Ask Not: The Kennedys and the Women They Destroyed

by Maureen Callahan

Through deep reporting and interviews with many who have never spoken before, this book seeks to understand what being a woman among Kennedy men felt like over the years. I have taken some creative license here, but each of these stories is anchored by years of research. Many of these women are complicated; they, too, were attracted to money, fame, power—and that’s okay. We have made great strides in realizing that few girls and women ever make perfect victims.

Think about this: Jacqueline Kennedy, a thirty-four-year-old widow and mother who held the nation together after narrowly escaping the assassin’s bullets that killed her husband—who signaled to the world that America would not only survive this trauma but emerge stronger—was, upon her remarriage five years later, castigated as a whore who had sold herself to the highest bidder. That mantle hung over Jackie’s fascinating, difficult, creative, controversial life until the day she died. A man would never have been so denigrated. What happened to Jackie would be unthinkable today.

We can answer only by fully reckoning with how the Kennedys have brutalized women throughout generations. The pattern originates with the ruthless patriarch, Joseph P. Kennedy Sr., a financially and sexually rapacious man who fathered nine children. His path to power would be through his sons; his daughters were bred for marriage and babies, worthless as anything else in his eyes. Ever

This book’s title comes from the most famous line of John F. Kennedy’s 1961 inaugural address: “Ask not what your country can do for you…”

His flying was a point of pride for him and fear for her. “I don’t trust him.”

Carolyn said this to family members, friends, the waitress at their favorite restaurant in Martha’s Vineyard. She didn’t think her husband had the patience, the diligence, the attention span, and, really, the humility to be a good pilot.

He didn’t take his training seriously. He hadn’t banked nearly the hours in the air, in daylight and at night, to pilot alone. He

would break the rules, sneak in solo flights when he was supposed to have an instructor fly with him, but not one person admonished him or threatened to take away his training certificate. Nope, it was just John being a Kennedy, a rogue and rebel like his father, risk in his blood.

He’d needed surgery on the ankle. John’s doctor had just removed the cast the day before, and even though John needed a cane to walk and would need months of physical therapy, he swore the doctor had cleared

him to fly. Not likely. But John was so confident. Overconfident, as usual.

No one said no to John F. Kennedy Jr., heir to Camelot, the only living son of the beloved slain president, with movie star looks and charm to match. “America’s Prince,” the media called him, and whenever John wanted to do something—to become a lawyer, start a magazine—hell, run for president of the United States, everyone knew that was coming—the answer was always ye...

She stood him up once. This was before everyone had cell phones, no way for her to reach John F. Kennedy Jr. as he sat in a darkening Broadway theater, all eyes on him and the empty seat next to him, to say she had to work late. Carolyn expected John to be furious with her, but it only made him want her more. And Carolyn realized her superpower. She became the only woman in the world to tell JFK Jr.: No, not okay, don’t behave like that, I won’t put up with it, say you’re sorry, do better.

Don’t take me for granted. And he got off on it. There was a picture that went around when they were going public, Carolyn on a boat in a thong bikini, John bent down in front of her, helping her into a wrap. That was their dynamic: Carolyn was the dominant, John the submissive. He liked to be bossed around by the women in his life.

George, meant to upend that image, was instead a failure on three fronts: commercially, critically, and as an intended triumph of public relations—one meant to give JFK Jr. the gravitas for a run for governor of New York or US Senate.

John sailed into those meetings without due diligence and met headwinds he’d never experienced or expected. One executive couldn’t believe John’s gall in asking for a $20 million investment without being able to answer the most basic stuff. Such as: Who was the magazine’s audience? What was the brand identity? Who would John hire to write? What stories would the magazine break? Who would make ideal profile subjects? Why would their as-yet-unnamed

magazine be successful when political magazines, by definition, were small and lucky to break even? How would they attract advertisers once, let’s face it, the novelty of being associated with JFK Jr. wore off? Carolyn knew all too well about that novelty wearing off. John was like Seinfeld’s Bubble Boy, so coddled and spoiled that he didn’t know what he sounded like to others. He could be prickly and impatient and something of a brat, really.

