The Stunning Transformation Of JFK's Grandson Jack Schlossberg

In 2018, a 25-year-old Jack Schlossberg appeared on "Today" to promote the JFK Library Foundation and the Profile in Courage Award. While Schlossberg was ready to talk all about that year's recipient, New Orleans Mayor Mitch Landrieu, host Savannah Guthrie had some other questions about the JFK Library committee member. After all, Schlossberg is the only grandson of President John F. Kennedy, and his dashing good looks seemed to position him perfectly to carry on his grandfather's legacy. 

"We always bother you about your future aspirations," Guthrie said. "Do you feel like you know what you want to do? You gonna be a lawyer? You gonna be a businessman?" Schlossberg confessed, "I don't know. That's why I'm in school trying to figure that out. ... I don't know what the future holds."

As Schlossberg has grown up and stepped into the spotlight, he's tried on numerous hats. He's been an actor, and he's written for his college newspaper. He co-founded a nonprofit while he was still in middle school, and he's spoken on national television to an audience of millions. He has tried to sidestep his family history, and he's also soaked up as much information as he could about his famous grandfather. In other words, Schlossberg's life has been one of constant reinvention and transformation ... even as he's captivated audiences online with shirtless lip-syncing videos. This is the stunning transformation of Jack Schlossberg.

John Bouvier "Jack" Kennedy Schlossberg was born on January 19, 1993, the first and only son of Caroline Kennedy and Edwin Schlossberg. He has two older sisters named Rose Schlossberg and Tatiana Schlossberg, making him the youngest member of that particular branch of the Kennedy family tree. Information about Jack's childhood is sparse, which is likely on purpose; Caroline's parents were Jackie Kennedy and John F. Kennedy, two people hounded by the media for much of their lives. The young Jack was occasionally photographed along with his mother on walks around New York City, but for the most part, he hasn't said too much about that time in his life.

Caroline, though, did speak with Parade about how her family has influenced the way she raised her children. In particular, she pointed out that her children resemble her historic parents. "They look a little bit like them," she said in 2011. "My son in particular is very interested in his grandfather, and he loved [Senator] Teddy [Kennedy]. Teddy made a huge effort over them, and I think it gave them a wonderful sense of connection with their grandparents. I can't wait to see who my children will become." Furthermore, Caroline shared well-wishes for their futures. "I hope that they'll find people that they love, and work that they find compelling," she said, "and that they're able to make the world around them better for everyone living in it."

In 2017, Jack Schlossberg appeared on "Today" alongside his mother, Caroline Kennedy. He spoke about feeling the pressure to live up to his family history, but he confessed that he wasn't sure quite yet what path he was going to take. "I'm inspired by my family's legacy of public service," he said. "It's something that ... I'm very proud of. But I'm still trying to make my own way, figure things out. And so, stay tuned. I don't know what I'm going to do."

When Schlossberg was in junior high, however, he dabbled in one career path: activism. Along with a group of friends, he co-founded ReLight NY, a group dedicated to installing better, more environmentally-friendly lighting in low-income neighborhoods. The group's website included a short bio of the young activist. "At 14, Jack is currently the youngest member of RelightNY," the website read. "Jack is not yet in high school, but he already demonstrates an avid interest in cooking, baseball and, of course, the environment. Jack helps round out the stellar group of young men."

Co-founder Avery Hairston was interviewed for a book called "The Green Teen," and he described the group's approach to changing the world, one lightbulb at a time. "Adults aren't going to see the effects of global warming," he reasoned. "So when someone young stands up and says, 'Hey, you're the one who has created the problem, help us fix it,' it's kind of powerful."

One might assume that Jack Schlossberg knew about his family's legacy from birth. In some ways, that's what happened; he later told Vogue that he grew up knowing exactly who he was. Still, he never looked too deeply into what that actually meant, until one particular day in tenth grade.

