Ask Not: The Kennedys and the Women They Destroyed

by Maureen Callahan

When John proposed, a part of her thought: This is it. As big as it gets. But she had her doubts. John expected her to cook, clean, and throw dinner parties—things she had had no interest in. She asked her friends what she was supposed to do as Mrs. JFK Jr: “Do I start my own foundation?” she would ask.

Carolyn’s mother was against the marriage. Her sister Lauren, who was currently working as a banker in Hong Kong, was not going to fly in. Her biological father, who hadn’t really been in her life since she was eight years old, would not be invited. Carolyn hated him yet was haunted by him. She remained very much a Bessette. On her forefinger she wore her mother’s wedding ring from that first marriage. She and her mother had dipped it first in holy water, as if to purify it. “Isn’t that fucked up?” she’d say. Yet she wore it constantly.

She had known, from a very young age, that she was destined for big things, but she didn’t know that for all her cool self-possession, her friends were deeply worried about this marriage.

That very public, very physical argument put John’s family and friends on edge. Carolyn, to them, looked like a liability, a shrew. Underneath that classy veneer was a feral girl, low-rent and trashy, sure to bring him down. No matter that paparazzi had photographed John taking his palm to Carolyn’s face and shoving her back by her head. Or that he tried to rip her engagement ring off her finger with such force that the stone broke off, or that he tried to pull their dog’s leash out of her hand so many times that she almost fell. They were a combustible match, toxic, and when Carolyn’s friends saw those pictures in the tabloids they almost felt sorry for John.

They were grooming Carolyn to be John Kennedy’s wife, and John Kennedy was being groomed to go into politics. I think the problem is that Carolyn created this Stepford political wife to please John. That’s when she started to die.”

“Each and every day… in each and every newspaper, I had to see the face of the man who raped me,” Bowman said. “That’s hard. Then I had to see the face of the man who raped me change into a man with a puppy, a man kissing schoolchildren.” Bowman later told the journalist Dominick Dunne that Smith’s was “the acquittal [that] money can buy,” and that after the rape—after she told Smith he had just raped her—“he looked at me, the calmest, smuggest, most arrogant man, and he said, ‘No one will believe you.’ And the jury came in and said, ‘Not guilty,’ and I was right back in that room with that man telling me no one would believe me.”

John would always circle those Kennedy wagons to protect the cesspool. He admitted as much during an interview with NBC’s Tom Brokaw, plugging George. Brokaw: “Can we expect some tough stories about Uncle Ted?” John: “Never.”

John took shots at lesser Kennedys: his cousin Joe Kennedy, who used Kennedy privilege to get an annulment against the wishes of his ex-wife, followed by thirty-nine-year-old Michael Kennedy, the married father of three who had been having what John called “an affair” with a fourteen-year-old babysitter.

John piously denigrated Joe and Michael in his editor’s letter for George, running it alongside an artsy black-and-white beefcake photo of John, shirtless and seated, looking up at a dangling apple. Hey—the fall of Eden was all Eve’s fault, right?

There was something ominous about Cumberland: the thousand-year-old oak trees, their thick branches twenty feet in circumference, knots the size of jagged boulders, curling and bending down toward the grass, hovering inches above in suspended animation. Witness trees, they call them, so old that they had lived through history, great and terrible. Ancient Spanish moss one hundred feet high, draping either side of the pathway to Greyfield Inn, two weblike, gothic green curtains daring visitors to pass through.

Spectral and eerie, at night especially, Cumberland still possessed its pre–Civil War colonialism; populated by anonymous titans of industry, Cumberland’s residents still talk about the slaves who had toiled on the island and farmed it as “lucky.” Well treated. Whipped only when they really deserved it. Cumberland did not augur well for this marriage. The night before, at the candlelit rehearsal dinner on the porch of the old Carnegie mansion, Carolyn wore a custom slinky pale-pink number handmade by one of her best friends at Calvin, Narciso Rodriguez, who had also designed her wedding dress.

The excitement, the daring in marrying America’s prince in a sexy slip dress—a dress as formfitting and soon-to-be-iconic as Marilyn Monroe’s—turned to shame, however, when she caught the eye of John’s friend Billy Noonan.

Carolyn’s mother rose and made a toast of her own. I don’t know if this marriage is good for my daughter, she said. I don’t know if John is right for her. John was stunned.

Ann wasn’t reacting only to that evening. She had known that the past three years had not been easy for her daughter. Carolyn had been met with suspicion by John’s family and their inner circle. John’s brother-in-law, Ed Schlossberg, was especially cold to Carolyn. His aunt Ethel, during Carolyn’s first visit to the Cape, brusquely suggested that Carolyn familiarize herself with geopolitics and policy if she wanted to be invited back.

