Will the Kennedy Name Help or Hurt Jack Schlossberg?

The "Good Kennedy" slot is empty. Can he bridge the divide between the aging Democratic establishment and impatient insurgency?

Illustration by Riley Levine

There’s a section of the country still yearning for a successor to the myths of American royalty and it forces Democrats to circle back every so often to the same name: Kennedy. And in 2025, the most likely heir to that impossible inheritance isn’t a senator, a governor, or a rising star in Congress – it’s Jack Schlossberg.

Since appearing on the Today show with his mother, Caroline Kennedy, in 2017, Schlossberg has hovered at the edges of public life like a political Rorschach test: part earnest idealist, part internet goofball, part legacy prince waiting for the right moment to step forward.

In one breath, he’s posting absurdist cosplay videos mocking Republicans while dressed like an everyday New Yorker; in the next, he’s slipping into the polished, almost diplomatic tone of a Harvard-trained Kennedy when the family – or the party establishment – calls on him. It made him a curiosity. A contradiction. A question mark with a famous jawline.

So what is he really? A Gen-Z adjacent avatar of authenticity who could win over young voters desperate for someone normal? Or the natural successor to the Schumer-Pelosi wing of the Democratic Party – a safe, pedigreed option built for the donor class and the Sunday shows?

The truth is somewhere between the myth and the meme. And that’s exactly where Jack Schlossberg’s political future begins.

The ‘Good Kennedy’ Slot Is Empty

For the first time in recent memory, the Kennedy name doesn’t stand for anything unified. It’s fractured – and the fractures start with RFK Jr., the conspiracy-driven dark star orbiting Trump’s regime. His anti-vaccine crusades, desecration of animals, unhinged public statements, and opportunistic alliance with Trump have turned the one-golden Kennedy brand into something moderates, liberals, and independents recoil from: Exploiting a legacy for money and political convenience.

On the other end of the spectrum, you have Caroline Kennedy: dignified, career diplomat, still deeply respected, but intentionally quiet. She represents the moral memory of Camelot, not the future of it. Her public life has been defined by service, not spectacle – which makes her the opposite of what the corporate media ecosystem rewards.

And then there’s the ghost that haunts every conversation about Jack: his uncle, John F. Kennedy Jr. For an entire generation – especially women – JFK Jr. wasn’t just a political heir; he was the golden child of America’s royal family. His sudden death in a 1999 plane crash didn’t just shock the country, it froze him in time, feeding decades of speculation about a “Kennedy curse” and mythologizing him into something no living person could ever match.

But the longing never went away. Liberal women have spent years quietly hoping for someone who could carry even a fraction of JFK Jr.’s charm, modernity, and promise. And with Joe Kennedy III, the Massachusetts congressman who bet his career on a Senate run, out of politics – Schlossberg has become the logical inheritor of that search – the first Kennedy male in decades who appears both politically serious and culturally relevant enough to step into a role the public has kept open since 1999.

Schlossberg’s Strengths – and Issues

If Jack Schlossberg is going to succeed in filling the retiring Jerry Nadler’s seat in New York’s 12th Congressional District, he has to prove he’s more than a famous name with a clever Instagram presence. And to his credit, he isn’t beginning the run as a blank slate. His résumé is practically engineered for a career in Democratic politics – the kind of upbringing that puts you in the halls of power long before you appreciate how different your life is from everyone else’s.

He was a Senate page at an age when most kids were just learning what Congress actually does. He delivered a primetime speech at the Democratic National Convention before he’d even finished college – the kind of spotlight usually reserved for former presidents, senators, or ambassadors. He spent years overseas during his mother’s diplomatic postings, absorbing international politics firsthand. He has done humanitarian and environmental work, built the kind of internship portfolio Ivy League kids fantasize about, and then capped it all off with a BA from Yale and a law degree from Harvard.

This isn’t a “privileged” background. It’s a dynastic one – and dynasties come with expectations that can’t be shrugged off.

