A conversation with The New York Times Magazine editor Jake Silverstein

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THIS EPISODE IS A SPECIAL COLLABORATION WITH OUR FRIENDS AT THE SPREAD AND IS MADE POSSIBLE BY OUR FRIENDS AT COMMERCIAL TYPE AND FREEPORT PRESS.

Clang! Clink! Bang! Hear that? It’s the sound of all the hardware that Jake Silverstein’s New York Times Magazine has racked up in his almost eleven years at its helm: Pulitzers and ASMEs are heavy, people!

When we were preparing to speak to Jake, we reached out to a handful of editors who have loyally worked with him for years to find out what makes him tick. They describe an incredible and notably drama-free editor who fosters an amazing vibe and a lover of both literary essay and enterprise reporting who holds both an MA and an MFA. As one New York Times Mag story editor put it, Jake’s superpower is his “vigorous and institutionally-shrewd support of skilled reporters with strong voices pursuing projects that were just a little beyond the paper’s ordinary comfort zone.”

Here’s a theory we set out to test in this interview—one that we’ve floated in our newsletter, The Spread, for years now: Is The New York Times Magazine the best women’s magazine out there?

Yes, we’re talking about the stories they produce under Jake, like Susan Dominus’s ASME-winning, game-changing story about menopause and hormone replacement therapy, and Linda Villarosa’s feature shining a light on the Black maternal health crisis.

But we’re also talking about the woman-loaded top of the Times Mag masthead, on which Gail Bichler, Jessica Lustig, Sasha Weiss, Ilena Silverman, and Adrienne Greene reign supreme—and seriously outnumber their male counterparts.

And we could spend all day name checking favorite writers, like Dominus and Villarosa, but also Emily Bazelon, Danyel Smith, Taffy Brodesser-Akner, Irina Aleksander, Jordan Kisner, Azmat Khan, Pam Colloff, Nikole Hannah-Jones, J Wortham, Wesley Morris. We could go on and on—you get the idea!

So, did Jake agree with our women’s mag theory? And what is it like to have the deep resources it takes to make these kinds of stories these days? You’ll have to listen to find out.

“We have this unusual opportunity to get to do magazine work, to get to do long-form storytelling, to get to write in the way that we write, but on this giant platform that is as giant as it is because it’s a news platform.”

Maggie Bullock: Okay, let’s pretend we weren’t just talking. Hi, Jake. How are you? What are you working on today for The New York Times Magazine?

Jake Silverstein: Oh man, so many things. Trying to figure out the weather and what to do with regard to the fires in LA. I have a person who just came out of Syria talking about that. I have a big sort of top secret media story for next week that I can’t talk about, but that we’re trying to put the finishing touches on and that all sounds really serious, but there’s probably some fun stuff in there too.

Maggie Bullock: No, you realize you just said our … four—I can’t count them—favorite words: “Top secret media story.” We’re like on the edge of our seats.

Rachel Baker: Okay. So we have an opening pitch for you, Jake. We’ve heard such nice things about you as a manager, which is not always the case with people in your line of work. And those magazines, especially your competitors, there’s a culture of fear and “keep everybody on their toes” to squeeze the most out of them. But everyone we talked to in advance of this interview said that your magazine couldn’t be more different, that it’s an amazing, drama-free, supportive, nurturing place to work, and it’s because of you.

Jake Silverstein: Oh, that’s nice.

Maggie Bullock: So here’s a game we want to play with you. Imagine we were one of your star editors with two heads. We just got this big fat competing offer from, let’s say, The Atlantic.

Jake Silverstein: Well it would definitely be The Atlantic, first of all.

Maggie Bullock: That’s what we figured.

Rachel Baker: I don’t know where we got that.

Maggie Bullock: What would you say to us to make us stay? Like what do you say to people to keep them?

Jake Silverstein: Okay I don’t say, “But we’re a drama-free workplace where everybody gets along because I’m such a nice guy.” I don’t say that. I’m glad to hear that is a perception. I tend to, in that type of situation—which of course does happen quite a bit, really—I often talk to people who are considering leaving about just how incredible it is to be doing this work from the platform of The New York Times.

That the reach and the resources and the kind of expertise that exists within the building on, like, a huge range of different types of media is just unparalleled. And the ability to get people to pick up the phone when you call them and tell them that you’re calling from The New York Times is truly remarkable.

And I often tell people that they have this incredibly lucky opportunity to be working on that platform, but doing the work that they know how to do as people in the magazine world on that platform, right? We have this unusual opportunity to get to do magazine work, to get to do long-form storytelling to get to write in the way that we write, to get to do the kind of incredible creative work that Gail does but on this like giant platform that is as giant as it is because it’s a news platform, right?

Because it wouldn’t really probably be that big if it was only a magazine platform. So that’s a unique proposition. And I’ve definitely used it to try to keep people who are entertaining the idea of leaving. And I think it’s worked more than it hasn’t.

Rachel Baker: We hear that when you took the job in 2014, you said you would only be in it for 10 years. That’s what we’ve heard in our reporting. And so here we are, the clock just struck. It’s 2025, baby.

Jake Silverstein: True. I think what I said was that I wouldn’t even think about whether I wasn’t going to be in the job until I had been in it for 10 years. That it didn’t seem worth doing unless you could do it for at least a decade, because then you could be like, “See that decade there, that was my decade.” That 10 years as a unit of time had a certain kind of meaning to it.