Carolyn had tried with the Kennedys and their sycophants—she really had. But with some of them, nothing was good enough. And now she was here, on the night before her wedding, about to make the biggest mistake of her life. Even the friends whom Carolyn had cast aside knew that John wasn’t for Carolyn.

Carolyn confessed to her mother that she still thought about her ex-boyfriend, the underwear model. She said that he understood her as no one else had—which would not have surprised her friends, the ones she had either abandoned or allowed John to push aside. One in particular thought that John was never going to be the love of Carolyn’s life.

The vows were said quickly, and the ceremony was over as soon as it began. The lone wedding picture released to the press—Carolyn and John exiting the chapel, not a hair out of place or a bead of sweat anywhere, John kissing Carolyn’s tulle-gloved hand—was a metaphor for the weekend and the marriage to come: a pre-Instagrammable image that looked perfect and effortless but was really a lie.

But many of Carolyn’s old friends were less optimistic. One thought Carolyn was in way over her head, a girl from the wrong side of the tracks now on board a high-speed train. He thought John, Carolyn’s Ultimate Trophy Husband, her knight in shining armor, was a loser wrapped in tinfoil. He thought, deep down, that Carolyn knew it, too.

He had once described her to Barlow as “nobody, really… a functionary of Calvin Klein’s.” But who was he, really? John Kennedy was a middle-aged man with no real accomplishments. Carolyn had worked her way up from a sales associate in a Boston mall to Calvin Klein’s most trusted adviser and something of an informal brand ambassador within the span of a few years. Not that John would understand that or find it all that important.

John asked her, too. Really, what was the problem? He didn’t like confrontation, mainly because he had lived his whole life without it—until Carolyn came along. Here was a nearly forty-year-old man who never heard no, who had everything so easy that he never really developed a personality or an edge. John was conditioned—enabled, really—to see himself not just as a good guy but a great guy, the complete package. “People often tell me I could be a great man,” he would say. “I’d rather be a good one.”

When your husband’s sister wouldn’t offer advice and barely tolerated you because you hadn’t been born into their world. Carolyn wasn’t a member of Camelot, not even a courtier. She was nothing. John had said it himself, more than once: Those who married into the Kennedy family weren’t really Kennedys.

“I don’t know how you put up with this,” her mother said. “I love him,” Carolyn replied. “It’s not worth it.” Warning Two.

She and John hadn’t even hit their third wedding anniversary, and already their marriage was in shambles. Multiple tabloid stories, many of them well sourced, were reporting that John was having affairs, that his ex-girlfriend Daryl was back in the picture, that John was disappointed that Carolyn couldn’t rise to the level of a Kennedy wife.

He had written in his editor’s letter for George—the same letter he had used to simultaneously attack and defend his cousins—that he was tempted to cheat on Carolyn.

There were reports he was getting ready to file for divorce.

“Maybe we should get divorced,” John said to her. “We fucking talk about it enough.” “Oh no,” Carolyn shot back. “We waited for your mother to die to get married. We’re waiting for my mother to die to get a divorce.”

He had logged only fifty-five hours of night flight and wasn’t instrument-rated—he didn’t know how to read and rely on his controls, which often contradicted what a pilot could actually see. “I don’t know if he’s ready yet to fly again,” Carolyn told the salesgirl. “I’m really not looking forward to it.”

John was still on crutches and taking Vicodin for bone pain, along with his regular Ritalin and thyroid medication. He carried a half-empty bottle of white wine. His doctor had warned him not to fly.

Without knowing which way the clueless pilot of a small prop plane was going, the American Airlines pilots had to divert from their flight path to avoid a midair collision. John kept on climbing. At 5,500 feet, despite warnings of extreme haze, John didn’t turn on his autopilot. He didn’t hug the lit-up coastline. Instead, he turned right and went out over the Atlantic, and before he knew it the sea and sky had turned into one seamless black mass and he couldn’t tell up from down.

Now would have been the time to radio ground control—but John, who loved to get himself into near-death situations, did not. Was he that sure he could get himself and Carolyn and Lauren out of it? Or was there a part of him, subconscious or not, that didn’t care if he died, taking his wife and sister-in-law with him? His magazine was on the verge of collapse. His marriage was failing. His sister, upset that John was trying to stop her from auctioning off their mother’s possessions—Jackie’s deathbed suggestion—was now barely talking to him.

The plane went into a graveyard spiral, falling 900 feet per minute. Carolyn and Lauren would have known they were going to die. The sheer force of gravity and speed would have been terrifying as they spun at 200 miles per hour, nose first, into the ocean.

