Reviving a political dynasty is best not left to chance. So on the morning that Jack Schlossberg, the grandson of John F. Kennedy, announced his campaign for a House seat in New York City, his team had a carefully choreographed plan.
Aides teed up calls with frenzied media outlets, Democratic luminaries and a roster of wealthy donors. The goal was to show that Mr. Schlossberg, a 33-year-old heir known for his good looks and madcap social media musings, was a serious candidate ready for what promised to be a grueling race.
But just hours into his Day 1 launch, the candidate abruptly announced a change of plans, according to three people familiar with the events. Forget dialing for dollars — Mr. Schlossberg said he needed a nap. He then effectively disappeared for the day, leaving his team reeling.
The incident would be unusual for any candidate for high office, especially one representing the beating heart of Manhattan. For Mr. Schlossberg, a first-time candidate with little traditional work experience, it was evidently par for the course.
In the months since, Mr. Schlossberg has translated his fame, charisma and creativity into a narrow polling lead ahead of June’s Democratic primary, and has been endorsed by the Democratic titan Nancy Pelosi. But behind the scenes, a group of fellow Democrats, family friends, union leaders and others with direct knowledge of the campaign described an operation so erratic and plagued by turnover that it raises questions about how he might handle himself as a member of Congress.
Especially early on, Mr. Schlossberg would regularly blow off weekly strategy meetings called for his benefit, and made a habit of disappearing for long stretches with little notice or explanation. (He did carve out time to swim or paddleboard in the Hudson most days.)
He has pushed boundaries on social media — so far, in one case, that a sitting congressman privately complained that Mr. Schlossberg had mimicked his Instagram commentary about President Trump and Venezuela without crediting him.
And Mr. Schlossberg has churned through staff at a head-turning pace. In the six months since he entered the race, he has had at least two campaign managers, two field directors, a handful of advisers and a rotating cast of consultants.
Some he fired after just weeks. Others inadvertently stayed on for weeks after Mr. Schlossberg decided to dismiss them, because he never bothered to tell them.
Jorge Muñiz Reyes, a canvassing coordinator, left the campaign last week, citing frustration with Mr. Schlossberg’s lack of engagement with community issues and the campaign’s management. Mr. Muñiz Reyes compared the campaign to a “dollar-store flower bouquet.”
“The colors might be nice to look at for a few days,” he said, “But since the flowers lack roots, they can’t last very long.”
Others who spoke to The New York Times about Mr. Schlossberg’s campaign agreed to do so only on the condition of anonymity, citing deference to Mr. Schlossberg’s famous family, but also concerns that he could turn his sometimes acerbic social media posts against them.
Mr. Schlossberg’s current aides and allies pushed back on aspects of this account, saying that sharp reversals are frequently a feature of political campaigns. Paige Phillips, who is now serving as his campaign manager, said that Mr. Schlossberg was campaigning “amid a deeply, deeply personal tragedy”: the death of his sister, Tatiana Schlossberg, in December.
“If an anonymous source thought he ‘disappeared’ at any point, they should remind themselves of that fact,” she said, without addressing the specifics of his campaign launch. She added that “no one works harder, cares more, or shows up like Jack Schlossberg.”
Ms. Phillips also played down the significance of staff turnover. She said Mr. Schlossberg was “decisive and honest about what (or who) works, and what doesn’t” — and said that was a good thing.
She added, “In a campaign that spans nine months, this stuff should not surprise anyone working in New York politics.”
A stranger to the professional world
Mr. Schlossberg was crisscrossing the country in a van last fall, filming a short-lived YouTube show (he described it as “serious — and insane. Just like me.”) when Jerrold Nadler, the district’s longtime representative, announced he would retire.
The news created a rare opening for a coveted, safely Democratic seat. Encompassing Midtown and the Upper East and West Sides, it includes more Fortune 500 companies and highly educated voters than any district in the country.
Other candidates jumped in, including two state assemblymen, Alex Bores and Micah Lasher; a global vaccine expert, Nina Schwalbe; and George T. Conway III, a former Republican turned Trump antagonist and cable news commentator.
Mr. Schlossberg was never going to be a conventional candidate.
The son of the ambassador Caroline Kennedy, he had grown up in elite political circles. But he made his name and accumulated millions of followers as a confounding social media presence whose scathing critiques of his cousin, Robert F. Kennedy Jr., were interspersed with videos of himself dancing shirtless or claims that he was “having a son” with the wife of the vice president.
And as he set out to build a congressional campaign last fall, Mr. Schlossberg had relatively little experience in a professional workplace.
After he earned undergraduate, law and business degrees at Yale and Harvard, one of his longest work engagements appears to have been a few months as a political correspondent for Vogue covering the 2024 campaign. He wrote six short articles, and a spokeswoman for the publication said he was considered a freelancer, not a staff writer.