But it didn’t mean that as soon as I hit 10 years, I’d be out the door. My 10-year anniversary was last May. And I will say that I did feel a certain sense of accomplishment hitting that mark. In part because with the weekly magazine you can look at—and the staff did a nice thing, which is they created a visual so that it could do this—you can look at all of the covers, hundreds and hundreds of covers that you’ve produced across 10 years. And it’s pretty interesting to look at many hundreds of covers and remember all the different twists and turns that you took to get to each one across a decade.

Rachel Baker: What’s your favorite cover?

Jake Silverstein: I knew you would ask that. I don’t have a favorite cover. It’s too impossible to ask that. But what I will say is that one of the incredible joys of doing a weekly magazine is that you do so many covers that you actually forget some of your favorite covers. And when you go back and you’re like, “Holy shit! I forgot! I love that cover. How could I have forgotten that cover?”

That ability to like, discover with all the pleasure of discovery, things that you yourself created—not alone, of course, like in this incredible team that we have—that’s pretty special. That I think was one of the, I think honestly was one of the sort of surprises of coming to a weekly magazine from a monthly. Which really terrified me. It seemed almost impossible to imagine you could put out a magazine in five days—how could anybody do that?

And it is hard. And it does require a whole different orientation, and staff, and approach, and you are working at a faster speed, of course. But the trade off of having that many at bats is such a treasure. It encourages a certain kind of fearlessness, I think, that you can take a swing because you’re going to get another swing and then 50 more after that.

Maggie Bullock: So you started out or you, I should say, you became known first as a writer for Harper’s and then the chance came up to work at Texas Monthly, which isn’t necessarily like a logical next step for a shiny star at Harper’s. What was the appeal of moving to Texas and working in that ecosystem?

Jake Silverstein: So I started writing for Harper’s—I was an intern at Harper’s as a lot of people have been and actually a fair number of people who are at The New York Times Magazine right now, there’s like maybe five or six of us who at one point or another were interns at Harper’s. Anyway, I was an intern at Harper’s and after doing that did a little freelancing for the magazine as a fact checker for, I don’t know, a few more months.

And then I moved to west Texas to work for a little small town paper in Marfa, The Big Bend Sentinel. After about a year of covering normal stuff for them—school board meetings and city council meetings and stuff like that—I wrote my first story for Harper’s. And then I bounced around a lot over the next, I don’t know, six years or so and was writing a little bit as I went for Harper’s, probably four stories over the next five or six years. So not a lot.

And at the tail end of that I ended up in Austin, Texas, and it was time to get a job. I went to talk to Evan Smith, who was then the editor-in-chief of Texas Monthly, and I was really hoping I could get a staff writer job. That was my dream. I imagined being like one of the old New Yorker writers, except in Texas. I wanted to be like Joseph Mitchell for Texas.

And he said, “I don’t have any jobs for staff writers. But actually I have an opening for an editor right now. That’s like a story editor. Would you want to apply for that?”

And I needed a job. So I said, “Yes!”

Even though I had real misgivings about being an editor—I still was really focused on primarily being a writer. He gave me the job and I found that I liked it quite a bit. And that was 2006. It moved rather quickly from there because Evan then left in 2009 to found The Texas Tribune. And by the time he left, I applied to get his job and got that. The rest is a blur, to be honest.

“It seemed impossible to imagine you could put out a magazine in five days—how could anybody do that? But the trade off of having that many at bats is such a treasure. It encourages a certain kind of fearlessness.”

Rachel Baker: You were at Texas Monthly for a while—like eight years.

Jake Silverstein: Yeah.

Rachel Baker: And then there was a big high profile search for the next editor of The New York Times Magazine. I remember very vividly. And you were the surprise winner.

Jake Silverstein: Right.

Rachel Baker: What was your pitch to the Times? “I’ve been doing this thing in Texas—the national magazine of Texas—but now I’m going to cover the world”?

Jake Silverstein: I think I probably had some of the advantage that comes from thinking that it’s a total long shot for you to get a job. So you’re just gonna go for it with your memo and you don’t maybe have the anxiety that comes from feeling like you have nothing to lose.

I definitely felt like a guy from far outside the center of where the decision would probably be getting made—or amongst the people the decision would probably be getting made with—and might as well just throw a crazy memo over the top.

I don’t remember everything I said in that memo. The gist of it was that I thought the magazine should be more literary. I thought that it was taking as its competition New York magazine and that it should be taking its competition as The New Yorker more. That it was, maybe not entirely, but that it was perhaps focused in the wrong direction at the time. That was my take.

I thought it needed to have a greater diversity of voices, I remember that was a big section of the memo. There was also a big idea in the memo that the writers who were writing for the magazine needed to have a much bigger presence online. In practice that didn’t work out as well for various reasons, which we can talk about. But everything else did play out the way that I had pitched it to them.

I don’t know if that’s why they hired me. I don’t exactly know what was the main thing that was appealing to Dean. Dean Baquet was making the decision for Jill Abramson. She was the executive editor at the time, but she had dispatched Dean to go find her a new magazine editor. And that was very lucky for me because then Jill got fired on my third day in the office. I had been primarily interacting with Dean up until that point.

Rachel Baker: What was it like when you got the call from Dean?

Maggie Bullock: This is, by the way, Rachel’s signature question: “Tell us about the call.”

