“Jackie Refuses to Meet Madonna”

Jackie Kennedy Onassis, America’s revered former First Lady, was already well aware of the whisperings of something romantic going on between her only son and Madonna. She used to purchase all the tabloids and other papers at a newsstand in the lobby of the publisher Doubleday’s Fifth Avenue offices (where she worked as an editor) to keep up on current events, and that’s where she first read the news about the growing romance. She quickly made it clear to John that she did not approve.

Thomas Luft, whose mother was close to Jackie, said, “He couldn’t decide if he was intrigued by her because he liked her, or because Jackie didn’t like her — not that Jackie ever met her. He said, ‘I don’t want to string her along if I’m really just rebelling against mother.’ His therapist had told him that Madonna represented insurrection to him, not romance.”

For her part, what most fascinated Madonna about John was his complete lack of pretense. “We were exercising with her, running through Central Park one day,” recalled Stephen Styles. “She had four bodyguards trailing her. John, of course, had none. It was so ludicrous, I said to him, ‘Why is it that she needs all of that security and you don’t need any?’ He laughed and facetiously answered, ‘I may be a Kennedy but, hey, man, she’s Madonna!’”

“He always introduced himself as just John, never John Kennedy,” another college friend, Richard Wiese, remembers. “The word ‘Kennedy’ never came willingly off his lips. He downplayed it as much as possible . . .”

“Johnny, do you know how big a star you could be if you only acted like a Kennedy instead of just any other person?” Madonna told him. She was nearly unrecognizable in a baseball cap, scruffy hair, and a T-shirt belted outside cycling shorts. She was chewing gum, as John liked to say, “like it’s going out of style.” She said, “I mean, my God! You could be absolutely huge!”

“Oh, don’t worry about me. I’m huge enough,” John said with a grin. He, too, was in tight biking shorts and a simple white T-shirt. A baseball cap was turned boyishly backward. His chiseled cheeks were shadowed by two days’ growth of beard. “I don’t want to be a star,” he said, dark eyes dancing. “I’m just me.”

Madonna seemed stunned. “But how could anyone not want to be a star?” she asked.

“Count me out,” John said, still jogging. “You can be the star in this family.” Then, with a grin back at her, he sprinted off.

While dating Madonna, John moved into a two-bedroom apartment near his mother’s penthouse on Fifth Avenue. As a surprise, Jackie hired a maid to help him organize his belongings. In the process, the maid apparently disposed of love letters Madonna had written to John. When John discovered the loss, he was angry because he thought that the maid had actually been following instructions given her by Jackie. However, those close to the family say Jackie had no idea what he was talking about when he confronted her about what had occurred. Also, she couldn’t believe that her son would accuse her of such behavior. She chalked it up to Madonna’s “bad influence on him.”

When John finally told Jackie that he had fallen for Madonna, she made it clear that she was unhappy about this turn of events. Jackie had been concerned about her children’s social status since they were young. Always protective of them, she was suspicious of most of their friends and unyielding in her demand that both John and his sister, Caroline, remain single until after graduating from law school.

“Jackie wanted her son to be with a woman of a certain breeding,” said a Kennedy family friend, Senator George Smathers of Florida (who was also very close to President John F. Kennedy). “She wanted both of her children to be with a person of class. But John always gravitated toward movie stars and flashy types, a lot like his father. Jack Kennedy ended up with Marilyn Monroe and, somehow, John ended up with Madonna. I don’t know which scenario most upset Jackie: her husband with Marilyn, or her son with Madonna.”

If Madonna had been single, perhaps Jackie would have been better able to deal with the relationship (though, no doubt, she would still have been unhappy with Madonna’s sexually charged image). She didn’t want to have to deal with the scandal it would have caused if word had gotten out that John was dating a married woman. Also, according to those who knew her, she had heard stories — many of which were probably accurate — about Sean Penn’s temper. She feared for her son’s safety. But, says Thomas Luft, who witnessed the scene, John told Jackie, “Mother, I can take that loud-mouthed little punk Penn blindfolded and with one arm tied behind my back.” “And he could have, too,” said Luft. Jackie shivered at the thought. “Oh, great! That’s all I need, John,” she said, “seeing you led away in handcuffs for getting into a fight with that hooligan. Don’t you dare!”

