Getting to Know Jack Schlossberg

Why JFK’s Grandson Is Running for Congress, and the Story Behind His Wild Social Media Videos

I recently met Jack Schlossberg at a campaign fundraiser hosted by his godmother, the author Alexandra Styron. It took place in one of those Upper East Side homes where the elevator opens directly onto the entire floor.

I’ve been closely following Schlossberg’s campaign to represent New York’s 12th District in the House of Representatives.

Bartenders served martinis while servers passed around mini lobster rolls. Caroline Kennedy, Jack’s mother, was there wearing a name tag that read “Ambassador Kennedy.” The crowd was a real mix of fashion designers, hoteliers, young professionals, and people whose family literally stepped off the Mayflower.

Before this evening, I was intrigued by his campaign. It’s exciting to have a young, enthusiastic, good-looking Kennedy running for office. The timing is also perfect: people are suddenly getting obsessed with the Kennedys again thanks to Love Story, the new FX series about JFK Jr. (Jack’s uncle) and Carolyn Bessette (I wrote in The Times about how the show may be giving his campaign a bump.)

But I wasn’t quite sure what to make of Jack himself. I’ve heard some wild stories from people who worked with him at Vogue, where he served as a political consultant. And I don’t always understand his social media videos.

However, I found him to be an extremely intelligent, well-spoken, and passionate candidate who cares deeply about current events and about this country. I was convinced enough to buy a Jack for New York sweatshirt.

Here are some excerpts from his speech where he explains why he is running, why he makes crazy social media videos, how he feels about the Democratic Party, and more.

Parts are quite funny so enjoy!

Why He Is Running

“When I look at the country, I ask myself: How did we get to this semi-dystopian point where our politics is unrecognizable from even ten years ago?

I think about the generations who sacrificed for all of us, who sent a man to the moon, who fought fascism overseas, who guaranteed the strongest civil rights protections anywhere on earth. How did that happen? Why did they do that?

To me, it’s because they believed. They believed in something. They believed we were all in this together.”

“Our campaign slogan is equal parts dumb and profound.”

“Our campaign slogan is equal parts dumb and profound. It’s ‘Believe in Something Again.’ I think that President Trump and the Republican Party win when nobody believes in anything.

We know Trump is lying to us. We expect cabinet secretaries to go to Capitol Hill and lie, and they don’t even care. We can’t even believe what the White House press secretary says. And that’s how they win. They win when we think the system is rigged against us, when our vote doesn’t count.

I’m running because I still believe in politics as a noble profession. I still believe that it’s the best way to solve big problems. And I think it’s our only way to address the major challenges we’re just not paying attention to right now.”

The Challenges on Jack’s Mind

“Climate change hasn’t gone anywhere. Immigration problems haven’t gone anywhere. China and Russia, our adversaries, aren’t resting, but we’re wasting our time watching content that the president is making to distract us.

If we don’t win the House of Representatives in the midterms, we can’t do anything to stop Trump from being on the ballot again. We can’t prosecute or hold anyone accountable for the crimes and blatant corruption that we see every single day.”

Why He Make Crazy Social Media Videos

“You basically have to run a mini production company now if you want to get your message out there and compete.

Look at what the other side does. They literally make content and then get to governing later. It’s all a show.

If you’re a guy and you watch one workout video, you’re suddenly swept into this right-wing media ecosystem. The whole internet has become right-wing.”

On His Cousin: RFK Jr.

“He is using my grandfather’s name and image to subvert everything our family stands for.”

Why He Loves Joe Biden

“Unapologetically, I love Joe Biden. I don’t think it was the right decision for him to run. But I think his first two years in office are the best-kept secret in politics.

It was a progressive person’s dream. They got more legislation passed than any president since FDR. There were historic investments in renewable energy and infrastructure. He stood up for civil rights and disadvantaged communities.

He did so much for our country, and nobody knew about it because he couldn’t talk.”

Why He Joined - and Then Quit - Biden’s Campaign

“They hired me to make social media videos and do young voter engagement, so I went to Wilmington and signed a contract. And I said, ‘Hey, how about we make this video now?’ They said, ‘Absolutely not.’ They wanted me to go into the basement and write a memo on something that doesn’t matter.

I said to myself, ‘I really don’t think this is going well, and if I don’t do something, if I don’t speak out and try this my own way, I won’t be able to live with myself.’ So I quit, and they said, ‘You entitled little shit. Who do you think you are?’”

How He Became a Star at the DNC

“I started making videos on my own, and everyone said I lost my mind. But a month later I got a call from the Biden campaign: ‘Hey, could you come speak at the DNC and campaign across the country by yourself?’ And that’s when I realized I was onto something.”

The Irony: He’s a Kennedy, but He’s an Outsider

“It sucks because there is a local political machine here, and they hate me so much. They don’t like somebody shaking things up.

They wish everyone would just stop paying attention to the race so they could do it the way it’s always been. Ironically, given where I come from, I’m an outsider in this race. That’s an awesome place to be, but it also makes it really hard.”

The Story He Told About His Grandpa

“My grandfather was serving in World War II in the South Pacific when his patrol boat, the PT-109, was rammed and sunk by a Japanese destroyer. Two people died, and Captain Kennedy swam with the eleven members of his crew to a desert island. It was basically a strip of sand with a couple palm trees. They had no food, no water, and no communication.

During the day they hid from the Japanese, who were trying to hunt and kill them. At night my grandfather swam into the channel and tried to flag down a rescue ship.

On the last day, when time was running out, he spotted a canoe on the horizon. He flagged down the boat, which was paddled by a Solomon Islander, and handed him a coconut husk carved with SOS and his coordinates.

That man paddled in a dugout canoe for 34 miles and delivered the coconut husk to an Australian coast guard officer, who then came and rescued JFK and his crew.

I went there with my mom two years ago and we recreated that swim. We went to Kennedy Island, where they had hidden out.

We met the grandson of the man who saved my grandfather. His name was John Kennedy.”

Why This Story Matters

“What happens in our politics really matters to our city, to our country, and to the rest of the world. What we do here ripples across the globe for generations. It’s our responsibility, as the most powerful economy in the world, to do right by the rest of the world and lead by example.

We’re not doing that right now, and there’s no reason for it. I find what’s going on completely unacceptable. I want better for all of us. I want us all to believe in something again. “