Jake Silverstein: It was a call from Janet Elder, who passed away not that long ago, but since then, and who was a wonderful presence in the newsroom at The New York Times and who I miss. She was the one who called me up and offered me the job. I don’t remember everything she said, although I did make a recording of it. I had a suspicion because you can tell when you get to the end of the road, so I made a recording of it.

But now I don’t know where that recording is. This was 11 years ago and was on like an old dictaphone that I used for interviews that I’ve since misplaced. But what I remember is that when it was over I ate an apple in 15 seconds. Like I just hoovered the apple down. I was so excited that I just devoured the apple. That’s what I have a vivid memory of.

Maggie Bullock: That is such a wholesome celebration. I thought you were gonna say I recorded it and I listen to it every morning when I’m getting ready.

Jake Silverstein: No, I remember there was like this apple sitting on my desk the whole time I was talking to Janet and when it was over, I had all this incredible pent up energy and I just ate this apple in a single bite, it seemed.

Maggie Bullock: And then you went outside and planted the core.

Jake Silverstein: Of course, I went outside and I fired my six shooter in the air.

Maggie Bullock: You were in Texas. In Texas, you had a pretty geographically -bound purview, right? But then you come to The New York Times Magazine and there’s no such boundaries, really. So I just wonder, how do you define what makes a great Times magazine story versus your competitors?

Jake Silverstein: At Texas Monthly it was always in the service of the kind of relationship of the story to the Texas myth or the sense of Texan identity that the reader might have or might be trying to have more of or whatever. There was a sense in which the magazine, even when it wasn’t doing service, was doing service in a way because it was helping people understand the place that they live and deepen their connection to it and so forth.

And obviously that’s not the case with the Times magazine. I think there’s so many different roles that we play for our readers. There’s so many different things that we do that our stories do for our readers that it’s impossible to say that there’s one thing that makes them successful. But we are often thinking about adding value to the experience of The New York Times.

I think this is probably a bit different perhaps than it was 10 years ago, in part because of the way that the business has changed in the past 10 years and the way that the magazine as a standalone kind of cohesive unified print product doesn’t quite have as much meaning as it did 10 years ago. So many more readers are encountering our stories individually online that we have to think, and this has been true for a while now, that we have to think in terms of the individual story.

And when you’re thinking in terms of the individual story, we often are thinking in terms of how that individual story comes across to a reader who’s finding it in the digital ecosystem of The New York Times. Which then of course leads us to think about what that story does might be different from what the other stuff around it is doing.

We think a lot about what kind of shade and color that we’re adding to the picture of the world that is different from what the news desks are adding to the picture of the world, and how do we not duplicate what’s happening elsewhere. How do we add our special something to this sort of incredible picture of the world that The New York Times offers readers every day.

Rachel Baker: That kind of answers my next question, but I’ll ask it anyway, which is that it feels like every department at the Times has become more magazine-y, like The Upshot is like a magazine, Opinion is its own magazine in the way that they package and tell stories. Does that change the way you think about the magazine? And also I’m curious about the turf wars between ideas.

Jake Silverstein: Yeah. That has been a process that has just intensified like every year since I’ve been there. And when I got to the Times it was already people were talking about the newsroom or the newspaper becoming more magazine-y. That was a thing you heard, and it’s just continued and continued. But that said, I think you can overstate that too.

The newsroom is so good at the core news journalism functions that it provides. And it’s gotten honestly a lot better because of the innovation of new things like the live briefing, for instance, like that didn’t exist 10 years ago. And it’s, I think, really revolutionized the way that we cover breaking news and it’s completely unlike anything that we do in the magazine world. And it provides a totally different service.

There’s a lot that the paper does that is, I think, pretty unlike what we do. I think you see more similarities that there’s more, there’s certainly more voicey-ness in the rest of the paper than there was 10 years ago, a lot more than there was 20 years ago. There’s more use of the first person. There’s more people who are breaking from the traditional Times voice. The opinion section is doing a lot more stuff that I would describe as just proper magazine stuff, it’s edited and even presented visually like magazine stories.

Yeah, we feel a little less different from the rest of the joint than perhaps we once did. But that’s okay. I think it makes it a little harder to do our job than once upon a time because the distinction is not always quite as obvious. But I think it’s also the case that one of the things that can be hard for The New York Times Magazine is that—and this is particularly true for a digital reader, which is most of our readers now—if they’re accustomed to nine times out of ten clicking on a link and it’s like a news story when they click on a link and it’s like a 7,000 word character-based narrative, they’re like, “What the hell is going on here?” And they bounce after two paragraphs.

That doesn’t always happen, of course, but it does sometimes happen. And so the idea that like a reader is starting to get a little more used to a wider variety of storytelling that’s not a bad thing for us, of course. That’s a good thing. We want a reader who is engaged and open minded about how they might be told the story.

**Silverstein at work with the magazine’s creative director Gail Bichler and features editor Ilena Silverman.**

Rachel Baker: We’ve heard that a big part of your job is actually outside of the magazine per se, like developing new ideas and franchises, like The Interview podcast and The Great Read. How does that work—that you’re this creative engine or incubator at the paper?

