The Good Son_JFK Jr. and the Mother He Loved

by Christopher Andersen

  Then, of course, there was the matinee idol face, the megawatt smile, the chiseled physique. John’s looks, even his closest male friends had to concede, were exceptional. “I am a heterosexual male,” John Perry Barlow said, “and there were times when he was sitting across me at the table and I would sort of be taken aback by how handsome he was. You’d sort of say to yourself, ‘God, this guy looks perfect.’ ”

  The editors of People agreed, anointing John as the world’s reigning male sex symbol by putting him on the cover of its September 2, 1988, issue as “The Sexiest Man Alive.” The story’s cloying first paragraph: “Okay, ladies, this one’s for you. But first some ground rules. GET YOUR EYES OFF THAT MAN’S CHEST! He’s a serious fellow. Third-year law student. Active with charities. Scion of the most charismatic family in American politics and heir to its most famous name.”

  The magazine’s “serious fellow” caveat aside, Jackie viewed John’s new Sexiest Man Alive image as a crass attempt to exploit the Kennedy name—and a serious setback to his embryonic public-service career. After all she had done to steer her son away from the glitz of show business, Jackie also worried about the impact all this attention was bound to have on John’s ego. “He already knows that he’s gorgeous,” she told her friend Bunny Mellon. “I hope all this doesn’t distract him from what’s really important.”

  John was determined to enjoy the moment, and poke fun at himself in the process. He put on a fig leaf and showed up at one Halloween party that year as Michelangelo’s David. He went to another party as “the Golden Boy,” attired in gold glitter and a loincloth. Later, he would offer the definitive answer to people who suggested all the attention was somehow beneath him. “Listen,” he told ABC’s Barbara Walters, “people can say a lot worse things about you than you are attractive and you look good in a bathing suit.”

  Now that he was a bona fide sex symbol, John’s love life was fair game for the tabloids. Not that this in any way inhibited him. John was “sleeping with every hot chick on the planet,” Billy Noonan said.

  John liked to call his best friend and leave a taunting message. “Check out the cover of People [or Vogue or Vanity Fair],” John would say. “I banged her last night. Just thought you might like to know.” Later, Noonan would get all the juicy particulars from John over the phone. “The possibilities were limitless,” he said, “and John played them out.”

  The temptation to draw parallels between the Sexiest Man Alive and his womanizing dad was irresistible. Ever since the revelations about JFK’s affairs began to emerge in the late 1970s—with Marilyn Monroe, Judith Campbell Exner, and others—Jackie and John just looked the other way. “Obviously,” Gore Vidal said, “it’s not the kind of thing a boy brings up to his mother. They just pretended none of it ever really happened. All the Kennedys are very good at that.”

  * * *

  ONE UNWELCOME REMINDER of JFK’s torrid affair with Marilyn—the affair that most troubled Jackie—arrived on her doorstep in the form of another blond bombshell by the name of Madonna. Already a pop icon, Madonna was best known at the time for her “Material Girl” video, an homage to Monroe’s “Diamonds Are a Girl’s Best Friend” number from the film Gentlemen Prefer Blondes.

  The Material Girl and JFK Jr. met briefly at a party following one of her concerts at Madison Square Garden in 1985. Three years later, after the breakup of her stormy marriage to Sean Penn, she went after John. Beyond the obvious—stories of her sexual escapades abounded—Madonna was convinced that destiny was taking a hand in bringing together the undisputed heiress to Monroe’s platinum persona with the son of JFK. She told friends she believed that her affair with JFK Jr. would be nothing less than “cosmic.”

  Like his mother, John was perfectly capable of being starstruck. “You could see it in his eyes that first time they met,” said dancer Erika Belle, one of Madonna’s closest friends at the time. “John was totally in awe.”

  In a clumsy effort to avoid detection, the couple rendezvoused at the health club where they both worked out and shared the same trainer, venturing outside together only for a quick morning jog through Central Park. She quickly came up with her own handles for John; Madonna called him either “Johnny,” or just “Kennedy.” It wasn’t long before John took Madonna to meet his mother.

