JFK’s Grandson Looks Like His Twin

Feb 02, 2022

In a video from August 2020's Democratic National Convention in Milwaukee, Wisconsin, the late President John F. Kennedy's grandson, 27-year-old Jack Schlossberg, appeared alongside his mother — and the resemblance to his grandfather is striking. We'll take a closer look at Schlossberg's life while also comparing him to his famous grandad, the 35th president of the United States.

As part of the DNC's mostly virtual convention last summer, Schlossberg and his mother, Caroline Kennedy, made an appearance in a short 2-minute clip, which also looked back on JFK's legacy as president. And while it certainly was not the focus of the video, Schlossberg's brief showing at the convention led people to discuss the uncanny similarities between the former president and his 27-year-old grandson.

According to Esquire, Jack Schlossberg is the third child of Caroline Kennedy –– the only surviving child of JFK –– and her husband, designer Edwin Schlossberg. As the unofficial Kennedy family tradition goes, Caroline entered public life in 1989 and has remained active since then. Her most recent high-profile job was as the US Ambassador to Japan, which she served between 2013 and 2017. 

During his mother's tenure as Ambassador, Schlossberg lived with her in Japan –– and experience, he said, profoundly shaped his upbringing. 

"I learned a lot about Japan. But the most important thing I learned was about my own country," Schlossberg said at the 2017 JFK Profile In Courage Awards. "It was something I had been told all my life but never fully grasped. I saw how people around the world see America: a beacon of opportunity, stability and strength in a world of uncertainty. America's historic role has been just that. America, as President Kennedy once described it 'has always been a lantern in the dark for those who love freedom but are persecuted, in misery, or in need.'"

Just like his famous grandfather, Schlossberg worked hard to obtain an Ivy League education. In an interview with the Today show from May 2020, the 27-year-old graduated from Yale University in 2015, after which he enrolled in JFK's alma matter Harvard, where he is currently pursuing a JD and an MBA. While Schlossberg might lead a privileged life thanks to his family name, the young student is nonetheless down-to-earth. In an interview with Boston.com, he admitted that he finds attending Harvard a "difficult" and "intense" experience. 

"Harvard Law School is great. I'm lucky to be here. It's a really difficult, intense experience," he said. "But I know so much more than I did the day before I got to law school, so that's a cool feeling."

Schlossberg also revealed that while he is grateful to be at Harvard, the rigorous studying required to keep up means he has little time for himself. 

"I don't have a life, but that's what I signed up for," he said. "It's cool, you just get to learn all day. Sometimes it's tough, but it's been a fun experience."

JFK's legacy is also very present around the campus in Cambridge, Massachusetts.  "My favorite restaurants are on JFK Street, so I definitely notice it. It's humbling, but overall it's nice that it's just out in the open. There's no pretending that it's not here when I'm at Harvard. The first few days it felt a little weird, but now I don't think about it so much."

While he might come from a world-famous family, Schlossberg says he's blended in quite well at his school. "Yeah, people have been very cool to me," he said. And once you start law school, people are too busy studying to care who you are."

Naturally, many wonder if Schlossberg plans on making a debut in politics just as much of his family has, although he says that he hasn't yet decided what he would like to do after Harvard. For now, he's focused on obtaining his Law degree. 

"I'm not sure what I want to do — business, law, something else," he admitted. "I came into law school thinking I really wanted to practice environmental law, and so far my favorite class is in property, which is something I never would have expected. Come three years from now, my interests could be completely different. I'll always be interested in climate issues, but my idea of what I want to do will probably change."

While it isn't yet clear if he will be joining politics later in his life, Schlossberg is nevertheless passionate about the causes he cares about –– especially climate change. He even started his first non-profit in the 8th grade, RelightNY, which aims to help low-income households become more environmentally friendly with the simple step of adopting energy-efficient lightbulbs. 

Schlossberg has also contributed to a few major publications like the New York Times and The Washington Post. 

In an interview with People magazine, Schlossberg revealed that he is The Rock's "biggest fan." The law-student revealed that a close friend even arranged for Johnson to send him a personal birthday message. "It was the happiest I've probably ever been," Schlossberg said. 

"He's just like the funniest, best guy," he continued. "And what I really love about him is that he is the hardest worker… I identify with that because I think hard work is very, very important, and so I just think he's the man."

While the 27-year-old claims he has a lot on his plate thanks to his studies, he did find the time to star in a beloved drama crime series. In 2018, Schlossberg made his acting debut in the season 8 finale of Blue Blood, in which he brought the character Officer Jack Hammer to life. Ecstatic about the experience, he took to Instagram to post about the exciting news with a photo of himself with the cast and his mom. He wrote:

"I don't make the rules, I just pretend to enforce them — Cash me tonight on season 8 finale of Blue Bloods my dream come true!! Best show in the entire world."