Jake Silverstein: Yeah, the paper has such a great track record of digital innovation and coming up with new ways to present stories digitally over the last 10 years. And it’s been exciting that the magazine rather than just being seen as like “the people who make the magazine over there” has started to become more integrated into that and seen as like a place that can be a home for new digital projects that, though they may be produced by the magazine or are overseen in some cases by the magazine, are not really the magazine, are actually just part of the digital experience of The New York Times. And the idea column that we’ve started running in the last year is a good example of that.

Part of it is that, I think there’s something interesting happening where our programming strategy as a newsroom, the way we program the digital feed is just naturally getting more sophisticated over time. The more time that we spend publishing journalism into this digital feed and understanding how readers are responding to it, and how that changes throughout the day, and how it’s different on the weekends, and how there’s patterns of behavior that we can begin to understand about what kinds of stories do better at what times of day.

The more that we learn about all of that, the more sophisticated our like strategy of how we program it is going to be. And I think the magazine is in a sense, the print magazine in a sense is the result of an earlier version of people thinking about programming strategy.

Obviously that’s a technical sounding term, but like at some point in time, in the late 19th century, it was believed that part of the programming, the editorial programming of The New York Times should be this like weekend magazine that would do something a little different and readers would—I don’t exactly know what the market research from 1896 was that indicated that there was an appetite on the part of the readers for such a thing.

I don’t know what that research was, but presumably there was some idea that there was like a moment in the week, or a type of reader, or a type of offering that would reach a reader at a certain time and it could be a little different and it could have pictures. It was the first part of The New York Times that had pictures.

And I think something vaguely analogous is happening now with the way we’re beginning to understand the incredibly complicated organism of this always-on, seven-day-a-week digital feed of stuff that obviously has to begin to get more organized as we become more sophisticated in our understanding of how people use it.

“I thought the magazine should be more literary. I thought that it was taking as its competition New York magazine and that it should be taking its competition as The New Yorker more.”

Rachel Baker: Do you have any new franchise babies in the incubator that you want to tell us about?

Jake Silverstein: None that are quite ripe enough to share. Franchises I think are an interesting part of that programming strategy that I was just talking about. The Great Read is a perfect example. That was an idea that Joe Kahn—it was even before he was executive editor—he had this notion that we should just simply have a destination for a really good piece of narrative journalism every single day. And not only would that be helpful for readers, it would give writers and editors inside the newsroom something to aspire to.

And in aspiring, they would perhaps even raise the level of their work higher because it’s always good to have a target to aim at. The idea was that the magazine as the kind of folks who do most of the long-form journalism, most of the narrative character-based journalism, should oversee that and should be the curator of that slot.

So that was in some ways of this recent group of franchises that you’re talking about, that was the original one. And the way that they function is really different from how the magazine has overseen in the past to function. In the past if we had a column in the magazine, literally in the magazine, we would essentially control the assignment and the creation and the editing and the publication of every single thing that went into that column.

But with these digital franchises there’s a balance between creation and curation. So sometimes we’re ginning something up from the ground floor and sometimes we’re finding stuff that exists. That’s a whole team. It’s run by a really talented editor named Claire Gutierrez—

Maggie Bullock: Our former colleague!

Rachel Baker: We worked with Claire at Elle. Shout out to Claire!

Jake Silverstein: I forgot. Since you worked with Claire, I will never hear the end of it if I don’t say her name in connection to The Great Read. I’m saying that “Claire runs The Great Read” and she does quite a good job of it.

Maggie Bullock: Okay, so switching gears somewhat, Jake, when you found out about this interview, you may have wondered why we were the ones doing it.

Jake Silverstein: I didn’t, but go ahead.

Maggie Bullock: Let me solve that mystery that’s been keeping you up at night. It’s because we really raised our hands for it, because we admire your work, but also because we do this newsletter called The Spread which is about women’s media, which is very much inspired by a moment in women’s media that crystallized for us three years ago, but who knows if it was happening way before that, which is that it wasn’t just that the traditional women’s mags were being decimated. It was also that we saw “dream” women’s magazine stories being produced in lots of big fancy places where you didn’t use to find them like your magazine. And so it was like you were seeing what we think of as being the women’s purview being really addressed in a much wider variety of sources, which was exciting, but also could feel like there was no centralized place for it. Anyway, that’s our raison d’etre. But we say often that your magazine is our favorite women’s magazine.

Jake Silverstein: What a great compliment! That’s funny. I’m so glad to hear that. So many of the stories that have been the standout stories and won awards and gotten the most readers and been the most celebrated are stories that—I hadn’t quite thought of it this way—but there are stories that totally could have appeared in a woman’s magazine.

We definitely, we’re not using the term ‘women’s magazine’ when we conceive of those stories, but we are thinking about stories that are often about women or about women’s health or are just about some broader topic that often does appear in women’s magazines like love, and relationships, and family, and so forth.

Those general topics are really important to us. And it just feels like there’s a lot of, as journalists, you always want to try to go to the place where you think there might be some untold stories and we have felt like there were some untold stories, at least for magazines like ours to cover in that area, but also just what do your readers care about?

It’s pretty obvious when we publish a story like Sue Dominus’s menopause story. It was very obvious that a huge number of our readers cared very deeply about that story and responded to it. And that didn’t us at all. We knew that going into it and we were excited about that.

Rachel Baker: That was one of the stories we’re going to ask you about, like specifically it felt like such a game changer. And we were curious: was that story idea an immediate yes for you or did it at some point, give you pause?

