Jack Schlossberg, the Kennedy rebel with a cause: ‘Trump is obsessed with my grandparents’

At 32, John Fitzgerald Kennedy was already a member of the United States House of Representatives. At the same age, Robert F. Kennedy was an advisor to the president and Ted Kennedy was a senator. At 32, John Bouvier Kennedy Schlossberg, better known as Jack, is a successful content creator. JFK’s only grandson has more than 1.5 million followers on TikTok and Instagram and a YouTube show, Test Drive, in which he dissects current events with irreverent humor, from Donald Trump’s tariffs to Sydney Sweeney’s controversial campaign for the clothing brand American Eagle.

Schlossberg’s videos never go unnoticed and often provoke confusion. One day he’s taking ballet classes or skateboarding while reciting verses by Lord Byron, and the next he’s criticizing Ryan Murphy for making a television series about his uncle, the late John F. Kennedy Jr., without consulting his family. He almost always attacks Trump or his own cousin, Robert F. Kennedy Jr., the controversial anti-vaxxer and conspiracy theorist whom the U.S. president appointed as Secretary of Health.

But it’s not all criticism and reproaches. He recently praised Spanish King Felipe VI’s style. “I spent a summer in Spain when I was in eighth grade and traveled all over the country. I have very fond memories, and yes, I think the king of Spain looks incredibly good,” Schlossberg said in a video call with EL PAÍS from his Chevy van, parked somewhere in Massachusetts, the birthplace of the Kennedys.

His intention is to inject some lightness and humor into a serious moment in U.S. politics. But since Trump’s victory in the 2024 elections, his criticism of the administration has grown in intensity. A few weeks ago, for example, he dressed up as Melania Trump — complete with a blond wig and foreign accent — and recorded himself reading the pacifist letter the first lady sent to Vladimir Putin during the Russian-American summit in Alaska.

“The media’s first reaction to the letter was, ‘Oh, the first lady is interested in Ukrainian children.’ That showed that a lot of people hadn’t read it. She doesn’t say the word Ukraine at any point. I put on a wig and this stupid voice so people could read her words,” he explains. “My imitation was maybe funny, maybe shocking, but in the end, it forced people to look at what she had said and consider whether or not it was a good idea to send that letter.”

Schlossberg shaved his head this summer. Although he’s gotten rid of his shock of dark, Kennedy-esque hair, he retains the athletic figure, the defined jawline, the eloquence, and the sex appeal of the men in his family. His parody of Melania Trump went viral on social media. The image of JFK’s cross-dressing grandson also caught the attention of the mainstream media. The pro-Trump press tries to portray him as crazy and often compares him to Edith Bouvier — an eccentric cousin of his grandmother, Jacqueline Kennedy Onassis — who lived out her final years in a ramshackle house in the Hamptons. The liberal press also doesn’t quite understand him.

He doesn’t care if the public is offended or if some consider him a freak. He says it’s intentional, a way to reach a younger audience, a generation that gets bored easily and is always looking for a little humor. And what does his family think about the content he shares on social media? “Ummm... I’m not going to speak for my family. But I would say that some of the funniest things I’ve done have been with them by my side,” he replies.

The heir to America’s most famous political dynasty maintains that the Jack people see on TikTok and Instagram is a persona. So who is the real Jack? “I’ve been called a silly goose and an edgelord, so I guess I’m somewhere in between,” he notes. “Everything I do on social media has one purpose: to draw attention to the serious issues my country is facing with the Trump administration.”

At close quarters, when he’s not recording one of his madcap videos, Schlossberg speaks seriously. The war in Ukraine is an issue close to his heart. His father’s family is Jewish and Ukrainian, originally from the city of Poltava, considered the spiritual center of that country. He doesn’t believe Trump will end the conflict. “I don’t believe anything Trump says. He lies to the American people every day from the Oval Office. Rather than paying attention to what he says, you have to look at what he’s done so far. His meeting with Zelenskiy at the White House earlier this year was one of the most horrifying things I’ve ever seen. Meanwhile, he treats Putin the exact opposite.”

Schlossberg was raised Catholic by his mother, but also in the Jewish traditions of his father. He is following with great concern the Israeli invasion of Gaza and the siege being imposed on the Palestinian people. “I don’t support Israel’s military policy. I think what’s happening is absolutely appalling. It bothers me that Judaism is somehow involved in something like this. And I’m frustrated that my country hasn’t made it clear where it stands,” he says. “Antisemitism is on the rise in the United States, and I take my Jewish pride very seriously. That said, the images and reports we’re hearing from Gaza are distressing.”