He’s so down-to-earth—give him a gold star! That was the line on John, from waitresses to movie stars, paparazzi to presidents. But he wasn’t down-to-earth, not really. Anyone who knew him behind closed doors knew that.

doubted Jackie’s intellect, or his sister Caroline’s, and certainly not his father’s. Why couldn’t he be taken as seriously? Carolyn had tried to tell him: If that’s what you want, treat other people and things with the respect you crave.

Responsibilities were for other people, not him. He rode around the city on his bicycle and never locked it up. He spent thousands of dollars replacing bike after bike.

The truth was that John was a terrible athlete, totally uncoordinated.

No one would ever have guessed he’d taken so many risks, had come close to death so many times in his teens and twenties.

Speeding, swimming too far out into the ocean, driving recklessly onto sidewalks or while high on pot, skiing in whiteout conditions, acting like

an expert in all sports when really he was just an amateur—there was little John wouldn’t dare, and he bullied almost everyone in his life to be as wild as he was.

The weird thing was the look in his eyes, like he was turned on. Dying, getting that close to it, was a high for him. No wonder the other near misses—almost smashing into a forty-nine-foot-long whale in Baja or kayaking straight toward the Staten Island Ferry or swimming far out into the ocean, way past shore—hadn’t stopped him. If anything, they electrified him.

John had given Christina valuable information that day: He had a death wish. It

He leveraged her fear that this would be their last time together, having told her that he needed to see other women before he married her, then telling her that she was too good for him, that she had a calling—acting—and he did not, and that he needed to find direction on his own. Alone. But then she would hear and read about the movie star he was seeing, Daryl. John and Daryl were all over the tabloids.

John was telling her something else: I’m too dangerous for you. For any woman, really.

John thought about marrying Daryl. When, years later, they finally broke up, everyone assumed it had to do with Jackie. Not so. The truth was Daryl dumped him. It was early 1994, and Jackie was suddenly battling a very aggressive cancer. John had an even tougher time focusing now. And so one day, John took Daryl’s dog for a walk and, when John wasn’t looking, the dog wandered into traffic, got hit by a car, and was killed.

There was the time Carolyn and John got pulled over on the Massachusetts Turnpike, the car reeking with the smell of pot, a starstruck cop letting them go without even a warning. “There’s an unwritten rule in Massachusetts,” John told her, “whereby members of my family can commit murder and mayhem”—after all, decades earlier his uncle Ted had left a young woman to die in three feet of water—“and nobody bats an eye.”

Carolyn was preparing for a big life, bigger than dating the C-list actors or club owners or male models or star athletes of her past. She excelled at pretending not to care about famous men but pretty much exclusively dated famous men.

Really, there was no one more famous than John F. Kennedy Jr., and when he walked into the Calvin Klein showroom for the first time, Carolyn knew exactly what to do. She ignored him.

Carolyn could be in a room full of supermodels and still make John Kennedy want her. And when he finally came around and asked her out, she’d just as often say no, that she had other plans. Really, Carolyn never had anything better to do. She’d just hole up in her crappy studio apartment all weekend, hoping that people would assume she had this fabulous, mysterious life full of wealthy suitors. She’d say, loudly, that she was not waiting around for JFK Jr. to call, but really she was waiting around for JFK Jr. to call. As they grew closer, she would insult him just to keep him back on his heels, off-kilter, but quietly she’d marvel at his beauty. She wanted him so badly.

Jackie wasn’t naïve. She knew Jack wouldn’t be faithful. But she hadn’t known just how promiscuous he was or how little he’d do to protect her. Later she’d learn, along with the whole world in news reports too numerous to bear, that Jack had likely infected her with his own constant sexually transmitted diseases, the asymptomatic chlamydia among them, and this was quite likely why she’d had so much trouble carrying her first two pregnancies to term.