Jake Silverstein: No, it actually took an interesting path. I don’t want to take credit for it because Sue deserves all the credit, but it originated with an idea that went to Sue that I gave to Sue and her editors Elena Silverman and Rachel Poser because a friend of mine was involved in a kind of menopause-related startup. And I was hearing stories that she was telling me about, first of all, just like how busy that space was. This was like three years ago, maybe.

This is a good lesson about how ideas get better over time because my original idea to Sue was, “You should do a story about how there’s all these menopause startups.” Which is a kind of boring version of the idea. It is true that there were a bunch. And so she went off and she started looking into that.

And then she came back and she said, “No, there’s a much more interesting story. And it has to do with HRT and the reasons why it hasn’t been as available to women.” And it’s sort of a science story. It’s a kind of blowing the whistle on a way in which the medical establishment has failed women. It’s a personal story. It’s all these different elements. And it’s such a ripe story.

And that was a thousand times better than the simple business story that I had initially proposed to her. And is a good example of why writers like Sue are invaluable to a magazine like ours because they often take a spark of an idea and with a little bit of reporting turn it into something truly special.

When she came back and she proposed that, I think there was like maybe 24 hours where we wondered whether the argumentative angle of that story would be the right angle to take. She was really going to come out and make a strong statement like “more women should be told that they are potentially candidates for this treatment.”

Any kind of big health-related statement like that, we always pause a little bit on because we just know how powerful The New York Times is as a recommender. And so we always want to think pretty hard. What we say is going to result in a lot of people going to their doctor and demanding X, so we want to think pretty hard about that.

So we didn’t just instantly say “yes” to Sue. We thought about it for a couple days but then talked to her about it and then said, “yes.” And she was completely right. It was a terrific story. And it’s obviously been a game changer.

Maggie Bullock: It’s interesting because we were talking about how magazines like yours are doing more quote unquote women’s stories, but you can do them in a way that, sadly, women’s magazines have never had the resources to do. Like that depth of the reporting, the word count, and also the gravitas of coming from the Times. It’s a combination of forces that makes it better women’s reporting than we’ve ever gotten before. Because the people who handled it—brilliant people—didn’t have those kinds of resources, usually. Also this idea that women would tear the pages out and take them to the doctor. That’s just a different level of power.

Jake Silverstein: Yeah, we heard stories about OB-GYNs that had QR codes that people were like, scanning to read the story. That doesn’t happen that often, to be clear, where a story really has that kind of cultural impact where people are talking months afterward about how it changed their lives and it’s incredibly gratifying.

It’s one of the things that I think, to go back to what your first question was, that’s the kind of thing I often trot out when somebody’s considering leaving the Times. That to me is an example of the kind of impact that we are lucky enough to be able to have in the world. There are lots of great places that publish really good health reporting but the level of reach that The New York Times Magazine has means that health reporting is able to have this impact on people’s lives. It’s truly incredible sometimes.

Rachel Baker: Didn’t that story win a bunch of awards? And according to our math, your magazine has won a Pulitzer Prize every year for the past five years, is that right?

Jake Silverstein: That story won a National Magazine Award. But yes, it is true that the magazine has won either independently or been involved in group entries that have won a Pulitzer for five years in a row. We’re pretty happy about that.

Maggie Bullock: That’s a hard record to keep up. Do you feel any pressure?

Jake Silverstein: It’s been a really tremendous run. Part of what I’m really proud about of that run is that the awards have all come from really different projects. So the first of those five awards was for Nicole Hannah Jones for commentary for her essay in The 1619 Project. The second was that Wesley Morris won his second Pulitzer prize for criticism.

And that was, as I said, some of these are group entries. So in that case, the culture desk had submitted some of Wesley’s reviews and one of the things that we’d submitted was this wonderful essay that he wrote about his mustache during COVID and the 2020 protests.

And then the year after that it was for Asmat Khan, who was part of this incredible project that we did on civilians who were killed by airstrikes in Syria, and Iraq, and Afghanistan. And she had a big part of that, which was also a group project.

So those three really different projects. And then the year after that, Mona Chalabi the prize was for illustrated reporting, and it was this visualization of Jeff Bezos as well. And then last year, Katie Engelhart won for this amazing story and feature writing about a mother with dementia and her daughter’s trying to deal with how to handle some legal issues that she was getting into as she slipped further and further away from the mom that they remembered.

So five very different stories and five very different writers doing very different types of things. We are always so proud of just the range of things that we get to work on at The Times magazine and the different styles that we get to work in. The different subject matter that we get to tackle. It’s just so fun.

“We’re not running all of our assignments up the flagpole by any means. It would become almost ungovernable for the top of the masthead if we were doing that.”

Maggie Bullock: I know the Asmat Khan story, she was gathering string for five years.

Jake Silverstein: Yeah.

Maggie Bullock: I wonder, is that the longest build up to a story? Or are there even longer term reporting projects?

Jake Silverstein: I don’t know what the record is, but I know that last year we published a story by Ronan Bergman and Mark Mazzetti about the impunity with which settlements have been built in the West Bank and how that has led to overtaking of of Israeli politics and society by a kind of radical element that was fostered in those settlements.

That is a project that Ronan, who is an Israeli reporter, has been working on for eight years. He’s done other stuff—and I don’t know how you want to measure it—he’s done other stuff as he was doing that. But yeah, that was a project that he reported for a really long time.