  At 1040, Madonna stepped off the elevator and signed the guestbook “Mrs. Sean Penn” (technically, she still was). Not surprisingly, Jackie was anything but thrilled with this particular liaison. There were many things about Madonna that rubbed Jackie the wrong way, not the least of which was her habit of thumbing her nose at Roman Catholic rituals. Madonna’s use of crucifixes and other Catholic images was deemed sacrilegious by the Vatican, and across the globe she was being condemned as a heretic. Nor did it help when Jackie picked up a copy of Life only to see Madonna dolled up as Marilyn on the cover. “I imagine it was all hitting a bit close to home,” Vidal said.

  Had she been able to look past Madonna’s brassy exterior, Jackie would have recognized an articulate, well-read young woman who could speak knowledgeably about art, dance, and fashion. Madonna also had a head for business. At that time, Forbes put Madonna on its cover as one of the wealthiest women in the entertainment industry, with a then-impressive personal net worth approaching $40 million (which would, according to Forbes, grow to over $500 million by 2013).

  John, of course, wasn’t interested in Madonna because of her head for business. One day while he was staying with Billy Noonan in Hyannis Port, John phoned New York to check his messages. On the other end, a woman with a familiar voice was calling from Rome. “Kennedy,” she began, “I’m drunk and when I see you next I’m going to take your . . .” The rest was decidedly X-rated, and after John played it for Noonan, his friend asked to hear it again.

  Unable to quite place the voice, Noonan begged John to tell him who it was. “Madonna,” John answered matter-of-factly.

  Noonan was speechless. “You are banging Madonna?” Noonan asked. “How do I not know this until now?”

  So what was it like sleeping with Madonna? “Let me tell you,” Kennedy replied, “she’s a sexual dynamo.”

  The only place the superstar couple could let their guard down was in Hyannis Port, where they bundled up in sweaters and jackets and jogged on the beach. Inside the compound, they curled up by the fire, sipping daiquiris from Waterford crystal glasses marked “Caroline” and “John-John”—souvenirs from the family’s first trip to Ireland after the assassination.

  If John sought during this period of his life to emulate his skirt-chasing father by having an affair with the 1980s’ answer to Marilyn, it was hard to think of anyone who fit the bill more perfectly than the Material Girl. Given the obvious and frequently drawn parallels between Madonna and Monroe, it was also difficult to imagine anyone whom Jackie would find more offensive or unacceptable as a love interest for her cherished only son. It is highly doubtful that John intended to hurt his mother, but his decision to carry on an affair with his generation’s reigning blond pop goddess appeared to offer a way—however far-fetched or ill-advised—for John to connect with his father by experiencing something akin to what Jack experienced.

  In New York, the JFK Jr.–Madonna affair stayed tightly under wraps. Amazingly, they managed to avoid detection largely by attending parties and plays separately, then getting together afterward.

  Somehow, John was managing to keep this clandestine liaison from his steady girlfriend, Christina. “She hasn’t a clue,” he told Noonan. After another midday lovemaking session at a New York hotel, John rushed to meet up with Haag. She leaned into his chest and inhaled. “Whose perfume is that?” she asked him.

  “Oh, that? I ran through Bloomies to get here,” he said, using shorthand for Bloomingdale’s department store. “I stopped at the perfume counter to get you something but all these salespeople ran up spritzing me, and it started attracting attention, so I just said to hell with it . . .”

  Christina was dubious, but let it slid
e. Madonna’s ex was less charitable. After a tribute to Robert De Niro at New York’s American Museum of the Moving Image, JFK Jr. joined Jeremy Irons, Liza Minnelli, Sean Penn, and other celebrities at a party in De Niro’s honor at the Tribeca Grill.

  At one point during the festivities, John walked up to Penn, stuck out his hand, and introduced himself.

  “I know who you are,” Penn glowered back. He was clearly still incensed over reports that John and his wife were sleeping together while she was still married. “You owe me an apology.” Aware of Penn’s fondness for fisticuffs, John beat a hasty retreat. The next morning, a funeral wreath of white roses bearing the inscription MY DEEPEST SYMPATHIES arrived at John’s front door. “Johnny,” the card read, “I heard about last night. m.”

