This is part of What We Learned, a series of reflections on the meaning and legacy of the Trump years.
For our series about journalists who covered Donald Trump from the beginning, I sought reporters who happened to be assigned to Trump’s presidential announcement at Trump Tower or his early rallies, back when his run was still widely seen as a stunt. But some writers have watched Trump’s political ambitions, such as they were, for a lot longer. Kurt Andersen, the former Studio 360 host and longtime American cultural statesman, recalls sparring with Trump as his national profile grew in the 1980s while at Spy magazine, which dubbed Trump a “short-fingered vulgarian” and helped shape his relationship with the press, for better or for worse. (“He was our clickbait,” one Spy editor told Vanity Fair in 2015.) I called Andersen just before Trump left office to talk about sparring with him in the ’80s and ’90s New York media, whether Trump was actually serious himself when he ran in 2015, and what it will be like to banish him from our minds, if we ever can. Our conversation has been edited and condensed for clarity.
Aymann Ismail: Do you remember the first moment you thought Trump might have a real shot at politics?
Kurt Andersen: Back when we were doing Spy magazine, I remember Trump beginning to flirt with politics as early as ’87. He said he was running for president. And that was a joke. Or we treated it like a joke. We did a poll asking people if they wanted him to run, and it was a joke. And so it became a joke every time because he kept doing it. Each time, I thought it was ridiculous. I just thought it was a new way to get attention. I would say I paid very little attention to him for 25 years, until he started doing the birther thing. That was so ugly and dangerous, I thought. I didn’t know quite how dangerous when he started, but that’s when I turned away from the like, “Oh, he’s funny, he’s entertaining.” Even as late as, like, 2006, I looked it up, I was writing about it in that way. I just thought he was a New York character asshole. When he started doing the birther thing, that’s when I really thought, “Nope! This is a real deal! And maybe he’ll win.” This is over 34 years of writing about Donald Trump. So in the spring of 2016, I’m half-way writing Fantasyland, my book about why America is mesmerized by conspiracy theories and entertainment and celebrity, and Trump is nominated for president. Everybody’s writing him off like it’s a joke. I thought, “No, this isn’t a joke.” He was in at the right moment, ready to exploit exactly what this whole media history of mine is about.
How has your temperament for thinking about Trump changed since the Spy magazine days?
In those days, it was like, “Let’s expose this guy because he’s a scumbag!” But it was fun then. He was mean to tenants—so are lots of landlords, but he was like a cartoon character. He was our villain. The Central Park Five was hideous at the time. We knew it. Everybody knew it. But he didn’t stick with that. He didn’t become a right-wing guy, he was still a Democrat, pro-abortion—he just thought you should execute these five kids who were arrested. He was a Queens white guy.
Do you regret taking him lightheartedly back then?
They were real pieces of investigative journalism. In fact, he threatened to sue us and had his lawyer send us letters. And then we just published those letters and had fun with that too. So no, we exposed him and took him seriously too and did real journalism about it. So I don’t regret it. I felt like we were tough enough. It was never like, “Oh, we were too nice.” He was Donald Trump! He built a couple of skyscrapers, you know? At the time, he did not represent an existential threat to democracy or the world then.
If I could travel in time, I would have said, “Stop him! He’s gonna be president!” I haven’t looked back at Spy to see how we handled the Central Park Five story. I’m sure we mentioned it and didn’t give him a pass for that, but that perhaps is something we could have focused on more. But no, I feel without regret with the writing I’ve done about Donald Trump for the last 35 years.
Have you lost all appetite for Trump the buffoon now?
I still made fun of him in the last few years. I think you can still make fun of him. It’s just that—I know we’re not supposed to compare him to Hitler, but it’s like making fun of Hitler in 1924 after he was arrested. I’ve consistently made fun of him and also examined him seriously. But I would say after the birther thing in the last decade, I gained a new sense of who he was and that he was dangerous.
Do you have any idea how Trump’s image in the media wasn’t totally annihilated after all of his public business and personal failures?
After his Atlantic City casino went bankrupt, he barely escaped financial death. Not long after that, he was on The Charlie Rose Show. I remember watching that episode, not then, but when he became president, and he was talking about how he turned it around. It was a comeback story. Then in ’90, ’91, he was doing all his stupid, cheesy failed projects, starting a football league, steaks, vodka, eventually Trump University—like, are you kidding me? A board game, there’s so many things. Then The Apprentice came along, ’03 or ’04. After a few years, it was a very successful show, and he became a big TV star.
