Ross Douthat and the Future of Digital Media

It has been over ten years since ESPN shuttered Grantland, a beloved online magazine that still has never been surpassed in online media, at least in my opinion. At its peak, Bill Simmons's outlet had an assembly of talent unlike anything seen before or since in online media and featured writing and storytelling that was consistently joyous, delightful, and amongst the finest work I've read in 20 years of working in online media. (Charles Pierce's piece on online gambling is particularly prescient given where we are today.)

But in 2015 ESPN, which had funded the site essentially as a vanity project to keep Simmons around without really understanding what they had, shut it down. And while Simmons and many of his staff would re-form as The Ringer, much of what made Grantland so unique and enjoyable died when ESPN pulled the plug.

Most significantly, Simmons's writing career basically ended when Grantland ended. In the 11 years since Grantland was shuttered, Simmons has barely written at all, becoming a full-time podcaster instead. Meanwhile, the magazine he built on ESPN's dime has never been replicated, even when most of their people eventually ended up at The Ringer.

Sadly, it isn't surprising that Grantland ended. The problem that doomed it was simple: We have a media environment in which producing great content day-to-day is relatively simple (simple, not easy) but producing it in a way that is sustainable over years is not. In the case of Grantland, it cost ESPN a lot of money to maintain, and no one had figured out a good way to monetize online writing. Keep in mind that this was 2015 and the only major outlet to successfully implement a paywall at that point was the New York Times. The Washington Post only launched their paywall in 2013, not long before the shuttering of Grantland. The Atlantic didn't fully implement theirs until 2019. The New Yorker went to a paywall in 2014. The rest of the big magazines: New York, Wired, Vanity Fair, etc. all launched their gates in the late 2010s as well.

This meant that Grantland, while an obvious success as a vehicle for publishing great writing, was out in the cold a bit when it came to the business side. The viral traffic models used by Buzzfeed or the Huffington Post didn't apply to Grantland because their traffic wasn't high enough. Combine that with ESPN's unwillingness to add a paywall and, well, Grantland was doomed from the beginning in some sense. Those four beautiful years we got of it were a joy because the media we got was exceptional, but it was never gonna last because the model supporting it couldn't last given the existing models for financing online media.

I have thought about Grantland and Simmons in particular many times as I reflect on the news that the best newspaper columnist in America is moving to a TV show and, presumably, will no longer be writing columns. That columnist, of course, is Ross Douthat, formerly of the New York Times and now bound for Bari Weiss's rebooted 60 Minutes.

In one sense, there is actually not anything that surprising about the move, even if it caught me (and most others) off guard when it was first announced last week. When you set aside the initial shock, consider these points: For the past year, Douthat has been a columnist, a newsletter author, and a podcaster (with a podcast that surely requires a great deal of research to do well). He has also traveled extensively, and he and his wife have five kids. (I'll note now: I have no personal knowledge of any of Douthat's thinking here; we have met maybe a half dozen times and have only spoken at any length once and that was in a Plough editorial meeting with many others present. So all I am saying here is based on what can be observed based on publicly available information.)

When you lay it out like that, it's not especially surprising that the man with that combination of a quite intense professional workload and a busy family life would be open to other opportunities. Additionally, given the amount of money that Paramount is investing in 60 Minutes under Weiss's leadership it is quite likely that Douthat was offered a fairly lucrative wage and, well, Douthat and his wife have five kids who will want to go to college someday... you can understand the rationale here. The move is likely to make for a significant improvement in the Douthat family's quality of life and as an admirer of Douthat's, even if a sometimes critical one, I'm delighted for him personally and for his family.

Yet while CBS and the Douthats figure to be big winners with the move, I can't help wondering if everyone else loses, for at least three significant reasons.

In the first place, for the 60 Minutes experiment to work we will need Weiss, a lifelong print media figure, to get very good very fast at running a complex broadcast news operation. This seems unlikely to me, not because Weiss lacks talent, but because a broadcast endeavor like 60 Minutes is a very different thing from a print endeavor like The Free Press. This is to say nothing of the fairly significant fact that Weiss's time at the show has been remarkably contentious already and, fair or not, any media endeavor funded by the Ellisons is going to be perceived as state-sponsored media by many, at least as long as President Trump is in the White House.

Second, it is not at all clear to me that the 60 Minutes format will port to new media environments, though that is obviously what Paramount is paying Weiss to figure out. The obvious video successes in our current media space are properties like the Joe Rogan Experience, Call Her Daddy, the Ezra Klein Show, Douthat's former podcast Interesting Times, and so on. None of these shows are reported journalistic projects; all of them are interview-based shows in which curious, engaging hosts who are good at asking questions have extended conversations with guests that their audience will find interesting. 60 Minutes has always had interviews as a component of their work, but the purpose of the interviews was not simply to feature an interesting guest, as with all those podcasts, but to use the interview to deepen the audience's knowledge of the story 60 Minutes was covering that week. In other words, it is an extremely different interviewing style than what is most popular today and I am not sure how well their style translates to today's media audiences. Indeed, I struggle to think of any video project built around longform reporting that is already thriving and serves as proof of concept for what Weiss's 60 Minutes might become. Others have tried such things–Vice Media did something like it for awhile, but, well, that didn't really pan out for them.

Doubtless 60 Minutes hired Douthat because they plan to use him as an interviewer and have him carry on his work with Interesting Times. Yet even there Weiss's own record at 60 Minutes so far suggests that Douthat will not have nearly as much freedom with them as he had at the Times, where he routinely asked very pointed questions of his guests and where his guests not infrequently struggled to answer. Will Douthat be allowed to push as hard as an interviewer with a legacy broadcast news outlet as he did while at the Times? I have my doubts, though obviously I would love to be wrong about this.

