Behind John F. Kennedy’s Revolving White House Door: Mistresses, Marilyn Monroe, and What Jackie Knew

As a young man President John F. Kennedy had identified with the aristocratic 19^th century British world, a society focused on pleasure, one in which there were no limits and no consequences. That was the personal world the president created for himself in the White House. And he wanted to memorialize some of his evenings. A Secret Service officer arrived on various mornings with photos just as Sidney Mickelson’s gallery and frame shop opened in downtown Washington. Some of the images were of beautiful naked women lying in a bed in the Lincoln bedroom. In one notable photo, the masked president lay next to two masked women.

Mickelson took measurements for a frame. The agent left with the picture, bringing it back at the end of the day for Mickelson to finish the framing. That way there was no chance anyone could copy the photo. Taking these pictures was a crazy thing to do in conservative Washington—let alone getting them professionally framed—but it was part of Jack’s drive, his compulsion, his obsession.

The Secret Service officers had a hard time protecting a president who was going to live his own life his own way. When twenty-eight-year-old William T. McIntyre arrived to take up protection duty on the night shift, he was startled at the visitors coming in and out of the White House. Night after night he saw “girls coming in—hookers.” Some may have been sex workers, but no doubt others were sent from lobbyists or upscale women who wanted their moment with the president. The officers feared one of these unvetted women might be carrying a recorder to set up in a bedroom, or, worse, might take it upon herself to harm the president or someone in his inner circle.

There were many women, each with her own small position in the president’s life. He had met Helen Chavchavadze in 1959, when Jackie invited the beautiful brunette divorcée to a dinner party at the Kennedys’ Georgetown house. Chavchavadze’s ex-husband was a Russian nobleman, and she and Jack spent much of the evening in their own dialogue about the Russian world.

Jack never forgot when it came to a woman he desired. Early the next summer, on the verge of the presidential nomination, he asked the columnist Charles Bartlett to invite Chavchavadze to one of his dinner parties. Afterward, Jack followed her Volkswagen Beetle home in his white convertible. It was hardly the car to drive to start a surreptitious affair, but it didn’t matter—their relationship began that evening. Chavchavadze’s two young daughters likely did not even know about this late-night visitor.

Jack appeared unworried that his secret sex life would become public. A janitor in the Senate Office Building might have taken the photo on his desk of him on a yacht with naked women and sold it to a scandal-chasing tabloid or Republican operatives. The FBI had information that an operative working for Teamsters president Jimmy Hoffa was “collecting information on the identity of prostitutes who might have had association with members of the Kennedy family” and that Hoffa was out to “bury the Kennedys.” Jack acted as if he lived on a plain so high that none of this could touch him.

Chavchavadze was the kind of socially sophisticated guest the Kennedys liked to have at their White House dinner parties, and she was a regular. Chavchavadze also frequently arrived at other times to be alone with the president. “I never knew if Jackie knew, but I felt uncomfortable about her,” Chavchavadze said. “I always felt ambivalent and wanted to end it.”

Most of Jack’s mistresses did not express much concern about Jackie. It wasn’t that these women were necessarily insensitive, but theirs was a totally different world in which Jackie did not exist. Beyond that, Jack was such an overwhelmingly powerful figure, not simply politically but emotionally, that everything else faded into insignificance.

Despite her qualms, Chavchavadze continued to see Jack throughout his presidency. “I was never someone who had extramarital affairs,” she said. “It was not my style, but it was irresistible with Jack.” Yet she knew something was terribly wrong. “It may have looked like beautiful convertibles and women and sophistication, but it was the shadow destroying the self.”

Some people in the White House treated Jackie as a cipher, ignorant of almost everything happening. But the elegant first lady could smell, hear, and see. She must have known of her husband’s long-term affair with Pamela Turnure, yet she brought the young woman into the East Wing as her press secretary.

Wherever the first lady looked, there were signs of her husband’s other women. One day, as she was showing a French journalist around the White House, she came upon Priscilla Wear, an aide in the press office. “This is the girl who is supposedly sleeping with my husband,” Jackie told the journalist in French. Wear spoke a measure of the language and probably understood what was being said.

