Last month, Slate Group chairman and editor-in-chief Jacob Weisberg announced he was leaving Slate to start a new audio company. After six years as a politics writer for the site—beginning around its launch in 1996—Weisberg became Slate’s editor. In those years, and in the decade since, he has been a constant presence and voice in and around the magazine via his writing, podcasting, event hosting, and much else. His departure therefore seemed like a proper occasion for some reminiscing. I spoke by phone with Weisberg on Monday, before his departure, to discuss the magazine’s ups and downs, how internet journalism and liberal commentary have changed over the past couple of decades, Slate’s best pieces, and much else. An edited and condensed version of our conversation is below.
Isaac Chotiner: Do you break the history of Slate up into different eras, and if so, what are they?
Jacob Weisberg: Yes, I do. There was the initial [founding editor Michael] Kinsley era when we didn’t know what would now be the most basic things about how digital media was going to work. Remember, when we started, you didn’t just have to tell people what an internet magazine was. You usually had to tell them what the internet was. We thought Slate would be like a weekly magazine and people would print it out, and we mainly thought of the web as kind of an instant distribution mechanism.
I think that was a brief period, of maybe only several months, before we figured out that things had to be updated regularly and that the tone was different, and started to play with all these different kinds of interactive features like diaries, and dialogues, and dispatches—things that were kind of proto-blog.
Then there was a fairly lengthy period at Microsoft that was an early sweet spot when the magazine was developing an identity and a voice. There was a pretty cohesive group of writers and regular contributors. I think of that period as stretching until Michael Kinsley decided to leave and I took over as editor, which was in 2002.
What do you think the relationship was between Slate and everything else when Slate started, and what’s the relationship between Slate and everything else now? What does it mean to be Slate in 1996 or 2006 or 2018 compared to other content online or in print?
At the beginning, we were one of the very few digital experiments in what we call legacy media, but people at newspapers and magazines were paying a lot of attention. Not because they particularly felt threatened or vulnerable in any way, but people loved Michael Kinsley and they were just really interested in it. I mean, Michael Kinsley was on the cover of Newsweek, moving to Seattle to found Slate.
The Microsoft connection created a certain glamorousness. In some of the old media world, there was just a lot of enthusiasm and interest. The new media people were a little less friendly, and vice versa. I think there were some that felt like they’d gotten there before we did and they were kind of cooler than we were.
This was before your time, but there was some early skirmishing between Mike Kinsley and David Talbot, who ran Salon. In a funny way, I think it was a lot more tribal. Someone who wrote for Slate wouldn’t have written for Salon, and vice versa.
You hear people say that a lot of internet commentary has come to reflect a Slate sensibility more broadly. To me, the paradox of that, and I’m curious whether you agree or disagree, is that left-of-center commentary on today’s internet is—even at Slate itself—incredibly distinct from the original Slate. Contrarianism is out, and the center left and left seem pretty united on a bunch of political issues. Hot takes about politics or culture that push against the liberal conventional wisdom are much less frequent.
Yeah. Well, I agree with you. I mean, I think Slate changed. I think other publications have changed. I think the world has changed. Kinsley was radical in a lot of ways. But one of the ways in which he was radical was that he thought thinking was more important than reporting.
Everyone else in journalism, I think, tends to valorize reporting as the way you add value. Kinsley thought you added value through thinking hard, analyzing things, and then presenting them in a really interesting, entertaining way. That sometimes got characterized as contrarianism. I think that was always a bit of a caricature, but part of the starting point for an article, if you were a writer who worked for Michael Kinsley, was coming up with a hypothesis. A pretty good hypothesis was always: What if everybody’s wrong about X?
It didn’t mean you always wrote an article arguing that everybody was wrong about X and that the world was flat or whatever it was, but it was about challenging and questioning a lot of assumptions. Because both of us were liberal, and the prevailing worldview was liberal, the assumptions that were questioned were liberal assumptions. I see that, as you point out, it’s sort of a less natural, habitual activity right now, because it’s not clear that the biggest problem is the flaws in liberal assumptions. The biggest problem is the assault on liberal values and norms from Trumpism and from a certain radical populism.
I think Slate is now functioning in a world that is much more about articulating and defending first principles than it is about the subtleties of which policy ideas liberals should get behind. It hasn’t completely changed things, but I do think the skeptical and contrarian mindset is … it doesn’t have quite the currency.
Maybe the question is what the original Slate would have been like if it had launched around something like the rise of Trump. Take someone like Kinsley, who obviously is a genius in our profession, but I get frustrated when he writes about Trump because it feels too contrarian to me and my attitude is like: “Oh, not in the mood for this.” It’s just interesting to think about how that original Slate sensibility, the contrarianism of it—even if you say it was overstated—would have played in the era we’re living in.
Slate launched in 1996, which was, in retrospect, a complacent era of peace and prosperity. We were on the verge of the only budget surplus we ever had. On the one hand, it was very much a missed opportunity for liberalism, because things were possible then that aren’t possible now. But as much as it felt like there was always a lot of fighting and politics, it wasn’t an embattling period the way it is now. I think the two things, obviously, that really changed this were 9/11 and the Iraq war, which created a bunch of different dynamics. The Iraq war, I think, was a factor in unifying the left and liberals. There were liberals who supported the war, some of them in Slate. But they quickly—and I had some affinity for this group, and I’m not speaking for myself exactly, but I would say that people pretty quickly changed their minds and there was a lot of unity on the left: that the war was a bad idea and Bush was pursuing it in a bad way and that Bush was a bad president. I actually think it was the Iraq war going badly very quickly that created the sea change you’re talking about and the sort of greater unity on the left.
Do you feel regret that maybe Slate published too many liberal hawkish cases around the eve of the war?
