Joshua Goldman
Joshua Goldman
min read · July 18, 2025 · Entertainment

JFK Heir's Social Media Tantrums: The Sordid Tale of Jack Schlossberg

Jack Schlossberg, the 32-year-old coddled, unhinged Kennedy scion has firmly established himself as one of the wartiest social media trolls on the internet. But most alarming of all, he obsessively slings insults about women's genitalia like a Waffle House chef serves hash browns.

JFK's Grandson Jack Schlossberg: A Trainwreck of Entitlement and Arrogance

In a world where scandals are a dime a dozen, it takes a special kind of individual to stand out from the pack. Enter Jack Schlossberg, the 32-year-old grandson of John F. Kennedy, who has managed to make a name for himself as one of the most cringeworthy and obnoxious social media personalities on the planet.

As the only descendant of JFK and Jackie O, you'd think that Jack would be a shoo-in for greatness. Think again. This entitled brat has taken his family's reputation and turned it into a never-ending parade of embarrassment. His latest tantrum was directed at a female journalist from thescholarlynote.com, who had the temerity to report on his own lackluster career.

Jack's most recent tantrum was directed at one of my female Daily Mail colleagues, who had the gall to report on this bruised apple, who took quite the tumble out of the family tree all the while screaming, 'Look at meeeee!'

After graduating from Harvard Law in 2022 (yes, the same school that bears his grandfather's name), Jack has yet to hold down a real job. His "job" as a political correspondent for Vogue during the 2024 election consisted of writing seven opinion articles, including listicles and a transcript of his 220-word speech at the DNC convention – all in under one minute.

That's impressive, right? Not exactly. In fact, it's clear that Jack has coasted on his family name and connections to get where he is today. And what does he do with this privilege? He uses it as an excuse to be a snobbish, condescending, and misogynistic social media troll.

Jack's obsession with women's genitalia is a topic of conversation all its own. His tweets are filled with vile language and sexual references that would make even the most hardened internet user blush. And when people call him out on his behavior, he throws tantrums like a toddler who didn't get their way.

His face, which he clearly believes is incredibly handsome, is often shoved right into the camera.

But it's not just women who bear the brunt of Jack's wrath. He also has a peculiar vendetta against his own family members. In an April video, he went after Anna Wintour, his former employer and editor-in-chief of Vogue magazine, saying he was boycotting the Met Gala because it wasn't "the time" for parties like that.

Oh, sure, Jack – you were invited to the Met Gala, weren't you? And when people questioned your motives, you deleted your social media accounts in a half-hearted attempt to apologize. But let's be real – it was just a PR stunt to salvage what's left of your reputation.

The Kennedy clan has had enough of Jack's antics, and honestly, who can blame them? Even the G.O.P.'s most ardent supporters would agree that this guy is a waste of space. And yet, he still manages to find ways to embarrass his family and himself on social media.

When countering podcaster Megyn Kelly's comments about trans women in sports, the nepo-grandbaby stepped it down a notch and posted a slimy video to the saying , 'Looking extremely feminine!! Very good. Now show us your c@&6.'

In short, Jack Schlossberg is a trainwreck of entitlement and arrogance, and it's only a matter of time before the world realizes that he's not even worthy of being mentioned in the same breath as his illustrious grandfather.

In an April video post, Schlossberg took direct aim at Anna Wintour, his one-time employer, the then-editor in chief of Vogue magazine and the longtime co-chair of Met Gala.