Presidents' Playground: JFK's desert ties included mob entanglements, affairs and political repercussions
Bruce Fessier, The Desert Sun Bruce Fessier
With files about JFK's assassination released by Thursday, this offers a timely look at the Kennedy family’s dealings in the desert.
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Palm Springs Desert Sun
Editor's note: With almost 2,900 document files about the 1963 assassination of President John F. Kennedy released on order of President Trump on Thursday, this installation of “Presidents’ Playground” offers a timely look at the Kennedy family’s dealings in the desert.

John F. Kennedy made his first visit to the Coachella Valley as president of the United States while his wife, Jackie, was on a two-week goodwill tour of India and Pakistan. He had planned to see his White House predecessor, Indian Wells resident Dwight Eisenhower, ostensibly to discuss the aftermath of the Bay of Pigs Invasion of Cuba, which had failed so terribly 11 months earlier, in April 1961. But he also had a date to meet Marilyn Monroe, the most famous sex symbol in Hollywood.

Kennedy's original plan was to meet swinging pals like Frank Sinatra, Jimmy Van Heusen and brother-in-law actor Peter Lawford at a party in the mid-Coachella Valley, presumably at Sinatra's house. Kennedy's aides would give the press corps accommodations at the swank Riviera Hotel in Palm Springs. Then Marilyn and JFK would sneak away for their own private party.

Sinatra and Lawford had arranged dates for Kennedy before. One with Jerry Lewis’s former assistant, Judy Campbell, hadn’t worked out well. Sinatra and Chicago mob boss Sam Giancana were having affairs with her around the same time. And that was just a subplot in the Giancana storyline. JFK’s brother, Attorney General Robert F. Kennedy, was trying to arrest Giancana for racketeering. He didn't know Eisenhower’s CIA had given Giancana a contract to kill Fidel Castro and he probably didn't know Sinatra had asked Giancana to swing the presidential election for JFK. He also probably didn't know his own father had asked Sinatra to approach Giancana.

But JFK was too preoccupied to be concerned about public appearances. He'd been dreaming of a date with Marilyn since she was a calendar girl. When he was going in for a serious back surgery, complicated by his Addison’s disease, in 1954, he had hung a pinup photo of Marilyn on his hospital wall. Marilyn had personally given him her phone number at a New York dinner party arranged by Lawford and JFK didn't want to miss an opportunity for a liaison while Jackie was out of the country.

Personal interviews over the past two decades with FBI officials, Peter Lawford's last wife, Patricia Seaton Lawford Stewart, and dozens of Frank Sinatra family members, friends, biographers and employees help paint a representative picture of JFK's relationship with the Sinatra Rat Pack and the mob.

The Coachella Valley had been a place for Kennedy extra-marital affairs for decades.

Joseph "Joe" Kennedy, the ambassador to England’s Court of St. James when World War II broke out, consummated his transition from banker to Hollywood mogul at Palm Springs’ El Mirador Hotel in 1928. Gloria Swanson, the biggest silent female star of the 1920s, had approached Kennedy in New York about reorganizing her independent production company while he was in the process of merging his Film Booking Offices with the French-founded Pathé studio. Kennedy seduced Swanson and assigned her husband to Pathé's Paris office. When Kennedy came west to take over his new studio, Swanson met him at El Mirador. They had a high-profile affair for two years, often seen publicly with publisher William Randolph Hearst and his mistress, Marion Davies, who would one day own the Desert Inn and hire Van Heusen as its lounge pianist.

JFK often went on “girl-hunting” expeditions to Hollywood after emerging from World War II as a Navy hero. He romanced actress Gene Tierney and was drawn to Palm Springs by the star magnet force of the Racquet Club. He visited Sinatra at his homes on Alejo and Wonder Palms roads in the 1950s while serving as a Massachusetts senator. When Lawford married JFK’s sister, Pat, and joined Sinatra’s Rat Pack, JFK hung out with them so often, it was nicknamed “the Jack Pack.”

Sinatra was staying at New York’s Waldorf Hotel when Joe Kennedy made a fateful request.

“You and I know the same people, and you know the people I mean," said the old man, who had dealt with mobsters while securing liquor distributorships before the repeal of Prohibition. "I can't go to those people. It might come back at Jack. But you can. "

Sinatra agreed to meet Giancana in the desert, where Giancana liked to golf.

JFK could offer no quid pro quo, Sinatra insisted. But he needed to win West Virginia and Illinois to beat Richard Nixon for the presidency. Giancana shrugged. “It’s a couple phone calls,” he said. “And tell the old man I said hello."

Sinatra celebrated the election by producing a star-studded inaugural gala. But the Ambassador banned Sammy Davis Jr. from coming because he was a black Jew married to a white woman. It turned a schism between Joe and Sinatra into an open wound. Joe told the director of the telecast, future desert resident Bill Asher, “Edit everything about Sinatra out. I don’t want him in it.”

The show didn’t get on TV for several reasons, and Joe and Sinatra seemed to patch things up in Rancho Mirage. Joe spent two weeks at Davies’ Wonder Palms estate and attended Palm Springs’ bucolic Desert Circus Days gala with movie stars Tony Curtis and Janet Leigh. His only other social outing, Palm Springs Life reported, was a dinner at Van Heusen’s house. He golfed mostly at the course where Giancana and Sinatra played: Tamarisk Country Club, which was formed by Jewish stars as an alternative to the restricted Thunderbird Country Club.

RFK, known as Bobby, stalked Giancana as part of his mission to eliminate the Mafia. But, on Feb. 27, 1962, FBI Director J. Edgar Hoover showed Bobby evidence of his brother’s affair with Judith Campbell. JFK's philandering was compromising his presidency, Hoover said, and now he wanted to stay at Sinatra’s desert compound? Where Giancana had slept?