Maggie Bullock: How does it work for you? You’re running the Times magazine, but yet, some of these projects require a long investment. I can’t imagine money, and time, and photography, et cetera. Do you have to pitch it and run it up the flagpole and get it greenlit? Or is your budget yours to do with what you want? I’m just interested in looking behind the scenes on that a little bit.

Jake Silverstein: It depends. I would say the majority of the stuff that we assign and move forward on at the magazine, we’re not running all of our assignments up the flagpole by any means. It would become almost ungovernable for the top of the masthead if we were doing that.

And historically, at least in recent times, maybe since Adam Moss wrested it away from its identity as truly like a newspaper supplement, it really was seen as an independent publication. And there was this sort of custom that the magazine editor, I don’t know how long back this goes, but when I got there, the custom was that the magazine editor would trot down to the third floor with a printout of the magazine cover for that week to show to the executive editor. So I would do that every week, show the cover to Dean.

The main way that the magazine would present itself to the executive editor for approval was via that cover meeting. That was really obviously pretty print-centric and now it’s completely different. We’re in much more—this also happened during Dean’s tenure—we were in a much more kind of constant dialogue about the magazine and what it has coming and what we’re assigning. If it’s a really big project, we’ll sometimes want to loop in and run our ideas past the masthead at an early stage.

In part because we want to coordinate with something else that might be happening. There’s so much always happening at The Times that level of coordination is really important. But there is a fair amount of independence granted to the magazine to pursue its own assignments. And I think that’s part of how you end up with a n output that feels different. It’s not like the same editorial impulses that are informing the decisions about all the different stories.

Rachel Baker: We’ve been talking about your wins—they’re really big wins. In your years at the Times magazine, you’ve also had your share of controversies. There was The 1619 Project, which was in many ways, a wild success, but also controversial. There was the Emily Bazelon story about trans kids. And then arguably one of the biggest journalistic controversies over the last couple years was around staff writer Jasmine Hughes, who was seen as such a star writer and who we covered all the time and still do in The Spread when she resigned after being disciplined for signing a letter protesting the Israel-Gaza war. As an editor and a boss, what would you say you learned from that experience and all these controversies?

Jake Silverstein: I don’t necessarily think you learn anything from these controversies. They’re all different, of course.

Rachel Baker: Dramatically. Yeah.

Jake Silverstein: I don’t think you necessarily learn things from controversy such as the ones that you’re just describing that will help you prevent them from happening, right? To some extent a magazine like The New York Times Magazine that is operating at the level that it is. It doesn’t need to be said that The New York Times is a kind of favorite target for a lot of people out there. And so there is a built in tendency to criticize things if people think there’s any reason to.

Which is, I think, part of the influence that we have. So it’s not necessarily unwelcome. I guess I think that the occasional criticism or controversy that erupts around a story is not an indication that we’re doing the wrong thing or whatever. It’s part of what comes from being bold about your story sense and trusting your writers and so forth.

And as far as management goes, we hire and work with hundreds of people over the years. And it also seems to me that it’s inevitable that sometimes those relationships aren’t going to work out in the long run and there’s going to be painful separations. And that’s also, kind of, part of doing business in a way.

I think what I have learned though, about all of those, and I just would say in general, what feels like a good lesson to take from any kind of difficulty that you encounter running a magazine like The Times is just that the more you’re able to communicate with your staff, you know, externally you can’t control what people are necessarily going to think.

I’ve also learned that people have a certain kind of bias against The New York Times—certain people. It just colors how they think in a way that becomes very difficult for us. You can’t necessarily control how an external audience is going to perceive something when a controversy like the ones that you’ve mentioned erupts, but you really can speak in a very forthright way to your staff and to your internal audience.

And it can be really hard for any group of people when their magazine, their institution, their team is being criticized. Because often you’re not even a part of the team or maybe not even part of the story or the decision that is getting criticized, but the place that you work is getting attacked by people on social media, maybe even by people in your friend group or whatever.

And it’s very helpful when the boss is able to speak in a very forthright and transparent way to the staff and answer questions. That can be hard. I don’t know that I’ve always done the best job of that, but I’ve certainly tried to get better at doing that with the staff.

You don’t want people to feel like there’s certain things that can’t be said internally, right? Everything we do is done collectively. And so whenever there’s any outside controversy that swirls around anything that we do it can disturb that. And I just really try to make sure that doesn’t happen.

Maggie Bullock: So we were really hoping that in the time that we have here you might do a little storytelling behind the storytelling. Give us the VH1 Behind the Music of a favorite production of yours or a story that either was very hard to make or was just weird and wild to make. Is there a favorite or one that sticks out in your memory?

Jake Silverstein: There’s so many.

Maggie Bullock: It’s hard to choose a baby, but try.

Jake Silverstein: Early on one of the most exciting projects that we undertook was this crazy virtual reality launch that we did in 2015 or 16 where we had this partnership with Google where they mailed these cardboard VR headsets to everybody. The number of different things that we had to figure out to make that happen was so complicated because first of all, we had to learn how to make a virtual reality film.

We did three films that were about displaced children. It was a moment when the global migrant crisis was really peaking and felt really serious and, at that point, something that readers had not yet read a lot about. We wanted to really take readers inside that in a profound way and we had started to experiment with VR and thought, This is cool. Let’s try to do something novel with this.

