JFK’s Only Grandson Follows in His Grandfather’s Footsteps & ‘Looks So Much Like’ JFK Jr – Pics of the 32-Year-Old Man

From his education and global experience to his growing political voice, here’s a look at the 32-year-old who’s carrying the Kennedy legacy forward but on his own terms.

John “Jack” Schlossberg, the youngest child of former president John F. Kennedy’s daughter Caroline Kennedy, has been stepping into the spotlight more and more.

With his sharp education, international experience, and a growing digital presence, he is drawing attention not only for his resemblance to his late uncle, JFK Jr., but also for the values and ambitions he’s carrying forward that reflect a modern take on a storied American legacy. Continue reading to learn more about him.

Caroline’s Youngest Carries the Kennedy Name

The Kennedy family name has endured through decades of American history, and Jack is part of its next chapter. The only grandson of the late President Kennedy, Jack was born on January 19, 1993, to Caroline and her husband Edwin Schlossberg.

He was named in honor of two men — his grandfather and his maternal great-grandfather, John Vernou “Black Jack” Bouvier. Caroline, who married artist and designer Edwin in 1986, raised Jack alongside his two older sisters, Rose and Tatiana.

After graduating from Yale in 2015, Jack moved to Tokyo, where his mother was serving as U.S. ambassador.

Much like her own parents, JFK and Jacqueline Kennedy, Caroline worked hard to keep her children out of the public eye while they were growing up. Despite the constant media attention surrounding her family, she remained committed to giving her children a sense of privacy and normalcy.

Time Abroad

In his youth, Jack attended the Collegiate School, an elite all-boys institution in New York City, where he was already showing signs of leadership and civic-mindedness.

While still in middle school, he co-founded ReLight New York, a nonprofit that helped install energy-efficient compact fluorescent lights in low-income housing developments across the city.

By the time he graduated in 2011, Jack had earned the title of valedictorian and delivered the school’s commencement speech. He then enrolled at Yale University, following in the footsteps of his sister Tatiana.

There, he majored in history with a concentration in Japanese studies and contributed to campus publications including the Yale Daily News and the Yale Herald. After graduating from Yale in 2015, Jack moved to Tokyo, where his mother was serving as U.S. ambassador.

He joined her during the final year of her term, working at Suntory, a distillery company, where he assisted the CEO’s office with research and speech writing. During that time, he also studied the Japanese language.

In January 2025, Jack reflected on Instagram about living overseas with his mother, “I lived [with] her in JAPAN during her time as Ambassador 2012–16 and I spent time with her in AUSTRALIA as Ambassador (2021–24).” He praised her leadership and diplomatic skills, adding:

“She’s a highly effective diplomat. In Japan, she secured critical economic partnerships, advanced the US–JAPAN military alliance, and most importantly represented America to the Japanese people who embraced her with open arms.”

He continued, “She was the first female ambassador to Japan, a country that despite what some feared completely welcomed a female as a strong independent force on her own.”

From Collegiate to Harvard

Following his stint in Japan, Jack returned to the U.S. and, in November 2017, began pursuing a joint degree at Harvard — splitting his time between the Law School and Business School.

During an interview, he described the experience, saying, “Harvard Law School is great. I’m lucky to be here. It’s a really difficult, intense experience. But I know so much more than I did the day before I got to law school, so that’s a cool feeling.” When asked if he had time for anything beyond studying, he replied:

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

In early 2022, Jack officially graduated from Harvard. In April of the following year, he celebrated passing the bar exam. He shared the news on Instagram with a photo of himself paddleboarding in Manhattan, writing, “TFW passed the bar — Jake Cyborg, Esq!”

By October 2023, at the Profile in Courage Award ceremony hosted at the John F. Kennedy Presidential Library, Jack confirmed that it “feels great” to have passed the bar on his first try.

Athletic and Adventurous – Just Like the Kennedys

Jack has long embraced the Kennedy family’s passion for the outdoors. In 2016, he ran his first triathlon on Long Island. A year later, he challenged himself with the Sea Paddle — a grueling charity race around Manhattan.

In March 2025, Jack shared another side of his active life, posting photos and videos on Instagram from a ballet performance he participated in — adding yet another unique skill to his already diverse interests.

He admitted that he initially signed up because it “sounded cool,” underestimating just how tough it would be. Training involved long hours on the Hudson River, where he often found himself trailing far behind much smaller competitors.

As the youngest of three siblings, he joked that the experience of watching them pull ahead felt all too familiar. The race started beneath the Brooklyn Bridge, but before it even began, Jack fell into the East River while adjusting his board.

“It’s true what they say: Nothing tastes quite like the East River,” he humorously shared. The rest of the race blurred together — a mix of caffeine, adrenaline, exhaustion, and Elvis blasting through his headphones. Nonetheless, he finished in just under five hours, placing eighth in his division.

In March 2025, Jack shared another side of his active life, posting photos and videos on Instagram from a ballet performance he participated in — adding yet another unique skill to his already diverse interests.

