Marion McKeone: Youngest Kennedy is not a knight on a white horse for Democrats
Jack Schlossberg, left, with Caroline Kennedy, former US vice president Mike Pence, and Karen Pence as Mr Pence received this year’s 2025 John F. Kennedy Profile in Courage Award. Picture: Getty
There remains a persistent belief in some sectors of the United States, against all evidence to the contrary, that the Kennedy clan will come riding to the rescue and save both the Democratic Party and American democracy from itself. That a new dawn of Camelot will usher in a golden age of American prosperity, power, and equality. That Trump’s dystopian world view and authoritarian creep will be replaced with a democratic Utopian ideal where diversity, equality, and inclusion are celebrated and American innovation will lead to prosperity for all and a return of the American Dream.
Somewhat surprisingly, the fringes that cling to this illusion transcend America’s fierce partisanship. The Maga crowd embraced Robert F Kennedy Jr so completely that Trump became concerned his popularity and profile would eclipse his own. And four years ago, Dallas police estimated that up to 2,000 QAnon conspiracists gathered at the site where John F Kennedy was assassinated 58 years earlier, convinced that his son John F Kennedy Jr would appear alive and well and wearing a Maga hat.
According to their reading of the QAnon runes, Kennedy Jr wasn’t aboard the plane that crashed into the Atlantic Ocean off the coast of Martha’s Vineyard in July 1999. He was just biding his time so he could become Donald Trump’s vice president when he returned to power in 2024.
They got the second part of the equation right; Trump did indeed return to power. But few Americans could have imagined in the aftermath of the January 6 insurrection that any Kennedy — even the brain-worm addled, dead-bear kidnapping, whale-head decapitating, anti-vaccine scion of Robert F Kennedy — would become Trump’s health secretary.
Long before RFK Jr turned Judas on the clan, the Kennedy name was in urgent need of a rebrand. The golden era, when young, handsome, idealistic Kennedys ran the White House, the Department of Justice, and the Senate, ended tragically and abruptly. The assassinations of JFK and RFK, who seemed destined to continue his legacy, inflicted a deep psychic scar, leaving America in a state of perennial yearning for the return of its ultimate era of prosperity and promise.
Even though the Kennedy legacy has been decimated by death and tragedy, tarnished by scandal and betrayed by RFK Jr, Democratic hopes are now pinned on what they fervently hope will emerge as a new star in the Kennedy firmament.
They’re in for a shock.
Jack Schlossberg, the only grandson of Jack Kennedy, announced his intention to run for Congress this week, seeking to fill the seat that has been occupied for almost 40 years by Jerry Nadler, a veteran Democrat who, unlike most of his political peers, recognised that it was time to allow some new blood to energise the Democratic Party’s sclerotic veins.
On paper, Schlossberg, 32, has everything it takes to reinvigorate the moribund Democratic brand. He has the JFK direct lineage, the Kennedy looks, the charisma, the dazzling smile, the confidence, and the smarts.
But he lacks the discipline and the filter, and any kind of message. As Zohran Mamdani, the mayor-elect of New York, has illustrated, Democrats are desperate for young, social-media savvy candidates who have a clear focus and a message that resonates.
Schlossberg thus far has skated by on the family name, flitting from soft-focus political commentator at to TikTok and Instagram influencer.
Even in this era of oversharing, Schlossberg's social media incontinence is notable, its content vacillating between the eccentric and the egocentric. He appears to post every unfiltered thought that enters his head — sometimes endearing, occasionally amusing, but overwhelmingly pointless content.
Like his cousin Robert, whom he viscerally loathes, Schlossberg likes to show off his physique. Scores of posts show him bare-chested in some form of sporting activity. Others show him in leggings and ballet tights, performing dance routines or skateboarding around New York and lip-synching to Taylor Swift. In others, he pleads for a girlfriend, or sobbingly recounts the demise of his latest romance. But mostly he trolls Maga and Trump apologists — and his favourite target is his cousin, who he has targeted with dozens of occasionally funny and invariably scathing videos.