And so our thought was to put people in the experience of children who have been displaced by war. We had to figure out how to make a virtual reality film. We hired people that knew how to do that, but still they didn’t really know how to do it, like for us. So we had to figure it out too.

We had to send writers around the world to find children, interview them. We had to build an app, a VR app, and then get a significant number of New York Times readers to download the app and know how to download it and then know how to use this Google cardboard.

So there was a lot of product design that we had to do. People would receive their paper on a Sunday, and they’d never heard about any of this before and all of a sudden there’s this confusing Google headset. The fact that we did all of that, and this was a project that Gail Bichler and I worked on really closely together, and a lot of other people too, but Gail was particularly important to it. Kathy Ryan as well.

It was just so satisfying to figure out all these new things. None of us had ever done any of this stuff before. Figure it all out and then pull it off to the point where we had created this moment where on a particular day, hundreds of thousands of people all across the country who get The New York Times were having an experience that they’d never had before.

That was very thrilling. So that was one project that springs to mind. That was a long time ago now. In 2019 Jonathan Mahler and Jim Rutenberg did their giant story about the Murdoch empire, which then became a CNN documentary.

**Silverstein, Bichler, and senior designer Claudia Rubín**

Rachel Baker: Yeah. Just a regular old story.

Jake Silverstein: Yeah.

Maggie Bullock: So satisfying. That one.

Jake Silverstein: Right before that the Times had renovated a bunch of its conference rooms and made them into whiteboards. And we would always joke about it because it was a sort of symbol of the fact that there are so many more product people, and tech people, and developers who have been hired—for good reason—at the Times in the last decade.

We didn’t really ever use the whiteboard walls, but you would sometimes walk around and you would see these crazy, like, A Beautiful Mind-type equations, like covering an entire wall. It would look really cool, but we would never do that over in our part of the operation.

But when we had to do this Murdoch story it was so complicated narratively. It had so much like different sections and structures and different characters, braided characters, and everything that we ended up filling a whole wall with a diagram essentially of the story. It looked pretty crazy by the end of doing it, it was all these scribbles all over the wall. And Jim has a photograph of that that we sometimes look at and remember that crazy long night of trying to diagram that story.

Maggie Bullock: I love that. That actually reminds me of the Prince story that you did. Remember the art in the Prince story? And I was like, I’m terrified and so attracted to this organizational system. Sorry.

Rachel Baker: We love that story.

Jake Silverstein: That was a great story. That was also a hard one to diagram, and we didn’t really diagram it the same way, but that was a story where Sasha Weiss, our deputy editor who looks at culture coverage and who’s also just a terrific writer and a wonderful editor of all stories, not just culture stories.

Sasha had the foresight to essentially embed with Ezra Edelman as he was working on this Prince documentary. And the idea was just to do a typical story about a really important film, documentary film in this case, that was being done. And we would publish the story when the film came out.

And then of course the Prince estate squashed the project and Netflix put it on ice and it became a completely different story, and a story about Ezra Edelman’s sort of thwarted attempt to make this film, and why it was being thwarted, and what was in the film that the reader was never going to be able to see for themselves.

And it was a really complicated story to tell because which one of those three things is the narrative? Is it a business story about why Netflix caves in? Or did Netflix get the wool pulled over its eyes by the estate? Or was the estate the bad actor in all of this? Or is it like what’s the film doing that was objectionable? Or is the film like a masterpiece that will never be seen?

And maybe it’s about the filmmaker himself and his sort of, Moby Dick-like effort to do a project that seems to stay beyond his reach. There were so many different ways that Sasha could have told that story. And she somehow figured out how to do it all in one story, which is the hardest thing.

Rachel Baker: It was ambitious.

Maggie Bullock: Is it fair to say that’s kind of a very Jake Silverstein story, though? I think about the book that you wrote that is blending memoir and journalism and fiction. And you have an MA and an MFA?

Jake Silverstein: I’m overeducated. Yes.

“The occasional criticism or controversy that erupts around a story is not an indication that we’re doing the wrong thing. It’s part of what comes from being bold about your story sense and trusting your writers.”

Maggie Bullock: I don’t know, can you be overeducated for your job, Jake?

Rachel Baker: Yeah, it’s going well. Seems to be going well. Seems to be working out.

Maggie Bullock: It serves. But anyway this newfangled way of blending different kinds of storytelling. It’s like a thing for you.

Jake Silverstein: Thank you for mentioning my book, which is still available on amazon.com.

Maggie Bullock: So is mine!

Jake Silverstein: I do like blended forms. You’re totally right about that. But I would say that what Sasha did in that story is something maybe a little different just in that it was like, I don’t even know that it’s right to say that she was blending forms exactly.

The hardest thing, I think, in magazine writing is that there are a lot of standard formulas that exist, like a basic profile of an individual who has something coming out. It’s just like a formula. We know how to do that. You can jazz it up one way, you can jazz it up another way.

Like the true crime narrative, there’s a basic formula. It can still require a huge degree of expertise to do really well. But there is a sort of sequence of steps that you tend to take each time. The same goes for so many different types of stories that we do.

Public interest health stories often have a kind of shape to them that’s familiar. It’s the stories that are like, what is this? Is it this type of story or is that type of story or is it the third type of story? It’s all three where you don’t know, should I start here? Should I start there after the first section? Do you go to this or do you go to that? Do you stay with this character? You move to that character? And there’s probably four right answers.