The son of diplomat Caroline Bouvier Kennedy (Barack Obama’s ambassador to Japan and Joe Biden’s ambassador to Australia) and the prestigious artist and designer Edwin Arthur Schlossberg, Jack grew up in a family home on the Upper East Side, New York’s most elite neighborhood. He attended the Collegiate School, the oldest private school in the United States, the same school where his uncle John-John Kennedy was a student. He spent his childhood and teenage summers between Martha’s Vineyard and his family’s home in Hyannis Port, Cape Cod. He studied history at Yale and earned a doctorate in jurisprudence and an MBA from Harvard.

In 2023, he passed the New York State bar exam on his first try, something very few aspiring lawyers achieve. He scored in the top 1% with a 332. With that resume and his family’s connections, he could be a successful lawyer at a large New York firm or a rising political hopeful in Washington. “Politics is what interests me. Who knows, maybe in the future…” he says. “Two years ago, I was in a library, buried in books. If you had told me two years ago that I was going to be a social media sensation, I would have said you were crazy. I have no idea what the future holds.” He doesn’t feel under pressure to go into politics. “But I genuinely care about my country because my family fought and died for a better country. Everything to me is politics. That’s how I see the world.”

That the grandson of John Fitzgerald Kennedy, the first television president in history, spends all day on the internet doesn’t seem so far-fetched. “My grandfather used television effectively and took advantage of new media to communicate with the American people. I think he’d be on every social network today, although he probably wouldn’t know how to use a cell phone. I don’t know...” he reflects.

His crusade against Trump began during Biden’s 2024 presidential campaign. He supported the Democratic president and Kamala Harris’ eventual run. After Trump’s victory, he realized he had to go further to capture the attention of young people. “I have to admit that when it comes to a sense of humor, Democrats don’t take risks. It’s not easy to make things funny. In fact, it’s difficult,” he acknowledges. He believes the Democratic Party needs a better social media strategy to ensure people understand why it’s important to continue defending essential progressive ideals such as reproductive freedom, marriage equality, and immigrant rights.

Last week, for example, he took advantage of the Labor Day celebrations in the United States to make a video in which he pointed out that the Trump administration is stripping workers of their rights (the president issued an executive order in May to eliminate union protections for hundreds of thousands of public employees, citing national security concerns). That same day, he published another video denouncing the fact that Americans eat 26 million chickens every day and that nine billion of these birds are killed each year.

In addition to his TikTok, Instagram, and YouTube posts, Schlossberg is very active on the X network. Many progressive users have fled Elon Musk’s platform, tired of the spread of hoaxes, insults, and far-right extremist slogans. He disagrees. “You can’t leave the site where they’re spreading information. You can’t leave because you don’t want to hear what they’re saying. Everything the other side says is to win votes, so it’s important to pay attention and be there.”

For generations, Americans have treated the Kennedys with indulgence and reverence, a rich, compelling, powerful, and tragic saga. There’s a certain nostalgia for JFK’s presidency. Americans often compare that era to the mythical kingdom of Camelot. Ryan Murphy is preparing a series about John-John Kennedy, and CNN is airing a documentary about the late president’s son, who died in a plane crash in 1999. “Now that some are questioning and attacking our progressive history, it’s only natural for people to look back,” Schlossberg reflects.

Trump seems determined to end this indulgence toward the dynasty. He has seized control of the Kennedy Center for the Performing Arts in Washington to, as he puts it, “change woke art to patriotic art,” and has threatened to add his name to the institution and turn the Kennedy Center’s opera company into the Melania Trump Opera House. The president has also destroyed the iconic rose garden Jacqueline Kennedy created in the West Wing of the White House in 1961 and ordered the declassification of thousands of documents and files about JFK. Schlossberg describes this latest move as “a huge distraction tactic, a disgusting thing.” “I don’t claim to know what’s going on in his head. But I have noticed that he is obsessed with my grandparents and with padding over their names,” he says. “Trump tries to undermine the heroes of our past in order to elevate himself, but I think that in the end he achieves the opposite.”

Schlossberg says there’s a growing fear in the United States of speaking out against Trump. “Last year, I followed the presidential campaign for Vogue magazine. At the time, Prada was sending me handbags, brands were giving me clothes… As soon as Trump won, everyone took a step back,” he recalls. “We’ve seen how he operates. He constantly threatens CEOs, and everyone across the country is looking out for their own interests. Nobody wants to take risks.”

At times, he resembles his uncle, John Kennedy Jr., the charismatic and attractive editor who revolutionized the media landscape of the 1990s with George magazine. He, though, doesn’t see any physical resemblance to his mother’s brother. “I think I’m a lot like my father. My uncle is a hero to me, someone I look up to and remember from my childhood. I miss him all the time. He was a media genius. I think I have a lot to learn from him... But I’d like to say that I’m much stronger than my uncle. I’m in better shape than he was,” he says with his unique sense of humor.

Now he wants to travel across the southern United States in his Chevy pickup truck to visit some of the places hardest-hit by the Republican administration’s cuts. “I’m definitely very afraid of Trump, too,” he admits. “But I don’t want that fear to stop me. I don’t want to be silent.”

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