Here's 5 of Jack Schlossberg's oddest social media posts
Jack Schlossberg, a member of the Kennedy family, has become a well-known social media personality over the last few years.
Whether he's trolling top Trump officials or making off-the-cuff comments, Schlossberg has said he regrets none of his posts.
His digital footprint has come under a microscope, however, after he announced his campaign for a New York City seat in Congress.
Here are some of his most outlandish posts over this past year.
Comparing the vice president's wife to his grandmother
In one of his most controversial posts, Schlossberg tweeted out: "True or false: Usha Vance is way hotter than Jackie O."
Schlossberg, 33, is the son of Caroline Kennedy, the daughter of John F. Kennedy and Jackie Kennedy. Many were confused on why Schlossberg made the post about his grandmother, but he has defended it.
"People are like, 'How could you say that about your grandmother?' And it’s like, well, of course it’s not me saying that. It’s me trying to hold up a mirror to say, how do we treat and objectify people in politics, family members and people in politics," Schlossberg said in a recent interview with Vanity Fair.
A post after the death of Pope Francis
On the day of Pope Francis' death, April 21, 2025, Schlossberg tweeted out: "Okay JD killed the pope."
One of the pope's final meetings before his passing was with the vice president.
Calling Trump a "fat cat"
In a post last April, Schlossberg slammed the president, writing that he was "KILLING USA."
"Trump is Funny, great on camera — VERY BAD AT THIS JOB
TRUMP POLICIES KILLING USA
DUMB FAT CAT," the tweet said.
Asking a conservative politician to be his dad
Last March, Vivek Ramaswamy, who's currently running for Ohio governor, tweeted out: "Get the cell phones out of the schools."
Schlossberg quoted the post, writing: "Just agree to be my dad and I’ll do whatever you want !!"
Calling his family member a Russian asset
In May last year, Schlossberg wrote: "RFKjr only makes sense as a Russian asset."
He finished the tweet with a simple ":)." (Robert F. Kennedy Jr., the US health secretary, is a member of his family.)
In another post from last year, Schlossberg said that he had never met RFK Jr.'s wife, Cheryl Hines, but if he did, he'd "tell her she looks super dehydrated."
Jack Schlossberg's defense on his posts
Schlossberg has said that his chaotic posts are intentional.
"You don’t have to be just boring all the time. You can show that you can be a politician, a Democrat, that’s fun and exciting, people resonate with, and can talk about policy," he said in an interview with Vanity Fair.
"If I tweet something or whatever that’s, that some find offensive or, or vulgar, I’m holding up a mirror right back to them and saying, 'Look what the president tweets every single day.'"