Lawford later said he never thought JFK was serious about staying at the compound. But he was given the task of telling Sinatra the Secret Service wanted JFK to stay at Bing Crosby’s Palm Desert home – next to Van Heusen's house – for security reasons. By then, Sinatra had spent thousands of dollars renovating his compound for a presidential visit. He was furious at Lawford and banned him from the Rat Pack. But Lawford went to the party with JFK and Van Heusen, who apparently invited some girlfriends.

Mimi Alford, a 19-year-old White House intern, said the party featured a fast Hollywood crowd. JFK wanted amyl nitrate – “poppers” – to enhance a sexual experience. Lawford stopped him for fear of giving him a coronary, but Alford wrote in her book, "Once Upon a Secret: My Affair with President John F. Kennedy and Its Aftermath," that JFK put a capsule to her nose and she had a panic attack. She and the president didn't have sex that night, she said, but JFK's plan was apparently to exit the party and sneak off to a Rancho Mirage love nest with Marilyn. Two witnesses said they saw and heard JFK and Marilyn that Saturday night in a rambling, Spanish-style house in Rancho Mirage. The White House press corps, meanwhile, was busy enjoying it own party in Palm Springs, set up by Press Secretary Pierre Salinger. They only reported seeing JFK the next morning at Sacred Heart Church in Palm Desert.

When he was diagnosed with Addison’s in 1947, he developed a sense that he wasn’t going to live past 45, motivating him to live like each day was his last. Peter Collier and David Horowitz, authors of “The Kennedys: An American Drama,” said JFK had affairs as part of a “search for self – an existential pinch on the arm to prove he was there. For him, as for the Ambassador, it was a game of numbers and he scored with impressive frequency.”

JFK was attracted to movie stars, but for more than their sex appeal. Collier and Horowitz quoted JFK’s Hollywood "wing man" of the 1940s, Jack Spalding, as saying, “Charisma wasn't a catchword yet, but Jack was very interested in that binding magnetism these screen personalities had. What exactly was it? How did you go about acquiring it? How did you make it work for you? He couldn't let the subject go."

Horowitz, who wrote the December 2016 Donald Trump book, “Big Agenda: President Trump’s Plan to Save America,” now thinks JFK’s attraction to Sinatra had less to do with their common rise from Catholic immigrant families than prurient interests.

“I think JFK was attracted to Sinatra because of his celebrity, his Mafia connections – after all Joe was tied in as well – and because of his access to women,” he told The Desert Sun. “I don’t put much stock in speculations about sons of immigrants, except that both of them probably had a certain contempt for WASPs and establishment types.”

If JFK and Jackie Kennedy were the Arthur and Guinevere of Camelot, Joe Kennedy was Merlin, the architect who made it happen before a stroke incapacitated him in December 1961.

Joe was reviled in England for trying to initiate appeasement talks with Hitler. But, Sinatra developed a sense of loyalty to him. In 1957, Joe's tax advice saved Sinatra more than $1 million in IRS penalties and interest. Like JFK, he also admired Joe’s Machiavellian instincts.

“I don’t for a second think that JFK did anything but worship his father,” said Horowitz, “and I don’t think Sinatra looked at him as representing something they despised. Both of them owed people they should have despised.”

Historians say Joe bragged to his sons about his sexual conquests while his wife, Rose, just ignored his philandering. So JFK absorbed a sense that adultery could be tolerated.

Ultimately, JFK’s treatment of women not only had a political backlash, it had tragic consequences for Monroe and Lawford, who died at age 61 after a long struggle with cocaine addiction and a failed stint in the Betty Ford Center.

Lawford hosted Kennedy’s 45th birthday party at Madison Square Garden on May 19, 10 days before his actual birthday. Neither Sinatra nor Jackie Kennedy were there to hear Monroe famously sing, “Happy Birthday (Mr. President).” But Asher was there, directing the show, and he observed, “Marilyn really was in trouble.”

JFK's distance from her that night made her realize he no longer wanted to see her. Her many calls to the White House had gone unreturned since their tryst in the desert. Then JFK sent Bobby to Los Angeles to tell her it was over. By many accounts, Bobby felt sympathy for Marilyn, and then fell into her arms.

“I think it’s pretty much established that both brothers had affairs with Monroe,” said Horowitz, “and that JFK pushed her off onto Bobby when he needed to get rid of her.”

According to “Goddess: The Secret Lives of Marilyn Monroe” by Anthony Summers, the LAPD placed Bobby in L.A. the night before Monroe died of an overdose of sleeping pills on Aug. 5, 1962. Other writers and documentary filmmakers have said he was trying to end their affair and destroy a tape recording of damning evidence.

Rancho Mirage resident Hal Wingo, who covered the JFK assassination for Life magazine, said the media cover-up of the president’s infidelities was so pervasive, Lyndon B. Johnson demanded the same “courtesy” when he became president.

Wingo was one of eight reporters at a Driscoll Hotel bar in Austin, Texas, on New Year’s Eve when Johnson walked in and began talking about how much he admired JFK.

“He talked to us for maybe 30 minutes,” said Wingo. “Then he put his hand on my knee and said, ‘Now boys, let me tell you something. While I’m in the White House, you may see me coming in and out of a few women’s bedrooms. But just remember. That’s none of your business.’ We just said, ‘Yes Mr. President. Yes Mr. President.’ Didn’t even dawn on us that he was asking – demanding – the same protection the press gave Kennedy when they knew he was a womanizer running all around.

“After Watergate, all the rules changed. Back then, he was in charge. He said, ‘Leave me alone.’ And we fell for it.”