News & Politics

Can Andrew Sullivan Re-Conquer Washington?

After 18 miserable months in New York, the pioneering blogger is back in DC with plans to transform journalism all over again.

Photograph of Sullivan by Joshua Cogan.

For almost a quarter of a century, or most of his career, one pundit or another called Andrew Sullivan the future of journalism. Twenty-three years ago, when he was appointed editor of the New Republic at age 28—a Brit, no less—the Washington Post noted that “there’s a heap of future in Sullivan’s life, and not much past.” In 2009, after more than a week in which his blog curated the best global coverage of the Iranian “green revolution” pretty much nonstop, the Week magazine declared, “The future belongs to Andrew Sullivan.”

Two years later, Tina Brown acquired Sullivan’s blog for the Daily Beast and extolled his “trailblazing journalism,” writing: “Andrew almost single-handedly defined the political blog and has been refining it as a form of journalism in real time nearly every day for the past decade.”

On a recent afternoon, the subject of all this praise—a writer-slash-thinker who has sojourned at virtually every major publication on the East Coast—is sitting in the window of the Duplex Diner in DC’s Adams Morgan, alternating sips of Jägermeister and Coke, hacking phlegm into a napkin (he has terrible asthma—sorry), and ogling a good-looking chef in a blue-and-white striped apron.

Sullivan is 50 now. After an openly miserable 18 months in New York that began while he was at the Beast, he’s back in Washington permanently—and thinking hard about the present.

Which at this moment includes a continuous parade of hot male specimens passing by outside. “I love home, and this is it,” he says, bearded and scruffy in a gray T-shirt but looking around with the air of a Victorian landowner surveying his acreage. “At some point in your life, I think you accept that and you think, I’ll be happy to die here. Lucky to die here. Lucky.”

The weight of the attention that was lavished on Sullivan’s future is ironic, mostly because 20 years ago he didn’t think he had one. In 1994, he bought a home in Provincetown, a gay haven on Cape Cod, so he’d have a place to go and die. The year before, he’d been diagnosed as HIV-positive and had seen his best friend and a number of acquaintances succumb to AIDS. He wrote a book, Virtually Normal, assuming he wouldn’t survive to see it published. But he did, and then he wrote another, Love Undetectable, in which he analyzed his own HIV status along with the fact that he might survive after all.

It didn’t matter that Sullivan wasn’t so focused on where his own life was headed. Because all that time he was pretty good at predicting what was to come for everyone else. In the ’80s, he started raging on behalf of marriage equality, writing a 1989 New Republic cover story advocating for gay marriage that was more than two decades ahead of its time. Beginning in the ’90s, he fought an immigration policy that barred HIV-positive aliens from traveling to or taking up residency in the US. In 2010, the ban was lifted.

Then there was his innovative medium. Sullivan basically created the political blog, spawning a new ADD-style, exhibitionist way of life on the internet and a generation of journalists who aspired to his cult of personality. He took his brand, the Daily Dish (now just the Dish after a Daily Beast-mandated name change), from one marquee news outlet to another before trailblazing all over again last year, when he departed the Beast and launched his own site.

And so, 20 years after his death seemed imminent, the only question to ask about Andrew Sullivan’s future at present may be: What now?

Sullivan and his husband, Aaron Tone, at the Duplex Diner, which Sullivan invested in 16 years ago, figuring that if he never recouped the cash, he might at least get free drinks. Photograph by Joshua Cogan.

• • •

Sullivan hated New York. So much so that he started a Dish thread called “New York Shitty” to rant about the indignity and difficulty of living in Manhattan—its endless crowds, spotty AT&T coverage, and lack of decent barbershops—which was mocked at length in a Gawker series titled “Andrew Sullivan’s Stations of the Cross.”

