You’d think being the only grandson of John F. Kennedy would come with some pressure to uphold the family legacy.
Instead, Jack Schlossberg seems more interested in going viral for all the wrong reasons.
At 32, the Harvard Law grad has turned into one of the internet’s most confusing—and cringeworthy—personalities.
From bizarre rants to vulgar social media posts, JFK’s grandson seems determined to torch the Kennedy mystique one video at a time.
A Legacy He Can’t Seem to Handle
Jack Schlossberg is the son of Caroline Kennedy and artist Edwin Schlossberg, and he carries the weighty lineage of JFK and Jackie O.
But rather than quietly carving his path, Jack appears more interested in stirring controversy.
He’s gained a reputation online as a troll who routinely crosses the line—especially when it comes to women.
His recent target? A female Daily Mail journalist who dared to write about him.
Jack didn’t just disagree—he lashed out with petty, over-the-top insults and mockery, making the whole ordeal feel more like a meltdown than a clapback.
Harvard Law Grad… but Doing What Exactly?
Since graduating from Harvard Law in 2022, Jack’s professional record has been less than impressive.
He had a short stint as a “political correspondent” for Vogue during the 2024 election—if you can call seven articles, mostly listicles and a short convention speech, a career.
When the Daily Mail pointed this out, Jack responded with, “Hate to break it to you but we have the same job.
I’m just better at it than you.”
Uh, really? That’s a bold statement for someone whose work barely fills a brochure.
Misogyny Masquerading as Internet Humor?
The troubling part isn’t just Jack’s defensive attitude.
It’s how often his comments cross into misogyny.
After a column by Maureen Callahan critiqued him, he responded with a vile nickname too offensive to repeat.
And in response to Megyn Kelly’s comments on trans athletes, Jack took it to a disgusting level, posting a video with a crude reference to female anatomy.
This isn’t “edgy.” It’s offensive—and not even clever.
Even Family Isn’t Off-Limits
Jack’s bizarre online behavior isn’t reserved for strangers.
He’s taken shots at his own relatives, including his mother’s cousin, RFK Jr., the U.S. Health and Human Services Secretary.
He once posted, “Why are you scared of me? Why don’t you ever respond? Are you busy pouring over the JFK files? Or is Cheryl just really dry down there?”
That last jab—aimed at RFK Jr.’s wife, Cheryl Hines—was disturbing, unnecessary, and wildly inappropriate.
Turning on Former Allies Too
Even those who once supported Jack aren’t safe.
In April, he dramatically announced on social media that he was “boycotting” the Met Gala, calling it inappropriate during such “serious times.”
The kicker? There’s no indication he was ever invited.
And the target of this statement? Anna Wintour, Vogue’s longtime editor—and Jack’s former boss.
It seems biting the hand that once fed you is another Schlossberg specialty.
A Cycle of Drama, Apology, Repeat
Jack’s pattern is clear: post something outrageous, face backlash, then offer a vague apology before disappearing for a while.
One of his recent messages read, “I’m sorry to everyone I hurt.
I was wrong. I’m deleting my social media. Forever.”
Of course, “forever” in internet time lasts about two weeks.
The Family Seems Over It
This year’s Kennedy 4th of July celebration in Hyannis Port was notable for who wasn’t there—Jack.
With the annual gathering often resembling a who’s-in-who’s-out social scoreboard, Jack’s absence spoke volumes.
Many believe the family is distancing themselves from his chaotic public presence.
Whether it’s his own doing or theirs, it seems the Kennedy clan has quietly shown him the exit.
More Schlossberg Than Kennedy?
Some speculate that Jack’s behavior reflects more of his father’s temperament than the famed Kennedy polish.
But let’s be real—the Kennedy history isn’t exactly squeaky clean either.
Still, Jack manages to stand out for the wrong reasons, even in a family known for high-profile scandals.
“Not as Bad as Hunter” Isn’t Much of a Defense
Sure, some defenders argue, “Well, he’s not Hunter Biden!” But that bar is in the basement.
At least Hunter had a brief art career. Jack, meanwhile, seems stuck in a loop of internet trolling and self-sabotage.
He’s only a laptop repair shop away from becoming the new poster child for disappointing political offspring.
A Legacy at Risk—Or Already Lost?
Jack Schlossberg had the kind of legacy most people can only dream of—famous bloodlines, elite education, connections galore.
But instead of building on it, he’s spent the last few years torching it online.
At this point, the only thing more surprising than Jack’s fall from grace is how fast he seems to be accelerating it.