Thirty years ago, when John F. Kennedy Jr. took on the role of editor-in-chief for his new magazine, “George,” the world eagerly awaited to see his next move.

With little to no background in journalism, especially in managing a publication that aimed to blend serious politics with light-hearted celebrity content, there were doubts. Would this be just another instance of Kennedy family privilege, with the former president’s son stepping into the limelight as a fresh face in media?

Contrary to expectations, Kennedy Jr. became an involved editor filled with creative concepts, though some were quite unconventional.

Among his most peculiar ideas was a 1996 cover proposal that involved dressing Madonna as his mother, Jackie Kennedy Onassis. The notion was unusual enough, but the fact that Madonna was his former lover added another layer of strangeness.

Such a suggestion was ripe for psychoanalytic exploration, given John Jr.’s history of dating women resembling Jackie. Actress Brooke Shields even recounted how he repeatedly mentioned her likeness to his mother before making romantic advances. However, the pop icon was not interested in entertaining the idea.

“John thought of having Madonna on the cover dressed like his mom,” remembered RoseMarie Terenzio, his personal assistant. “The plan was to outfit her in a suit, signature sunglasses, and a pillbox hat, seated atop a stack of books.”

Madonna turned him down in a fax message, saying: ‘Dear Johnny boy, Thanks for asking me to be your mother, but I’m afraid, I could never do her justice. My eyebrows aren’t thick enough for one.’

‘When you want me to portray Eva Braun [Hitler’s lover] or [socialite and politician] Pamela Harriman I might say yes! Hope you’re well. Love, Madonna.’

JFK Jr proved to be a hands-on editor brimming with ideas, but the weirdest of them all was his suggestion for a front cover for a 1996 issue that involved dressing Madonna up as his mother (Pictured together in 1997)

Madonna turned him down in a fax message, saying, in part: ‘Dear Johnny boy, Thanks for asking me to be your mother, but I’m afraid, I could never do her justice’

Ouch. That said, there was never much love lost between the Material Girl and the former First Lady when John Jr had a brief affair with her in the late 1980s.

She was long gone from his romantic life by the time he met future wife Carolyn Bessette and started the doomed love affair revisited in the FX drama series Love Story: John F Kennedy & Carolyn Bessette.

So, it should be no surprise that, apart from the odd reference, the relationship barely gets a mention in the wildly popular drama series. (Her non-appearance also spared Love Story’s producers the nightmare of trying to cast an actress in the role.)

Madonna was the world’s biggest pop star and Kennedy America’s most eligible bachelor when they met.

‘For his part, John, who was not above being star-struck, was dazzled by the notion of dating Madonna, the most glamorous, celebrated and, by all accounts, exciting woman of her generation,’ said Christopher Andersen, who has written biographies of them both.

Dancer Erika Belle, one of Madonna’s closest friends at the time, said: ‘You could see it in his eyes that first time they met, John was totally in awe.’

Jackie O, however, was decidedly less blown away by the prospect of her son’s dalliance with the racy star, which she saw as a publicity stunt cooked up by Madonna.

In those days, John Jr was on every showbusiness guest list – the pop icon and political scion first ran into each other briefly at an after-show party following a Madonna concert at New York’s Madison Square Garden in 1985.

That same year she married actor Sean Penn but, three years later, with the turbulent marriage already on the rocks (although it wouldn’t formally end until the following year), Madonna was searching for romantic pastures new.

According to Andersen, she ‘went after John,’ telling friends she believed an affair between them would be ‘cosmic.’

At the time, Kennedy was not only dating actress Christina Haag – a former classmate at Brown and his girlfriend since 1985 – but also secretly seeing actress Daryl Hannah and model Julie Baker (one of the women who looked considerably like his mother).

Jackie O was decidedly less blown away by the prospect of her son’s dalliance with the racy star, which she saw as a publicity stunt cooked up by Madonna

At the time that the two met, Kennedy was dating actress Christina Haag (right, in 1986)

Madonna, meanwhile, had married the actor Sean Penn (right, in 1987)

It was a crowded field, but in keeping with his father’s reckless philandering, there was always room for one more. Especially if she was a super-hot pop star. Anxious to avoid detection, they decided to meet each other at the health club where they both worked out religiously with the same trainer.

They only went outside together to go jogging around Central Park. It didn’t take long before the devoted son took his latest catch to see his mother at her apartment at 1040 Fifth Avenue.

Madonna signed the guestbook ‘Mrs Sean Penn’ but if that was an attempt at levity, her hostess didn’t appreciate it. According to Andersen, Mrs Kennedy Onassis disliked various things about her son’s new friend, starting with her relentless trashing of Roman Catholic rituals and traditions.

The Vatican had denounced the Like a Virgin singer for her disrespectful use of crucifixes (she festooned herself in them in her highly sexed videos), and other Catholic imagery and paraphernalia which it regarded as sacrilegious.

Jackie also wasn’t impressed when she saw Madonna on the cover of Life magazine made up to look like Marilyn Monroe, the most notorious of her late husband John Sr’s reported lovers.

The biographer wondered whether John Jr was seeking to emulate his ‘skirt-chasing’ father by having an affair ‘with the 1980s answer to Marilyn.’ If so, ‘it was also difficult to imagine anyone whom Jackie would find more offensive or unacceptable as a love interest for her cherished only son.’