Eventually, last fall, after a deluge of reader e-mails pointing out how much happier he’d be in Brooklyn, he went to visit a high-rise there with gorgeous views and had an epiphany: He liked the area because it reminded him of Adams Morgan. It was time to leave. “Not that there aren’t lots of lovely people in New York, but in general you have to be an asshole to live there,” Sullivan says. “I guess I can say that in Washingtonian magazine.”

Maybe Washington really is much more civilized than New York. Or perhaps the center of the media universe didn’t embrace Sullivan as much as he might have liked it to. Maybe he’s just getting old.

Whatever the real reason for his return, Sullivan’s domestic routine in DC—roll out of bed, read the news, spend a few hours firing off blog posts, hit the gym by 6, the diner by 8, play a shit-ton of Angry Birds, and wind down with some South Park—is nothing if not comfortable.

It’s definitely at odds with the brash fervor of his rise in the ’90s, back when he posed for a Gap ad shot by Annie Leibovitz as a hauntingly beautiful young man in black-and-white with a quizzical, almost vulnerable expression.

Back then, his idiosyncrasies were fascinating to predictable Washington—here was a British, Oxford-educated, Catholic, gay conservative who resisted categorization.

“I loved the freedom here,” he says of his arrival in the US on a Harvard fellowship in 1984, eager to shed years-old insecurities about his sexuality and middling middle-class upbringing. “I loved the informality. I loved that people were respected for what they did rather than who they were—that people were generally enthusiastic about my own enthusiasm.”

In loud, brash, outspoken, unapologetic America, loud, brash, outspoken, unapologetic Andrew Sullivan found out he belonged. He was in love with his new country, and it reciprocated, inviting him to weekend in Hyannis with the Kennedys and to go to parties with David Geffen and to dance all night to house music in underground clubs at 14th and U with “punch bowls, helium balloons, and all these beautiful, beautiful black men.”

In 1993, two years into his editorship at the New Republic, Sullivan applied for a green card, only to learn during a physical that he was HIV-positive. “My first response wasn’t ‘Shit, I’m going to die,’ ” he says. “It was ‘Shit, I can’t become an American. What am I going to do?’ I had a real legal problem.”

At that time, the policy banning HIV-positive immigrants in the US was in effect. Sullivan decided to withdraw his green-card application and apply instead for an O visa, granted to people with extraordinary ability in the arts or sciences. For 17 years, he lived in the US on O visas, paid taxes, and bought property, knowing he could be thrown out at any minute because of his HIV status.

“The longer I survived, which wasn’t a given, the worse it got,” he says. “The greater my roots and connections here, the greater the upheaval would be if I had to go back to square one.”

Sullivan lived both in spite and because of Washington: his church, his doctor, and his shrink—not necessarily in that order—and a network of gay friends. He starred as Benedick in Washington Shakespeare Company’s production of Much Ado About Nothing. He was persuaded by a friend to invest in his now beloved Duplex Diner, reluctantly forking over $5,000 on the presumption that he’d never see it again but might get free Jägermeister for life. (He got all his money back, plus interest, and still occasionally gets free drinks.)

Sullivan still lives in the Adams Morgan loft he bought while at the New Republic, in a building once known as “the kindergarten” because two other precocious New Republic staffers, Jacob Weisberg and Michael Lewis, also lived there. He shares his home with his husband, Aaron Tone, an actor he married in 2007, and their two dogs, Eddy and Bowie (the latter a replacement for Dusty, who died last year and was such an integral part of the Dish that she appears in its logo). He got a green card in 2011—after the HIV immigration ban was finally lifted—and two years from now, he can apply for US citizenship.

Sullivan has done more than he ever could have hoped. And yet, thanks to his regimen of antiretroviral drugs, he may live another 20 or 30 years, which is why, oddly perhaps, the future seems so uncertain.

“To have been at this level of visibility in this city for a great length of time,” he says, “and still be only—I say only, I feel terribly old—but to still be only 50 years old? I should be about to make my mark instead of feeling like a has-been.