Those are the really hard stories. And that Prince story was totally one of those stories. And, it was partly why the editing process was complicated. And those are also, I would say some of the most fun stories to work on because they’re just really challenging to figure out the structure of.

Structure is one of my favorite things to work on as an editor. I do also enjoy—although I really don’t do much of it any longer—working at line level comments and so forth. I really enjoy working with our editors on how to structure stories because, you know, there’s just a lot of interesting thinking that can go into that.

And I think it’s also changing too, because structure is, to some extent, related to your understanding of who the reader is and how the reader is going to encounter the story. What will they expect from the first section or what do they need from the first section to keep going? And that’s definitely evolved over the last decade as we think more and more about a reader encountering a story on their phone. Our sense of how to structure stories has adapted to that a little bit.

Rachel Baker: You seem so wistful about writing. Do you think you’re going to go back to writing?

Jake Silverstein: Yeah.

Rachel Baker: At some point? And is there a book happening? Somebody told us about a book.

Jake Silverstein: Yeah, I am working on a book that’s a book of history. It’s a history of American history. But I’m working on it rather slowly.

Maggie Bullock: Do you want to say anything else about it? What’s your spin on history?

Jake Silverstein: I got very interested in historiography after we did The 1619 Project and wrote an essay for the magazine about the kind of dialogue between the way that what we would consider standard American history, the kind of dominant narrative of American history of the founding and and so forth and how that has evolved over the last 250 years. And the dialogue between that and a more critical take on American history that has slowly emerged.

And it’s not only that it’s critical, it’s that it’s also a telling of American history that broadens the frame and that is more inclusive and includes a lot more actors, and characters, and subjects, and types of people, and points of view, and so forth than what was traditionally included in the narrative.

And that there’s been an interesting dialogue or tension between those two ways of telling our story over the last 250 years that the dialogue itself, I think, has become the product of a certain aspect of American historical identity. And that’s what the book is trying to do.

Maggie Bullock: Just a little light writing assignment—to get your feet wet again. Okay, so Jake—Rachel, what’s the amount of money?

Rachel Baker: A hundred million.

Maggie Bullock: This podcast has a standard kicker and—it’s a hundred million?

Jake Silverstein: —I get for doing the podcast?

Maggie Bullock & Rachel Baker: Yes!!

Rachel Baker: Your check is in the mail. There’s somebody at the door for you right now.

Maggie Bullock: Put your feet up, Jake, your work here is done. If we were to give you—it’s a hundred million? Okay, sure, I’ll give you a hundred million dollars.

Rachel Baker: It might be more than that. I think it’s more than that. It’s a billion. I think it’s a billion!

Maggie Bullock: It's a billion dollars, Jake. But let’s take it down, because then there’s no challenge. A hundred million dollars to start a new media endeavor. At this point, knowing what we know about what works and doesn’t and what’s promising, what kind of thing would you start?

Jake Silverstein: Does it have to be promising? Because I don’t know what’s promising.

Maggie Bullock: Don’t throw my hundred million away!

Jake Silverstein: If I had a hundred million dollars to start a new magazine—I do like this question and I’m always interested, on this podcast, to hear how people answer it. Which is to say, I have thought about it because I’ve heard other people answer this question.

I really love doing special issues. I mentioned maybe one or two of them in our conversation, but there’s so many more that I could mention. I love the sense of total freedom that they give you and the ability to surprise readers with some twist, not just on the typical content of a magazine, but often we’ve tried to really put a twist on the idea of the magazine itself.

Once we did—and Gail gets a lot of credit for how this finally came across—but once we did a special issue of the magazine about voyages that you would take to places in the world to hear a particular cool sound that was only able to be heard in that place. And the issue, other than a little brief text that introduced the issue, had no words in it. It was just photographs. So also lots of credit to Kathy and her photo team.

And there was a podcast or an audio track that you could listen to that would tell you what you were hearing, what you were looking at, and play the sound. That was the kind of reason you would go to that place. But it was very unusual to just get a magazine that was just one full bleed photo after another for the entirety of the magazine with no words. And it was such a thrill to be able to give readers something that would truly stupefy them and make them stop in their tracks and wonder, “What the heck is this?”

Or another one that Gail and her team get a lot of credit for—I think this was her deputy Matt Willey’s idea—was when we did a story about the super-tall buildings in New York City, to turn the magazine on its side so that we get the maximum height from the—

Rachel Baker: Magazine-y!

Jake Silverstein: Yeah. So just like, you know, and so many more special issues that we’ve done over the years that were just like really outside the box kind of creative ideas.

So if I had a hundred million dollars—that’s a lot of money. So you could build a team that would basically do a magazine that was a special issue every single week. Where every single week we were reinventing the idea of a magazine. And there was essentially no front of book, no back of book, no standard features. It was essentially like a free form special issue from scratch every single week.

Maggie Bullock: So you don’t like sleep is what you’re saying.

Jake Silverstein: No, but you’ve given me enough money to hire almost like multiple staffs.

Rachel Baker: Special Issue magazine.

Maggie Bullock: I saw Rachel got a little nervous when we said it wouldn’t have a front of book. Rachel loves a front of book.

Jake Silverstein: I do love a front of book too, although it’s hard—

Rachel Baker: Maybe the front of the book is in the middle of the book. Who knows?

Jake Silverstein: Exactly.

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