The first lady was far too sophisticated to think she could steer her husband back onto the straight and narrow—a path he had never followed. Instead, she amused herself by playing around with his predilections. At dinner parties, she would seat an attractive woman next to him and watch Jack salivate. Even then, her husband had no boundaries. One evening, he passed a note over dinner to an attractive guest. Later that evening, he called the woman and told her he was sending a car. “For Christ’s sake,” she implored him. “I’m your wife’s friend.”

Judith Exner met Jack in February 1960 in Las Vegas during a primary campaign stopover when she spent an afternoon in his hotel room. Exner took great pride that she was sleeping with the president of the United States. Although Jack saw Exner various times, during the White House years at least half a dozen other women had longer, more intimate relationships with him. Exner’s notoriety is due to something different: her simultaneous affair with Sam Giancana and Johnny Rosselli, the Mafia chieftains in Chicago and Los Angeles. The FBI was wiretapping Giancana and Rosselli and monitoring their activities. The FBI had enough information to add Rosselli to Exner’s list of lovers, referring to him as her “paramour.”

Exner was a busy woman, moving between Rosselli in Los Angeles and Giancana in Chicago, while, in the blunt words of one private investigator interviewed by the FBI, “shacking up with Kennedy in the east.” Exner had no job or obvious means of support, yet she rented an expensive home in Palm Springs and another place in Malibu. Most interesting of all, her phone records showed her making calls to Jack’s secretary Evelyn Lincoln at the White House.

J. Edgar Hoover had survived for nearly three decades as the head of the FBI in part by collecting gossip and using it as a tool of power in the most adept way imaginable. Instead of directly suggesting to the president that he had information Jack was likely having an affair with a gangster’s moll, in February 1962, he wrote a subtle bureaucratic letter to White House special assistant Kenneth O’Donnell. “The relationship between Campbell [Exner] and Mrs. Lincoln or the purpose of these calls is not known,” the FBI director wrote.

About a month later, Hoover had lunch with the president at the White House. There is no record of their conversation, but afterward Jack called Exner. Even he must have known there sometimes had to be a limit to his philandering, and that was the end of his time with Exner.

Back in 1954, during the filming of The Seven Year Itch, a still photographer had captured an image of Marilyn Monroe standing over a New York subway grate as steam lifted her white dress above her head. It became one of the most erotically enticing images of the era and helped establish Monroe as the world’s leading sex symbol. Not only did the blond actress possess a strikingly voluptuous figure, but she also played with her image, aware of the power she held over men and sometimes even mocking it.

Jack had wanted to have an affair with the glamorous movie star for some time. But Monroe was constantly pursued by paparazzi and gossip columnists, making it difficult for him to approach. With Jack’s ascension to the presidency, she focused her passionate interest on him, believing he was the leader who could change America as no president had since Franklin Roosevelt. This preoccupied her to such an extent that she discussed it in depth with her psychoanalyst. “No child will go hungry, no person will sleep in the street and get his meals from garbage cans,” she told Dr. Ralph Greenson.”

Monroe now felt involved with what she considered the greatest man of the era. At a luncheon at the beach house of Jack’s brother-in-law Lawford in Santa Monica, Monroe was among the guests. The president would have been appalled to learn that the FBI had a source at the private party who noted that Monroe “asked the President a lot of socially significant questions concerning the morality of atomic testing and the future of youth in America.” These were not subjects Jack typically discussed over a casual lunch, but they demonstrated how Monroe viewed her affair with the president as elevating her into a realm far above that of a mere movie star.

Monroe came to Washington, and Jack took her out on the Potomac on the presidential yacht with a group of his friends. This was a shrewd move, as he could always claim the actress was with one of them. Senator George Smathers had seen his friend’s women come and go, but Monroe was different. Her love was overwhelming. “And God, she loved Jack,” Smathers said. “She was all over him. Of course, he liked her very much, but he was already married and everything, so he had to be reasonably discreet.”

It was hardly discreet to invite Monroe to Jack’s massive forty-fifth birthday celebration at Madison Square Garden in May 1962. Her devotion to him was such that she flew to New York during the filming of Something’s Got to Give, violating her contract and causing the production to be shut down.

That evening, Monroe arrived at the event in a silver sequined dress so tight it looked as if the sequins had been applied with a riveting gun. “Happy Birthday” has been sung a billion times, but never the way Monroe sang it to the president that evening—slowly, languidly, turning it into an erotic ballad, suggesting by her sheer provocativeness that she might be the desired birthday gift. By the time she finished, there were nothing but dry mouths at the Garden.