Mr. Schlossberg likes to mention his work at the State Department, where he helped plan a conference on oceans, but his tenure there as a staff assistant under Secretary John F. Kerry, a family friend, lasted less than four months, according to a department spokesman.
And on the financial disclosure form that Congress requires candidates to submit, Mr. Schlossberg reported no earned income for 2025, but did disclose trust funds and other assets worth as much as $32 million. (Ms. Phillips said Mr. Schlossberg “refused roughly $1 million in brand deals last year.”)
Mr. Schlossberg has bristled when questioned about his qualifications on the campaign trail.
At a recent candidate forum, for example, the candidates were asked to name their top accomplishments in public service. Ms. Schwalbe said she had distributed 500 million Covid-19 vaccines; another candidate discussed helping launch a ferry service in the East River.
Mr. Schlossberg pointed to his current campaign, saying it had excited voters. When a moderator followed up to say that his answer might “raise flags” about his experience, Mr. Schlossberg grew visibly irritated.
He said he had volunteered on campaigns since 2008 and as an E.M.T. in college; cited his State Department stint and his role helping his family hand out an award each year; and added that he had passed the bar exam “in the top 1 percent.”
“While you may not think that content creation and building a following based on speaking out for what you believe in at a time when others were unwilling, taking on your family members, traveling the country to every single swing state, serving as a delegate at the D.N.C., is an experience, I do,” Mr. Schlossberg told the moderator.
A fast-churning campaign
Once he set his sights on Congress, Mr. Schlossberg’s stature and his family’s connections meant he had little trouble finding experienced strategists willing to help him get started. Scott Fay, a former aide to Senator Edward F. Kennedy, helped with headhunting. Angelo Roefaro, a longtime spokesman for Senator Chuck Schumer and friend of Mr. Schlossberg, became an important unpaid adviser.
Volunteers, résumés and $2.3 million in donations have poured in.
Ron Klain, a former White House chief of staff who taught Mr. Schlossberg at Harvard Law School, agreed to help the candidate put together his policy positions, and came away impressed by Mr. Schlossberg’s acumen in weekly calls.
“Of all the congressional candidates I’ve ever worked with, Jack is one of the ones who has been most serious about policy,” he said.
But the campaign’s operations have sometimes been as chaotic as the candidate’s public persona suggests.
In November, for example, Mr. Schlossberg posted a “serious message” to nearly 900,000 followers on Instagram about Mr. Trump’s military provocations in Venezuela and how Congress should respond. The video was shared widely.
When aides to Representative Seth Moulton, a Massachusetts Democrat, saw it, they were taken aback. Mr. Schlossberg’s message was nearly identical (though not verbatim) to one Mr. Moulton, a Marine combat veteran, had posted a day earlier. His campaign reached out to Mr. Schlossberg’s seeking an explanation, and a representative was told that the candidate had admitted to copying the video — because he liked it, according to two people familiar with the incident. He updated the post to credit Mr. Moulton, who decided not to make the complaint public.
A spokeswoman for Mr. Moulton’s campaign declined to comment.
Ms. Phillips did not dispute this account, but said, “It’s hard to have a straight face and say Jack Schlossberg copies anyone on social media.”
Outside the online realm, Mr. Schlossberg has often agonized over decisions about policy positions, campaign events, media appearances and strategy — routinely greenlighting plans only to scrap them hours or days later.
Mr. Schlossberg has also struggled to find a staff to his liking. He hired a campaign manager, Annabel Lassally, well before his public launch, but fired her a few weeks after the campaign officially began. He told donors and reporters he was his own campaign manager, but recently acknowledged that Ms. Phillips, his former fund-raiser, was doing the job, too, leaving more junior aides and allies to wonder who was in charge.
(Mr. Schlossberg is now also working with Alex Voetsch, a strategist whose firm worked for Kanye West’s 2020 presidential campaign and for Tony Simone, a local assemblyman.)
Among others he laid off or cut ties with were his ad maker and mail consultant. Mr. Schlossberg told New York Magazine that some of his staff turnover took place after he realized “how corporate campaigning is and how stupid it is.”
One woman who interviewed for a job with Mr. Schlossberg said the experience was surreal. The woman, who would speak only on the condition of anonymity, said that they met one-on-one on Zoom, and the conversation was initially courteous, substantive, even inspiring.
But toward the end of the session, Mr. Schlossberg unexpectedly slammed his hands on the table and pushed his face close to the camera to address her.
She recalled him using her name and repeating that he wanted her, that he needed her. She said she believed he was referring to working on the campaign but that his flirtatious tone made her uncomfortable.
Ms. Phillips said she sits in on every interview and that “this did not happen.”
The woman who was interviewed, though, said Ms. Phillips had not been a part of the video call. She did not take the job.
Nicholas Fandos is a Times reporter covering New York politics and government.
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