  Jackie, who became a grandmother for the first time when Caroline gave birth to Rose Schlossberg on June 25, 1988, was still rooting for John to marry Christina Haag. After running into Christina at a performance of Macbeth starring Christopher Plummer and Glenda Jackson one evening, she and Maurice Tempelsman offered Haag a ride home. As their limo passed the marquee for Speed-the-Plow, the David Mamet play in which Madonna was making her Broadway debut, Jackie grabbed Haag’s arm.

  “Oh!” Jackie said. “Have you seen it?”

  “Not yet,” Haag replied. Both Jackie and Haag knew about John’s rumored affair with Madonna, but for now all Christina could do was accept John’s fervent denials.

  Jackie, of course, knew otherwise.

  “The play was good, but Madonna was terrible,” Jackie said, laughing between puffs on a cigarette (by this time she had switched to Marlboros). “I think you should go. I think you should go next week—and have John take you. And go backstage!”

  Fortunately for everyone involved, Haag did not take the bait. But whether it was out of a desire to see Christina confront Madonna or simply to make her skirt-chasing son squirm, it was clear that Jackie did not approve of John’s romantic entanglement with the woman who billed herself as the 1980’s answer to Norma Jean.

  * * *

  EVEN BEFORE HE ended his affair with Madonna, John racked up other celebrity conquests. Returning from a trip to Los Angeles, John arrived at the Delta terminal at JFK Airport and was walking outside to find his waiting car when he heard someone call his name. The door of a limousine opened, and out popped Sarah Jessica Parker, who later became best known for television’s Sex in the City. Taking her cue from swimwear model Ashley Richardson, Parker wore a mink, high heels, and—as a titillating flash of her coat revealed to John—nothing else.

  The Kennedy-Parker affair, which John conducted while he was seeing Madonna, among others, lasted only a few months. “The body’s beautiful,” Parker acknowledged, but added that she found it impossible to deal with constantly being upstaged by him. “What you have is wrong,” she joked with him. “It’s not right. It’s unfair, as a woman, to have to stand next to you.”

  Another of John’s celebrity romances lasted longer; it would jolt along in a series of fits and starts for more than five years. John had actually met Daryl Hannah when they were both eighteen and vacationing with their families on St. Martin. The stepdaughter of billionaire Chicago financier (and major Democratic Party contributor) Jerry Wexler, leggy, blond Hannah was not about to go unnoticed. To make certain of this, she toted around a teddy bear on the beach, at restaurants and clubs—wherever she went.

  By the summer of 1988, Uncle Teddy was trying to curry favor with Wexler by setting John up with Hannah. But it wasn’t until that September that they finally met again, at the wedding of Lee Radziwill to director Herb Ross. Hannah no longer needed a teddy bear to be noticed. She was now a major box-office draw with such hits as Splash, Wall Street, Roxanne, and Ross’s Steel Magnolias under her belt.

  Hannah lived with rocker Jackson Browne at the time and John was still stringing Haag along. But within weeks they were spotted dining in a West Village restaurant, then shooting pool almost until dawn at S.T.P., a bar in TriBeCa. Hannah missed John’s graduation from NYU Law School in May 1989—Christina was there alongside Jackie and Caroline—but it was Daryl, not Haag, who was chosen by John to accompany him aboard a forty-six-foot yacht cruising Virginia’s Smith Mountain Lake.

  Yet as long as she knew John was seeing other women—publicly he made a point of referring to Haag as his girlfriend—Hannah was not about to end her often-stormy relationship with Browne. Over the years she ricocheted between the two men, leaving John confused and at times heartbroken. “Until she was the only woman in John’s life,” said Daryl’s former assistant, Natalie Cross, “she wasn’t about to give Jackson up.”

  Meanwhile, John was studying for the brutal New York State bar exam in July 1989 when Hannah abruptly picked up and returned to her mercurial rock star boyfriend for the first time. One week later, John failed the bar exam along with 2,187 others.

  “I failed the bar exam, too,” former New York City mayor Ed Koch wrote John. “It didn’t stop me and it won’t stop you.” Still, John was humiliated by THE HUNK FLUNKS headlines. After all, his sister had aced the bar exam on her first try, was already writing a book on the Bill of Rights, and had to juggle all this with being a full-time mom. (Caroline gave birth to her second child, Tatiana Celia Kennedy Schlossberg, on May 5, 1990.)