Also, Jackie feared that Madonna might influence John to reconsider a future as an actor, something she definitely did not want to occur. He had appeared in a couple of plays in college and, though she attended the performances to demonstrate her support, she asked him not to become an actor. Her dream was to see her son as an attorney.

“I was there at her home on Martha’s Vineyard when Jackie told John, ‘I need you to think about this, carefully. Madonna may be a nice girl, but until she is single, she will be nothing but trouble,’” says Thomas Luft.

“But I like her,” John said, trying to reason with Jackie. “She’s quite intelligent. You should know her, Mother. You’re an editor! She’s just the kind of woman you would find fascinating.”

Luft says that Jackie rolled her eyes and shook her head in what appeared to be complete dismay.

“My goodness, there are millions of intelligent women on this planet, John,” she told him. “And you have to go out with the only one who calls herself a ‘Material Girl’? I just don’t understand it. I mean, really!”

“John got angry,” says Luft. “Even though I was standing right there, and he never talked back to his mother in front of others, he shot back, ‘Mother, let me ask you this: who in this world has been more materialistic than you?’”

Luft recalls that Jackie shot him a look. Then, without warning, tears came to her eyes. She rushed from the room. John was immediately overwhelmed by regret. “Mother, please, I didn’t mean that,” he said, following her. “I’m sorry.” Then, for the rest of the day, he was angry with himself. “How could I be so stupid and mean,” he said. “Stupid, stupid, stupid,” he muttered, chastising himself. “But I like Madonna,” he told Thomas Luft, “and, damn it, I’m going to date her.”

One wonders if Madonna ever imagined the impact she had on these denizens of so-called Camelot . . . and if ever she would have believed any of it possible just a few short years earlier.

*

With Sean Penn in Asia filming Casualties of War, Madonna was free to explore a number of life options. In her personal life, there was the possibility of a long-term relationship with John Kennedy, Jr., though that seemed a long shot. As adorable as he may have been, she would later have to admit that something was “missing.” She liked strong-willed, powerful men. John seemed too reliant on his mother, his family, for strength. She needed time to marshal her thoughts, but it did seem that her future with Kennedy had certain limitations.

Professionally, Madonna was considering a Broadway show which, she hoped, would allow her to shine so brightly that she would be able to eradicate the memory of the many bad reviews generated by her last two films. She wanted to prove that she could act. Film director Mike Nichols had mentioned to her a part in David Mamet’s Speed-the-Plow. Madonna was a huge fan of Mamet’s earlier works and has said that she went after the role in his new play “with a vengeance.” She personally called Mamet and requested an audition.

The plot of Speed-the-Plow involved a plain, seemingly naive secretary, Karen (Madonna), who comes between two movie moguls (Joe Mantegna and Ron Silver) known for their production of surefire, commercial Hollywood films. Mantegna bets Silver $500 that he can bed Karen. However, she turns the tables by seducing him. She then tries to convince him to put up the money to turn a brainy, pretentious book she has been reading, one with absolutely no commercial appeal, into a film. Mesmerized by the dynamic woman masquerading as a plain office worker, he agrees to her request — almost enabling Karen to destroy the commercial deal that Mantegna and Silver virtually have in the bag. Madonna described her character as, “honest, sincere and naive, and hungry for power, like everybody else.” Her observation proved that, at first, Madonna didn’t even realize that her character was not what she seemed to be; she was anything but naive. “It was a real mind-fuck of a script,” she discovered midway through rehearsals. “Little did I know that everyone else involved saw me as a vixen, a dark evil spirit.”

Whether or not Madonna agreed with the interpretation of the role, her name on the marquee meant big business for the show. It sold out for six months in advance, which meant millions of dollars in ticket sales. Although the three-character play did much to confirm Madonna’s drawing power, it did little to reverse critical reaction to her acting skills. Madonna’s opening night on May 3, 1988, at the Royale Theater in New York City attracted celebrities such as Brooke Shields, Jennifer Grey, Jennifer Beals, Tatum O’Neal, Christie Brinkley and Billy Joel.

