Jack Schlossberg, the Kennedy family scion, is facing significant challenges in his congressional campaign, marked by what insiders describe as a “dollar store” approach. His campaign strategy has reportedly led to frustration among his aides and a rapid turnover of staff.
At 33, Schlossberg, who is the grandson of former President John F. Kennedy, is vying for a highly coveted seat representing a major portion of Manhattan, drawing considerable public attention.
However, as revealed by sources speaking to the New York Times, his campaign has been riddled with unusual conduct, frequent unexplained absences, and an unstable team dynamic.
Concerns about Schlossberg’s preparedness for the congressional role surfaced from the onset of his campaign in November. His well-compensated team had organized a packed schedule of media engagements and meetings with Democratic financiers.
Yet, just hours into the campaign’s debut, Schlossberg reportedly cancelled these plans unexpectedly. He informed his team of a sudden decision to take a nap, after which he departed for the day.
According to insiders, this incident typifies what they describe as Schlossberg’s ongoing erratic behavior during his campaign efforts, casting doubt on his suitability for office.
In response to the report about him avoiding campaigning to take naps, Schlossberg appeared to mock the allegations as he shared a picture to X on Thursday morning showing him falling asleep at a table.
‘Needed a quick nap !! Even though I just woke up. Rest of the day / month wide open lmk if you wanna hang?’ he captioned the post. ‘Wait nvm changed my mind really busy can’t make it.’
Despite being the scion of one of America’s most powerful political families, critics of Schlossberg say he has done little in his career to warrant a congressional seat.
Jorge Muniz Reyes, a canvassing coordinator, said he left the campaign a week ago due to Schlossberg’s lack of community engagement, telling the Times that the candidate has run a campaign akin to a ‘dollar-store flower bouquet.’
Kennedy heir Jack Schlossberg has run a ‘dollar store’ campaign for Congress that has infuriated aides and forced out staffers at a fast pace, reports say
The grandson of President John F Kennedy’s apparent lack of experience has come under scrutiny as a scion of one of America’s most powerful political families
In response to the report about him avoiding campaigning to take naps, the 33-year-old appeared to mock the allegations as he shared a picture on X on Thursday showing him falling asleep at a table
Reyes said he grew frustrated with Schlossberg’s apparent lack of interest in learning about the district he is running to represent, which encompasses much of midtown Manhattan and the Upper East and Upper West Sides.
He compared the campaign to a cheap flower bouquet as ‘the colors might be nice to look at for a few days… but since the flowers lack roots, they can’t last very long.’
Schlossberg’s work experience includes a short stint as a political correspondent for Vogue, where he published six short pieces about US politics.
A Vogue spokesman told the Times that he was considered a freelancer and not a staff writer.
He also spent less than four months working at the State Department as an assistant to then-Secretary of State John Kerry, a friend of his family, and has cited his social media following as one of his credentials.
In financial disclosure forms required by Congress, Schlossberg said he made no income at all in 2025, but disclosed trust funds and assets worth up to $32 million.
Best known for his social media antics, Schlossberg has raised eyebrows in the past with some of his online antics, which have ranged from bizarre and humorous to grotesque.
Best known for his social media antics, the 33-year-old has raised eyebrows in the past with some of his online posts, which have ranged from bizarre and humorous to grotesque
In the six months that he has been running for office, Schlossberg has seen two campaign managers quit, along with two field directors and a number of consultants
Schlossberg with his mother Caroline Kennedy, the child of President JFK who served as US Ambassador to Japan
In one instance in June last year, he came under scrutiny for launching a sexually-charged attack at Megyn Kelly after the conservative commentator criticized Israeli Prime Minister Benjamin Netanyahu.
In response to Kelly’s comments, he responded: ‘Looking very feminine! Very good – now show us your c***.’
When questioned about his experience and readiness for office on the campaign trail, Schlossberg has reportedly grown agitated.
This included a recent candidate forum where he appeared to bristle at a moderator who asked the candidates to name their top accomplishments in public service.
Schlossberg said it was his current campaign and how he had excited voters – and then flew into a rant when the moderator said the answer may ‘raise flags’ about his experience.
He then cited his months in the State Department and volunteering on other campaigns, his help in handing out an award from his family each year, and that he had passed the bar exam.
He continued: ‘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 DNC, is an experience, I do.’
According to insiders, Schlossberg’s campaign has reportedly been plagued by bizarre behavior, strange absences and a high staff turnover rate
The social media influencer has bristled at questions over his lack of experience, with Schlossberg best known as a social media influencer
In the six months that he has been running for office, Schlossberg has seen two campaign managers quit, along with two field directors and a number of consultants.
Some critics have accused Schlossberg of mismanaging his own campaign, including one instance soon after he launched his campaign last year.
In November, he shared a message to his almost one million followers on Instagram, condemning President Trump’s military moves in Venezuela and calling on Congress to step in.
Aides to Massachusetts Democrat Seth Moulton alleged to the Times that they were stunned by how close Schlossberg’s video message was to his, saying it was nearly identical.
According to the report, a representative for Schlossberg said he admitted to copying the video because he liked it, and he later added a credit to Moulton in his post.
Critics also accused Schlossberg of copying a political message first issued by Massachusetts Democrat Seth Moulton (above)
Responding to allegations that he has been erratic on the campaign trail, Schlossberg’s current campaign manager Paige Phillips told the Times that he was campaigning ‘amid a deeply, deeply personal tragedy’ – the death of his sister Tatiana from cancer in December.
‘If an anonymous source thought he ‘disappeared’ at any point, they should remind themselves of that fact,’ Phillips said.
She added that she disagreed with accounts that Schlossberg was not engaged with his campaign, arguing that ‘no one works harder, cares more, or shows up like Jack Schlossberg.’
Phillips also did not dispute the allegations that he ‘copied’ Moulton, but hit back, ‘It is hard to have a straight face and say Jack Schlossberg copies anyone on social media.’
The Daily Mail has contacted Schlossberg’s campaign for comment.
