In a moment so rich in symbolism and emotion, even the legendary Greek playwrights would have been moved to tears.

On the day marking his third birthday, John F. Kennedy Jr. stood solemnly as his father’s casket passed by. With a gentle twist, he freed his small hand from his mother’s black-gloved grip, turned to face the coffin, and offered a heartfelt salute.

It was a scene so evocative that even the great Sophocles might have struggled to craft a more compelling narrative of tragedy, duty, family conflict, and a legendary curse.

Yet, it is perhaps the central theme of Sophocles’ most renowned work, “Oedipus Rex,” that resonates most strongly.

This classic play was the foundation for Sigmund Freud’s exploration of what he called the Oedipus Complex—a theory suggesting that men harbor unconscious desires for their mothers and feel envious of their fathers’ relationship with them.

And Kennedy Jr certainly made no secret of his love for his mother Jackie.

In the mid-1980s, he met Brooke Shields: the child star was 19 or 20 at the time and Kennedy was 25.

‘He kept saying I look like his mother,’ she told Howard Stern in 2023. ‘Which is really interesting, and a compliment. But it was also like: “I don’t know how to feel about this.’”

John F. Kennedy Jr, on the day of his third birthday, watched as his father’s casket passed before him and raised his right hand in a salute

‘He kept saying I look like his mother,’ Brooke Shields (right) told Howard Stern in 2023. ‘Which is really interesting, and a compliment’

By the 1990s he was dating model Julie Baker, and Kennedy’s childhood friend Sasha Chermayeff noticed a striking resemblance between the elegant brunette and Jackie Kennedy.

‘She was a lingerie model,’ said Chermayeff, in an interview with author Elizabeth Beller. ‘She was nice and friendly. She looked like his mother in a way. He liked that sometimes.’

Edward Klein, author of The Kennedy Curse, writes that it wasn’t just his mother’s looks he found enticing.

‘John once told a friend: “I’m attracted to strong-willed women like my mother,”‘ Klein wrote.

Certainly, his eventual wife, Carolyn Bessette, was strong-willed. Many noted that she also shared Jackie’s refined elegance and dislike of the spotlight. The two women never met: Jackie died aged 64 at around the time the pair began dating seriously, in May 1994.

Dr Sabrina Romanoff, a New York-based licensed psychologist, told the Daily Mail that such attractions were not uncommon.

‘The pattern of gravitating towards women who resemble your own maternal figure – whether through their image, like Brooke Shields, or through their temperament – can often reflect an unconscious attempt to recreate and master early attachment dynamics,’ she said.

Romanoff said that the smash-hit dramatization of Kennedy’s romance with Bessette, Love Story, depicted how ‘his mother was a bit unavailable’.

‘There was a heartbreaking moment in the series where he was afraid of losing Carolyn, and that’s bringing back memories of having lost his mom, who had died shortly before. So we see in the show that there’s many different ways that we can be drawn in to people – not just in how they look, but really how they operate in the world.’

By the 1990s he was dating model Julie Baker (right), and Kennedy’s childhood friend Sasha Chermayeff noticed a striking resemblance between the elegant brunette and Jackie Kennedy. ‘She looked like his mother in a way. He liked that sometimes,’ said Chermayeff

‘John once told a friend: “I’m attracted to strong-willed women like my mother,”‘ Edward Klein, author of The Kennedy Curse, wrote

Like his father and grandfather before him, John Jr was a ladies’ man

Alivia Hall, a licensed psychotherapist and clinical director of New York-based therapy practice LiteMinded, agreed that men were often, as in Kennedy’s case, drawn to women who resemble their mother.

‘It’s actually common for people to feel drawn to partners who share qualities with a caregiver. From an attachment perspective, our first close relationships are what really shape what feels familiar, emotionally meaningful and sometimes even “attractive” later in life,’ she told the Daily Mail.

But, she cautioned, ‘that doesn’t mean someone is consciously “looking for their mother” in a partner. More often, they’re responding to a sense of psychological familiarity. If there’s a pattern of multiple partners resembling a parent in personality or presentation, it can suggest that the person has a particularly strong template for what intimacy is supposed to feel like.

