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Who is the real Schlossberg —serious politician, fantasist, internet troll, or all three?

March 7, 2026
in News
Who is the real Schlossberg —serious politician, fantasist, internet troll, or all three?

With the Camelot legacy behind him, it makes sense that Jack Schlossberg — the only grandson of President John F. Kennedy — is running for political office, just like so many of his family before him.

But the 33-year-old, who is running for Congress to represent Manhattan’s 12th district, is weighed down by his history of controversial online antics, a lackluster job history and a platform that, so far, has few specifics.

Schlossberg has got a lot of attention for being a firebrand on social media, and when he met with The Post this week, he returned to a frequent target who is very close to him, in Secretary of Health and Human Services secretary Robert F. Kennedy Jr., whose views on science and vaccines he is against.

Jack Schlossberg at the Elliot-Chelsea NYCHA housing complex in Manhattan.
Jack Schlossberg says he is running a grassroots campaign, and has appointed himself campaign manager. Emmy Park for NY Post

“I wish he hadn’t been doing what he’s doing,” said Schlossberg, referring to RFK Jr. “Nobody wants to be the one who’s fighting with your family in public.”

He told The Post his mother, US ambassador Caroline Kennedy Schlossberg, was reluctant to speak out against their cousin when she issued a public letter to Senators, calling Kennedy Jr. “a predator” with “dangerous views” on the eve of his confirmation hearings for the cabinet-level post last year.

“My mother didn’t want to put the letter up,” he said, adding that he posted the letter on his social media platforms.

“She wishes that it wasn’t happening but it wasn’t her choice. We were pushed into the pool and we didn’t want anyone to be confused about what we believe and what President’s Kennedy’s support would be and how dangerous it was to our future.”

The Trump administration is another of Schlosberg’s frequent targets, which he also credits as a source of his popularity, having amassed 874,000 followers on Instagram.

Jack Schlossberg speaking with tenants at the Elliot-Chelsea NYCHA housing complex.
Jack Schlossberg launched “Fix It Now!” an initiative to help NYCHA residents with long neglected repairs in the 12th district. Emmy Park for NY Post
Prince William, Jack Kennedy Schlossberg, Tatiana Kennedy Schlossberg, and Caroline Kennedy standing together.
Following the death of his older sister Tatiana Schlossberg in December, Jack Schlossberg said his family has rallied around his campaign to help ease their grief. AFP via Getty Images

“Social media is an amazing way to build trust and people who come up to me, who know my Instagram, often thank me. At first I couldn’t believe it,” he said.

“Especially at the beginning of the Trump administration … There weren’t that many people challenging, and so they associate me with somebody who’s willing to say things.”

Some of his more bizarre online posts have included donning a wig to mock First Lady Melania Trump and making a post where he claimed he and Second Lady Usha Vance were “having a baby,” and “might get married,” with a picture of her holding a child with his face photoshopped onto it.

Collage of Jack Schlossberg's face edited onto a baby held by a woman, with an Instagram post text.
Before he announced his Congressional campaign, Jack Schlossberg regularly posted on social media that he was in love with Second Lady Usha Vance. Jack Schlossberg/Instagram
Jack Schlossberg mocking Melania Trump, wearing a blonde wig and with images of Trump and her letter to Putin in the background.
Before announcing his campaign in November, 2025, Jack Schlossberg’s Instagram campaign featured posts in which he mocked First Lady Melania Trump and his cousin Robert Kennedy Jr., the Secretary of Health and Human Services. @jackuno/Instagram

Trolling RFK Jr., Schlossberg previously wrote a recipe for a Make America Healthy Again “energy ball” cocktail, which he claimed should include: “2 oz of Jew blood (ashkenazi not Sephardic). 4 cups of male j–z. Baked at 300 degrees until totally dry like your wife,” referring to actress Cheryl Hines.

Since announcing his campaign, Schlossberg has adopted a more corporate demeanor and was dressed in a black overcoat and crisp white shirt when he met The Post.

He proudly states he’s his own campaign manager and that he’s been doing almost everything in the “Jack for New York” campaign himself. This is not exactly true. Annabel Lassally, a former special assistant to New York Governor Kathy Hochul left the leadership of the campaign in December, after two months on the job. Lassally did not return a request for comment.

Lorne Michaels in a black tuxedo with a black bow tie and a flower pin on the lapel, standing in front of a blue background with the Emmys logo.
Saturday Night Live producer Lorne Michaels is among the celebrity donors to Jack Schlossberg’s Congressional campaign. AFP via Getty Images
Paul Simon performing on stage, singing into a microphone and playing an acoustic guitar.
Musician Paul Simon donated the individual maximum of $7,000 to Jack Schlossberg’s campaign. Getty Images

Schlossberg has a law degree and MBA from Harvard, but his opponents have criticized an apparent lack of real-world work experience, accusing him of trading on his family history.

“Jack has no clue why he’s running, so it stands to reason no one else does either,” said a Democratic strategist for one of his opponents. “His campaign’s most substantial document is his birth certificate.”