In history, Schlossberg studied his grandfather's administration. "I felt uncomfortable, so I was goofing off," he recalled. "The teacher called on me and tried to make me look stupid by asking me what the Kennedy administration's policy was in Laos." Schlossberg had no idea, and he realized he needed to commit himself to learning more about what his grandfather's legacy actually was. "That day I went home and started reading," Schlossberg remembered. He became "nerdy" about learning as much as he could about JFK, and one historic speech in particular really resonated. "One gift that [President Kennedy] gave me was his speech at Rice University, his famous moon speech," Schlossberg explained. "That line, 'not because they are easy but because they are hard,' is something that really resonates with me. It's a timeless message."

Those words would echo through the rest of Schlossberg's career, as he committed himself to upholding his family's history. "I've always felt super lucky that there's this massive historical record about my family that I can learn from," he said. "A lot of people don't get to have that kind of relationship with their ancestors."

Even though Jack Schlossberg had grown up around politics and politicians, and even though he'd done a deep dive on his own family, it was Barack Obama's candidacy for president in 2007 and 2008 that really energized the young political scion. He told Vogue years later that his uncle, longtime Senator Ted Kennedy, was the one who first included him in politics. "My uncle Teddy — Senator Edward Kennedy — asked me what I thought of [Obama], and I said how much I loved him and thought he was the real deal," Schlossberg recalled. The high schooler went on to add that he was excited to share his perspective with the veteran politician. "I also felt like he wanted to hear the opinion of a young person and took it seriously," he said.

After that conversation, Ted and Caroline Kennedy endorsed Obama, helping jump-start a groundswell of support that carried him into the White House. "I felt so involved, so heard, so excited about politics," Schlossberg remembered, "and felt that anything could happen and I could make a difference."

In 2017, Schlossberg presented President Barack Obama with the John F. Kennedy Profile in Courage Award. "We can live in the just, inclusive, strong and compassionate nation that President Kennedy imagined and fought for if we choose the type of courageous leadership that defined President Obama's eight years in office," Schlossberg said. "That is our responsibility as citizens, and it is as important today as it ever has been."

Like many Kennedy men before him, Jack Schlossberg received an impressive, Ivy League education. He studied at Yale, where he wrote for the Yale Daily News, and then he went on to both Harvard Law School and Harvard Business School. While there, he participated in several events related to his famous family, including presenting the John F. Kennedy New Frontier Awards. "People have been very cool to me," he told Boston.com, insisting that despite his pedigree, he wasn't treated any differently even though there were buildings on campus bearing the family name. "Once you start law school," he said, "people are too busy studying to care who you are. Overall, I've had an amazing experience here." We have to wonder if Malia Obama had the same experience at Harvard; she was even there the same time Schlossberg was.

At the time, Schlossberg told the outlet that he wasn't exactly sure what he wanted to do with his law degree. Years later, looking back at his education, he told Vogue that he was grateful for the way Harvard helped him become better-informed. "I just read and read and read, and it made me way smarter and a way clearer thinker," he said. "I went to law school super liberal, and I came out of the program with the same thinking — just realizing that I was still right but that I had not known what I was talking about before."

Though Jack Schlossberg has been active on social media for several years, he went viral in early 2024 thanks to a series of quirky videos where he danced shirtless. In one video that got cross-posted to X, formerly Twitter, he danced to "Ticket to Ride" by The Beatles, racking up 34.6 million views on that upload alone as of press time. Sample reactions include, "Love him – funny, charming & right on many issues." Another person wrote simply, "Hot like Uncle JFKJr."

"I think I've broken through to a younger audience," Schlossberg told Town & Country. "I think everyone's looking for a little bit of levity and humor here, and if it's all so serious all the time, it's just too heavy."

At the same time, Schlossberg has received some criticism for his videos, which sometimes include him playing various characters, occasionally with heavy regional accents. One Kennedy family friend told the same outlet, "When he does working-class accents, he's playing with fire. Here's this rich kid making fun." Still, the friend acknowledged that the benefits probably outweighed the risks. "He's got all the stuff," they said. "He's got the humor and the talent and the intelligence to be a really powerful force on social media."

