronald Reagan for governor of California.