No, I think what was really great was that Slate hosted that debate. I put together this forum where we had maybe 25 different writers arguing about that and explaining why they were for and against it. I actually have looked back at that. I provisionally supported the war. I think that was a mistake on my part, but when I look at what I wrote and what a lot of other people wrote, it was so hedged and conditional.
I think that also highlights one of the things we were talking about earlier. If something equivalent to the Iraq war happened now and Slate was having a debate about it, it feels like 12 out of 13 of the contributors would be very strongly anti-war.
Yeah, I think you’re right. It’s probably generational shift, and it’s partly the loss of any credibility on the conservative side. I mean, nobody in Slate is going to give Republicans the benefit of the doubt on anything again, because we’ve learned to mistrust their motives in a more fundamental way. There weren’t a lot of Bush supporters at Slate either, but I do think there were conservatives who had credibility in the early 2000s. Now you can count them on the fingers of one hand.
What do you think you do and don’t understand about running a magazine in the modern era?
I think it’s a lot harder to be the editor of any magazine right now. The staffs at magazines tend to be young. I think millennial journalists have a different set of attitudes about authority, about hierarchy, about loyalty, about what their careers are going to look like. Without passing any judgment on it, it’s a different mindset.
At several of the most prominent magazines, including the Atlantic, the New Yorker, and the New York Review of Books, the editors have all had the experience of being challenged by their young staffs about decisions they made, and challenged very vigorously in public. I think that represents a change. At Slate we always had a vigorous debate about everything, but the staff didn’t go over the head of the editor to appeal to Twitter if there was a decision they didn’t like.
I think there’s a different presumption around publication. Again, I’m not talking primarily about Slate here. I’m talking about what the job of the editor of an intellectually inclined magazine is. In my earlier days in the business, the instinct was, well, if people find it interesting, let’s publish it so they can debate it and that’ll be good because people will be talking about it. Now I think there’s much more debate about the threshold for publication, and there’s more of an instinct to constrain certain things that are considered across a boundary of one type to another—an opinion boundary or prejudicial boundary. It feels like a very fraught moment when there’s just a lot of anger around politics and ideas and social arrangements. I think editors are on the front line of it, and the challenge they’re getting is not just from political opponents but even inside the house.
You said you don’t want to be judgmental about it, but I’m sensing from the way you’re saying this that you do have some judgments about this.
I mean, I’m glad that I was an editor when it was an easier job than it is now. I think the kinds of management you have to be good at, and the kinds of challenges you are likely to face as an editor—it’s very intense right now. It’s a reflection of the political moment. I don’t know that it’s a kind of permanent situation. I think the job of being an editor has gotten really, really difficult because … I mean primarily because good journalism is under assault from the White House.
There’s not an acceptance of the basic accountability and truth-telling function in the press. On the one hand, that creates tremendous momentum and energy about what journalists do, and it’s great to stand up for such principles, but it’s also very hard to be under assault all day long. I think that stress comes out in different ways.
What’s your favorite piece that you personally have written for Slate?
I’ll read it and if it’s good enough we’ll link to it.
I do think for a long time the piece that got the most traffic was a piece I wrote about whether Teletubbies were gay.
What about the one you thought was the best?
I answered it wrongly because I couldn’t think of any. I think I’ve probably had 1,000 bylines in Slate. Especially during campaigns, I wrote pieces every day. I did a weekly column forever. I remember times I was early on something that people came around to thinking, and that maybe had some impact. Just as an example, I fell in love with The Wire early on, before people had caught on to it as a good show. I wrote a piece saying that it was the best show that had ever been on American television. This was the beginning of Season 4, and it was in jeopardy of being canceled by HBO at that point. I said we’ve got to start a campaign to keep the show on the air.
How much effect did that have?
Well, it’s not for me to say exactly, but the show got renewed very soon after that, and it became a critical darling soon thereafter. It was the fourth season when they broke through.
So you’re basically to blame for the mediocre fifth season of The Wire after arguably the best four seasons in television history. Is that what you’re saying?
Yeah, exactly. Well, but I thought the fifth season pulled it out in the end. I think that by the end of the show it was really—
That’s an old-fashioned Slate take.
Yeah, but if you said what’s the best season of The Wire, it’s obviously the fourth season.
What are three pieces in Slate history that you come back to? Three phenomenal things written in Slate. Please, no more than two out of the three should be my own pieces.
Right. Exactly. It’s funny. I’m so bad at questions like this. My mind goes blank when people ask me about anything I’ve written or anything anybody else has written. And then of course I’ll think of 200 things when we get off the phone …
When I was editing the magazine, the people I brought in—partly in the atmosphere after Sept. 11 and around the Iraq war—it was Anne Applebaum, and Christopher Hitchens, and Fred Kaplan. I felt we had such exciting and dynamic debates around everything that mattered in Slate. We launched Atul Gawande as a writer. He’d never published anything before he started writing for Slate. Michael Lewis wrote a couple of series for us, including this one about fatherhood that became his book. Those were all things that I edited and worked on and brought in, in one way or another, that I think still stand up.
I think a crucial function Slate has played has been discovering talent. Most magazines buy talent after it’s already established. Slate takes people at the beginning of their careers and gives them space to write with an audience and to really find their voice. But I think the kinds of writers, when you look down the list of people who got started at Slate—it’s Dahlia Lithwick, and it’s Frank Foer. It’s Katy Waldman. There’s just a long list of people who I think are such powerful voices. Amanda Hess. It’s often frustrating because then they get discovered and poached by the New Yorker or the New York Times. But Slate has always been a place for writers—because that can happen, and because of the freedom and the intelligence with which you can write—where talent always comes in the door even if it ends up going out another door.
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