JFK Grandson Jack Schlossberg Explains His Wacky Political Posts

Jack Schlossberg – the grandson of John F. Kennedy – is well-known for his off-the-wall, politics-infused posts. He opened up about it in a podcast appearance.

"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," People Magazine reported the the 32-year-old writer telling former White House Press Secretary Jen Psaki on the inaugural episode of Psaki's podcast "The Blueprint with Jen Psaki."

"And I think that I see that Democrats play that game not as well as we could."

Another aspect to the game he's seeking to crack? Schlossberg told Psaki that it's "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."

In that, Schlossberg has been proving his mastery lately, with his response to a Megyn Kelly post slamming him and his mother, Caroline Kennedy, after Kennedy recorded a video in which she read a letter detailing why she thought her cousin, Robert F. Kennedy, Jr., a vaccine skeptic, was not fit to be named the head of Health and Human Services. Schlossberg's response to Kelly prompted UK newspaper the Daily Mail to label him "unhinged."

Far from a fuming rant, though, Schlossberg's video rebuttal, which he posted to Instagram, was an almost-jocular exemplar of comic timing in which he greeted Kelly by saying he wanted to "check in" and "start a dialogue" before getting in a few digs.

"The two genders rule must be tough," Schlossberg addressed Kelly, evidently in reference to a Donald Trump executive order that purported to confine gender to two narrow silos. "None of us know which one you are," Schlossberg went on to say, "so let us know."

JFK's grandson went on to ask Kelly to "stop attacking trans people. You do it for a living, professionally, on your show. I don't really get that. I don't get what makes that so fun for you. The trans people I know? Just people, okay? Not great people, but you don't need to be great to be treated with respect."

Schlossberg ended his video with, "Do not ever attack me."

He captioned the post with: "Manly lady ? Or ladies man ? @megynkelly" and added: "She attacks trans people and talks about masculinity for a living. But why ?"

"Ahhhh... it's deep... repression... be well !!"

Schlossberg then posted a video in which he gently chided the Daily Mail for its coverage of his spat with the former Fox News commentator, upbraiding the paper for having supposedly "edited" his video in a way that excised "the only funny part and the reason I made it."

"You can post about me – love you guys – but you can't cut out my joke, okay?" Schlossberg said.

Schlossberg also laid out his rationale for the Megyn Kelly response video.

"Public humiliation is the only way that we can fight back," Schlossberg declared, before expanding on that by saying that "humiliat[ing]" and "mak[ing] fun" of right-wing figures is "the only thing they respond to."

"Don't bother arguing them on the facts," Schlossberg added with a wave of his hand. "They don't care."

"Don't take it seriously," Schlossberg advised, "because they don't."

To Psaki, Schlossberg said, "I love my country, I love politics. I really care what happens. And I've been – like everybody, like you – paying attention to what's happening in our country and in our politics and our media."

"And I'm developing instincts," he added, "as this changes and we get more used to misinformation."

But even Schlossberg seemed to take things too far when he "sparked controversy when he asked whether his grandma, Jackie Kennedy Onassis, was 'hotter' than second lady Usha Vance," People noted, adding that Schlossberg "deactivat[ed] his social media accounts on Feb. 6."

In a valedictory message, Schlossberg posted: "I'm sorry to everyone I hurt," he wrote. "I was wrong. I'm deleting all my social media. Forever. It's been fun. Thanks anyways everyone."

To Psaki he acknowledged that his question had been "Creepy" and "weird," but, he posited, "The internet is a place to be weird."

Added Schlossberg: "I use my judgment to make posts that I think are funny or silly but have a purpose, either to make you think this guy's crazy. 'Why is he talking about his own family that way?'"

"But to be honest, then you get all these retweets, quotes, and everybody flips out about it."

Which was, according to his own rationale, the point. A more successful illustration of how he used absurdity to underscore a message was when – as People recalled – Schlossberg falsely claimed to be "Justin Baldoni's lawyer amid the actor's ongoing legal battle with Blake Lively," a prank he undertook because, the magazine said, "the conflict between the two high-profile celebrities was gaining more traction than the transition of power in the United States government."

"People will print and believe anything," Schlossberg said of the stunt.

People recalled the posts Schlossberg made late last year in which he seemed to be grieving the end of a romantic relationship – including a thirst-inspiring shirtless selfie that showed off his toned torso.

"I couldn't stop laughing when I recorded that video," Schlossberg told Psaki. "I thought it was one of the funniest things I've ever done, because I would never.... If I was actually going through a breakup, I don't think I would want anyone to know how sad I was."