He cheerfully quotes his mother, Caroline Schlossberg, who tells him he’s "a little different" and admits he’s "not for everybody".
In an era where the political trolling tent is big enough — or indiscriminate enough — to include Marjorie Taylor Greene, Laura Loomer, and Nick Fuentes, there’s plenty of room for Schlossberg’s offbeat musings, even if they break no new liberal ground. He has around 2m followers — no small feat, but fewer than you might expect given his brand and the access he enjoys to mainstream media. Every national media outlet positioned his decision to run for Congress in 2026 as headline news.
The main problem (apart from his online presence which conveys the musings of a privileged, self-absorbed, and shockingly immature dilettante) is that Schlossberg, who likes to quote Shakespeare, is something of a lightweight Hamlet — constantly changing his mind, contradicting himself, announcing new projects and then abruptly pulling out of them. He tearfully announces he’s quitting social media, only to pop up hours later, reciting Byron while skating through Central Park.
His much-vaunted mission to crisscross all 50 states in a campervan to talk to ordinary Americans and “get the truth out” quickly ran out of gas.
In short, Schlossberg is running purely as a Kennedy. If he has a political platform, he hasn’t shared it. Aside from occasional posts about the importance of voting and the dangers of gerrymandering, most of his political content consists of pot shots at his cousin and his Maga buddies.
'If he wasn’t a Kennedy...'
Several of his relatives — including his mother — quickly discovered that the Kennedy name is enough to launch, but not to land, a career in Congress. But in politics, timing is everything. And there are some who believe that even — or especially — in a hyperkinetic news cycle, Schlossberg may have found his moment as an impudent insurgent challenging the Democratic old guard.
Schlossberg is a regular at Democratic beauty pageants when the party wants to trot out proof of life of a party suffocated by the gerontocracy and establishment figures that have controlled its ranks for decades.
“If he wasn’t a Kennedy, they wouldn’t let him near a mic,” a New York delegate remarked as we watched him take the stage at the 2024 Democratic Convention to thunderous applause.
Democrat boomers who remember the glory days of the Kennedy White House, and the Generation X crowd who recall Ted Kennedy’s powerful oratory and his relentless social justice crusades, would be foolish to place their hopes in this erratic repository of liberal dreams. Whether Generation Z will embrace him as the antithesis of everything they revile about America’s toxic political scene remains to be seen.
Aside from the current health secretary, attempts by half a dozen second- and third-generation Kennedys to keep the dynastic flag flying didn’t survive contact with America’s brutal political battlefield. Caroline Kennedy’s 2009 bid for a US Senate seat was torpedoed by the New York governor — assisted by the Clintons. Voters rebuffed Jean Kennedy Townsend’s bid to become governor of Massachusetts, and Mark Shriver’s 2002 congressional bid received a similar response.
Those who want to bet on a Kennedy resurgence would find it's best placed on Joe Kennedy III, who served four terms as a Massachusetts congressman. Effective, hardworking, and popular with his fellow Democrats, he was tipped as a future presidential candidate.
But a case of Kennedy entitlement prompted an ill-advised decision in 2020 to challenge Ed Markey, the popular Massachusetts senator, for his seat. It led to an ignominious defeat and, having yielded his safe seat in Congress, he was rescued by Biden.
His appointment as economic envoy to Northern Ireland yielded limited results, but it wasn’t for lack of effort on Kennedy’s part. His low-key, relentlessly hard-working approach has as little in common with RFK Jr’s unprincipled power grab as it has with Schlossberg’s online preening. At 44, he’s said to be biding his time for an opening in the Senate or Congress.
The Kennedy dynasty is the most enduring of all political brands; between 1946 and 2021, only two years passed without a Kennedy in Congress. In 2008, there were five Kennedys in elected office — three on Capitol Hill, one in Maryland’s lieutenant governor’s office, and another dominating its state legislature.
Their return to political prominence — with RFK Jr’s Maga defection — wasn’t what the Kennedy clan had in mind. It’s unlikely Schlossberg will be the Kennedy who rehabilitates the tarnished brand, but in the rollercoaster world of American politics, anything is possible.
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