In 2017, Schlossberg debuted his puppy to his Instagram followers, where he humorously listed some potential names for the new pet. 

"Gonna name him Fuki or Nutroll or Rabbit or Maestro or Big Data or Richard or maybe Pickle or Angus. He's my brother," he wrote. 

In the end, Schlossberg ended up going for another name, which might come as a surprise to many. Speaking to People, the law student said he named his dog Chester because "he looks exactly like [former president] Chester A. Arthur." While Chester looks quite like a pooch, Schlossberg says he isn't too sure about the little guy's origins. "He's a mix of two different types of dogs, but I don't remember the exact breed," he said.

Unlike the rest of the Kennedy clan, Schlossberg isn't too shy to give the public a peek into his personal life and keeps an active presence on Instagram. An avid lover of the English language, the 27-year-old uses his profile to share wordplay-memes, with which he explains the difference between similar phrases and words. In his most recent post, Schlossberg explained the different meanings of the word "key."

Fans of the Kennedy Family cannot seem to get over Schlossberg's striking resemblance to his uncle, the late John F. Kennedy Jr, who dies in a plane crash in 1999. From the eyes to the dark hair to the impressive jawline, many fans have dubbed Schlossberg his uncle's "reincarnation." In a tweet comparing the two from last summer, one user said they got "chills" upon seeing their similarities. 

"Gave me chills to see how much he looks like his uncle," they wrote. "What a legacy and a gift that family has been and continues to be!"

Following Schlossberg's high profile at the 2020 DNC convention, others also took to Twitter to write about his eerily close looks to Kennedy Jr. 

"Those Kennedy genes are SCRONG! Jack Schlossberg is giving me all the JFK Jr feels," reads another Tweet.

Perhaps most obviously, Schlossberg shares his grandfather's killer good looks. It's not a stretch to say that most of us remember JFK as a bit of a hunk. After all, one of Kennedy's most famous photos is of him sporting stylish Ray-Bans with the wind in his hair on his private yacht, the Manitou. And countless publications have called the 35th president a "style icon," with guides on "How to dress like JFK." 

In a few years, magazines might be writing the same thing about Schlossberg because the 27-year-old not only knows how to dress — look at him in a suit! — but he also has that old-world Kennedy charm.

While Schlossberg might not be following his family in politics for now, his role in carrying on the Kennedy legacy isn't lost on him. 

"I'm inspired by my family's legacy of public service," he told Today in 2017. "It's something that I'm very proud of." 

In the summer of 2017, Jack Schlossberg did the unthinkable by making a round of Manhattan's island on a stand-up paddleboard. And he did it for charity. 

In a piece he wrote for Cut at the time, the Harvard matriculate revealed that he took part in a 25-mile circumnavigation race around Manhattan. The event aimed to raise funds for environmental and autism charities, two causes for which Schlossberg cares deeply. To raise funds, he asked his friends and loved ones to sponsor him in and, in exchange, he would let them choose a slogan for him to print on the t-shirt he would be wearing on the day. "I wouldn't dare reprint their many slogans in this esteemed publication," he joked.

The race started on the East River, underneath Brooklyn bridge. According to his narrative, Schlossberg managed to fall out of his kayak just before the whistle blew." Nothing tastes quite like the East River," he wrote.

"I signed up for the race because I thought it sounded cool. 'Paddle around Manhattan? Sweet, man! How hard could it be?' Of course, when I asked around, everyone said it was really hard and that I'd better start training," Schlossberg recalled.

With that advice in mind, Schlossberg sought out a coach or rowing group to whip him into shape in time for the race. He eventually found a group to help him at a boathouse that offered board storage and lessons in stand-up paddling, kayak, and canoe. He admits that while he was born and raised in Manhattan, it was the first time he had experienced the rivers that surround it. 

Schlossberg revealed that three women "half [his] height and weight" had trained him for the event, taking him on rigorous training sessions on the Hudson. He jokes that he tried desperately to catch up with them but "never came close."

"In fact, I spent the entire race on Saturday watching them get farther and farther ahead of me — this, a familiar feeling for a younger brother of two older sisters," he wrote.

The experience was both exhilarating and exhausting for Schlossberg, who says the combination of "coffee, adrenaline, exhaustion, and Elvis hits blasting in [his] ears" have blurred his memory of the day. The race took him five hours, and he ended up coming in eighth place. 

Were you surprised to see how much Jack Schlossberg resembles his legendary grandfather? Or do you think he resembles his famous uncle even more? Let us know in the comments, and make sure you pass this along to your friends and family!