Third, and this is my largest concern: As the above examples make clear, we have shifted into a media environment in which individuals are far more powerful than institutions. Columnists and essayists who are good at those roles have a tendency to build platforms that surpass their employer's, in some ways. Over time they cease to be "columnists" or even "writers" and instead become "media personalities." And as media personalities, they often have a kind of power that can rival or even surpass that of their employers. I expect that the Times will lose many subscribers over Douthat's departure.

But we have seen this pattern play out many times before: Tucker Carlson left Fox News and while his audience is not as broad as it once was and he is somewhat quarantined on Twitter in a way he was not while at Fox, he still has a meaningful audience and clearly has a sustainable media operation behind him. Candace Owens's departure from The Daily Wire played out in a similar way: Her audience is almost certainly larger at this point than that of her former boss Ben Shapiro, who has remained rooted in the institution he built. Obviously both Carlson and Owens are extremely different figures from Douthat. It may be that their commercial success as independent producers is not replicable because it depends on a particular sort of audience that is toxic enough to alienate anyone not already part of it and large enough to sustain some larger media operations. Douthat obviously will not profit from that same arrangement, nor would most other media figures.

Even so, the functional reality of our current media ecosystem is that for complex reasons likely related to media format (lots of audio and video content especially), the loneliness epidemic, and the ubiquity of smartphones, we now exist in a media space in which personalities are supreme. In a past age, we read columnists in search of delight, provocation, and wisdom. Today I worry that we treat our media personalities less like professionals with a skill we value and more like a kind of conversation partner and friend we turn to in order to fill up the time with something that interests us. That shift has significant ramifications for what it means to work in media.

Smart institutions, such as the Times, understand this. That's why they brought Douthat into the podcast space: His column style always suggested he would be a great interviewer. Before Douthat they had already made a similar move with Ezra Klein, who they hired away from Vox to be both a columnist and podcaster, as he had done for some time at Vox already. It isn't a surprise that they would look at Klein's success, look at Douthat's style as a writer, and reasonably conclude that he'd be an excellent podcaster. The note sent to Times staff about his departure said it well:

He arrived already fluent in a kind of thinking and writing many pundits never learn; the essay that changes its own mind partway through, in public, on purpose.... He was right about things early, wrong about things honestly and never, not once, boring.

A year ago, Ross took on something new and harder: He agreed to help us build a show, putting himself in front of a camera and an audience in ways a print columnist rarely has to. "Interesting Times" became appointment viewing for a simple reason: Ross would let a conversation go somewhere he hadn't planned. With respect and humor, he pressed JD Vance and Peter Thiel hard enough to surface something true about each of them. He wrestled with guests like Chase Strangio and Helen Andrews but never let their provocative conversations curdle into a partisan debate. And when Ben Sasse sat across from him to talk about dying, Ross let himself feel it on air instead of remaining at a distance. All of this asked Ross to be exposed in a different way than the page demands, and he did it with the same rigor and the same refusal to perform certainty he brought to all his work.

That is precisely correct. But it implies what I take to be a serious problem for our media environment: Because media endeavors are today largely built around personalities there is always a strong incentive to find more ways to put that personality in front of your desired audience. And when the person is as talented as Douthat, it goes very well. But, like Grantland, it can't last.

The work of simply writing 1-2 columns a week at the level Douthat did for so many years is already enormous. To be lucid, clever, and creative in such a tight space is almost impossible because doing so requires enormous levels of verbal dexterity and precision on the part of the writer. He has to be able to be penetrating and engaging without showing any of his work because there simply isn't room for it. There are very few writers who can do that well and none do it as well as Douthat.

In the evangelical space, Tish Warren, David French, and Bonnie Kristian can do it. Amongst Catholic writers, Leah Sargeant, Matt Schmitz, and Matt Walther are all good. But those who can are rare. Even columnists who have had success in the shorter format, like David Brooks or Elizabeth Bruenig, often turn out to be far stronger writers when given more space. Other good writers are largely defeated by the space constraint and need much more room to be at their best—Kevin Williamson at The Dispatch would fit here. So too, I think, would writers like Andrew Sullivan, George Packer, Wesley Morris, Jelani Cobb, Ta-Nehisi Coates, or Caitlin Flanagan. These are all excellent writers, but like most good writers they struggle to be forced into an 800 word suit. The writer who wears such clothing well is rare.

Likewise, the work of prepping sufficiently to have longform conversations of the caliber Douthat routinely managed on Interesting Times is immensely demanding and difficult. You will never be able to read all the things you'd like to read before talking to someone. You'll always feel a little unprepared. But the time for the interview arrives and you have to do it. And Douthat consistently did it at quite a high level, after taking a bit of time to find his footing.

Now layer on top of that a fairly demanding travel schedule as well as book projects which must somehow be fitted in. The workload we are describing here is immense and, honestly, not terribly human. My point here is not that you should feel sorry for media people. I recently spent time talking to an immigrant man who drives Uber 72 hours a week to pay the bills. Anyone who makes a living from their pen is absurdly blessed. But, even so, to make a living from one's pen in a way that can be maintained over years or decades is difficult.

And this is what I worry will happen if nothing changes in our media environment: Because all the momentum and incentives in our environment push toward maximizing the value of individuals, we will keep seeing individual producers put into positions that cannot ultimately be sustained long term. What will win out is what promises a relative degree of stability for the producer in terms of money and work routine. That's why Bill Simmons, once one of our best sports writers, stopped writing. And it's why the best newspaper columnist in America no longer works at a newspaper and almost certainly is done being a columnist.

For those of us who love the written word and who believe writing is a superior form of media for its unique power to shape thought and force clarity, the loss of a generational columnist is a loss that touches us all, and one we should all grieve.