An Elegy for the Elite
A conversation with Empire of the Elite author Michael Grynbaum. Interview by Sean Plottner
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Michael Grynbaum is a correspondent for The New York Times, where he has covered media, politics, and culture for 18 years. He’s reported on three presidential campaigns, two New York City mayors—they're always so boring—and the transformation of the media world in the Trump era. He lives in Manhattan and he’s a graduate of Harvard.
His first book, Empire of the Elite: Inside Condé Nast, the Media Dynasty that Reshaped America, was published by Simon & Schuster in June, 2025. In the book, Michael chronicles the origins of the company, its go-go boom days in the eighties and nineties, and its more recent post-print transformation into whatever Condé Nast is these days. We’ll figure that out later.
Michael’s bestseller captured a lot of attention when it was published—it’s a bestseller and it’s the latest in the line of books by and about Condé Nast magazine makers—full of great anecdotes and good stories. The kind of stuff we love here on Print Is Dead (Long Live Print!), and it’s extremely readable.
Sean Plottner: Tell us how the book came to be.
Michael Grynbaum: Back in 2017 the news broke in The New York Times that Graydon Carter was leaving Vanity Fair. I’d gotten to know Graydon a little bit as a journalist and he called me one day and invited me to his Bank Street townhouse—purchased in part with an interest-free loan from Si Newhouse—and gave me the scoop.
It was a grandly choreographed affair. I believe that I knew about it before the Newhouses did. When I wrote that story it felt like I was writing an elegy for this era of celebrity editor and certainly of when glossy magazines were at the peak of their power, Graydon leaving felt like this real turning point.
Of course, Anna Wintour was still there, but this felt like a real moment and I had so much fun writing that story. It just felt so redolent of a certain time and era in the American media, in New York City, in the creative world, that I started thinking that it could be something, maybe there was something bigger there.
And what I found was that the last real independent history of Condé dated all the way back to the late 1990s. There are many great memoirs about Condé that I’m sure your listeners have enjoyed. I’ve enjoyed many of them myself, but they tend to be narrow. It’s one editor’s subjective experience, and I thought that there was something that an independent journalist could bring here.
Kind of a wider aperture in assessing Condé Nast, looking at its importance in the culture. Looking at how the culture shaped the magazines and vice versa. And I thought there was a real need for that. And that was the origins of how Empire of the Elite got started.
Sean Plottner: Was that your pitch to publishers?
Michael Grynbaum: It was. And to be honest with you I was expecting the boomers and the older editors to respond to this and maybe getting crickets from people under the age of 50. And what was so encouraging for me was when I went around pitching the proposal, often book editors have assistants and junior editors who are in their twenties who are on the call.
I’d be telling these stories about the Concord flights and the black town car services and the younger editors, their eyes were like saucers. They were so riveted and it felt like they were almost nostalgic for this great era, the media that they themselves had missed out on.
And there was a real fascination about a lost world. I found it very hopeful that this was a book that could find readers beyond just people who worked at Condé Nast. And so that was a really positive feedback.
Sean Plottner: That’s part of the reason why it became a bestseller. And I’ve come across a lot of people that I know who happen to be reading it at the moment and enjoying it. So you do a great job of quickly explaining the origins of Condé Nast. I’m going to just briefly go over that. There was a guy named Condé Montrose Nast, and he helped his college buddy make a Colliers magazine a success. And, Condé decided to go out on his own and start his own company. He eventually bought Vogue magazine in 1909 and he named the company after himself minus the Montrose. And Condé was aware of pince-nez—those old style eyeglasses with no earpieces—so we’re going way back. And then the company suffers through the Wall Street crash of the late thirties. In 1929, Condé Nast dies. There’s a fire sale, and in 1959, a man named Sam Newhouse comes along. Who was Sam Newhouse?
Michael Grynbaum: A very rich man—of modest social stature. Sam Newhouse was an up-from-the-bootstraps newspaper magnate born into poverty on the Lower East Side, an immigrant son who straps together this network of mid-market newspapers.
The Star Ledger in New Jersey, the Staten Island Advance, the Syracuse papers, New Orleans, Portland—all solid publications, but in like B-tier cities around the country. And I mean that in terms of advertising reach and social clout. And so he became a very wealthy man and even lived on Park Avenue.