‘Familiarity often feels like compatibility, even when people aren’t consciously aware of why they’re drawn to someone.’

And it’s not just Kennedy’s relationship to his mother that would have the Greek playwrights salivating.

His connection to his father, uncles and grandfather would also provide plenty of fodder for the scribes. Women, it is fair to say, were the Kennedys’ Achilles heel. And they spared no effort in chasing them.

‘Joe Jr, Jack, Bobby and Teddy were full of longing for a warm and tender mother,’ writes Klein in The Kennedy Curse.

‘They had an overpowering craving to be close to a woman, and yet they hated this feeling because they feared it meant that they were weak as men. As a result, they put on a tremendous show of Don Juanish behavior to demonstrate that they were in actuality strong, powerful men. But this was a compensatory image.

‘Deep down, they felt like tiny, powerless boys. The physical and emotional absence of a loving mother was keenly felt by these powerless boy-men.’

Like his father and grandfather before him, John Jr was a ladies’ man.

But it went beyond that – both his father and grandfather slept with the same woman.

Joe Kennedy Sr in 1938 had begun an affair with Marlene Dietrich, according to a 2009 Vanity Fair article – sparked by the two staying, with their respective spouses and children, at the Hotel du Cap on the French Riviera.

Twenty-five years later, when Kennedy Sr’s son was in the White House, Dietrich would enjoy an evening with the president, according to Vanity Fair and Gore Vidal.

The magazine reported that Vidal told how a 62-year-old Dietrich initially protested the 43-year-old’s advances, telling him: ‘You know, Mr President, I am not very young.’

But, as was often the way with JFK, he won her over.

Vidal claimed that after their liaison, the president, a towel around his waist, escorted Dietrich to ‘the small elevator across the hall from the bedroom and “shook her hand as if she were the mayor of San Antonio.”‘

Vidal says that JFK asked Dietrich: ‘If I ask you a question, will you tell me the truth? Did you ever go to bed with my old man?’

The magazine reports: ‘Knowing exactly what he wanted to hear, Marlene demurred. “He tried,” she responded after a brief pause, “but I never did.” Jack was triumphant, exclaiming, “I always knew the son of a b***h was lying.”‘

It wasn’t the only time JFK was competitive over his women.

Both he and his brother Bobby were said to be rivals for Marilyn Monroe’s affection.

Actress Shirley MacLaine, in her 2024 memoir, describes the infamous night of Monroe’s 1962 ‘Happy Birthday, Mr President’, and seeing Bobby enter the room where she was, shortly after his brother left.

‘It’s actually common for people to feel drawn to partners who share qualities with a caregiver,’ said licensed psychotherapist Alivia Hall

Women, it is fair to say, were the Kennedys’ Achilles Heel

Marlene Dietrich enjoyed an evening with JFK while he was president, according to Vanity Fair and Gore Vidal

On the infamous night of Marilyn Monroe’s 1962 ‘Happy Birthday, Mr President’, Bobby entered the room shortly after his brother left

MacLaine implies it was not the first time there was a ‘revolving door’ into Monroe’s bedroom.

In a later photograph, from 1984, she writes: ‘Here I’m telling Teddy Kennedy that story… and he’s laughing about how the boys got away with it all the time.’

Ryan Murphy, producer of Love Story, has taken these threads and run with them.

Critics, including Kennedy Jr’s own nephew, Jack Schlossberg, have taken issue with the dramatization.

But the parallels are not new.

Kennedy Jr died with his wife and her sister in July 1999, when he evoked Icarus and arrogantly flew his plane in poor visibility, without sufficient training.

At the time, The Times of London commented on the Greek tragedy.

The Oedipus story survives, the paper said, ‘because it embodies the deep human sense that free will is a fragile thing, and no inheritance, however noble, frees one from the mark of sin.

‘The fate of John Kennedy Jr reinforces in every mind that melancholy truth.’