Meet JFK’s Grandson Jack Schlossberg, the Democrats' New Hope

Caroline Kennedy’s son isn’t just the latest light of America’s quasi-royal family. Championing social causes and sporting a presidential look, he may be aiming very high

Jack Schlossberg on May 5, 2017, when he appeared on "The Today Show" in New York with his mother, Caroline Kennedy.
Nathan Congleton / NBC Universal via Getty Images

On July 16, 1999, a single-engine Piper plane plunged into the Atlantic not far off Martha’s Vineyard. Five days later, three bodies were pulled from the water. The pilot was John F. Kennedy Jr. and the passengers were his wife, Carolyn, and her sister, Lauren. The three had been on their way to the wedding of John’s cousin, Rory Kennedy.

The bride is the embodiment of the family tragedy. Her father Bobby was assassinated six months before she was born. When she was 15, one of her brothers died of a drug overdose, and a decade and a half later another was killed when he crashed into a tree during a game of ski-football in Aspen, Colorado. When her cousin perished in the plane crash, her wedding day essentially turned into a funeral ceremony.

When the Piper plummeted into the ocean, so did the hopes of many Americans. JFK Jr., the son of the beloved president, was the great promise. From a young age he was expected to run for president one day to continue the legacy of his father. He was good-looking, interested in politics and projected the image of a success story – even though that wasn’t quite the case.

For much of his 38 years, he gained a reputation as a playboy and eternal bachelor whom the paparazzi would snap as he rolled shirtless around Central Park on in-line skates. Toward the end of his life he was the publisher of George, a failed political magazine, and his fairly recent marriage also seemed on the verge of collapse. But none of that really mattered.

The family mythology, combined with John Jr.’s charm and ideals, were supposed to take him as far as one can go in America. And he never said he wasn’t interested in that. In the lean years of the ‘80s, when it seemed the Republicans would remain in power forever, JFK Jr. was supposed to be the one to pull the Democrats out of the depths.

John-John was the last Kennedy who inspired Americans. In the two decades since his death, the family hasn’t put into the public arena anyone who could breathe hope into battered Democratic souls. But now they have. He hasn’t even finished graduate school but is generating a buzz. The moment he hinted he has political ambitions, he sent blood coursing through parts of the body politic that had hitherto seemed moribund.

Jack Schlossberg, 27, is the grandson of President Kennedy, the son of his daughter Caroline. It’s no surprise that he stirs nostalgia for JFK's son. Young Schlossberg bears a striking resemblance to his late uncle. When he appears at public events with his shock of hair, superbly fitting suit and talks about public service and courage in politics, he’s echoing the promises that his uncle didn’t live long enough to keep. Most of all, he’s putting a little blush back into the cheeks of a family and party whose glory days have been nearly forgotten.

Caroline Kennedy and her son, Jack Schlossberg, at a Metropolitan Museum of Art gala, May 1, 2017.
Evan Agostini / Invision/ AP

More than a hunk

In May 2017, Caroline Kennedy arrived for a gala at the Metropolitan Museum of Art accompanied by Jack, then 24. She may have been wearing an elaborately crafted gown with layers of floral prints, but all eyes were on the young man in the dark suit and black-and-gray tie. This was Jack’s first exposure to the public at large. Many people wondered who this young man was who looked so much like JFK Jr. It almost looked as if Caroline were stepping out with her brother – the version from 30 years earlier. Jack was immediately marked as a promising hunk, but lately he has shown he’s a lot more.

Schlossberg was back in the headlines last month after Vice President Mike Pence cited President Kennedy’s legacy in a Wall Street Journal op-ed on the impeachment proceedings against President Donald Trump. Young Schlossberg didn’t like seeing his grandfather used this way; he scolded the vice president on Twitter and gave him a history lesson.

“I would argue instead that today, as in 1865, political courage might require a Republican Senator to risk his or her own political future by breaking lockstep from the President and agree to hear from witnesses, review the evidence, and put the national interest above their own,” Schlossberg wrote.