And in the late fifties, he was interested in expanding into the magazine industry and he was known—basically he was what we would now call a distressed-asset specialist. He would go after publications that were near bankruptcy or casualties of family feuds and buy them up cheap. And at the time Condé Nast did have Vogue magazine, but even in the 1950s, Harper’s Bazaar was really at the vanguard of fashion journalism. Diana Vreeland was the fashion editor at Bazaar and Vogue was the second tier magazine. So this was a damaged goods that he bought up and he bought it for a song.
The joke was that his wife Mitzi, who was a social climber, asked Sam to go out and buy her Vogue at the newsstand, and he came back with the entire company. This is how the Newhouses came to own this kind of Gilded Age relic that was Condé Nast. And Sam ended up putting his eldest son Si in charge of the place.
Sean Plottner: We quickly move forward to get Si into the story here. In 1964, Sam assigns Si the job of publisher at Vogue. You call this, Sam’s appointing, a mix of pragmatism and desperation. Why?
Michael Grynbaum: So a lot of people, when I set out to write this book, told me that I was going to have a big problem, which is that Si Newhouse was too enigmatic and too unknowable a character, and that the book would suffer from that.
What I discovered and I actually even dug up some of Si’s letters as a teenager to his friends. A lot of archival research. He was a very awkward and lost young man. He was the eldest son of this magnate with all the responsibility that comes with that, his father expected him to inherit the family business.
But he was very awkward. He got married young, had kids, divorced, became an aimless bachelor. He also loved material goods and arts and culture, the kind of attributes that his father had no use for and at worst considered feminine.
And he didn’t really thrive in the newspaper business. And by the way, Sam Newhouse, it was the newspapers that mattered to this family. Those were the prestige properties. So when his father had him go learn the magazine business, it was oh, go run the women’s magazines, this extraneous arm of the family empire.
So that’s how Si ends up at Vogue in 1964 and his father thinks, Listen, you know my kid, he’s lost. Let’s give him a project that he can play with. And this is where Si finds his niche.
Condé Nast—and I didn’t even realize this because by the time I moved to New York and in the mid aughts—Condé was already this great empire, but it really was Si Newhouse who was the architect of this and from the mid seventies onward really transforms this company into a global publishing powerhouse as we then came to know it.
Sean Plottner: Yeah. His father did him a favor in a way, and he took it on and took it farther than I think his father—thinking of it just as a way station or a layover or a stepping stone to something. So Si is the oddball, enigmatic character. He is front and center in the book, but there in the shadows, not center stage, as you dealt to all the editors. Tina, Anna, Art, Graydon, David Remnick. Sorry, David, I don’t know if you’re a first-name-only kind of guy yet. And of course some of these folks have been on this podcast, thank you very much. You just offer up a great serving of anecdotes and stories about their reigns at the various magazines. And Si is always lurking in the shadows. Of course he’s the Great Manipulator. He had his successes and he was shrewd, I want to say. Got Self going, certainly drove in ad pages, he made what could be called some great hires or lucky hires, and he also got something called The Art of the Deal, a book by Donald Trump, into motion. And we’ll talk about that a little later. But I think he made people uncomfortably uncomfortable.
Michael Grynbaum: That’s right.
Sean Plottner: What explains him? Why was he the way he was?
Michael Grynbaum: He certainly made people uncomfortable. Including editors and advertisers. And he spoke very haltingly and minimally. And some of that is the privilege of a very wealthy man who ran the place. He could behave however he wanted and he could slouch into the office in his faded New Yorker sweatshirt.
All the fashionistas around him would cower in fear, who were all dressed to the nines. It’s funny to think about it today because we actually live in an era where these billionaires are buying and selling media assets like so many ticky-tack items on the street.
But Si really cared about what Condé Nast produced and was this emblem of refinement and discernment and status. He really was like this kind of modern Medici—he was the benefactor for all of these editors and writers and photographers and artists.
And he was mercurial and he would fire people on a whim and hire people on a whim. It was a court, it was really a royal court at Condé Nast where everyone kind of bob and weave around what Si’s wants were. At the same time, he actually gave his editors quite a bit of autonomy.
He would hire someone and let them do their thing and he believed in allowing the creative people around him to pursue their interests and their instincts, and if it didn’t work out, he would fire them. But it was on the editor to make it work. And he was not one to meddle. Which came across again and again in my interviews with former editors-in-chief.
