JFK's Grandson Explains Reason Behind His Bizarre And Controversial Tweets—And He's Got A Point

Jack Schlossberg, grandson of late President John F. Kennedy and Jacqueline Kennedy Onassis, explained to MSNBC host Jen Psaki the thinking behind his "controversial" social media posts after his tweet comparing Second Lady Usha Vance's looks to his famous grandmother's sparked backlash.

Last month, Schlossberg dedicated a TikTok tribute to Vance, calling her “the most beautiful woman in the world.” The video features Schlossberg wandering the streets of New York City while singing along to the 2001 romantic pop hit "Drops of Jupiter."

He declares:

“This one goes out to Usha Vance, the most beautiful woman in the world. Whenever you’re ready, I’m here for you.”

He then launches into the song, pausing between verses to add:

We’ll all forgive you. We’ll all understand. Just be with me—Valentine’s Day.”

Schlossberg had earlier weirded out social media users by making a poll comparing Vance's looks to those of his late grandmother, one of the 20th century's greatest fashion icons, in a post on Inauguration Day:

“True or false: Usha Vance is way hotter than Jackie O."

Schlossberg later deleted his social media accounts, and in comments on Psaki's podcast, said he was making a point about political messaging:

"I think that the internet is a place where it's difficult to break through, especially if you're not saying something that's controversial, or at least, somehow unexpected. I think that Democrats play that game not as well as we could."

"I use my judgment to make posts that I think are funny or silly but have a purpose to make you think, 'That guy's crazy. Why is he talking about his own family that way?' Then, you get all these retweets and quotes and everybody flips out about it."

"I think that that's the game that the other side has been playing really well, which is flipping people out and getting a reaction."

Schlossberg also addressed one of his most baffling stunts—claiming to be Justin Baldoni's lawyer during the actor’s ongoing lawsuit with It Ends With Us co-star Blake Lively:

"It just came to me one night. I see everybody arguing online about Justin Baldoni and Blake Lively, two people that otherwise I don't know anything about or have much invested in. I saw the entire country, seemingly, the entire internet, flipping out over this while I was focused on the change of administration and all the serious things that were going on."

"Our culture is obsessed with certain things. Some are more important than others, you might say. How do you inject yourself and shine a light on that in a way that is totally out of the box?"

"I knew no one's going to remember this in a week. Everyone's going to forget about it because they've forgotten about a lot of way more serious things. At first, I was freaked out because everyone was mad."

Then, once people started to understand it was a joke or that it was satire, I think people started to understand the game I was playing."

He added:

"Not every post is going to be hilarious or risky in some way. Some of them have to be serious and boring, but they can't all be serious and boring."

"It's very important to switch it up and to take risks because that's not only entertaining for me as I laugh and post it on my phone but also a good way to signal to people that you're willing to either fight for them or speak your own mind."

You can hear what he said in the video below.

Schlossberg's observations about political messaging definitely struck a chord.

Well played, Jack.