  John offered no excuses. “Now I have to suck it up,” he said, “and give it all I have next time so I won’t have to do this again.” In the meantime, he was still permitted to earn thirty thousand dollars a year working as one of sixty-four rookie assistant prosecutors under longtime Manhattan district attorney Robert Morgenthau. He would be allowed to prosecute low-level cases once he passed the bar, but for now he was restricted to doing legal research and interviewing defendants.

  At this point, John’s scofflaw past caught up with him. A quick background check revealed that John had accumulated $2,300 in unpaid parking tickets and that there were several outstanding moving violations, including driving an unregistered vehicle, making an illegal turn, and, of course, speeding.

  Once those infractions were quietly cleared away by John’s lawyers, he was allowed to report for work at the DA’s office on Hogan Place. That day, a mob of reporters blocked his way. Uniformed police escorted him inside and onto the elevator—then asked for his autograph. A tabloid offered one paralegal ten thousand dollars just to surreptitiously take a photo of John at his desk.

  JFK Jr. was the only assistant DA permitted to have his own secretary just to handle the mail addressed to him at the office. “There were love letters, invitations to parties, lots of pictures of naked girls,” said Jill Konviser, whose office was next to John’s. “The other idiots in my office would fight over them.”

  Another of his colleagues at the DA’s office, Owen Carragher Jr., praised John for “fitting in. In ways that are most meaningful, he was just one of us—except with better girlfriends.”

  With Carragher and the other new arrivals, John was assigned to the complaint room, where the prosecutors meet with defendants twice a week. “It was disgusting, it was filthy,” Konviser said, “and it stinks, and people scream at you.” Everyone complained—everyone but John.

  Still coping with his ADD and a mild form of dyslexia, John took several bar review courses but was “unable to sit still for more than ten minutes at a time,” said a fellow lawyer. There was a door off the classroom opening onto a balcony, and, according to his colleague, John jumped up three or four times during the class to open it “for really no reason. He just seemed to have this need to constantly be in motion.”

  When John failed the bar a second time in early 1990, the headlines were merciless. THE HUNK FLUNKS—AGAIN! blared the front page of the New York Post. Confronting the mob of reporters that waited outside the district attorney’s office, John struck a hopeful if vaguely defiant tone. “Obviously, I’m very disappointed,” he said, pointing out that he had fallen just eleven points short of a passing grade of 660. “Close is only good for horseshoes,” he has
tened to add, “not for the bar exam. But you know, God willing, I’ll go back there in July and I’ll pass it then. Or I’ll pass it the next time, or I’ll pass it when I’m ninety-five. I’m clearly not a major legal genius.”

  Maybe not, but no one who knew John thought he was dumb. “That whole notion that he was stupid is a myth,” Barlow said. “John was very, very intelligent. A little scattered, but really smart.” John’s boss in the DA’s office, Michael Cherkasky, agreed. “He was very smart, very committed,” Cherkasky said, “and a good lawyer.”

  Once again, John put a brave face on things. But privately he was, in Barlow’s words, “crushed.” This failure was so bad, Littell added, “it drove him to drink.” John climbed into his newly purchased truck, a blue GMC Typhoon, and checked into a motel in Lake George, some 215 miles north of Manhattan. Alone, he holed up with a bottle of Macallan Scotch.

  As upset as John was about the drubbing he was getting in the press, it was no match for Jackie’s rage. She concealed her true feelings from the public, as did her son, but privately Jackie railed against the newspaper editors who delighted in portraying John as dim. “They’re really having a field day with this,” she told Ed Koch. “It’s so unfair, and it just makes me so furious.”

  Failing the bar a second time and the media frenzy it ignited did more than just drive John to drink. It drove him to see a therapist. His entire life, John had been held up to the impossibly high standard set by his father. Now he was forced to take a long, hard look at how he stacked up to the slain president. At twenty-nine—John’s age now—his father had already distinguished himself as a war hero, written two bestselling books (one of which won the Pulitzer Prize), and been elected to Congress. Just a few days after John failed the bar exam a second time, a senior prosecutor in his office made a cutting remark about how far JFK had gotten by this age.