He also had, I think, the benefit of being both an outsider and an insider. He was born into wealth. His mother attended Truman Capote’s black and white ball. He had this front row seat to society, but because he was so awkward and because he had no social graces he wasn’t accepted by that world, he could observe it at a distance.
And I think if you look at the history of great magazine editors, going back to Harold Ross and Clay Felker and all these giants of the magazine trade, they all came to New York City. And by the way, the same goes for Anna, Graydon, and Tina, who are on the cover of my book now.
My book’s subtitle is The Media Dynasty That Reshaped America. And on the cover I have a Canadian and two women from England. So I think it speaks to the idea that even though Condé Nast became the ultimate arbitrator of insider-dom, its regents were outsiders and strivers and people who came to preside over a social world that they weren’t necessarily born into.
Sean Plottner: Interesting. Did he ultimately have a good or bad relationship with his father?
Michael Grynbaum: They fought quite a bit. When Si was a teenager, his father I think, felt much more comfortable with Si’s younger brother Donald who did come to take over the newspaper business. And by the way, proved himself to be a shrewd businessman.
He invested in cable television and telecom back in the seventies and eighties. Investments had paid off hugely for the family. But Donald really was much more loyal. Donald and his wife moved into the apartment directly below their parents and lived there for many decades.
Si went off and had a bachelor pad designed by Billy Baldwin with a fur rug from the skins of 50 French jackals and became this decorated collector of great modern contemporary art. He really loved sort of living a sensual life in a way that I think his father, who was much more of a workaholic, never understood. So I pinpoint 1979 as this key turning point year in Condé Nast.
It’s when Self magazine starts, it’s when they acquire GQ. And it’s shortly before Si purchases Random House. And ’79 is the year that Sam Newhouse dies. And I think that even though they had a rocky relationship, having the shadow of his father lurking held Si back in a lot of ways. I think he was quite intimidated by his father. And I think he starts coming into his own as a businessman in the wake of his father’s death.
Sean Plottner: When Si Newhouse came calling people were usually very happy to pick up the phone and entertain his offers. And you tell those stories about those other editors. There’s an interesting anecdote. I’d love for you to read this for our listeners about his courting of Michael Kinsley in 1998. Tina Brown was leaving the New Yorker and Kinsley had edited the New Republic. He had started Slate in 1996. He was someone who was on Si’s radar, and so they met. And Michael, could you go ahead and just read this section about their meeting?
Michael Grynbaum: Yes, and I’ll just set it up that Tina abdicating The New Yorker job was sudden and abrupt and a shock to Si and the rest of Condé Nast. So that’s a bit of the backdrop here.
It was a Friday morning in Seattle when Si reached Kinsley. By Saturday, the editor was standing in Si’s apartment admiring the Andy Warhol “Marilyn” on the wall. Three hours later, Si offered him the editorship of The New Yorker with a $1 million salary and a $5 million signing bonus.“To the extent he had a strategy at all, it was to bowl me over with money,” Kinsley recalled. And he succeeded at that. Kinsley was elated but disoriented. Things were moving very fast, and he asked for a beat to speak with his wife.
Si, who wanted to announce Tina’s successor by Monday reluctantly agreed. They met again on Sunday for a dinner with Donald Newhouse, and upon parting Kinsley promised a final decision by morning. Fifteen minutes later, he walked into his room at the Helmsley Hotel and found a message to call Si.
The publisher’s voice crackled over the receiver. “You seem reluctant.”
“It is a big decision,” Kinsley replied, “But if I do it I assure you, I’ll be energetic and enthusiastic.”
“I’m starting to feel reluctant too,” Si said. “I think it would be better to call it off.”
Kinsley froze. Grasping for words, he told Si, “This is going to be embarrassing for both of us.” A few Newhousian mumbles later, the call and the prospective editorship was finished.
“I was really angry,” Kinsley told me, “I sulked for a while. What annoyed me in some ways was that he offered it to me and then withdrew it with the same, ‘Who cares?’ attitude about the consequences. That’s something that only a rich man would do.”
At the time, Kinsley considered himself adept at handling wealthy benefactors, but Si’s caprice left him confounded. “He was very nice,” Kinsley told me, “until the last phone call.”
Sean Plottner: Great anecdote. Condé Nast was his passion project and he wanted folks to share the passion, fully.