When the shattered plane was recovered five days later, its cabin was upside down. The debris field spanned 120 feet. Only five of the six passenger seats were found. John’s body was bent backwards at the waist, his head touching his feet. It was rumored on the Cape that the force of impact caused Carolyn’s seat belt to sever her body. Reports were that Lauren may have been in the missing seat.

Ann was terrified that the Kennedys would use their power to bury what remained of Carolyn and Lauren at the family plot in Brookline, Massachusetts. Ann wanted her girls close to her in Connecticut, and she needn’t have worried: the Kennedys told Ann that they did not care. John’s remains, however, belonged to them, and he would be buried separately in Brookline.

When Ann came down to NYC, however, Caroline didn’t show. Instead she sent [her husband] Ed and Vickie Reggie [Ted’s second wife]. All the Bessette family knows that Ed hated Carolyn and did everything he could to make her life miserable. He bullied, bullied, bullied the shattered, grieving mother.

In death, as in life, they never considered Carolyn Bessette a real Kennedy. And as per Kennedy tradition, burying troublesome women alone was nothing new to them.

Mimi had always planned to keep her relationship with the president secret. Only her first husband, Tony, had known about it.

She had built a life, had two daughters, divorced Tony and remarried, found rewarding work as an administrator at the Fifth Avenue Presbyterian Church in Manhattan.

Robert Dallek, while working on a JFK biography, unsealed an oral history that named Mimi as the president’s in-house teenage mistress. Another biographer had reached out to Mimi one year before. It was only a matter of time before the front-page headline in the New York Daily News, which ran in May 2003. “Fun and Ga...

After the Daily News outed her, she decided: the only person to tell her story would be Mimi Alford. It took no time for her to find a literary agent and to sell her book to a major publishing house. Mimi wasn’t going to be anyone’s victim.

the president had persuaded Jackie and the children to go to her beloved Glen Ora in Virginia. And as soon as the First Lady was gone, Dave Powers had called for Mimi, who arrived at once. She had spent the next two days in the White House watching the president go downstairs for lengthy meetings, hiding from a disapproving Bobby Kennedy and feeling safe, swaddled like a baby in the finest bedsheets, as the president set about saving America’s eastern seaboard from nuclear oblivion—a catastrophe, really, of his own making.

So more people had known about the affair than Mimi had believed, or had wanted to believe.

Mimi discovered another bombshell while reading Grace and Power: She hadn’t been the only mistress of JFK’s who was still in school. Here she learned of Diana de Vegh, the beautiful, high-class Radcliffe girl whom JFK also brought to the White House when Jackie wasn’t there.

JFK had sex with Diana in the Lincoln Bedroom multiple times, another desecration. Not enough that the president took Mimi’s virginity on Jackie’s bed; he had to defile his wife’s favorite room in the White House, a room she compared to a church.

The adult Mimi learned that the president said that “the chase is more fun than the kill,” that he called his paramours “kiddo” or “sweetie” because there were so many that he couldn’t remember their names.

JFK couldn’t abide women who were as smart as or smarter than he was. In choosing Mimi and Diana, two well-bred girls from the right schools and social class, JFK had gifted them with extraordinary acces...

Diana proceeded to go home, get drunk, throw up, and wake the next day—and the next, and the next—waiting for Jack Kennedy to call. Now she was left with no illusion that theirs had ever been a relationship of equals.

Mimi was finding herself on a downward trajectory, stashed in cheap motel rooms and told never to leave, not for anything, until she was summoned to the president’s five-star hotel or family estate. She called it “The Waiting Game.” Mimi could feel the disdain among the president’s closest aides but she didn’t care; she was more worried about pleasing the most powerful man in the world

It never occurred to her to ask herself: Why was she the target of other staffers’ contempt? Why didn’t they blame the president, whose newborn son, Patrick, had lived less than two days? Why didn’t they give him hell for traveling around with a teenage intern when he should have been at home, comforting Jackie?

He took the capsule, popped it, and put it under Mimi’s nose anyway. Her heart began pounding so fast she thought she was having a heart attack. She fled in tears. The president did not go after her. He did not check on her. He spent the night in a private room on the other side of the estate with a guest Mimi did not know was there: Marilyn Monroe.

“Mr. Powers looks a little tense,” the president whispered to Mimi. “Would you take care of it?” Mimi was shocked. But what if she didn’t do as JFK had asked? Would the president think her a prude? He could have any woman he wanted. She needed to keep him. And Dave, seated poolside in his suit with his feet in the water, laughed as Mimi made her way to him, stood up, and performed oral sex on him. The president watched avidly, never saying a word.