This wasn’t the first time Schlossberg had dipped his hand into the political swamp. At 23, he defended his grandfather’s legacy in a forceful piece in Politico in which he responded to Senator Ted Cruz’s claim that JFK wouldn’t have felt at home in today’s Democratic Party. In the article, Schlossberg contrasted what he described as today’s racist and backward Republican Party with his grandfather’s enlightened and progressive legacy.

Schlossberg has shown that he’s unafraid to go after more seasoned political rivals to defend his family’s honor and values. It’s clear that this guy is much more than his mom’s hunky date to gala events. In a joint interview with his mother on NBC’s “The Today Show,” he was asked whether he was considering a future in politics.

“I’m inspired by my family’s legacy of public service,” he replied. “It’s something that I’m very proud of, but I’m still trying to make my own way, figure things out, so stay tuned.” This diplomatic answer was enough to signal that a new Kennedy was planning his first steps in politics.

John F. Kennedy Jr. and his wife, Carolyn Bessette Kennedy, leaving a party in New York, October 10, 1996.
Douglas Healey / AP

Jewish father, Catholic education

John Bouvier Kennedy Schlossberg was born on January 19, 1993, the day before Bill Clinton was sworn in as president, opening a new Democratic era in the White House. His father is designer and author Edwin Schlossberg, who married Caroline Kennedy in 1986.

Caroline was 6 years old when her father was killed. Since then her public life has gone on in the shadow of the assassination and the family legacy. After years of working as a lawyer and in volunteer positions, at 50 she decided she was ready to enter politics and announced she was aiming for the Senate seat that Hillary Clinton was vacating.

She seemed to have a good shot until it became clear she wasn’t a particularly deft politician – and was someone who hadn’t bothered to vote since 1988. After a catastrophic television interview in which she said “you know” 168 times in half an hour, she dropped out of the race. Later that year, 2013, President Barack Obama offered her a consolation prize, ambassador to Japan, a post she held for more than three years until Trump was elected.

Jack Schlossberg grew up a chubby kid in Manhattan. In keeping with the family tradition, he enjoyed boating and fishing trips. Though his father is Jewish, like a real Kennedy, Jack received a Catholic education. He says he keeps some of the Jewish tradition and celebrates Jewish holidays, but the religion clearly doesn’t play a central role in his life.

His oldest sister, Rose, created and stars in a web series about two girls who manage to stay well-groomed even post-apocalypse. His other sister, Tatiana, has approached the apocalypse from a more serious angle as the climate change reporter for The New York Times. She has also written a book on the subject.

Jack attended the prestigious Collegiate private school on Manhattan’s Upper West Side; it claims to be the oldest school in the United States. In the eighth grade, he and a few classmates founded the nonprofit organization ReLight New York. The aim was to provide economical compact fluorescent bulbs to low-income housing developments; the boys raised over $100,000 for the cause. Schlossberg cited the initiative’s dual social message: supporting the needy and increasing awareness of environmentally friendly energy. Since then, the climate agenda has become one of his flagship causes.

He earned his bachelor’s degree at Yale, where he studied history, majored in Japanese studies and wrote for the school newspaper. At the time his parents were living in Japan while his mother was ambassador. Jack lived with them part of the time and when not, went back for frequent visits. He learned Japanese and accompanied his mother to many of her meetings.

In Japan, he gained his first exposure to international diplomacy up close. He took part in meetings with Japanese Prime Minister Shinzo Abe, and with U.S. Secretary of State John Kerry and Michelle Obama when they visited the country. He joined his mother when she toured the Fukushima nuclear plant that was damaged in the 2011 earthquake and tsunami. While workers were still clearing away fuel rods, Kennedy and her son toured the site dressed in protective suits, helmets and gas masks.

Schlossberg said he had joined his mother to boost awareness of the disaster among young people. “I hope my peers, my generation in the United States, will keep Fukushima in mind and understand that there is still work to be done and we can all do something to help,” he said.

In Japan he also learned the art of networking. Through his mother he met the CEO of Japanese e-commerce company Rakuten, who gave him his first job after he graduated from Yale. He later had a temporary job at the State Department and for Japanese beverage company Suntory.