Michael Grynbaum: The New Yorker, I would argue, mattered more to Si than almost any other property. Because when he purchased The New Yorker in 1985, he did so really against the wishes of his brother and the other Newhouse on the family’s board. He overpaid for it. It mattered to Si because he considered it this literary treasure.
It was a magazine he had grown up reading as a teenager. Of course the purchase of The New Yorker was greeted by the literary establishment as this act of vandalism. The idea that Si, this ‘philistine,’ would take over this vaunted magazine to the degree that I actually dug up and quoted in the book.
But Lillian Ross, who was the mistress of William Shawn, quit in protest when Shawn left as editor. And Shawn and Ross actually collaborated on a full-length motion picture screenplay that dramatizes the purchase of a magazine very much like The New Yorker by a billionaire philistine very much like Si Newhouse. And it’s an incredible document that readers will find in the book.
But let me go back to Kinsley. So that’s the backdrop of Si offering what is in some ways the most desirable job in American letters to Michael Kinsley. From Kinsley’s perspective—he started Slate with Bill Gates, he would’ve had to move his family to New York. He needed to talk to his wife.
This was a pretty major life decision, but Si wanted this passion. He wanted no hesitation. He wanted someone who saw what a gift this was and would grasp it with both hands. And for whatever reason, he felt that Kinsley’s Hamlet routine turned him off. And decided, as he often did, to just go with his gut and said, “Maybe this isn’t the right fit.”
David Remnick, who Si had also had a conversation with earlier that week, didn’t hesitate to spend that weekend, that same weekend, writing an extensive memo about what he, David Remnick, would do with The New Yorker. And by that Monday, Remnick had the job.
Sean Plottner: Yes. Yes. Did you speak to Michael Kinsley?
Michael Grynbaum: I did. Yes.
Sean Plottner: How is he?
Michael Grynbaum: Oh Michael he’s had a long, lengthy chronic illness. But we spoke and he was incredibly lucid, down to detail about staying at the Helmsley Hotel and the phone call, which he remembered with great vivid recall. We had a lovely conversation about it. I wouldn’t say he feels any rancor, but I think that he’s miffed at the way he was treated by Si. He’s a treasure of journalism and it was an honor to be able to speak with him for the book.
Sean Plottner: Yeah it’s great to see him in here and it’s great to hear that he’s hanging in there. So anyway, thank you very much.
Michael Grynbaum: I should add, Sean, that Condé Nast officially would not cooperate with me. I approached them very early on. I wrote letters to the Newhouses and the word came back that they did not want to have anything to do with the book. I wasn’t shocked, they’re an extremely private family. They don’t like being written about that often in the press.
But one corollary that was at the Condé Nast HQ prohibited the current editors from sitting down with me for interviews, which I had hoped to do. Now without naming names, I’ll say that there are certainly people currently at Condé Nast who did speak with me on background.
And their perspective is reflected in the book. But one person who didn’t speak with me for an interview was David Remnick. And so I was pleased that you had done a great interview with David on the podcast and was able to include it.
Sean Plottner: That’s terrific. That’s good. Good to be able to find some other sources there if you can’t go directly. Super. So let’s move on to talk just briefly about what you call the last great magazine launch. And I just think it’s a story, and a magazine, that doesn’t get the attention that the other big Condé Nast titles do. Of course, it didn’t last very long. And that’s Portfolio magazine. Can you just give us a quick take on what was the last great magazine launch?
Michael Grynbaum: What makes Portfolio to me such a compelling chapter of the Condé story is that the project gets going in 2006. By this point, the writing is on the wall about print media. The advertising market is starting to collapse. Publishers are putting their resources into the internet and coming up with digital outposts for their magazines. And here’s Si Newhouse who really loved, loved magazines.
We didn’t talk about the print-order meetings, where when an editor-in-chief was getting their monthly issue ready to go, there would be a presentation. Not just Si, but there’d be a presentation of every page of it. And Si would come in and look at the rhythm and the cadence of the issue. And this is a guy who just had such a passion for it.
He decides there’s a market for a great magazine of business journalism—in some ways modeled after in the 1930s, which is still very collectible as a really great print product. So he commits over a hundred million dollars to this project, thinking that well, maybe there’s an advertising market and they pull out all the stops in terms of hiring all the most prominent financial journalists of the day. And it’s exceedingly lavish, in the Condé Nast style.
