Inside, JFK heard the commotion, quickly pulled on his robe, and fled the pool just before he could be caught. Agents would later recall that his large wet footprints and the smaller prints of his female swim partners left a very clear trail, which Jackie did not see, having left in a huff.

*   *   *

Even as one part of the president’s brain strategizes clever ways to deal with Fidel Castro, Nikita Khrushchev, and Charles de Gaulle, another part strategizes ways to have as much sex as he wants without Jackie walking in on him. And as Kennedy gets more and more comfortable in the White House, his affairs get more and more outrageous.

“We got to the point where we’d say, ‘What else is new?’” one member of the Kennedy Secret Service detail later remembered. “There were women everywhere. Very often, depending on what shift you were on, you’d either see them going up, or you’d see them coming out in the morning. People were vacuuming and the ushers were around. There were several of them that were regular visitors. Not when Jackie was there, however.”

When Kennedy goes more than a few days without extramarital sex, he becomes a different man—so much so that the Secret Service breathes a sigh of relief whenever Jackie takes the kids away for the weekend. “When she was there, it was no fun,” a longtime agent would later admit. “He just had headaches. You’d really see him droop because he wasn’t getting laid. He was like a rooster getting hit with a water hose.”

Sex is John Kennedy’s Achilles’ heel. Why in the world does he do this to Jackie? And what is he doing to the nation in the process?

*   *   *

Just a few short weeks after being named attorney general, Bobby Kennedy received a special file from J. Edgar Hoover, the pug-nosed and Machiavellian head of the Federal Bureau of Investigation. In the file was evidence about the president’s extramarital affairs. It turns out that while the newspapers were looking the other way, the FBI had been tracking JFK’s liaisons since the late 1940s, because he was seeing a woman thought to be a spy for Nazi Germany. The file is Hoover’s idea of job security. He wants everybody to know the FBI will never be diminished—and that there’s nothing illicit going on in America that he doesn’t know about. For reasons of national security, not even the president of the United States is above the scrutiny of the FBI.

In early 1962, as President Kennedy’s visit to Palm Springs is being planned, a Justice Department investigation into organized crime reveals that singer Frank Sinatra is deeply involved with the Mafia. This is trouble for the Kennedys—Americans know that Sinatra not only supports the president but is also a close personal friend. And if that isn’t enough to compromise the attorney general and the president of the United States, their sister Patricia’s husband, movie actor Peter Lawford, is a member of Sinatra’s famous Rat Pack.

Making the matter more delicate is a brand-new file from Hoover delivered to Bobby just a few weeks before the Palm Springs trip. This one indicates that the president of the United States is having sex with a consort of Sam Giancana, not only one of the most notorious mobsters in the country, but also at the top of the list of Mafia kingpins whom Bobby Kennedy is trying to bring down. The woman’s name is Judith Campbell, and Hoover is describing her as a major security risk. Unbeknownst to Patricia Kennedy Lawford, her husband owes that affiliation to her family heritage. Sinatra has long wanted to be closer to the throne of power. Once he realized that the Kennedys were on the verge of becoming the most powerful family in America, he allowed Lawford into his inner circle. In addition, it was Patricia Kennedy Lawford who bankrolled the script for Oceans 11, assuming her husband would costar with Sinatra. But Dean Martin was given the role instead. Sinatra treats Peter Lawford like a hanger-on, suspecting that Patricia Kennedy Lawford, like most people outside the Hollywood bubble, will do almost anything to bask in the reflected glow of movie stars’ fame.

And Sinatra is correct. Despite numerous snubs, the Lawfords remain keen to be part of the Rat Pack “vibe.”

Thus, the woman who extended Sinatra’s invitation for JFK to stay in his Palm Springs home on his visit to the city is none other than Patricia Kennedy Lawford.

After reading Hoover’s Sinatra file, Bobby Kennedy tells the president to stay somewhere else in Palm Springs. Bobby doesn’t care that this slight might sever a long-standing political relationship with Sinatra, who not only campaigned extensively on behalf of Kennedy in 1960, but also worked overtime to coordinate the inaugural gala.

The truth is that Bobby has no choice. Sinatra has had repeated contact with ten of the biggest names in organized crime. The FBI reports detail not only the times and dates when the singer is phoning Mafia heads from home, but also reveal that the mobsters are dialing his private number. “The nature of Sinatra’s work may, on occasion, bring him into contact with underworld figures,” reads the report. “But this does not account for his friendship and/or financial involvement with people such as Joe and Rocco Fischetti, cousins of Al Capone, Paul Emilio D’Amato, John Formosa and Sam Giancana—all of whom are on the list of racketeers.”

The FBI has been keeping files on Sinatra since the late 1940s, chronicling his associations with other famous gangsters such as Lucky Luciano and Mickey Cohen. As early as February 1947 there were reports that he had vacationed in Havana with Luciano and his bodyguards, and that the trio were seen together at “the race track, the gambling casino, and at private parties.” What made these sightings so extraordinary was that Luciano had recently been paroled from prison and deported to Sicily. Such a high-profile appearance in Havana was his way of thumbing his nose at U.S. law enforcement.

President Kennedy was once close friends with Frank Sinatra, shown here in California. (AFP/Getty Images)

The list of alleged associations goes on and on. Bobby’s true surprise about Sinatra, however, is not that the singer is connected with the Mafia. Rather, it’s that the FBI has evidence linking the Kennedy White House with organized crime through the singer. In fact, Hoover has years of files documenting the close relationship between Sinatra, the Kennedys, and high-profile members of the Mafia such as Giancana—who wears a sapphire pinkie ring given to him by none other than Frank Sinatra. The most damning bits of the report state that Giancana frequently visits Sinatra’s Palm Springs estate. Agents also found a number of calls from Giancana’s good friend Judith Campbell to Evelyn Lincoln, the president’s secretary, suggesting a clear link between the Kennedy White House and organized crime.

Frank Sinatra and John Kennedy have shared many laughs, many drinks, and, as the FBI suggests, a woman or two. In a separate investigation in February 1960, the FBI observed JFK at the Sands Hotel in Las Vegas with the Rat Pack and noted that “show girls from all over town were running in and out of the Senator’s suite.” Sinatra and the Rat Pack sang the national anthem to open the 1960 Democratic National Convention in Los Angeles. Sinatra has visited the Kennedys’ family estate at Hyannis Port and once startled guests by performing an impromptu concert at the living room piano. Sinatra even reworded his 1959 hit song “High Hopes” to make it an anthem for the Kennedy campaign.

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