What would the world say if the President hooked up with Hollywood’s top actress after she dated the most famous singer in the biz? Well, that actually happened, and while the racy details of the relationships between Frank Sinatra and his Rat Pack, Marilyn Monroe, and the President of the United States, John F. Kennedy, lay beneath the surface, the group often flaunted it without a care in the world.

“It’s an amazing moment,” said Author Shawn Levy, who’s written two books about the Rat Pack — The Rat Pack, and The Rat Pack: Uncensored. “Where show biz, politics, organized crime, and for lack of another word, ‘adult sensations,’ were all at a very high level in one sort of vessel, and out in the open!”

Las Vegas was their ‘stomping ground’

The “vessel” Levy is referring to carrying the whole bunch and was a haven for gangsters created by the mafia — Las Vegas.

“[The Rat Pack] carried on in plain sight,” added Levy. “They were the most popular entertainers in the world and running around with a presidential candidate and the Chicago mob. It was kind of crazy.” The gathering of the “Summit” in 1960, as the Rat Pack preferred to be called, culminated in the making of the box office smash, Ocean’s 11. “Ocean’s 11 was like a commercial for Vegas,” explains Levy. “[The Rat Pack] saved Las Vegas — they made Las Vegas with that movie.”

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Getty Images – From left to right: Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, Joey Bishop – posed outside Sands Casino, Las Vegas, 1960 at “Summit At Sands.” All five men starred in Ocean’s 11.

One month after announcing his candidacy for president, at a Rat Pack show at the Sands Casino in Vegas, Sinatra looked to the crowd between songs and singled out one individual seated next to the state. A spotlight revealed the man, and Sinatra said, “I’d like to introduce the next president of the United States, John Kennedy!”

The two had cemented their relationship years earlier, as Kennedy’s younger sister Pat married fellow Rat Packer, Peter Lawford. Sinatra and Kennedy got along famously, with a special bond that was difficult to fully appreciate. “They were men cut from the same cloth — they always got what they wanted,” Levy explained. “There were very few people at this altitude, and they saw one another in each other… it was a special relationship.”

By 1960 each man was doing favors for the other. When a book called The Manchurian Candidate was published in April 1957, Sinatra wanted desperately to make a movie about it. The idea fell flat as Hollywood producers were skeptical about making a movie about a presidential assassination. Ironically, Kennedy was a fan of the book, and had friends on the board of United Artists, and used his influence to convince the studio to make the movie.

The relationship worked both ways, as it’s largely understood that Sinatra used his connections with the mafia in Chicago to deliver the vote there. “In Chicago, they used to say, ‘vote early, and vote often,’” said Levy. “But it’s largely understood that because the Eisenhower administration was starting to crack down on organized crime, Kennedy would loosen up on that in exchange for the mafia delivering Illinois.” 

Enter the beautiful blonde

It was a glorious time for these men of power and prestige, and yet there was one more actor with equal clout that had a part to play — Marilyn Monroe. Monroe was a common thread between the bunch, as Sinatra and she had previously dated, was a close friend of Pat Kennedy and Peter Lawford, and of course, rumors about her and Kennedy are especially steamy. 

“When you look at who Monroe was,” said Levy. “It makes sense that she married the greatest playwright (Arthur Miller), greatest Baseball player (Joe Dimaggio), dated the greatest showman (Frank Sinatra), and slept with the president of the United States (John Kennedy). She carved her own way in the world, and she was gonna do whatever she wanted.”

By early 1961, Kennedy had been elected in the closest election in American history at the time, and for his pre-inauguration gala, Sinatra delivered a number of his star friends to perform, which included Gene Kelly, Nat King Cole, Milton Berle, and Ella Fitzgerald. Sinatra himself took turns performing and keeping the president-elect company in his box.

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Getty Images – American actor and singer Frank Sinatra (left) with US President John F. Kennedy (right) at Kennedy’s inaugural ball at the Mayflower Hotel in Washington D.C, 20th January 1961.

Their relationship began to take a turn when Kennedy appointed his younger brother Robert to the post of Attorney General. Robert had already done much to disrupt organized crimes’ influence over labor unions, and now he set his sights on the mafia itself. Then, in March 1962 everything unraveled prior to a scheduled visit by Kennedy to Sinatra’s Palm Springs home. 

Stories conflict, but what is known is that either Robert Kennedy or FBI Director, J. Edgar Hoover, interceded to dissuade Kennedy from staying at Sinatra’s house. On its surface, it was a bad look for the president, especially since Chicago Mob boss Sam Giancana, had been known to have previously stayed at Sinatra’s house (Giancana and Kennedy were also having an affair with the same woman, Judith Campbell).

The snub heard ’round the world

Kennedy was forced to cancel, and Lawford was given the dubious task of delivering the news to Sinatra. Sinatra had recently completed construction of a helipad on his grounds to accommodate the president’s helicopter, and when Lawford told him he got so angry that he proceeded to smash it to bits with a sledgehammer. He then banished Lawford from the Rat Pack for good and even had him replaced by Bing Crosby in his upcoming movie.

It’s interesting that Crosby got the nod because instead of Kennedy going to Sinatra’s house on that night in March 1962, he went to Crosby’s home. There’s no disputing it, as that fateful night was when Kennedy and Monroe actually did meet. It’s not a leap to think that the two had thought about each other before, as they had powerful and promiscuous sexual appetites and sought the most prominent of partners.

People close to Monroe have reported that that was the night the two were intimate together, culminating in probably the most notorious affair in American history. While our imaginations run wild about a steamy night it probably didn’t mean much to them other than another notch on their belts. They did, however, have one last meeting, and it… was… hot!

On the night of May 19, 1962, in front of a packed house in Madison Square Garden, Monroe took to the stage to sing to the man of the hour, John Kennedy. “Happy birthdayyyy, Mr. Pres-i-dent,” she sang in a near-pornographic tone. After then singing a rendition of “Thanks for the Memory,” Kennedy took to the stage and said that he could “retire after having had ‘Happy Birthday’ sung to me in such a sweet, wholesome way.”

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During a party at the home of movie executive Arthur Krim, American actress Marilyn Monroe stands between Robert Kennedy (left) and John F. Kennedy, New York, New York, May 19, 1962. The party followed a democratic fundraiser at Madison Square Garden honoring John F. Kennedy’s birthday where Monroe famously sang “Happy Birthday.’

After the show, the two met at the movie executive’s home with others in attendance, and that’s where the only known photo of the two exists. Monroe would die of a drug overdose just three months later, and evidently, her last phone call was to Lawford. Lawford’s career was railroaded by events and later divorced Pat. Kennedy was killed the next year, and Sinatra wept for days at the news, though he wasn’t invited to the funeral. As for the Rat Pack, 1964 was the death knell for their reign at the top, thanks to a long-haired group of rockers named the Beatles and their appearance on the Ed Sullivan show in February 1964.

“After the rise of Kennedy, and rise of hippie and teen culture that stuck around for good, and was never to be rebuffed again,” explained Levy. “Men in nice suits rubbing elbows with mobsters, womanizing, and smoking cigarettes while drinking liquor seemed old.” Never again would, “A” listers, the mafia, and politicians share such an intimate relationship, leaving us gawking at the past, while the sizzling stories fill our wild imaginations.