His pedigree gives him immediate credibility – a member of the White House Press Corps called him “a rising star in the Democratic Party” and was mentioned in a question to press secretary Karoline Leavitt for simply announcing his candidacy. That pedigree also creates a contradiction that has defined him since he first dipped a toe into public life. Schlossberg presents two selves at once: the polished heir who hangs with Chuck Schumer while being bestowed with a committee seat to decide how New York City will celebrate America’s 250th birthday – and the buzz-cut New Yorker filming absurdist van-life videos like he’s doing character improv on Staten Island. Both versions are authentic to him, but neither is enough on its own – and the tension between them is impossible to ignore.

Not because he’s full of shit. Not because he comes off as malicious. But because the political moment makes the joke harder to laugh at without thinking of the privilege behind it.

In 2025, the most viral political video in New York didn’t come from the mayor, the governor, or any congressional hopeful. It came from Zohran Mamdani – an assemblyman delivering a no bullshit, plain-spoken breakdown of why rent is crushing his district. It blew up because it wasn’t content, it was him listening. It was the language of young workers and families balancing panic over rent with panic over healthcare, gig jobs, childcare, and the fear that one emergency will blow up their entire month.

In that world – in that reality – a Kennedy joking around in a panel van doesn’t read as “relatable.” It reads as a costume. A clever costume, maybe, and a sincere one in its own way, but still something he can take off and switch out for a $3,000 Brioni suit for his first MSNBC interview since announcing his candidacy. He can step out of ‘trolling for a cause’ and immediately back into a life built on generational access: the donor circles, the diplomatic networks, the institutional connections, the media oxygen, the doors that swing open without him touching the handle.

Most young New Yorkers, or Americans for that matter, can’t do that. They don’t get to toggle between survival and comfort. They don’t get to play around with versions of themselves for fun. They wake up in one version only: the one where rent spikes, where insurance evaporates, where a broken hand means a broken bank account, where groceries cost more than they did the week before, where the heat doesn’t work and the landlord ignores emails. That’s the electorate he’s walking into – one that is permanently aware of how thin the line is between stability and disaster.

And that’s the paradox of Jack Schlossberg. For all the contradictions, he’s not an empty suit. He’s not a bored rich kid looking for a hobby in politics. There seems to be something real there – a sharpness, an awkward sincerity, a kind of unvarnished earnestness that isn’t manufactured. His call outs of RFK Jr. aren’t just clever; they’re morally grounded and politically necessary. His comfort on camera isn’t robotic. His humor doesn’t feel like it’s written by a consultant. And unlike a lot of legacy candidates, he doesn’t seem terrified of sounding like an actual human being.

Democrats are starving for someone under 50 who can speak plainly without melting down on contact with reality. He may be the only member of his generation in the party with instant name recognition who also seems willing to say something real. But charisma and opportunity don’t answer the fundamental question he now has to face: does he understand the people he wants to represent, or does he only understand how to perform for them?

That’s the difference between winning a seat and earning the respect of the people who put you there. And that brings us to what matters most – not the résumé he inherited, but the path he builds from here.

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The Path Forward

If Jack Schlossberg wants more than a viral launch and a Kennedy-curious press cycle, he has to win over a very specific universe of voters – and they are nothing like the national audience watching clips on social media.

New York’s 12th District is not some swingy outer-borough district. It’s the densest slice of power in the country: the Upper East Side, Upper West Side, Midtown, Chelsea, Gramercy, Lincoln Square, Roosevelt Island – 100% urban, overwhelmingly white and highly educated, with a median household income of about $153,000 and the highest per-capita income of any congressional district in the United States. It’s also a deep blue D+33 seat where Democrats routinely clear 80% in statewide races.

That’s why Jerry Nadler kept getting sent back to Washington. For decades, his districts have been in Democratic hands and he has never dropped below 75% in a general election. Nadler built that durability on a clear profile of being liberal, pro-civil rights, pro-LGBTQ equality, and deeply embedded in local transit, housing, and Jewish community politics.