“But I don’t, I suppose, because everything I’m doing is so overwhelming and demanding that I don’t have time to reflect on all that.”

Sullivan became the New Republic’s editor at age 28 (right). Top left: at a 2012 state dinner with his husband. Below left: speaking with writer Michael Lewis at George Washington University this year. Photograph of Sullivan at age 28 courtesy of The New Republic. Photograph of State Dinner by Charles Dharapak/AP Photo. Photograph of Sullivan with Lewis by T.J. Kirkpatrick/Getty Images.

• • •

The career path from blogger to journalist is commonplace today, particularly for young, obsessive types like Ezra Klein (Vox) and Brian Stelter (CNN). To go in the other direction—to embrace the grind of churning out 20 posts a day as a late-thirties former magazine editor—was unheard of back in 2000 when Sullivan started publishing his thoughts on the internet with maniacal devotion.

At first, he had a friend do the posting for him. But his pace was frantic. From the moment the rapidly-getting-ticked-off friend informed Sullivan about a newish self-publishing site called Blogger, he was hooked. Here, at last, was technology that allowed writers to communicate exactly as they wanted, without pesky editors interfering or space issues or the interminable delays of print journalism. Here was his very own podium.

Early on, Sullivan sought input from right-wing blogger Matt Drudge. His advice—that blogging is more akin to broadcast journalism than it is to print—helped shape the Dish’s unrelenting production cycle when news breaks. During a big news day, Sullivan’s term for holing up to follow a developing story is “going cable.”

For the first six years, the Dish was just Sullivan, and in the early days he juggled it with his job writing for the New York Times Magazine. But eventually the two didn’t mix. He often used the Dish—the space where he raved about Ronald Reagan, argued initially for the Iraq War, and defended then attorney general John Ashcroft—to take swipes at the liberal Times, and in 2002 the paper fired him. After that, Sullivan threw himself into his own site, an obsession that led to its being adopted by Time in 2006, by the Atlantic in 2007, and then by the Beast.

While his fusion of breaking-news bites, personal essays, and aggregation eventually brought traffic to those sites in droves, it took a while for his distinct style to take hold.

“ sets a standard for narcissistic egocentricity that makes Henry Kissinger look like St. Francis of Assisi,” Eric Alterman wrote in the Nation in 2002. “Readers are informed, for instance, that Andy’s toilet recently overflowed; that he had a rollicking dinner chez [Christopher] Hitchens; that he might have seen Tina Brown across a hotel lobby, but he’s not sure; and that, in separate, apparently unrelated incidents, he had a nightmare and ate a bad tuna-fish sandwich that upset his tummy, requiring many stomach ‘evacuations.’ ”

Back then, this much oversharing was anathema to journalism’s old guard. These days, it gets you a killer beat at BuzzFeed.

And Sullivan will happily take credit for the evolution. “What struck me about blogging,” he says, “is that you don’t often get to be of a generation in charge of creating and helping form an entirely new medium.”

• • •

What’s remarkable about the Dish is how little it’s changed since Sullivan launched it.

The blog still follows the formula he and then others adopted in the early 2000s: Posts are primarily aggregated from elsewhere, couched under a direct, chatty headline (“Face of the Day,” “Creepy Ad Watch,” “Paul Ryan’s Zombie Reaganomics”), with a few paragraphs excerpted and sometimes with Sullivan’s really quick or really long take attached. The Dish still has an eclectic, scattered range of focus, covering everything from foreign policy to TV to religion.

And it still navel-gazes. “If you’re blogging every day in real time, you just can’t hide it—your personality, your prejudices, your biases, your tics, your pet peeves, your blind spots, your temperament,” Sullivan says. “So at some point—and a lot of people get to this point—you have to ask yourself: Do I want to be picked over every day by so many people?

“Twelve years ago, being told I was an asshole and that I get things wrong A LOT, all caps, would have given me a little pierce. But the scar tissue is so deep and thick now that I feel nothing.”

