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A Carriage Named Desire

by Sharon Churcher Photographed by Yamaguchi Haruyoshi/Corbis via Getty Images, Jeffrey R. Staab/CBS via Getty Images and Carl Timpone/
Friday, October 6, 2017

The buzz about her being the “goddess-in-waiting’’—as Truman Capote once called Caroline Kennedy—started barely two weeks after she arrived back at her elegant Park Avenue co-op in January. Invoking her three years of foreign policy experience as Barack Obama’s ambassador to Japan in a February appearance on the Today show, she excoriated Donald Trump for his “alarming’’ America First rhetoric.

Ramping up the speculation was a sparkly performance at this spring’s Costume Institute Gala, where she was honorary cochair alongside Anna Wintour, as well as Katy Perry, Gisele Bündchen and Tom Brady, and Pharrell Williams, and attended along with the usual Hollywood and fashion A-list rabble. While they walked the red carpet with their age-appropriate significant others, Caroline’s drop-dead gorgeous choice of escort was Jack Schlossberg, her 24-year-old son.

Kennedy’s gown provided one of the evening’s topmost talking points. Its bizarre floral-layered tiers were specially designed for her by the evening’s honoree, Comme des Garçons’ Rei Kawakubo. “It took a lot of trial and error,’’ Caroline giggled.

Once known as the “shy’’ Kennedy, Caroline, at 59, finally has come out of her shell. Diplomatic insiders say she acquired a taste for the limelight in Japan, where cheering crowds turned out to watch her arrive in a gilded horse-drawn carriage to present her credentials to the emperor. Booted out of her job by The Donald, she is said to be determined to win a seat in Congress and rebrand the Kennedy name after decades in which it has become synonymous with tragedy and scandal rather than the liberal idealism that she hopes will be her ticket to power. “We each need to figure out what we believe in, and how to stand for something,’’ she declared at a Met Gala presser.

But has she? And is she really ready to seek elective office?

“If her brother wasn’t gone, he’d probably be running for president,’’ says Kathy McKeon, Jackie Kennedy’s former personal assistant, who helped bring up Caroline and brother John Jr. “When Caroline was growing up, she always said she wanted to be a wife and mother, and she is a very good mother. But the Kennedys are go-getters who never give up, and after John died, I think Caroline had that sense of duty in her to follow in her father’s footsteps, and I believe she’ll pull it off.

“I really think she might be the first lady president.’’

But then…this is a nation that hasn’t always been kind to Kennedys. And Caroline comes from the wing of the family that knows that best, even if it is the one that gave it its godlike status, and has paid most dearly for that hubristic inheritance.

Though no one doubts that Caroline has the name recognition and funds—with her estimated Kennedy/Onassis fortune of $500 million—to mount a race, she faces skepticism from some Democratic Party power players, who recall how she bowed out of her 2008 effort to be appointed to the New York Senate seat vacated when Hillary Clinton became secretary of state. Despite a public policy background that included interning in her uncle Ted’s Senate office, she was woefully unprepared to answer even the most basic questions about her qualifications for the job, stammering “you know” some 235 times during a 41-minute New York Post interview. She also was dismayed by lurid rumors—denounced by all concerned as totally false—that she was cheating on her husband, Edwin Schlossberg, with Times publisher Arthur Ochs Sulzberger Jr.

“Amazingly, Caroline believed that there was such public affection for her as the last child of Camelot that she’d be treated with kid gloves,” Christopher Andersen, the author of a 2003 biography, Sweet Caroline, says of the 2008 fiasco. “The truth came as a quite a rude shock. That she might actually have to answer questions about her private life, especially her marriage? Unthinkable!” 

Presiding over an embassy has honed her self-confidence, however. And while she remains notoriously press-shy (she didn’t even respond to multiple requests for cooperation with this article) her daughter Tatiana is in a perfect position to serve as an advisor or surrogate, having just left a position as a Times reporter specializing in President Trump’s pet peeves, climate change and the environment. And she certainly has a ready-made constituency in liberals who hunger for someone with the fame and ideological cred to reverse the electoral debacle of 2016. She is “the next Hillary Clinton, but without Hillary’s baggage,” says one supporter.

So Kennedy is believed to be eyeing the Lower Hudson district occupied by the 80-year-old Democratic congresswoman Nita Lowey. As a backstop, with Lowey insisting she has no plans to retire, sources who claim to speak for Kennedy say she also is interested in being appointed to replace New York’s junior senator, Kirsten Gillibrand, who now occupies Clinton’s former seat, if Gillibrand mounts a 2020 White House run.

Andersen concurs that the last survivor of Camelot “has an absolute obsession with posterity. That’s what drives her more than anything else, that her father be remembered.” But there’s also a school of thought which says that desire can be fulfilled by, to paraphrase her father, passing the torch to a new generation, born in the waning days of the last century, tempered by this one, and disciplined by tragedies both personal and historic to face a hard and bitter fight.

