Why did you decide to run into the teeth of such grief?
Well, I wasn’t planning on running for office now. I wasn’t plotting and waiting in the wings for a seat to run for. It’s an unlikely path that led me here, and it kind of started at the end of 2023. I went to law school, business school. I graduated, took the bar, and I finished all that, and I thought I was going to be an environmental lawyer. I was excited, because that’s what I studied and that was what I cared about. But at the same time, I still am—and always will be, irrespective of his decision to run for a second term—a huge Joe Biden fan.
I knew the truth, which was that he had accomplished so much in the first years of his term. I mean—biggest investment in energy and infrastructure in decades, ended our longest war, ended the pandemic. And nobody knew about this at the time. And if you think back, it was a different world. R.F.K., Jr., was a Democrat running for President, and a Trump victory did not seem like an inevitability.
So I decided to go work on the Biden campaign. And, long story short, we didn’t really . . . They hired me to help with youth-voter engagement, but we didn’t really see eye to eye on video stuff. So I left the campaign—
Tell me about that. What did you want to do and what did they want you—
I wanted to go hard after R.F.K., Jr., and at the time, there was a lot of risk aversion there. So I quit, because I couldn’t live with myself if I didn’t speak out in the way I wanted to. And I got a lot of heat for that, but I knew I had to do it my way.
I spent about a month writing draft over draft about what kind of statement I wanted to release about R.F.K., Jr. And, one day, I just took my phone out and started talking to it and posted it. It went viral in a way that I never imagined, and overnight I built a fan base that I was as surprised as anyone to have.
About a month later, I got a call from the Biden campaign, asking me to come back to make more videos, to speak at the D.N.C., to be a delegate from New York, and to travel to every swing state across the country—which I wasn’t paid to do, and took upon myself. I had a lot of success doing it, and I’m really proud of that.
And it showed me that I had something to offer the Party in the kind of social-media engagement that I was getting, not because I was in an ad campaign or was a movie star, but because I was speaking truth to power about our political systems.
Do you think there are things that you did before, on TikTok, that you wouldn’t do these days, now that you’re wearing a shirt and tie and campaigning? Would you put on a blond wig and imitate Putin or do some of the crazier things you did?
Yeah, I mean, I wouldn’t call them crazy. I think satire is a really powerful political tool, and it’s not like I was making videos that nobody was watching. I was breaking through pretty well.
Yeah, you were.
And, I think, raising awareness on issues for people who otherwise might not receive that information. But the internet and social media change rapidly. The first stage of me going viral was very much happy, comedy, silly. This was a time when, you know, the ’24 election hadn’t happened yet.
You’ve said, “I’ve got a legal education and a lifetime of working on the issues I care about.” But you haven’t worked as a lawyer post—
Not at a law firm.
But, then, how so?
How so what?
How did you use your legal education?
Well, I understand that content creation is a new profession and that for a lot of people it’s not synonymous with a quote-unquote real job. But I’ve been arguing with evidence supported by facts, very clear arguments made on behalf of the issues that I think are important, and those issues are: corruption of the Trump Administration; his terrible, irresponsible foreign-policy decisions; advocating and arguing for why the Democratic Party—its history and current policies—reflect putting a priority on organized labor and working families.
And on social media, it’s not like I was successful just because of my name. You have to make an argument in ninety seconds, with a lot of complicated information. And synthesizing that information, breaking it down into one, two, and three points and having a conclusion—that’s the exercise of law school.
Jack, you know, somebody my age, my first memory is the death of your grandfather. That’s a big set of imperatives to carry on your shoulders. When did this sort of enter your life, that there was something unusual attached to your future?
There is one moment that sticks out. It’s tenth-grade history class, and we’re learning about President Kennedy, and I—
This is at the Collegiate School—
This is at the Collegiate School, on the Upper West Side. And Dr. Grossberg was giving us a lecture about the Kennedy Administration, and I felt uncomfortable, and I was goofing off in the back of class.
And she called on me, because she knew I was making trouble, and she asked me about the Kennedy Administration’s policy in Laos, and I wasn’t familiar with that at the time. And it was mortifying because I wanted . . . You know, I said I didn’t know. And I went home and started reading Ted Sorensen’s book on my grandfather, and I started listening to and watching his speeches every single day after school.
I made myself do that before I started my homework every day: listen to one speech or read a chapter of a book about him. And I got really inspired by the story that I read. J.F.K. sent a man to the moon. He drafted the Civil Rights Act, established the Peace Corps. There are so many things about the progressive agenda, supporting the arts, that he represented and that trace their origins back to the early nineteen-sixties.
But it’s a complex legacy as well, even for a liberal. Included in that is the beginnings of Vietnam, of the Bay of Pigs, all kinds of things, on both a personal level and on a political level. How do you take all that in? And I return to my original question: When did you start feeling that voice in your head, in the ambient sound of your life, that you’ve got to do something about that?