Schlossberg isn’t running in a district that’s deciding whether it likes Democrats. He’s running in a district that expects its Democrats to be smart, competent, and reliable on democracy and civil rights – and at least minimally credible on housing and cost of living, even in a wealthy seat where a huge share of the population are high-earning renters.

That’s the real test behind the MSNBC rollout. When he sat down with Jackie Alemany to announce his campaign, Schlossberg framed the race around what he called a cost-of-living and corruption crisis, insisting that “none of it has to be this way” and pitching himself as part of a younger generation of Democrats who aren’t sleepwalking through the moment. He used the platform to draw a hard, public line inside his own family, too – calling RFK Jr. “a dangerous person” and “a rabid dog” who’s now making life-and-death decisions at HHS. In one interview, he did what half the Democratic Party still won’t do: name the threat and look directly into the camera while doing it.

That’s where his path forward starts, becoming the anti-RFK Jr. Kennedy, not in the tabloid sense but in the governing sense. In NY-12, a district stacked with doctors, lawyers, media workers, nonprofit directors, professors, and highly educated voters, leading with science, public health, competence, and reality isn’t optional. It’s the floor. His MSNBC rhetoric hit the right tones: public health, corruption, affordability. Now he has to prove it wasn’t just a clean five-minute segment on the corporate media launch tour.

Because substantively, the voters aren’t looking for nostalgia. They’re looking for someone who won’t embarrass them. This is one of the richest districts in the country, but also one of the most rent-burdened – young professionals paying $3,500 for a studio, families squeezed by daycare and medical bills, seniors holding onto stabilized apartments like a liferaft. What wins here is competence: protecting democracy and civil liberties, fighting for transit and climate resilience, defending reproductive rights and LGBTQ equality, and actually being able to talk about rent and healthcare without sounding like someone gave you the talking point.

What makes this even trickier is that the voters he needs aren’t the ones drowning under every part of the broken system he’s talking about. They’re not the baristas splitting rent four ways in Bushwick or the home health aides getting crushed by childcare bills. NY-12’s electorate is different. Wealthier. Older. More institution-minded. This is a district that admires Pelosi and Schumer for keeping the machine running. They want stability, competence, and someone who won’t set their hair on fire on cable news. They want a Democrat who can navigate power without torching it.

But the party he needs a future in isn’t the same party as his district. Nationally, Democrats are being pulled left by a generation that doesn’t worship institutions, doesn’t trust legacy politics, and doesn’t care about Camelot. They want someone who fights corruption, takes on corporate power, defends renters, and treats affordability as a national emergency – not an optional paragraph at the end of a policy proposal.

That is the line Schlossberg has to walk now. He has to convince NY-12 that he can be the polished, competent, reality-based Kennedy Democrat they expect, while convincing the rest of the Democratic Party that he’s not just another dynasty kid cosplaying as regular while being molded in the Schumer-Pelosi tradition. He has to prove that he can talk to wealthy Manhattan voters without losing the younger, more populist coalition that will determine who rises in the party over the next decade.

If he can do that – if he can stay earnest without seeming naïve, sharp without seeming entitled, serious without seeming rehearsed – he could become something the Democratic Party hasn’t had in a long time: a legacy candidate who actually meets the moment instead of hiding from it.

And if he can’t thread that needle – if he veers too close to the privilege that keeps him in elite circles – he’ll be swallowed by an electorate that doesn’t have time for contradiction between his last name and what they’re looking for.

The Democratic Party is in a populist push that just saw New York City elect the youngest and first democratic socialist mayor in history – where transparency and affordability were the main concerns – and Schlossberg must thread his family legacy and a younger left-leaning party with one of the richest districts in the country and the politics that entails.

Evan Fields is a veteran who writes the Weekly Wrap and Fouth & Democracy newsletters for Lincoln Square and the News from Underground Substack.