Jack Schlossberg's increased viral fame gave him a platform to speak out about the 2024 election, which not-so-coincidentally included another member of the Kennedy family. While most of the Kennedy clan are lifelong Democrats, Robert F. Kennedy Jr. campaigned for the presidency as an Independent. (RFK Jr. is Schlossberg's mother's first cousin, making him Schlossberg's first cousin once removed.) The campaign was marked by controversies, including the fact that he promotes anti-vaccine conspiracy theories. Some headlines have even been quite bizarre, like the revelation that the candidate once dumped a dead bear in Central Park and staged it to look like a bicycle accident. 

While many members of the Kennedy family have lifted one another up through the political ranks, Schlossberg did not want to see RFK Jr. become president. Many of Schlossberg's viral videos have been silly, but to that end he also became an outspoken critic of his cousin. In one Instagram video, Schlossberg put it simply. "I've listened to him. I know him," he said in the video, which appears to have been recorded in his car. "I have no idea why anyone thinks he should be president," Schlossberg continued. "What I do know is his candidacy is an embarrassment."

Schlossberg's cousin's quest for the presidency didn't last. On August 23, 2024, RFK Jr. officially withdrew from the race and endorsed Donald Trump. 

In July 2024, after months of public attention paid to his wacky online persona, Jack Schlossberg landed a new gig. Ahead of the 2024 election season, Schlossberg joined the team at Vogue, serving as a political correspondent for the magazine. Politics are the family business, but magazines are, too; his uncle, John F. Kennedy Jr., founded George Magazine in the 1990s. Depending on who you talk to, George may or may not have put a strain on JFK Jr. and Carolyn Bessette-Kennedy's love story.

Schlossberg, though, told the magazine that he hopes his new gig will allow him to bring attention to important political issues facing younger generations. "I am inspired by my family's legacy of public service. I take that very seriously, and I want to contribute in my own way," he said. "I have big dreams, but I also know that I'm trying to make a positive impact today."

To that end, Schlossberg called himself a "silly goose" and said that he hoped he'd be able to use his public persona to inform the public. "If you're going to ask people to think about something serious, you need to make it entertaining or fun. That's what all the great leaders do," he said. "You've got to bring some positivity and good energy to the things you think are important. That's the only strategy I have."

In 2018, Jack Schlossberg appeared on an episode of "Blue Bloods" as a character cheekily named Officer Jack Hammer. "That was really fun for me. It's my favorite show," he told "Today." "It was a dream come true to be able to do that, so it was a lot of fun." Still, though, he insisted that it was a one-time experience and that he had no plans to act again.

Something seems to have changed, as Schlossberg has come to be known for the wacky impressions he does online. While speaking with Town & Country, Schlossberg revealed that he's been in talks to try his hand at acting again, though he didn't reveal what, exactly, he'd been auditioning for. Schlossberg wouldn't be the first Kennedy to tread the boards, as they say; his uncle, John F. Kennedy Jr., loved acting when he was younger.

In that same interview, Schlossberg revealed that he was trying something else, too: he was working at becoming an author. "My book is about my method and how I see the world," he revealed. The idea that Schlossberg wants to write a book might come as a surprise to longtime followers of his account on X, formerly Twitter. In 2024, he revealed that he had big plans for that year's Lenten season, writing, "I'm going to read a novel. My first novel."

In August 2024, Jack Schlossberg gave a speech at the Democratic National Convention in support of Vice President Kamala Harris' historic campaign for the presidency. He'd spoken to the DNC before, appearing alongside his mother virtually in 2020, but this time Schlossberg also served as a delegate. In his address to the party, he acknowledged the politically influential family he'd grown up in, talking about how his grandfather's legacy gave him an insight into this particular moment in American history. "He inspired a new generation to ask what they could do for our country," Schlossberg said. "Tonight, JFK's call to action is ours to answer, because once again the torch has been passed to a new generation — to a leader who shares my grandfather's energy, vision, and optimism for America. That leader is Vice President Kamala Harris."

He also echoed the quote from his grandfather that first got him interested in studying his family legacy. "Like President Kennedy, Vice President Harris has dedicated her life to public service," he said. "She believes in America like my grandfather did — that we do things not because they are easy, but because they are hard."

It's unclear what future Schlossberg wants in politics for himself, but after that convention address, it's clear that he's grown up to become an influential voice. Not a surprising path for a Kennedy.