I spoke to the editors who worked on the prototype, and they would do these elaborate photo shoots. They were trying to figure out the cover shot and so they actually coordinated a photo shoot one afternoon with a helicopter, a boat, cars that were like, it was like an overhead helicopter shot of the Brooklyn Bridge of a boat passing under, and it was supposed to represent New York as a capital of industry and they pulled off the shot and then they said, “Oh, it doesn’t work.” And they threw it out.
So you know, there’s tens of thousands of dollars gone. And so there’s a huge amount of skepticism about the project. It launched in 2007, Tom Wolfe got paid $12/word to write a fictional story about hedge fund guys.
And listen, if it had been 1983 when Vanity Fair was revived, what a fantastic project to do. But the market wasn’t quite there. And then of course, in a bit of perverse timing, the stock market collapses and, the entire raison d’etre for this magazine goes up in smoke.
And I see that moment in 2008 as the end of the old Condé. I think that was the final gasp of the lavish print years at Condé Nast. And so I unspool that story in the book in a chapter that I call “The Elephant.”
Sean Plottner: Yes. And the elephant in the room, you have an anecdote in there about getting a real elephant to photograph that concept. And what strikes me is that nobody was aware of what the real elephant in the room was, which was publishing like this. But to their credit that first issue, and I still have it, 332 pages, 185 ad pages. Oh, the glory days! It lasted two years.
Michael Grynbaum: I have it too. It cost me $40 on eBay to get my copy.
Sean Plottner: I can say I bought it on a newsstand … for whatever that’s worth.
Michael Grynbaum: It is a collector’s item now.
Sean Plottner: Yeah. Yeah. Okay. You talk about that as like the beginning of the end. Portfolio was basically a disaster. We had the 2008 market crash, and then if there was a third nail in the Condé coffin so to speak. It was the big shift in our culture. You have just an excellent couple graphs about this as you introduce this topic, and I’d love for you to read those now too. Thank you.
Michael Grynbaum: Sure.
One day in the mid 2010s, Condé Nast staffers were summoned to a series of company-wide seminars on diversity held by an outside firm. The watchword for the event was inclusiveness. During one meeting, an attendee piped up to point out that the entire company had been founded on—and sustained for decades by—the celebration and fostering of exclusivity. An awkward silence filled the room.
The economic damage wrought by the 2008 market crash was one thing. Condé’s magazines had weathered recessions in the past, but the company now faced a more existential threat. Condé’s métier was privilege, and privilege had become a dirty word. The elites whose lives were romanticized, packaged, and sold to the masses by Condé as exemplars of American success were suddenly being recast as villains amid a populist surge. Wealth porn, long a core appeal of the Condé stable, was no longer sexy. In the immediate aftermath of the crash, it could even be seen as borderline obscene.
I am glad you pinpoint this because I think, as much as the economic problems of 2008, as much as the fact that the iPhone is introduced around then which puts all the power of a magazine in somebody’s pocket, there was a real turn in American culture against what Condé Nast had represented successfully for almost a century.
I think that the aspiration that Condé represented was something that people used to celebrate: How do I live the good life as a successful American? And there wasn’t this kind of resentment and bitterness directed against the elites who were in Condé’s pages.
But when opportunities began to crumble in the wake of that crash and I think that there was a new generation that felt like the American Dream was passing them by that was much less accessible than it had been to previous cohorts of Americans.
I think what Condé represented became less and less palatable to its former readership. I think this was another, as you said, a nail in the coffin that I think editors and executives just had no idea how to pivot around.
Sean Plottner: Yeah. And the shift was slightly ahead of the rise of Trump and the state that we’re currently in. Let’s talk about Trump for a second. I mentioned that Si Newhouse had actually come up with the idea, I believe, of The Art of the Deal. Can you tell us just a brief take on how that came to be?
Michael Grynbaum: This w as a historic footnote. And Jane Mayer in The New Yorker did some of the original reporting on this. Trump was on the cover of GQ magazine in 1984. The profile was written by E. Graydon Carter. And any listeners of yours—I’m sure your listeners have mostly read the story—but It’s a fantastic piece. You can read it on the GQ website. It’s brilliantly written. That issue sold like gangbusters and Si Newhouse who had recently purchased Random House, and decided, This guy should write a book, could be a big bestseller for us.
