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#JFK’s grandson may be the last hope for the Kennedys’ political dynasty

#JFK’s grandson may be the last hope for the Kennedys’ political dynasty

He’s the tall, dark, and handsome princeling of American politics. But will John Bouvier Kennedy Schlossberg ever actually enter the arena?

Twitter had a meltdown after Jack, as the 27-year-old is known, appeared with his mother at the Democratic National Convention in a video pushing for the election of Joe Biden to fulfill the words of Pres. John F. Kennedy’s own acceptance speech 60 years ago.

“The themes of my grandfather’s speech — courage, unity and patriotism — are as important today as they were in 1960,” said the Harvard Law School student, who is JFK’s only grandson. “And once again, we need a leader who believes America’s best days are yet to come. We need Joe Biden.”

His comments lasted all of 50 seconds, but they set social-media hearts aflutter. Fans gushed over Schlossberg’s resemblance to his late uncle, John F. Kennedy Jr. – and over his leonine head of presidential hair.

But despite the mane, the pedigree and the tentative steps he’s taken along a pathway to political power ever since high school, Jack has always been coy about his future plans.

“That’s why I’m in school, to try to figure that out,” he said in 2018, one year into his stint in Harvard’s joint degree program in law and business.

If he does figure it out, he might be the last hope for his family’s crumbling political dynasty.

But one Kennedy cousin told The Post that Jack and his sisters — Rose, 32, an aspiring actress, and 30-year-old Tatiana, an environmental writer — have always been separate from the larger Kennedy fray. Portions of the extended family were noticeably absent from Tatiana’s 2017 wedding to medical resident George Moran.

“Caroline’s family summered on Martha’s Vineyard, not Hyannis Port,” the cousin said. “Caroline has the same sensibility as her mother. She’s not a joiner … Jackie did the same thing.

“There’s a younger clique … Jack is kind of apart from all of them. He’s not as much of a partier or as Hollywood as Bobby’s kids. He’s super smart and strategic.”

Is he too smart and strategic to delve into the kind of high-profile public-service life that has brought his family fame, but also tragedy? He may not have a choice.

“I definitely see Jack doing some type of public service — but I’m not even sure it’s what he wants,” a family insider said. “He is very, very close to his mother. I think he’d like to do something to make her really happy, and that would be public service or politics of some kind. But not necessarily old-school politics. That’s been a dead-end for Kennedy kids. If he did run for office someday, he’d probably aim very big, though.”

Jack Kennedy Schlossberg, Tatiana Kennedy Schlossberg and Rose Kennedy Schlossberg in 2002.
Jack Kennedy Schlossberg, Tatiana Kennedy Schlossberg and Rose Kennedy Schlossberg in 2002.Kevin Wisniewski/Shutterstock

Born in 1993 and raised in Manhattan, Jack was shielded from the press throughout his childhood by his protective mother and his publicity-shy father, artist Ed Schlossberg.

“There are so many generations of Kennedys now that no one is going to be singled out for the kind of attention his mother or his uncle got,” said Jack’s friend and former Yale classmate Paul Wasserman, now a policy analyst at the Department of Defense. “He’s been able to be his own person.”

But Jack was schooled in the Democratic Party canon by his godfather and uncle, the late Sen. Ted Kennedy of Massachusetts. In 2010, Jack spent a high-school summer working at the US Senate as an intern and page for then-Sen. John Kerry.

The next year, Jack was chosen by classmates to give a commencement speech at Collegiate, his NYC prep school — and Kerry read the entire address, replete with bawdy teenage jokes, into the Congressional Record.

Jack indulged a passion for politics in his undergraduate years at Yale, where he studied history. On the side, he ran a student group to support Sen. Chris Murphy (D-Conn.) and wrote columns for campus publications.

“Democrats should never publicly criticize Obama,” he declared in one article as the 2012 presidential race heated up.

In his first TV interview, a chat with CNN on the floor of the 2012 DNC, he said: “Politics definitely interests me. But I haven’t even picked what classes I’m taking this semester yet, so I’m not thinking about a political career right now.”