Schlossberg dismisses the criticisms, saying: “I have work experience and I really enjoy the criticism that I’ve never had a job, especially when it’s coming from other opponents who have hired fancy consulting firms to do their social media.”

He added he has worked for the State Department in the past at the Bureau of Oceans and Environment.

On his rather short resume, he also listed himself in his 2025 congressional disclosure as correspondent for Vogue magazine. However, a representative told The Post Schlossberg “was Vogue’s election correspondent through the 2024 election, so he did not work with us in 2025.”

He also claimed he worked for, then quit, ex-President Joe Biden’s re-election social media team in 2023.

Nancy Pelosi touches a man's face at the 2024 Democratic National Convention.
Nancy Pelosi endorsed Jack Schlossberg in his run for Congress. Jack Schlossberg/ Instagram

“I said, ‘I have an instinct about how Democrats need to communicate.’ They said ‘no’ to every idea I had. I quit, and started making my own videos.”

A senior Biden campaign official told The Post Schlossberg never worked in any official capacity for them, although he interviewed at several different departments, including social media.

And, to his detractors’ point, as hands-on as Schlossberg may be with his campaign, he’s decidedly hands-off when it comes to earning cash.

In his financial disclosures, revealed this week, Schlossberg listed no earned income in 2025. He does, however, have four family trusts, which suggest he is worth between just under $11 million and nearly $32 million.

Nancy Pelosi accepting the Profile in Courage Award, flanked by Caroline Kennedy and Jack Schlossberg.
Caroline Kennedy and Jack Schlossberg present Nancy Pelosi with the Profile in Courage Award in 2019. The award is named in honor of President John F. Kennedy. Boston Globe via Getty Images

Schlossberg claims his man-of-the-people image is bolstered by his donations, adding: “We are creating a new way of doing things … You see it in the numbers. Our fundraising average donation is under 40 bucks. I think we’re up to 45,000 individual contributions.”

While that may be the case, the duality of being a grassroots fundraiser and the scion of a political dynasty is on full display in Schlossberg’s backers.

Many of the big money individual donations come from wealthy family friends and celebrities. Musician Paul Simon donated $7,000, Saturday Night Live creator Lorne Michaels gave $3,500, cookbook author Ina Garten gave $2,000 and fashion designer Lisa Perry gave $3,500 to Jack for New York, among many other bold face names.

Donors can contribute a maximum of $3,500 to the primary race, which takes place in June, and another $3,500 for the general election in November, according to FEC rules.

Thousands more came from his parents and extended family, including aunt Vicki Kennedy who pledged $7,000, cousin Kerry Kennedy who gave $500, and older sister Tatiana, 35, who contributed $5,000 before her deathfrom a rare form of leukemia in December.

“She [Tatiana] was really excited about the campaign,” said Schlossberg, adding that his whole family is rooting for him. “I think it’s been a lot of fun for my family to have something to cheer for, and become invested in when experiencing loss.”

Jack Schlossberg and Tatiana Schlossberg lying in bed, both wearing beanies.
Jack Schlossberg said that his sister Tatiana was very excited when he told her he was running for Congress. She contributed $5,000 to his campaign a month before she died of leukemia. Instagram/@jackuno

Contributions to Schlossberg’s campaign currently total nearly $2 million, according to a campaign volunteer, although those numbers are not yet reflected on the Federal Election Commission’s (FEC) web site — which lists his campaign’s totals at $1.1 million.

Schlossberg also has the endorsement of former House Speaker Nancy Pelosi. He told The Post she only agreed to back him after an hourlong “interview” in which she asked him all about why he wanted to run.

However, other sources in the Democratic party claimed they thought San Francisco-based Pelosi’s real reason for backing Schlossberg was to get back at 17-term Democratic Rep. Jerry Nadler, who announced his retirement last year. He has handpicked  Micah Lasher to be his successor in the sprawling 12th district, which Schlossberg is also competing for.

The district encompasses Midtown, Gramercy Park, Hell’s Kitchen, Chelsea, the Upper East Side and Upper West Side as well as Roosevelt Island, and the democratic primary faces a crowded field, with 13 candidates.

Schlossberg certainly has an advantage over his opponents when it comes to online visibility, with the next most popular candidate, Lasher, having just 7,200 followers on Instagram.

During The Post’s visit Schlossberg towered over many New York City Housing Authority residents he was visiting in Chelsea, many of whom vied for his attention.

In order to help residents, Schlossberg unveiled his “Fix-It Now” initiative, with volunteers urging tenants to add their names to a form with a description of what they needed repairing in their units.

“His last name isn’t Kennedy and he doesn’t have the experience,” said Hank Sheinkopf, a political strategist. “His appeal might be glamor and the politics of the past, but in the harsh world of  New York City politics, that’s not going to work.”

The post Who is the real Schlossberg —serious politician, fantasist, internet troll, or all three? appeared first on New York Post.

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