JFK's legacy lives on in his grandson, Jack Schlossberg – but he's carving his own path

News24

10-05-2025

With his chiselled jawline, shock of dark hair and camera-ready smile, there's no doubt about it – he's a Kennedy.
As the only grandson of former president John F Kennedy, it was inevitable that Jack Schlossberg would draw a lot of attention – and the fact that he looks so much like JFK's handsome son, John Kennedy Jnr, who died tragically in a plane crash in 1999, only adds to his appeal.
And like other members of the famous family, Jack (32), the son of Caroline Kennedy (67) – JFK and Jackie Kennedy Onassis' only surviving child – is blessed with natural charisma and loves being in the spotlight.
His Instagram and X accounts have become must-follow destinations for those fascinated by the intersection of American political royalty and millennial outspokenness.
One day he's posing shirtless in workout videos, the next he's launching critiques of political figures – including, most controversially, members of his own extended family.
Jack has made no secret of the fact he's horrified by the outspoken devotion his mom's cousin, Robert F Kennedy Jnr, bestows on President Donald Trump.
The family have always been staunch supporters of the Democratic Party so it was a shock when Robert (71) – the son of Robert F Kennedy who was assassinated in 1968 during his own run for president – threw his weight behind the Republicans when he abandoned his run for the presidency.
Since Trump appointed Robert Jnr his secretary of health, Jack has become even more vocal on social media about how disgusted he is by his relative's politics.
In a scathing series of posts earlier this year, Jack called him a 'liar' and a 'guru shaman', taking particular issue with Robert's views on abortion, chronic diseases and his belief that childhood vaccines trigger autism.
'My family has always stood for science, for truth, for moving forward,' Jack declared in one heated video. 'Using our name to spread misinformation isn't just wrong – it's a betrayal of everything we've built.'
In April he threw down the gauntlet in another video tirade.
'RFK Jnr . . . I have got a challenge for you,' he said. 'Me and you, one-on-one, locked in a room, we hash this out. Nobody comes out until one of us has autism. What do you say?'
The feud marks a dramatic departure from the way the family have traditionally handled disagreements.
'The Kennedys were always known for their dignity in public,' says political commentator Eleanor Hayes. 'There was this unspoken code – you might disagree fiercely in private, but you maintained a certain decorum before the cameras. Jack's throwing that playbook out the window.'
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As a three-year-old Jack endeared himself to millions when he served as ring bearer at JFK Jnr and Carolyn Bessette's 1996 wedding.
But other than this, his mom and father Edwin Schlossberg, a museum curator and author, largely kept Jack – whose full name is John Bouvier Kennedy Schlossberg – and his sisters, Rose (36) and Tatiana (35), out of the spotlight.
But behind the scenes, Jack, who grew up in New York, was developing a keen interest in politics.
In high school he was a committed member of the Young Democrats club and helped canvass for Barack Obama's presidential campaign. When he was in Grade 8 he co-founded ReLight New York, a non-profit organisation that installed energy-efficient lightbulbs in low-income households.
After graduating from Yale University in 2015 with a degree in history, he went to Harvard to do a law degree and an MBA.
After passing his bar exam, he had a brief stint working as a political correspondent at Vogue magazine ahead of the 2024 US election.
'I am inspired by my family's legacy of public service,' he said at the time. 'I take that very seriously and I want to contribute in my own way. I have big dreams but I also know that I'm trying to make a positive impact today.'
Growing up as a bearer of America's most mythologised political surname has shaped Jack's world view in complex ways, insiders say.
In interviews he describes his grandfather, who was assassinated in 1963, as his hero.
'The first thing I ever got really nerdy about was him.'
But being a Kennedy also presents challenges.
'You grow up with this incredible privilege but also this weight of expectation,' he says. 'Everyone's waiting to see if you'll run for office, if you'll get in trouble, if you'll live up to the legacy or crash and burn.'
The comparisons to his uncle JFK Jnr, who served as editor of political magazine George before his death, have followed Jack all his life. Beyond the physical resemblance that's inspired countless side-by-side photo compilations, friends say he shares his uncle's easy charm and humour.
'They both have this quality of being completely comfortable in their own skin,' an insider says. 'John had that magical ability to make everyone feel special when he spoke to them, and Jack has that same gift.'
Despite this, Jack, who had a cameo role in the eighth season finale of Blue Bloods in 2018, has been careful not to position himself as his uncle's successor.
'I respect his memory enormously but I'm walking my own path.'
That path has increasingly involved forays into television and digital media.
In August 2024 Jack delivered a widely praised speech at the Democratic National Convention and he recently announced plans to launch a live news programme.
Meanwhile, he continues to stir up controversy with his social media posts.
'The internet is a place where it's difficult to break through,' he says. 'Especially if you're not saying something that's controversial. I use my judgement to make posts that I think are funny or silly but have a purpose.'
One subject he does shy away from is his love life. For several years he was involved with fitness influencer Krissy Jones but kept their relationship under the radar. They broke up last year and there hasn't been any sign of anyone new in his life.
Meanwhile he seems determined to rewrite the rules, whether that means a future in politics or media. And one thing seems certain – he won't be doing it quietly.