Rather than subject herself to the slings and arrows of another campaign, Andersen surmises that she really may be stoking desires for a Kennedy revival while grooming her son for a race. “My bet is on Jack,” Caroline’s biographer says. “He has been at his mother’s side during most of her recent TV interviews, and it’s pretty clear Caroline is pushing him into politics. He’s helped by the fact that he doesn’t have to contend with the ghosts and demons that swirl around her to this day.’’

Quizzed on Today about whether Jack is eyeing a congressional race, Caroline deftly ducked the question: “I will support whatever decision he makes,” she said slyly.

In a three-hanky Kennedy Library video commemorating this year’s 100th anniversary of her father’s birth, Caroline confides, “I have thought about him and missed him every day of my life.’’ Reminiscing about his crusades for universal healthcare, human rights and a “nation of immigrants,’’ she vows, “As my father said in his inaugural address, ‘This work will not be finished in our lifetime, it’s up to us to continue to pass these values on to our children and grandchildren.” Political observers inevitably have interpreted the film—which also features Jack and his sisters, Tatiana and Rose—as the cynical season opener for a forthcoming campaign.

Family insiders say that for all of JFK’s shortcomings, “Buttons,’’ as he nicknamed his cherubic blond daughter, iconized him. Caroline was just short of her sixth birthday when he was gunned down on November 22, 1963, and McKeon—who recently published a bestselling memoir, Jackie’s Girl—says the little girl’s grief was heartbreaking. 

“She said a Hail Mary for him in her prayers every night,’’ McKeon, now 72, told AVENUE. ‘’It was so sad. She didn’t trust people that well. She was very caring about people, but she had a kind of fear of the world. She’d say, ‘You never know who’s going to get you, Kath.’’’

Andersen says: “Caroline has had to endure one emotional hammer blow after another. Ignore that toothy Kennedy grin and focus on the eyes. You will see a lot of anguish there, even now.”

Living up to the expectations of a Capote “goddess’’ was a different kind of burden. Caroline was a brilliant student who aced classes at her private schools and as a Radcliffe fine arts major, but Jackie’s concern, Andy Warhol recorded in his diary, was that “her behind is so big.” Her mother, who subsisted on a social X-ray regimen of boiled eggs and cottage cheese, had to march her to a doctor who prescribed diet pills. “You’re not going to order dessert, Caroline,” she snapped at a meal in a Paris restaurant in a tirade overheard by other diners. “You’re much too fat. Nobody will ever want to marry you.”

With her charismatic brother designated as the family’s president-in-waiting, Caroline dutifully followed in Jackie’s footsteps as a patron of culture and the arts. In July 1986, she married 41-year-old interactive media designer Ed Schlossberg and devoted herself to their three children: Tatiana; Rose, a budding actress; and Yale grad Jack, who is heading to Harvard Law School. “She is first and foremost a wife and mother,’’ stressed Paul Kirk Jr., a Kennedy Library official after the immaculately groomed Caroline dipped a tentative toe into public life and joined its board as president in 1987.

After graduating Columbia Law School in 1988, she cowrote a book with a former classmate, Ellen Alderman, about the Bill of Rights. In 1995, a year after Jackie’s death, the pair brought out a tome titled The Right to Privacy. Unquestionably Caroline has inherited her mother’s distaste for the media, as well as her ability to carve out personal space for herself and her family despite being in the public eye. Friends who made flattering comments about her for a 2009 New Yorker story about her Senate campaign subsequently withdrew them for fear of “banishment’’ from her inner circle, the magazine reported.

Her image of old-money rectitude has been eroded, however, by two auctions she helped to organize of such family chattels as John Jr.’s high chair, Jackie’s fake pearl choker and JFK’s rocking chair. The sales raised about $40 million. Privacy, in her lexicon, is about maximizing control over the family fortune, say critics, who recall how she led a Kennedy effort to challenge businessman Robert L. White’s right to sell a collection of Kennedy tchotchkes he claimed he had accumulated legitimately, such as her father’s Hermès briefcase and Cartier watch.

The case cost White nearly $1 million in legal fees and was still going on in 2003 when he died of a heart attack at age 54. ‘’He had a heart problem, but I think the case stressed him out and he died prematurely,’’ says a family member.

Caroline and her husband also have enraged conservationists by subdividing Jackie’s beloved Martha’s Vineyard estate, Red Gate Farm. Two parcels fronting the ocean and Squibnocket Pond are on the market for $27 million. The Boston Globe reported in August that Barack and Michele Obama were  “looking to buy” the land. A source close to the ex-president told AVENUE, however, that the report was untrue and that he suspected it was a ploy to attract purchasers because the lots “aren’t moving. They’re so overpriced.”

