Kennedy heir Jack Schlossberg has reportedly run a 'dollar store' campaign for Congress that has infuriated aides and forced out staffers at a rapid pace, according to insiders. Schlossberg, 33, the grandson of President John F. Kennedy, is competing in one of the most closely watched congressional races in the nation, aiming to represent much of Manhattan.
Campaign plagued by issues
According to sources speaking to the New York Times, Schlossberg's campaign has been plagued by bizarre behavior, unexplained absences, and a high staff turnover rate. Aides indicated that concerns about his readiness for office surfaced on the very first day of his campaign in November. After his high-priced staff arranged a series of media interviews and discussions with Democratic donors, Schlossberg abruptly canceled the plans, telling his team he was leaving to take a nap and departed for the day.
Sources told the Times that this incident was emblematic of Schlossberg's immature behavior on the campaign trail, which they allege has persisted throughout his run for office. Despite being the scion of one of America's most powerful political families, critics argue that Schlossberg has done little in his career to warrant a congressional seat.
Staff departures and comparisons
Jorge Muniz Reyes, a canvassing coordinator, said he left the campaign a week ago due to Schlossberg's lack of community engagement, describing the campaign as akin to a 'dollar-store flower bouquet.' Reyes explained that he grew frustrated with Schlossberg's apparent disinterest in learning about the district he seeks to represent, which includes much of midtown Manhattan and the Upper East and Upper West Sides. He compared the campaign to a cheap flower bouquet, noting that '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 brief stint as a political correspondent for Vogue, where he published six short pieces about US politics. A Vogue spokeswoman told the Times that he was considered a freelancer, not a staff writer. He also spent less than four months at the State Department as an assistant to then-Secretary of State John Kerry, a family friend, and has cited his social media following as one of his credentials. In financial disclosure forms required by Congress, Schlossberg stated he made no income in 2025 but disclosed trust funds and assets worth up to $32 million.
Social media antics and controversies
Best known for his social media antics, Schlossberg has previously raised eyebrows with online behavior ranging from bizarre and humorous to grotesque. In June 2025, 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 wrote: '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. At a recent candidate forum, he appeared to bristle at a moderator who asked candidates to name their top accomplishments in public service. Schlossberg cited his current campaign and his ability to excite voters, then launched into a rant when the moderator suggested the answer might 'raise flags' about his experience. He referenced his months as an assistant at the State Department, volunteering on other campaigns, helping to hand out a family award each year, and passing the bar exam. He added: '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.'
High staff turnover and copying allegations
In the six months since he began his campaign, Schlossberg has seen two campaign managers quit, along with two field directors and several consultants. Some critics have accused him of mismanaging his own campaign. In November, he shared a message on Instagram condemning President Trump's military moves in Venezuela and calling on Congress to intervene. Aides to Massachusetts Democrat Seth Moulton alleged to the Times that they were stunned by how closely Schlossberg's video resembled Moulton's, saying it was nearly identical. A representative for Schlossberg reportedly admitted he copied the video because he liked it, later adding a credit to Moulton in his post.
Campaign manager defends Schlossberg
Responding to allegations of erratic behavior, 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 did not dispute the allegations that he 'copied' Moulton but retorted, '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.