While the critics praised the play, they panned Madonna. “She moves as if she were operated by a remote control unit several cities away,” said Dennis Cunningham of CBS, adding that “her ineptitude is scandalously thorough.” John Simon of New York magazine complained that “she could afford to pay for a few acting lessons.” The Washington Post’s David Richards said simply, “she’s the weakest thing in it.” Madonna, though, was happy with her performance. “It’s like having really good sex,” she said of the experience.

“I hated to love it and I loved to hate it,” she said, later. “It was just grueling having to do the same thing every night, playing a character who is so unlike me. I didn’t have a glamorous or flamboyant part. I was a scapegoat. That’s one of the things that attracted me to it. Still, night after night, the character failed in the context of the play. To continue to fail each night and to walk off that stage crying, with my heart wrenched . . . it just got to me after a while.”

Also in that first-night audience, perhaps to check out her son’s latest romantic interest, was Jackie Kennedy Onassis.

“John told me that Jackie thought she was ‘fascinating’,” said Stephen Styles. “I asked him, ‘What does that mean?’ and he laughed. ‘That’s Mother’s way of saying that Madonna isn’t her cup of tea,’ he said.”

“Madonna didn’t know Jackie was in the house [the theater],” said Diane Giordano. “If she had known, as fascinated as she was with Jackie, she might have had trouble going on, she would have been that nervous.”

After the show, when Madonna was told that Jackie had been in the audience, she waited backstage for an hour, hoping the former First Lady would come back and say hello. She had applied a pale, almost white foundation to her face, which contrasted dramatically with her bright red lips. Carefully she penciled in her eyebrows and then shaded her beauty spot. She pulled her dark hair back severely and dressed in a natty, gray, pinstriped Armani trouser suit with a white silk blouse — buttoned all the way to the top. Three friends joined her. Someone fixed martinis. Then they waited . . . and waited. Jackie never showed up.

Later, Madonna would say that Jackie’s absence backstage “ruined” her opening night. “The only reason a person doesn’t come backstage after a show is if they didn’t like what they saw and don’t know how to tell you that,” Madonna said, sadly. “If I had only known she was out there, I swear to God, I would have been much, much better. I would have tried so much harder. Why didn’t Johnny tell me she was coming?”

Madonna loved a good icon, always had. She was such an admirer of Jackie, she desperately wanted her approval, especially now that she was dating her son. She was certain, she told friends, that she would be able to convince Jackie that she wasn’t as notorious as the former First Lady believed her to be. However, Jackie steadfastly refused to meet her. “How can she not take my calls?” a perplexed Madonna was reported as having said. “Doesn’t she know who I am?”

Privately, Jackie told a colleague at Doubleday, “I don’t want to validate the relationship by meeting her. I’m not going to have her going around saying that she and I are friends.” If circumstances had been different, no doubt Jackie would have wanted to meet Madonna and discuss with her the writing of her memoirs for Doubleday, just as her son had observed. In fact, she asked certain people in the publishing company’s editorial division if they thought Madonna had a compelling story to tell. She was told that such an autobiography would definitely translate into a best-seller. When she asked for details, she was duly intrigued but also more sure than ever that this woman was not for her son. “Yes, she has had an amazing life,” Jackie said to a source, “but I simply don’t want my son to now be a part of it.”

In July 1988, Madonna pleaded with John to arrange a meeting with his mother. Two other people were present at John’s Upper West Side apartment in New York with John and Madonna while they engaged in a conversation about meeting Jackie. John was in red sweats and a black T-shirt with the words “Man Power” emblazoned across his chest in big, white letters. In an odd contrast of fashion, Madonna wore a slinky, short black dress that appeared to be designed by Yves Saint Laurent, with heels. She was smoking. John never smoked. He asked Madonna why she was so certain his mother would be interested in meeting her. His tone, the witnesses recall, was sarcastic and inconsiderate.

Madonna, as per usual, was unruffled. “She’d want to meet me because I’m Madonna,” she said, exasperated. “Who wouldn’t want to meet me? After all, John,” she concluded, “your mother is probably the only woman on earth more popular than I am.”

“Can’t happen,” John declared. “Mother would make sure we never see each other again if she meets you. I can guarantee it.”