Do you think his run for president was a PR thing, even in 2015?
I have no basis for knowing, but I certainly believe that. The expectation that he’d win was always low, so I think that was the plan. I really do. Obviously, you can think it’s funny that it was a brand promotion endeavor. And it worked! I’ve always thought that his desire for attention of any kind was unlike anybody I’ve ever seen. And then becoming president made him the most famous person in history.
Do you think the media attention he got for being ridiculous played a role in his rise?
Sure? Because they didn’t depict him as the ridiculous hustler, the liar, the bully, all those things. If you want to say I had my little role in giving him attention, sure. But I was always saying, “Look, here’s what he is. He’s a horrible scumbag.” I think that writers like us who have contempt for him and mock him gave him his contempt for the media and the elite, even for a rich guy living in New York. And I think that, yes, his political base saw that and understood. Then again, in terms of the media responsibility, there’s a sense of “We shouldn’t have mocked him, or been contemptuous of him. Because that’s what inflamed his rebellion, you know?” Is that part of it, 100 percent? I don’t know. Back then, that’s what he was, so what can you do? I wouldn’t blame a reporter just for writing whatever. Trump was this different creature that required a different way of reporting. I blame certain individuals and certain institutions for not doing what they should, and I would say the last five to 10 years, there is media culpability, for sure.
Was there a conversation behind the scenes at your show on how to cover Trump when he became the Republican nominee and then president?
Yeah, on an episode of Studio 360 in the summer of 2016, I interviewed my friend and former colleague Susan Morrison from the New Yorker. At the end of the show, she asked, “Uh, what if he wins?” It was a stunning moment. I really hadn’t thought about it until that moment in a serious way. I thought I had an opportunity for us to take this lens on the world of art and culture and all the rest and see how it overlapped with Trumpism and everything else. We didn’t do it. I remember when the Huffington Post decided on not covering him and his campaign as politics, but cover it as entertainment. I get why they did that. It was an understandable misstep, because they thought taking him seriously would be a problem. But no, that’s the fucking problem. You aren’t taking him seriously. You don’t understand that entertainment and politics have long since merged in this country. And so saying he’s not a politician because he’s an entertainer was and is a fallacy.
True. The WWE entertainer did become president, and nobody can say that he didn’t. Did Trump suck the soul and joy out of us journalists, creatively?
I don’t think we’ll know until it’s done. Depending on how this all plays out, if he begins melting and goes away, then we’ll be able to answer that question. Journalists can’t get Trump out of their head. It’s not just our fraction of America who’s thinking about politics and society, it’s millions and millions and millions of people who every hour, or certainly ever day, can’t go by without thinking about what’s going on with Trump, which of course is his intention: “Pay attention to me! Let me be in your head!” It’s so unlike how media has been for a long time. We have yet to reckon with Trump, as far as journalism goes. He was the subject for every journalist, not just political journalists. And he will likely remain the subject. That was like an atom bomb. And we’ll still be living with its effects—certainly it will be interesting for everybody and a relief for most people not to have him in your head every hour of every day. I grew up with the Soviet-versus-us, communist-versus-us. We had one big enemy for the first 35 years of my life. Trump in this analogy serves that same purpose of being this total focus of every attention that the Soviet union was until 1990. When Trumpism ends, we can go back to some normal multiplicity of opinions and positions and everything else. That’s what will be different. Trump has been this unifying thing that made all discourse binary.
What will it take for us to get there?
The “two versions of reality” problem is a real problem, and it’s kind of insolvable. It’s not a very fixable problem because of cable television and the internet, which made it the problem that it is. You can start maybe regulating the way Facebook does what it does, but the fact is that we can’t live in this country with these two separate realities. There’s always going to be one minority, that loud alternate reality, like the Trumpworld, and then the rest of us. It’s hard to fix, but maybe it is fixable. It’s kind of my nature to be 51 percent hopeful—until I’m not. And if he’d won reelection, that would have changed. But now I’m back to 51 percent.
This is part of What We Learned, a series of reflections on the meaning and legacy of the Trump years.