Moreover, the LBJ Presidential Library archivist Jennifer Cuddeback has told AVENUE that in a particularly unusual and controversial move, Caroline copyrighted her mother’s handwriting before giving her correspondence to the center. “I reconfirmed this with the supervisory archivist at the Kennedy Library, Karen Abramson. Ms. Abramson informed me that according to the deeds of gift signed June 2009 and December 2010, copyright was assigned to Caroline Kennedy and her children,” Cuddeback says.

“In my experience, handwriting is not typically copyrighted in personal papers collections.”

Oliver Herzfeld, the general counsel to a New York brand

licensing firm, Beanstalk, predicts that if a legal challenge arises, Caroline will have a tough time defending her right to profit from her mother’s John Hancock. “In the United States, the shapes of typefaces are generally not copyrightable,” he says. “I think Caroline is not on the winning side of this issue.”

Kennedy has profited handsomely from her legacy, publishing, among her many books and collections, transcripts of her mother’s conversations with Kennedy friend and house historian Arthur M. Schlesinger (which came with a CD of their interviews); an update of her father’s book Profiles in Courage; and a volume of her mother’s favorite poems. Her obsession with squeezing the last cent from her inheritance is defended by Christopher Andersen as yet another hangover from her unhappy childhood: “Despite his great wealth, JFK complained bitterly about Jackie’s spending. Caroline was raised from childhood with the nagging fear that, while they were indeed rich, they would never be rich enough,” he says. “That’s the Bouvier curse.”

While her fortune gave her the means to mount her 2008 Senate race, it quickly turned into a curse when she was pilloried by Democratic Party power players such as Hank Sheinkopf, a member of Bill Clinton’s 1996 presidential reelection team. Charging that she had shown no interest in policy issues, he portrayed her in a CNN commentary as being cocooned by her wealth and the Camelot “fairy tale.”

Some of the vicious coverage of her that year is said to have been orchestrated by Sidney Blumenthal, a longtime Clinton henchman who also was a consultant to the Daily Beast. He reportedly commissioned and edited two pieces for the site that lampooned her campaign as a “puppet show.” Daily Beast founder and then editor-in-chief Tina Brown also weighed in: “Caroline has led a parochial, socially timid life centered on Manhattan’s most cosseted enclave, remote from the competitive cut and thrust of local or national politics, the blood-coursing challenges of winning and losing that defined her father’s side of the clan,” she sniped.

A Clinton confidant told AVENUE that the attacks were revenge for Caroline’s endorsement of Barack Obama over Hillary in the 2008 Democratic Presidential race. Clinton loyalists also allegedly spread the scuttlebutt about her marriage: “Bill Clinton was always loyal to the Kennedys. They were his role models and heroes,” the confidant says. “So when Caroline led the family, including Teddy, Maria [Shriver], and the whole crew except Bobby’s older child, Kathleen, in supporting Obama, the Clintons felt betrayed. It hurt. Deeply hurt.

“And when you betray the Clintons, Sidney is like an attack dog who will go after any legitimate target, including the state of an opponent’s marriage. That’s how the rough-and-tumble of politics works. Caroline didn’t have the stomach for it.”

Members of the couple’s inner circle were appalled: “[The Schlossbergs] are very happy and will live happy ever after,” says Marta Sgubin, Caroline and John Jr.’s former governess, who went on to help raise Jack, Tatiana, and Rose. A Times spokesman also shot down the gossip about an affair: “Mr. Sulzberger is not and never has been romantically involved with Ms. Kennedy.”

Caroline succeeded an unassuming Silicon Valley lawyer and political activist, John Roos, as U.S. ambassador to Japan. Thousands of onlookers waved as she clopped in her coach to the imperial palace escorted by a footman in breeches. “John Roos went by car to present his credentials,” says Roland Kelts, the Tokyo-based author of a book about Japanese culture, Japanamerica. “But Caroline agreed to arrive in a carriage. She knew the value of the Kennedy name, and during her time in Japan she used this soft power very effectively.”

The question is whether her time in Japan will help her if she runs for Congress. And whether the Clinton family will seek to foil her again. “Chelsea Clinton is hungering to succeed Nita Lowey or Gillibrand—whichever of them steps down first,” says a Clinton insider. “If Caroline runs against Chelsea, all the dirt will be wheeled out against her again and then some. The golden carriage is a great attack ad.

“My bet is that Caroline knows that and will make the smart move and run Jack. The boy is 24. He has the magical Kennedy name.” He also has the advantage of being a bachelor. “Female voters will love him,” the insider predicts.

Cue in Jack’s bare-chested August photo for New York magazine, accompanying an essay about how he paddleboarded, with “beet juice pulsing through my veins,” in a 25-mile Manhattan charity race.

That old black Irish magic may just have us under its spell again. 


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