Jack Schlossberg, the 33-year-old grandson of President John F. Kennedy, is running for Congress in one of Manhattan's most coveted districts. By most accounts, including those of his own former staff, the campaign is falling apart before early voting even begins.
Multiple reports published this week paint a picture of a congressional campaign defined not by policy or grassroots energy but by chronic staff turnover, missed meetings, and a candidate who, on the very first day of his campaign, reportedly skipped donor and media engagements to take a nap.
The Hollywood Reporter detailed the turmoil surrounding Schlossberg's bid for New York's 12th Congressional District, which covers Midtown and stretches across parts of the Upper East and Upper West Sides. At least two campaign managers, two field directors, a handful of advisers, and a roster of consultants have all been let go so far. That is a staggering body count for a campaign that has been operational for only nine months.
The New York Times, in an account published Thursday, reported that Schlossberg skipped an opportunity to build energy among staffers on the very first day of his campaign. Citing three people familiar with the situation, the paper said staffers were "reeling" when the candidate disappeared for the remainder of the day. The reason? He said he needed a nap.
Schlossberg leaned into the anecdote rather than running from it. On May 14, he posted on X:
"Needed a quick nap!! Even though I just woke up. Rest of the day / month wide open lmk if you wanna hang?"
He followed up moments later: "Wait nvm changed my mind really busy can't make it." Whether the posts were meant as self-deprecating humor or damage control, they did little to quiet the growing chorus of concern from former staffers and political observers.
The New York Post reported that sources told the Times Schlossberg has since missed strategy meetings and gone off the radar for stretches, a pattern that extends well beyond launch day. Multiple staffers reportedly left amid complaints of chaotic management, erratic behavior, and repeated no-shows.
One former canvassing coordinator, Jorge Muñiz Reyes, told the Times he quit over Schlossberg's lack of engagement with community issues. His assessment was blunt:
"The colors might be nice to look at for a few days. But since the flowers lack roots, they can't last very long."
Muñiz Reyes compared the operation to a "dollar-store flower bouquet." Not exactly the kind of endorsement a frontrunner wants from someone who was knocking on doors for him.
The staff churn goes beyond anonymous grumbling. The Washington Free Beacon reported that Schlossberg's campaign manager, Annabel Lassally, exited after only one month on the job. Neither Lassally nor the campaign gave a reason for her departure. The campaign did not say who would replace her.
That kind of silence speaks volumes. Losing a campaign manager a month in, with no explanation and no named successor, is not a sign of a tight ship running lean. It is a sign of disorder.
The Free Beacon also noted that the campaign has faced blowback over Schlossberg's past social media posts, including offensive comments about RFK Jr., a resurfaced video, and other posts that were later deleted after he launched his campaign. A source told the New York Post that his mother, Caroline Kennedy, "pleaded with Jack not to run." When your own family is reportedly urging you to stay out of the race, voters have reason to wonder what they know that you won't say publicly.
Schlossberg's troubles fit a broader pattern of Democratic candidates losing the confidence of their own side before they ever face Republican opposition.
Schlossberg is not without advantages. A March poll reported by Patch showed him with 25 percent support among likely Democratic voters in the district, a meaningful lead in a crowded primary field that includes state assemblymen Alex Bores and Micah Lasher, along with Lincoln Project co-founder George Conway. Nancy Pelosi has endorsed him.
But name recognition and an elite endorsement can only carry a campaign so far when the candidate's own staff keeps walking out the door. Schlossberg has staked out what his coverage describes as a "blue-chip centrist lane" focused mostly on opposing President Trump. He has defended continued U.S. funding of Israel's Iron Dome, proposed that the federal government bill Trump Tower for its own security costs, called for a freeze on tariffs, and branded himself "No PAC Jack" for his stance on campaign finance reform.
On CNN, Schlossberg pushed back against the wave of negative coverage. "I work harder than anybody I know, and we're doing it all and making it look easy," he said. That claim sits uneasily beside the reports of missed meetings, vanished afternoons, and a parade of fired or departed staff.
He also told reporters:
"There's a lot in that article that's not true, but you know how this works: once you're declared the frontrunner and early voting starts in less than a month, everyone's got something to say."
Fair enough, frontrunners do attract scrutiny. But the complaints are not coming from rival campaigns or opposition researchers. They are coming from the people Schlossberg hired to help him win.
Supporters have offered an explanation for the candidate's uneven conduct. They argued that the death of his sister, Tatiana Schlossberg, in December helps explain behavior otherwise uncharacteristic of a young politician. Grief is real, and no one should minimize it. But voters in NY-12 are not choosing a grief counselor. They are choosing a representative. And the question of whether a candidate can manage a congressional office starts with whether he can manage a campaign.
Vanity Fair's reporting described volunteer enthusiasm and events at venues including the Tap Room overlooking the Hudson River and art world heir Peter Brant Jr.'s family townhouse. The social circuit is not the problem. The problem is the gap between the glossy public image and the operational reality behind it.
Schlossberg has also worked to restore buildings in Chelsea, which gives him at least one tangible local credential. But credentials on paper matter less than the day-to-day grind of running a district-level campaign, showing up, staying engaged, and keeping your team intact long enough to reach Election Day.
Democrats nationally are already watching their polling advantages erode, and the party can ill afford to hand winnable seats to candidates who cannot hold a staff together.
The NY-12 primary features more experienced hopefuls who have spent years in state government or political organizing. Bores and Lasher both carry the résumé of working legislators. Conway brings national media exposure and anti-Trump credentials that overlap heavily with Schlossberg's own lane. With early voting approaching in less than a month, Schlossberg's team, whatever remains of it, has a shrinking window to right the ship.
The broader Democratic landscape offers no shortage of similar cautionary tales. Voters in Illinois recently rejected far-left candidates in decisive fashion, and internal party divisions have surfaced everywhere from Senate leadership fights in Maine to primary challenges in Pennsylvania. The common thread is a party struggling to match its candidates to the seriousness of the moment.
Schlossberg's last name gets him in the door. His poll numbers, for now, keep him at the front of the pack. But a 25-percent share in a multi-candidate field is a lead built on sand if the organization underneath it keeps crumbling.
At some point, the Kennedy mystique runs out, and voters are left with the candidate in front of them, not the grandfather behind him.