Andersen doesn’t believe, however, that John Jr intended to hurt his mother but rather that he wanted to ‘connect’ with a father he barely knew by ‘experiencing something akin to what Jack experienced.’

Mother’s views of Madonna certainly didn’t appear to matter too much to JFK Jr, particularly when his interest in the star appeared to be purely carnal. His mother wanted him to marry Haag but there never seemed to be any indication that he saw Madonna in that way.

They were just going to enjoy it while it lasted, insiders recalled. John was once staying with a close friend, Billy Noonan, in Hyannis Port, Massachusetts, when he rang his New York home to check his phone messages.

There was one from Madonna who was in Rome: ‘Kennedy, I’m drunk and when I see you next I’m going to take your…’ The rest was unprintable.

Madonna was the world’s biggest pop star and Kennedy America’s most eligible bachelor when they met in 1985. (Pictured together in 1997)

According to Andersen, Mrs Kennedy Onassis disliked various things about Madonna

The biographer wondered whether John Jr was seeking to emulate his ‘skirt-chasing’ father by having an affair ‘with the 1980s answer to Marilyn.’ (Pictured: Madonna performing at the 63rd Academy Awards in 1991 emulating the look of Marilyn Monroe)

Noonan was stunned when his friend played the tape back for him. He had been unaware of the affair and wanted to know why John Jr hadn’t told him, but more important, he wanted to know what she was like between the sheets. ‘Let me tell you, she’s a sexual dynamo,’ replied Kennedy.

The Kennedy family compound in Hyannis Port was, says Andersen, the only place where John Jr and Madonna ‘could let their guard down… where they bundled up in sweaters and jackets and jogged on the beach.’

He continued: ‘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.’

Back in New York, the couple initially managed to keep their affair secret. They never attended events together but would meet up afterwards, leaving Haag to accept John’s repeated denials of infidelity.

According to Noonan, JFK Jr told him how he once arranged an assignation with Madonna in a hotel suite, then had to rush off to meet Haag. When he arrived late, smelling of Madonna’s scent, Haag quizzed him about the unusual perfume.

Without missing a beat, he told her that he’d been trying out scents in a department store to give to her as a gift but, with store assistants charging up to spritz him, he’d created too much of a stir by being in the store so he gave up on the idea.

‘He grimaced when I asked if she really believed him,’ wrote Noonan in his own book about his famous bosom pal.

According to Andersen’s The Good Son, his 2014 book on JFK Jr and his mother, the latter was determined to cause trouble when it came to his fling with Madonna.

Once, in 1988, when Jackie and Haag were passing the theater where Madonna was making her Broadway debut in the David Mamet play Speed-the-Plow, she mischievously asked Haag if she’d seen it. She hadn’t.

‘The play was good but Madonna was terrible,’ said Jackie. ‘I think you should go. I think you should go next week – and have John take you. And go backstage!’ Haag, says Andersen, ‘didn’t take the bait’ and that particular confrontation was averted.

But if Haag let John off the hook, Sean Penn wasn’t so forgiving. Although John and Madonna tried to be discreet, they couldn’t stop rumors from circulating.

During a party at New York’s Tribeca Grill restaurant to celebrate the career of actor Robert De Niro, the notoriously hot-tempered Penn didn’t react well when Kennedy introduced himself – even though he and Madonna were separated.

Noonan had been unaware of the affair and wanted to know why John Jr hadn’t told him, but more important, he wanted to know what she was like between the sheets. ‘Let me tell you, she’s a sexual dynamo,’ replied Kennedy

During a party at New York’s Tribeca Grill restaurant to celebrate the career of actor Robert De Niro, the notoriously hot-tempered Penn didn’t react well when Kennedy introduced himself

Years later, JFK Jr would go on to marry Carolyn Bessette. (Pictured together in 1995)

‘I know who you are,’ the pugnacious Penn told him. ‘You owe me an apology.’ 

Kennedy wisely extricated himself rapidly and the following morning Madonna sent him a funeral wreath of white roses inscribed with the words ‘My Deepest Sympathies.’ An accompanying note read: ‘Johnny, I heard about last night. m.’

It’s unclear exactly when John and Madonna stopped seeing each other – some say they were no longer romantically entangled when he was her ‘date’ at a party she threw in her brother Christopher’s loft apartment in September 1989.

By then, he was busy with other women, especially his on-off relationship with Splash and Steel Magnolias star Hannah, and a briefer dalliance with Sex and the City actress Sarah Jessica Parker. Later, of course, there was Carolyn Bessette, who married John in September 1996.

And although those cozy days in Hyannis Port and Madonna being introduced to Jackie suggest there was more to the relationship, some of JFK’s friends said the coupling was no more than glittering ships passing in the night.

‘Madonna was totally a fling. Nothing more. Barely a fling at that,’ JFK Jr’s college friend, Robert Littell, said in the 2024 book JFK Jr: An Intimate Oral Biography.

An unnamed friend interviewed for the same book went so far as to insist that the couple never even had sex with each other – although, said the source, they were prevented on one occasion while Madonna was on tour because ‘they didn’t have the proper protection measures and she was very on top of HIV prevention.’

In 1991, the Queen of Pop starred in her own documentary, In Bed With Madonna (also known as Madonna: Truth or Dare) – sadly, she didn’t disclose to what extent that suggestive title ever applied to John F Kennedy Jr.