The other connection there is that Si Newhouse and Roy Cohn were best friends from childhood. Truly Si’s best friend. He attended every day of Roy’s corruption trials. They carpooled to Horace Mann together as teenage boys. Certainly Si had gotten to know Trump through Roy at some point in the late seventies and early eighties.
And so they pitched the idea of the book to Donald Trump. They actually bring in a big, thick book with a mockup of the cover to his office, and Trump says, “Oh, I like it, but my name needs to be a lot bigger on the cover.”
And the book party in 1987, which is in the atrium of Trump Tower, there’s a great Ron Galella photograph of Donald, Ivana and Si Newhouse greeting the well wishers at the book party. And of course it’s a huge bestseller. To me, it’s really the moment when Trump leaps from being a New York City figure to a person of national prominence.And in that kind of butterfly effect, I think sets the groundwork that leads us to President Trump.
I interviewed Si Newhouse’s daughter Pamela, she told me that the family regrets that her father had said into motion this series of events. Although she says, and I think fairly, of course, “How could anyone have known what the future might have brought?”
Sean Plottner: You were talking about Pamela. The quote is fascinating. “I just don’t know whether Trump would’ve gotten that show (The Apprentice) but for the success of that book. “My father, in a way, put Donald Trump on the map. It is a source of deep regret to everybody to think that, but how would he have ever known?” Oh, that’s just fascinating. And Roy and Si—is that the prequel to the screenplay we were talking about earlier? And by the way, who would play Si in that? Who would play Si—that’s something to contemplate. Mike Myers comes to mind.
Michael Grynbaum: It’s funny because Jeremy Strong, who played an incredible Roy Cohn in the movie, The Apprentice—I thought Oscar worthy—actually, I think, could be a fantastic Si Newhouse. He would really inhabit that character in a really fascinating way.
Sean Plottner: Great idea. Okay we’re taking care of some Hollywood business here. In your reporting on the media these days and over the last 18 years for the Times, what do you have to say about the transformation of the media under Trump—post-Condé Nast, certainly magazines—but what’s your soundbite on Trump and the media and where are we headed?
Michael Grynbaum: I covered New York City Hall for many years when I was first starting at the Times. And so I took on the media beat actually in the early months of 2016. And I’ll tell you that, that beat became something very different than it used to be like, What network anchor is getting, what time slot? And it’s become this existential assignment about the future of free expression and press freedoms in the United States.
That’s been a very long process. I interviewed Steve Bannon right after Trump was first elected. His description of the media as the opposition party originates from that interview I had with him, when he told that quote to me. That kind of complete change in the public perception of the mainstream media, which in many ways has been accelerated by the demonization that Trump has led among his political supporters.
But also the fact that the media is just more atomized than ever. That people are bombarded with information from so many different outlets throughout the day, every hour of the day, from social media to television, to streaming, to podcasts.
And so I think we’re in a moment where. I think media literacy has really been eroded. I think that people have a much harder time ascertaining what’s trustworthy, and I think you now see traditional news outlets struggling to find new ways of reaching readers. Not just get their content in front of their eyes, but to present it in a way that feels credible and trustworthy.
Which in some ways is as much an aesthetic kind of decision as it is a journalistic one. So it’s a pretty hugely transformative existential moment. I’ve had a front row seat to it. It doesn’t feel like I’m going to run out of things to write about anytime soon.
And I’ll just say that in a way, what I loved writing and researching this book was it’s such a simpler time in the media. It’s nice just to live in that moment of a simpler culture. So there is a bit of nostalgia to the book too.
Sean Plottner: Oh, so true. And maybe a longing. And yeah, it would be nice to have that simplicity because it seems like we’re on some slippery, scary slopes here and where we’re headed with the media is anybody’s guess. Two more quick things. One, digitally Condé Nast never got their act together and embraced the digital revolution. We have plenty of examples of that in the book. “Computers? It’s a phase,” says one executive in the eighties at Condé Nast.
Michael Grynbaum: Not just one executive. Alexander Liberman says that!
Sean Plottner: Yes. Yeah. And please explain to our listeners who he was.
Michael Grynbaum: Some of your listeners will know Alexander Liberman and some won’t. I actually hope my book will revive his reputation a bit. He was the longtime editorial director of Condé Nast joined in the 1940s and was, like, the autocrat in charge of all creative output of the company for more than 40 years.
