It’s hard to figure out what Jack Schlossberg wants, or why we read it.
The son of Caroline Kennedy and grandson of President John F. Kennedy has become more and more contentious and officious in his online rants.
Initially eccentric, Schlossberg has veered into obnoxious, unproductive rants that take no prisoners. He is literally against everyone: his extended family, his parents’ friends and relations, political associates of the Kennedys. He’s become the kid who yells “fire!” in a movie theater, and makes no attempt to help anyone escape.
After vicious attacks against Trump, his whole ilk, and cousin Robert Kennedy Jr., Jack now turns his attention to former President Barack Obama.
In a screed today, Schlossberg comments on Obama’s words from a recent speech. The beloved former president advised Democrats to “tough up” in their fight against Trump.
Schlossberg’s response? He presents an emotional non sequitir, the deaths of Minnesota politician Rep. Melissa Hortman and her husband. What is he talking about? He’s drawing lines from dot to dot that make no sense.
Obama said: “You know, don’t tell me you’re a Democrat, but you’re kind of disappointed right now, so you’re not doing anything. No, now is exactly the time that you get in there and do something,” he said. “Don’t say that you care deeply about free speech and then you’re quiet. No, you stand up for free speech when it’s hard. When somebody says something that you don’t like, but you still say, ‘You know what, that person has the right to speak.’ … What’s needed now is courage.”
Schlossberg’s retort: “Tell that to the 2 Dems murdered last month. Used to love you more than God,” he says, referring to Obama, “— n”now you’re just lost and unhelpful. Stick to Netflix , or have Clooney execute another coup.”
Your first reaction is to slap him silly. But of course Schlossberg has no interest in a political career. He’s not savvy enough to pull it off. He prefers being the outlier, a path he can take since has no job, but he’s got the family money. He can take pot shots randomly and run for cover. There’s no downside.
Schlossberg has embraced the AOC-Zohar Mamdani extreme leftist corner of the Democratic party. His grandfather is rolling in his grave. For a 32 year old who comes from such a serious background, Schlossberg comes off as naive. In this message, he’s asking Obama to ignore him. I’m sure the former president will oblige.