When Jackie came out of anesthesia hours later, at two in the morning, it wasn’t her husband at her bedside but her brother-in-law Bobby. It was he who broke the news, who held Jackie’s hand, who told her he would take care of everything—by which he meant the baby’s burial—and who made the excuse Jackie wanted to believe: Jack was still at sea, unreachable in the Med. Of course, Jack was reachable in the Med. Bobby knew, because he’d already spoken to his brother. “What’s done is done,” Jack told Bobby

over the phone. “The baby is lost.” Jack saw no point in cutting his vacation short. Her husband had given no greater rejection. Mourning a child she never got to see or hold, Jackie lay in the hospital absorbing the message that her husband’s absence, the lack of so much as a phone call, had sent. I would rather be off with random women than comforting you. I’m not sad about the baby. Someone else can take care of the funeral. What does it matter? She’s dead.

Jackie never even had a honeymoon period with her husband. In fact, days into their actual honeymoon, Jack suggested she fly home alone so he could travel with “friends.” Jackie declined.

He was hardly in a position to be so callous now that Jackie needed him. It was as if his own body waited for him to have a partner before it broke down. Jack’s back was such a mess that he couldn’t bend over to tie his shoes, or climb stairs without help, or tolerate riding in a car. He walked with crutches, an obscenity to him. They both knew a wheelchair was next. There was a surgery that might help, but it could very well kill him. Joe begged him not to have it; he had already lost three children and he couldn’t bear the idea of losing Jack, his favorite.

Jackie was so weak and depressed that she couldn’t even attend her daughter’s burial.

Bobby stood over the baby’s coffin while Jack was still sailing with his starlets and bikini babes off the south of France, drinking, smoking cigars, having fun. She knew he was cheating on her.

What kind of narcissist had she married? A week went by, and Jackie was still in the hospital with no word from Jack. He intended to keep cruising around the Med till September—and as soon as he got home, he was going off to campaign for the next three ...

Jackie wanted an annulment. Divorce was not enough. She wanted the Catholic Church to nullify this marriage, negate it, treat it as a great nothing just as her husband had done. “I’m never going back,” Jackie said. Jack’s self-preservation must have kicked in, because three days after the baby’s funeral, he was suddenly in her hospital room. Ten days had gone by. Any suspicions Jackie had about why he was there, why the change ...

George Smathers, was the one who got Jack back home to her. It was hardly the stuff of romance. If you ever want to be president, Smathers said, “you better haul your ass back to your wife.” When Jack finally landed in the States, he told a reporter that Jackie had not let him know about the stillbirth because she didn’t wa...

That was true, Jackie had to admit. Despite everything, she was still deeply in love with Jack. He was the smartest, the cleverest, the best gossip, the brightest light in any room. When she had his attention there was nothing like it.

Jackie had caught Jack getting a blow job in his Senate office, a young girl under his desk, just after they were married. He didn’t even try to hide his affairs.

As Jack and the Old Man said more than once, Jackie really classed up the Kennedys.

It irked Jack’s sisters to no end.

The dressed-down Kennedy sisters had packed beer and hot dogs, while Jackie showed up immaculate in a white Christian Dior sheath dress, toting a basket filled with foie gras, caviar, and cold champagne. “Pat Lawford and Eunice Shriver never got over that,” Cassini said. “Years later, they were still jabbering away about it.”

For Jack and Old Joe, that level of refinement was Jackie’s superpower.

This second encounter would set the tone for their relationship. Mimi would be welcomed upstairs only when the First Lady was away, and it was her job to remind him of simple pleasures: small talk, shared bubble baths, and sex, hasty though it always was. They never discussed the big stuff, the pressures of the presidency or the state of his

marriage. He didn’t seem to care whether she slept over or not, but when he offered she always did. Wearing the same dress to work, two days in a row, never embarrassed her. It was Mimi’s nonverbal way of letting all those other women in her department know: she had special privileges. She was the president’s favorite. The White House was her dominion.