Anna Wintour in this role she has now as chief content officer of Condé Nast is really the true successor to Alex because he had his hands in every part of the company. He was also Si’s mentor in art and refinement. He was a Russian exile, educated in Europe, very snobbish and had great panache, could be very scary and imposing, but was really the creative heart of Condé Nast throughout the mid-century.
And so he was the one in the 1980s when Linda Rice was showing him some new IBM machine he said, “Computers? That’s just a phase.”
Sean Plottner: It’s interesting though that they did eventually invest in Wired magazine, for what that’s worth. And you spell out very briefly how the farthest cry from Condé Nast that I can think of—Reddit, the social aggregation news site. I guess the Newhouses did have a financial interest in that and made a killing when it went public, what, last year?
Michael Grynbaum: The truth is that the Newhouses, there was a lot they missed. They just didn’t invest in the digital side when they had a chance to. They could have created big websites for the magazines early on and they didn’t. It was Style.com for a long time before they built out Vogue.com.
Stephen Newhouse had invested in Reddit early on, and in fact, they purchased Reddit outright. Today, Condé Nast itself, actually Wired is a good example because I actually think Wired and The New Yorker, which were certainly not the essential titles of Condé Nast are actually probably, The New Yorker, has a very healthy digital subscription business, makes good revenue, and has live events.
David Remnick has really turned that around as a business. Wired in the last few months has been breaking a ton of news about Elon Musk and DOGE and the Trump administration—really thriving. Wired was a very shrewd early investment early on. Si wanted to get a piece of the tech rush. For all the mistakes that the company made there were a few good picks too.
Sean Plottner: Oh yeah. And there’s still a nice stable of Condé Nast magazines. Si died in 2014. At the time, his daughter, I think, made the understatement of the century saying, “He was not comfortable with intimacy or with people’s emotions.” Who runs the company now and what is the company?
Michael Grynbaum: Stephen Newhouse, who is Si’s nephew and Donald Newhouse’s son, is the Newhouse who has the most power overseeing Condé Nast. There’s a small board. Jonathan, a cousin who ran the European editions for a long time was handicapped as Si’s successor.
Si had even identified him as a successor, but Jonathan ultimately was sidelined in this sort of corporate battle. And Roger Lynch is the CEO of Condé Nast, and he is a digital executive. He came from Pandora, the music-streaming business. He had no experience with magazines.
And listen, that was by design. The Newhouses thought, Look, we need someone who's more of a digital native who can help guide our company into the 21st century. So you know, Roger’s tenure, I think the jury’s still out on it. They’ve shuttered a lot of print titles. I don’t know if their digital strategy has been that successful. I think Anna Wintour has taken over editorial control of every magazine except The New Yorker with mixed success.
I think the big question now will be when Anna does eventually actually leave the company who becomes like the creative driving force of Condé Nast. And that’s a question that has no answer at the moment.
Sean Plottner: And we’ll all be watching and waiting. Condé Nast will always live long in our memories for what it was and we’ll continue to be fascinated by whatever it does and whatever it becomes.
Michael Grynbaum: I’ll add one thing. I was intrigued that Chloe Malle, who was recently announced as the head of editorial content of American Vogue, actually floated an idea to publish Vogue’s print edition less frequently and to make each of the print editions more of a collectible object, more of an event.
Talking about the future of print, in a lot of ways there is a thriving world of smaller, more artistic print magazines. Does Vogue become something where it publishes a print edition a few times a year, maybe on higher quality paper, maybe it’s something that’s more, feels more like something you collect and really enjoy the tactile nature of it?
While the brand every day is churning out other content online—that’s a way to preserve print while also acknowledging that the brand is going to have to migrate into the digital world to sustain itself. I’m not sure, but I think you know this question of what happens to print media. I still think Condé Nast will be at the center of that moving forward.
Sean Plottner: Oh, yes. Thank you Michael. Is there anything else you’d like to say? Anything you want to talk about here at the last minute.
Michael Grynbaum: No, this is great. And like I said some of the interviews that you’ve done with Condé alums were very helpful for me as I was researching the book. You’ll find Print Is Dead (Long Live Print!) in the end notes. And the book is out now. I hope your listeners enjoy it. It’s just such a fun topic. I love discussing it.
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