No doubt, the fact that Jackie Kennedy Onassis refused to meet her tapped into Madonna’s deep inferiority complex. Beneath all of the bravado, she has always been insecure — it doesn’t take a psychiatrist to discern that much about her. During this time, she kept saying to friends, “His mother would love me, if she gave me a chance.” Jackie’s refusal even to give Madonna “a chance” quickly became a source of hurt for her. Then, as often happened in her life, hurt turned to anger. By the end of 1988, Madonna told friends that she was bored with John.

Besides the Jackie factor, another issue in her relationship with John was her communication with him. One had to know how to deal with John Kennedy, Jr., when he was angry. John was a shouter. If he was upset, he’d scream at full volume, his own face just inches from the object of his aggression. Though such a thing could be daunting to some people, it certainly was not to Madonna. She was equipped with the skills to handle this kind of explosive personality, simply because of who she was married to and what she put up with on an almost daily basis. However, for some reason, she didn’t seem to be able to meet John at that hot level during a disagreement. Perhaps she was awed by him because of his family’s almost regal history. Maybe she wished to appear dignified in his presence. Or, maybe she just didn’t care enough about him, didn’t feel passionate enough about him, to engage in the kind of fracas with him that she would customarily have with Sean.

Apparently, a defining moment in Madonna’s relationship with John occurred when he thought she had told someone else something personal about him — and that this person had then gone to the press with the information. When Madonna denied having done as much, he didn’t believe her. “What the hell is wrong with you?” he screamed at her at full volume in front of friends. Everyone in the room who knew Madonna held on to his chair for dear life, probably expecting the outbreak of World War III. However, instead of firing back as expected, Madonna was quiet. Her startled expression indicated that she was stunned by John’s outburst. She dropped her eyes, unable to meet his accusatory gaze. Then, she ran from the room. This was odd behavior from a woman used to taking as much as she could dish out in an argument. Mystified by her conduct, John turned to his friends and sputtered, “What’d I say? What’d I say?”

After that incident, Madonna seemed to lose all interest in John Kennedy, Jr. Some intimates believed she thought he was a “hothead,” and since she already had one of those at home she didn’t need another. Others said that the intensity of the physical intimacy they shared had waned and it now wasn’t worth her tolerating him and his domineering mother. Madonna didn’t say much about any of it. To one friend, she called the situation with Kennedy “toxic and sad,” and said “I needed out of it.” She asked that friend, “Don’t you think the need for companionship is a weakness? Because I do. And I refuse to be weak.”

After a two-week cooling-off period at the end of July, John invited Madonna to dinner at a trendy West Side restaurant to discuss their relationship. According to law school classmate Chris Meyer (whom John brought to the dinner because, as he put it, “I don’t want to be alone with her. She scares the hell out of me.”) John told Madonna that he was sorry for all that had happened in their relationship concerning his mother. He hoped that they could still be friends. He also indicated that there could be nothing more than that between them because his mother would not approve, “and her approval means everything to me.”

“Madonna was annoyed by the whole thing,” said Chris Meyer. “He thought he was letting her down easy, but she was clearly finished with John. He didn’t need to be gentle with her. My impression of her was that she had already given him the heave-ho in her mind, anyway. John’s ego, though, would not allow him to believe that she had lost interest.”

A week later, Chris Meyer had an appointment with an attorney at the same New York high-rise that houses Doubleday when he happened upon John Kennedy, Jr., in the men’s room. John was probably visiting Jackie at work. As they stood beside each other at adjoining urinals, Meyer asked Kennedy about Madonna. “How’s it going, buddy?” he wanted to know. “Is it really over with Madonna?”

Staring straight ahead, Kennedy smiled thinly and said, “She’s great, but, yes, it’s over between us, Chris.”

“Because of your mother?”

Kennedy shrugged. “Not really,” he said, sounding vague. “But any excuse will do, I guess. That’s as good as any other when you’re trying to break it off with someone gently.”

“Wow,” Chris said. “Too bad.”

Without a reaction, John zipped up, walked over to the basin and washed his hands. As he dried off with a paper towel, he turned to Chris who was finishing up at the urinal. “We had some good times,” John observed. “I like her a lot. Oh well. Easy come,” John said while crumpling the towel, “easy go,” he concluded as he tossed it into a trash can.⁹