Jack Kennedy Schlossberg at the 50th anniversary program of the Cuban Missile Crisis at the Kennedy Library in 2012.
Jack Kennedy Schlossberg at the 50th anniversary program of the Cuban Missile Crisis at the Kennedy Library in 2012.Alamy Stock Photo

And in the years since, his focus seemed to shift.

In 2013, as his mother began a post as US Ambassador to Japan, Jack took an increasingly visible role as a Kennedy family representative. He appeared at formal events at the JFK Presidential Library in Boston, the Kennedy Center in Washington, DC, and at ceremonies marking the 50th anniversary of Kennedy’s 1963 assassination, where he chatted easily with Barack Obama and Bill Clinton.

He also turned attention to hands-on service efforts, training as an emergency medical technician to serve Yale’s New Haven neighborhood and taking a summer job removing toxic waste from polluted sites in Massachusetts.

He graduated from Yale in 2015 and joined his mother in Tokyo, working short-term for the US Department of State. But Jack slowly began to increase his political profile once he and his mother returned to the US in 2016.

The two have made regular appearances to announce winners of the annual Profile in Courage Award, given by the Kennedy Library to honor displays of courage reminiscent of those described by JFK in his 1956 book of that title.

John (Jack) Bouvier Kennedy Schlossberg
John (Jack) Bouvier Kennedy SchlossbergGetty Images

And Jack took to Twitter earlier this year to lash out at Mike Pence for quoting his grandfather’s book in an op-ed that urged Senate Democrats to break ranks on the impeachment of President Trump.

“A total perversion of JFK’s legacy and the meaning of courage,” Jack railed.

But he rarely uses his social media accounts for political messaging. Instead, he cultivates a goofy persona on Instagram, with posts on vocabulary trivia, off-key renditions of pop songs and the occasional beefcake photo — including a spate of shirtless shots that emerged once he started seeing yoga celeb Krissy Jones, co-founder of Sky Ting studio.

Jack and Jones traveled to Indiana for a down-home Fourth of July celebration with her family in 2019. But they split soon after amid rumors that he had “snuck around,” according to Radar Online. Previous reports also linked him to Cazzie David, “Curb Your Enthusiasm” star Larry David’s daughter and the ex of “Saturday Night Live” comedian Pete Davidson.

A photo from Krissy Jones' Instagram.
A photo from Krissy Jones’ Instagram.Instagram

“Girls love Jack but he isn’t as smooth as JFK Jr.,” said the family insider. “He’s got the same hair but he’s nerdier.”

Like his late uncle, he can’t seem to resist the allure of Hollywood. While JFK Jr. was romantically linked to famous beauties including Darryl Hannah, Cindy Crawford and Brooke Shields, and ran a magazine, George, devoted to pop culture and politics, Jack has pursued acting via a 2018 cameo role on the CBS series “Blue Bloods.”

It’s pretty safe to assume that Jack’s wait-and-see attitude toward politics is colored by the Kennedy dynasty’s checkered electoral history in recent years.

One Democratic strategist admitted that the Kennedy name will still open doors: “In this era it still gets you looked at in a way that other Democrats just starting out just don’t get looked at.” But it certainly doesn’t guarantee votes.

Jack’s mother Caroline’s only attempt to win office crashed and burned in 2008, when she angled to be appointed to the US Senate as Hilary Clinton’s replacement. Her stumbling response to reporters when asked why she deserved the job — along with a New York Times interview punctuated by 142 uses of the term “you know” — doomed the effort.

And this week, Jack’s cousin Joe Kennedy III could provide another cautionary tale.

Joe, 39, a four-term congressman from Massachusetts, is attempting to unseat incumbent Democratic Sen. Ed Markey in a Tuesday primary — and, if pollsters are correct, may go down in flames. Two polls last week showed Markey, 74, with a double-digit lead — and much of his support coming from Kennedy’s generation of under-40 voters.

And that group may not care much about Jack’s politics either.

“He made no strong impression on me one way or the other,” said Felix Biederman, co-host of Chapo Trap House, the influential left-wing podcast. “He said about two sentences.”

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