Caroline Kennedy’s 32-year-old son Jack Schlossberg is ensuring the Kennedy reputation for being pigs doesn’t skip his generation.
The grandson of former President John F. Kennedy is using social media to openly fantasize about having a baby with Vice President JD Vance’s wife, Usha.
“I’m having a son !! So excited about this. Cannot wait for the birth of my next child because today was the best day of my life,” Schlossberg wrote on his Instagram account.
“Out of wedlock, yes. But we might get married,” he added.
Attached to the birth announcement was a photo of the lovely Usha Vance holding a baby with Jack Schlossberg’s smug face. Honestly, this guy makes Lyle Menéndez look like Mr. Rogers.
I would’ve thought the real news is that Schlossberg’s not gay, but no one made me the sheriff of the news cycle.
This is not the first time Schlossberg has targeted the Second Lady for creepitude. Back in February, Schlossberg posted a photo of the Vice President and his wife holding their newborn daughter and wrote, “Could have been US !!”
Granted, I did see that post at the time but just assumed he was flirting with JD Vance, not Usha — you know, because gay.
What I didn’t know is that he’d already been obsessed with her for some time.
“This is for Usha whom I love,” he captioned in a viral video posted in February. “Whenever you’re ready I’m here for you.” He then proceeded to sing her a love song.
“True or false: Usha Vance is way hotter than Jackie O,” he published on X in January.
What are we supposed to think of a guy who finds his own grandmother “hot?”
The bottom line is that this entitled left-wing activist born with a silver spoon up his tight ass finds himself adorable: “I think that the internet is a place where it’s difficult to break through, and it’s difficult to break through especially if you’re not saying something that’s controversial, or at least, somehow unexpected,” he told MSNBC’s Jen Psaki on a podcast.
“And I think that I see that Democrats play that game not as well as we could,” he explained. “And I think that’s kind of the game that the other side’s been playing really well, which is flipping people out — and getting a reaction is almost half the battle.”
He’s obviously correct about a big part of the Democrat party’s problem, but he’s also a symptom of a party with absolutely no self-awareness or sense of humor. Hey, there is no place I’m not willing to go for a laugh, no matter how dark or inappropriate, but publicly hitting on the Vice President’s wife with a cheap cut and paste? A good joke requires misdirection, self-deprecation, and wit. He’s basically screaming, “I want to have a baby with Usha Vance!” and then waiting for everyone to laugh because he’s the only one who doesn’t understand that I want to have a baby with Usha Vance is the set-up, not the punchline.
Here’s a better example of Schlossberg’s misguided comedic approach:
Not to overthink this, but it’s difficult to incorporate someone in a joke who is not defined beyond an attractive and dignified young woman. In that way, Usha Vance is like Jackie Onassis. On the other hand, it’s easy to mock a Hillary Clinton, and not just because she’s fat. Hillary has a larger-than-life personality. She’s defined. So that I’m not accused of being partisan, it’s the same with President Trump… And dog-snuffing jokes will never not be funny about Homeland Security Secretary Kristi Noem. That’s how the world works.
Schlossberg is so insulated and in love with himself, he reads a room with all the skill of Helen Keller.
John Nolte’s first and last novel, Borrowed Time, is winning five-star raves from everyday readers. You can read an excerpt here and an in-depth review here. Also available in hardcover and on Kindle and Audiobook.