Reminders of JFK Jr. Run Deep

Jack has openly called himself a “student of [his grandfather’s] life, legacy, and administration,” but those closest to him often see echoes of his late uncle, John F. Kennedy Jr. Those close to John Jr. have noted striking similarities between uncle and nephew. One friend revealed in 2015:

“Jack is very much interested in John. He has an ease and a sense of humor. And he loves being compared to him. John was a rare kind of celebrity who grew up with being famous and had fun with it and didn’t let it take over his life.”

Jack and his late uncle’s similarities are not lost on netizens either, as one commented on one of his Instagram posts, “Jack, you look so much like your Uncle John John, in this photo especially ❤️❤️❤️.”

Motivated by his grandfather’s ideals, Jack has made it his mission to engage a new generation in politics — and he’s doing it with humor and heart.

Someone else said of another post where Jack resembled JFK Jr., “Waou u look just like your uncle in this pic. Insane.” A third person typed, “The resemblance to your uncle is uncanny!!” while a fourth added, “Your uncle’s twin. 🩶”

Another person wrote, “I thought that was JFK Jr, he’s a mirror copy of his uncle. Wow 😯” Someone else remarked, “Oh wow!! He looks so much like his uncle Jon-Jon !! Very handsome!”

John Jr. died alongside his wife, Carolyn Bessette, on July 16, 1999, following a tragic plane crash. In a final bid to mend their strained relationship, Carolyn agreed to go with him to his cousin Rory’s wedding in Hyannis Port. The plan involved a stopover at Martha’s Vineyard to drop off Carolyn’s sister, Lauren.

John Jr., an experienced pilot, would then fly his Piper Saratoga plane, which he had bought earlier that spring, to Hyannis Port. On July 16, after a day at the office, he met Lauren at 6 p.m. for the drive to Caldwell Airport in New Jersey. Carolyn arrived separately via car service.

For decades, rumors swirled that Carolyn was late to arrive at the airport because of a spa appointment. However, eyewitnesses clarified that she had left the spa by 5 p.m. and had made a quick stop at Saks to buy a dress for the wedding.

As Carolyn departed, a salesgirl wished her good luck. By the time their plane took off at 8:38 p.m., the sun was setting, and visibility was poor due to worsening weather conditions. At some point after 10 p.m., Rose Marie Terenzio, John Jr.’s assistant and close friend, received a phone call.

On the other end was Carole Radziwill, the wife of his cousin, Anthony Radziwill. Her voice carried a note of urgency — the plane had yet to land in Martha’s Vineyard. Their whereabouts remained a mystery.

That night, after Carole’s call, Rose frantically searched for answers. She contacted the Caldwell airport and reached out to Carolyn’s mother, Ann Freeman.

Ann was overcome with emotion. “She was panic-stricken,” Rose recalled in her book. “She said something like, ‘I told him never to take two of my girls up at the same time.’ She was in shock — crying, panicked, unable to believe what was happening.”

Tragically, John Jr. and Carolyn never made it to Hyannis Port. The plane crashed into the waters about seven miles from Martha’s Vineyard, killing them and Lauren. The National Transportation Safety Board (NTSB) thoroughly investigated the crash.

Their findings pointed to spatial disorientation as the primary cause. The report concluded that the “probable cause(s) of this accident to be the pilot’s failure to maintain control of the airplane during a descent over water at night. Factors in the accident were haze and the dark night.”

Carrying the Torch – On His Own Terms

In 2024, Jack took a step further into the political spotlight when he was named Political Correspondent for Vogue. Speaking about his role, he said:

“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. I have big dreams, but I also know that I’m trying to make a positive impact today.”

Motivated by his grandfather’s ideals, Jack has made it his mission to engage a new generation in politics — and he’s doing it with humor and heart. Rather than echoing traditional political messaging, he focuses on delivering important information through accessible, entertaining videos.

Jack’s political efforts have resonated strongly with younger audiences, especially on TikTok.

His content covers everything from presidential debate analysis to Supreme Court rulings, including a recent breakdown of the Loper Bright Enterprises v. Raimondo decision.

“If you’re going to ask people to think about something serious, you need to make it entertaining or fun,” he told Vogue. “That’s what all the great leaders do.”

He added, “You can’t just hammer people with how bad stuff is. You’ve got to bring some positivity and good energy to the things you think are important. That’s the only strategy I have.” Jack’s political efforts have resonated strongly with younger audiences, especially on TikTok.

When asked to describe his online presence, he replied, “It would be for others to describe. I’m just having a good time. I’m a fun, wacky guy. I’m a silly goose — a silly goose who’s trying, just trying, to get the truth out there.”

As for why people are tuning in, Jack believes authenticity is key. “I try to say things that I think are important. People can tell when people are being authentic and don’t have any other agenda,” he revealed.

“That comes through in ways that are intangible but people pick up on, especially younger people who are super fluent with social media. There are things that you can tell are authentic versus not, and people respond well to that with me,” Jack continued.

Jack has honored his family’s legacy while forging his own path — through education, global experience, athletic challenges, and a rising voice in politics.

At 32, he reflects the best of former president John J. Kennedy, his late son John Jr., and his family’s name, and signals a new chapter built on purpose, presence, and authenticity.