After Yale came Harvard, where Schlossberg is now studying in a joint law and MBA program. At this stage he began cultivating a public persona and has gained tens of thousands of followers on Instagram. His friends in a Harvard study group voted him most likely to live longer than the rest of the group, apparently an ironic nod to the family tendency to fall short of old age.

A crush on Kendall Jenner

As part of his internship in the family business, Schlossberg takes part in foundations that grant awards named after his grandfather. He’s the family representative on the John F. Kennedy New Frontier Awards committee that honors public servants who fight for their communities, and he’s on the panel that bestows the Profiles in Courage Award to leaders who show extraordinary political courage. Schlossberg has become the spokesman for these awards – in media appearances he enthusiastically explains why the recipients were chosen and promotes the issues he cares about.

He has handed awards to people like May Boeve, leader of 350.org, to President Obama for health care reform and to New Orleans Mayor Mitch Landrieu, who removed statues of Confederate leaders from public spaces. While many young members of the Kennedy clan are focusing on careers in show business, Schlossberg focuses on the family’s ideological side, the one that still champions liberal values and isn’t afraid to say so to protect them. Among the causes he highlights are climate change, women’s rights and diversity.

Even though this is a guy who has been wearing suits since age 20 and is more than comfortable discussing momentous issues with the utmost seriousness, Schlossberg isn’t ashamed to laugh at himself or act silly in public. His Instagram page is filled with private jokes, shirtless photos and pictures of him from university costume parties. Sample costume: a bull market – apparently a hilarious joke in business school circles. An unabashed nerd, much of his Instagram page is devoted to the differences between “concrete” and “cement,” or “memoir” versus “autobiography.” Stuff like that.

Nor does he hide his admiration for Emmanuel Macron and Justin Trudeau, the two main icons of young and liberal (and handsome) world leadership with whom Schlossberg evidently feels a kinship.

So far, Schlossberg’s history with women isn't that rich. His most notable relationship was with yoga teacher Krissy Jones. Schlossberg even passed up the traditional Kennedy family Fourth of July party to be with her. The relationship didn’t last very long. Jones reportedly dumped him after she discovered he had “snuck around” on her – another family tendency that apparently didn’t die with JFK. Before Jones, Schlossberg was reported to have spent time with screenwriter Casey David (daughter of Larry David), and he was also said to have had an unrequited crush on Kendall Jenner.

Schlossberg checked off the acting-career box when he appeared in an episode of “Blue Bloods” as Officer Jack Hammer. He said he did it because it’s the best show in the world and he has no ambitions to pursue acting. He seems to combine a life of moderate pleasure-seeking, an Elvis-type image, enthusiasm for sports like paddleboarding and a great passion for politics and public service.

In 2017, when Schlossberg circled Manhattan on a paddleboard, he wrote about the experience for New York Magazine. The accompanying photos – black-and-white shots of him paddling bare-chested – again called to mind Uncle JFK Jr., who also worked as a journalist and had no qualms about appearing in public shirtless. Again the question was raised, not for the last time, whether here was a political heir – and would Schlossberg have a happier ending.

In some ways, the sun appears to be setting on the Kennedy family empire. The money is still old, but the brand, like that of other royal or quasi-royal families around the world, no longer inspires the awe it once did. Yet Jack Schlossberg is a living reminder of how the Kennedy surname, like a sleeping tiger, can suddenly pounce on you.

Schlossberg reminds us of his grandfather’s glamour, but beyond the family affiliation, he makes a mark as a millennial who isn’t preoccupied with himself. His political activism, unlike that of many of his peers, goes beyond a superficial presence on social media. He genuinely aspires to devote himself to public service.

At a time when the Democratic candidates are fighting for what could be the right to lose to Trump in November, young Schlossberg offers hope and a reminder of the fighting spirit, glamour and nobility that the party once possessed. In the Kennedy family, the only two things that get in the way of political ambition are an assassin’s bullets and reckless arrogance that leads to an early death. Young Jack Schlossberg should be careful out there.