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Ask not what Jack Schlossberg is talking about, ask why his parents haven’t had him committed yet.
For something is seriously wrong with JFK’s grandson.
Jack Schlossberg, a 32-year-old member of the Kennedy family, has gained a notorious reputation as a provocative figure on social media. The most concerning aspect of his behavior is his tendency to make derogatory comments about women’s anatomy with unsettling frequency.
Calling Camelot… you may have yet another misogynist in your midst (it runs in the family).
Sloppy Schloss is the son of Caroline Kennedy and artist Edwin Schlossberg and he is the sole descendent of John F Kennedy and wife Jackie.
Recently, Jack targeted one of my female colleagues at the Daily Mail, simply because she dared to report on his controversial antics and attention-seeking behavior.
Even though he graduated from Harvard Law in 2022, from an institution that bears his grandfather’s name, it doesn’t seem like Jack has pursued a conventional career since. However, when the Daily Mail pointed this out – following Jack’s online outburst about mangoes – he became particularly irate.
‘Hate to break it to you but we have the same job,’ he posted to the Daily Mail scribe. ‘I’m just a lot better at it than you.’

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.

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!’
Really?
Jack’s ‘job’ as a political correspondent for Vogue during the 2024 election consisted of a whopping seven inane opinion articles, including listicles and the transcript of his 220-word speech at the 2024 DNC convention, which takes less than one minute to read.
Wow, Jack. That’s quite a high bar to clear. An intern with head trauma could have been more prolific.
I’m sure everyone at Conde Nast wholly regrets their association with you.
Here’s the thing: Schlossberg won the genetic lottery and he’s whizzed it all away. That’s his business. What irks me is his insufferable arrogance, thin-skinned whining and bizarre fixation with ladyparts.
After fellow Daily Mail columnist Maureen Callahan penned a piece about his antics, he tagged her with a vile, sexual nickname that I won’t reprint.
And 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 saying: ‘Looking extremely feminine!! Very good. Now show us your c@&6.’
Jack’s really giving Hunter Biden a run for his money for the Most Massive Disappointment of the Century award.
And when Jack isn’t wreaking gynecological warfare only on strangers, he spews his smut on family.
He appears to carry an especially unsavory hatred for his mom’s cousin Health and Human Services Secretary RFK Jr, whom he has described as a ‘liar’ and once posted: ‘Why are you scared of me? Why don’t you ever respond? Are you busy pouring [sic] over the JFK files? Or is Cheryl just really dry down there?’
That creepy zinger was, of course, intended for another woman – Bobby’s wife Cheryl Hines, who certainly didn’t sign up for these demented jibes.
And, it seems, Jack’s not one for loyalty either.
In an April video, 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.
‘Hey Anna Wintour! I am boycotting the Met Gala this year. With so much happening at home and around the world, it’s not the time, it’s not the time for a party like that—at least for me. So I am boycotting the Met Gala this year. I will not be going to the Met Gala. Thank you all so much. I will be boycotting the Met Gala and I think others should as well.’
But were you ever invited, Jack?

Here’s the thing: Jack Schlossberg won the genetic lottery and he’s whizzed it all away. That’s his business. What irks me is his insufferable arrogance, thin-skinned whining and bizarre fixation with ladyparts.

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 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.
In the whiplash world of trading on your name and likeness for clicks, we all need a neck brace for the amount of times Jack steps in a steaming pile of his own making.
Later he squeaks out some half-hearted apology before going dark, like this insincere mea culpa from the spring when he posted: ‘I’m sorry to everyone I hurt. I was wrong. I’m deleting my social media. Forever. It’s been fun.’
Has it?
Honestly, what can you expect from someone who has likely been told he’s mommy’s special little commander-in-chief since the cradle? Sadly, this charmed, once-handsome only grandson of JFK has turned into a worthless, uninteresting, unemployable funk bucket, who will likely be an embarrassing anchor on the family name forever.
Even the gently bred Kennedy clan appears to be all but done with Jittery Jack and would probably love a long hiatus from the troubled kid at Trembling Hills, as well as, maybe, a restraining order.
Jack wasn’t in attendance at this year’s Masshole 4th of July celebration in Hyannis Port, which has turned into a cruel annual ‘who-wasn’t-invited’ national sport.
They’ve washed their hands of Secretary Brainworm as well as Janky Jack. Maybe it’s that these huckleberries sniff that Jack is more Schlossberg than Kennedy – but then again, the historical record is overflowing with Kennedy relations who went all gas and no breaks right into the drink.
Jack’s defenders say, ‘Well he’s not as bad as Hunter!’
That’s true, but at least Hunter picked up a paint brush for a few months.
This kid is a laptop repair shop away from eclipsing the most embarrassing political offspring in modern history!