Sullivan’s unfiltered style certainly enticed his community of readers into feeling like they know him intimately, and for a time anyway it also regularly led him into controversy. His early, aggressively vocal support for the Iraq War appalled liberals as much as his change of heart later in 2003 dismayed and alienated his stolidly conservative readers. (“I supported it like a teenage girl supporting the Jonas Brothers,” he once said.)

In 2008, Sullivan repeatedly questioned the circumstances surrounding the birth of vice-presidential candidate Sarah Palin’s youngest son, Trig—asking, for instance, why there were no photos of Palin with a visible baby bump and why she would fly from Alaska to Texas and back while eight months pregnant with a special-needs baby when she was leaking amniotic fluid before the flight home. Republicans who hadn’t already been turned off by Sullivan’s vocal affection for Barack Obama were horrified, with many comparing him to the “birthers” who insisted on seeing Obama’s birth certificate.

That ability to provoke—to draw eyeballs—was what had prompted media mogul David Bradley to lure Sullivan away from Time to the Atlantic in 2007 with an irresistible offer pegging the writer’s salary to his page views. It was an arrangement that proved very productive, until it became untenable. By the end of 2010, Sullivan was bringing in a quarter of the magazine’s web traffic—and had to go. As he explained it later, “I got too expensive.”

Tina Brown promised him a share of the ad revenue at the Daily Beast, he says, along with a budget of about $800,000 a year, which was enough to expand his team (and give them health insurance). He went for it. But by the middle of 2012, the flaw revealed itself.

“One of the big advantages of it was getting some share of the advertising revenues,” Sullivan says, “which I think was only fair given what we were bringing to the table, and would have been a great deal had there been any advertising revenues. But there were no advertising revenues to speak of.”

Sullivan and his two so-called underbloggers, Patrick Appel and Chris Bodenner, decided to become partners and go independent. “Patrick got LLC for Dummies,” Sullivan says. “He and Chris basically carried me through it because I said to them, ‘I can’t handle business. I can’t handle administrative stuff. I’m not good at it.’ ”

The new Dish is an ad-free site, paid for with $19.99-a-year or $1.99-a-month subscriptions. In its first year, the site very nearly brought in $900,000, as Sullivan and his partners hoped for. About 83 percent of subscribers renew.

What the Dish hasn’t done is drive the conversation, as Washingtonians like to say, the way it used to. Since the site went independent in early 2013, only five of its most-viewed posts have attracted more than 100,000 page views. About 781,000 people visit the site every month, a not-unrespectable showing. Then again, that’s fewer readers than Sullivan was attracting at the Atlantic site 3½ years ago. Meanwhile, the number of eyeballs has only grown, and most online media companies are doing everything possible to capture them. The Atlantic, for instance, expanded its site and more than tripled traffic after Sullivan left; it had 16.6 million readers this past March.

• • •

“Michael Wolff, who’s an asshole, wrote this supercilious piece with a back-of-the-envelope calculation about our revenue last year, and got it wrong, and then at the end said, ‘Well, I suppose it’s a living,’ ” Sullivan says of the media writer who these days pens a column for the Guardian. “I’m not Roger Ailes. I’m not going to earn Bill O’Reilly’s fortune for traducing the life of my savior. I have enough money. To earn a living with total freedom as a writer—if he can’t see that that’s the greatest possible thing to have, then he’s not in the same business that I’m in.”

Sullivan and Tone,who married in 2007, in Meridian Hill Park with their beagle, Bowie, and their mutt, Eddy, who sometimes make appearances in the Dish. Photograph by Joshua Cogan.

Which is to say Sullivan is feeling pretty good about his blog.

He still has an income from a column in the Sunday Times of London, he owns his apartment, and he makes money off speeches. Plus, the site’s finances are healthy: In the first four months of 2014, the Dish collected $727,000, a solid start toward its target of $1 million by year’s end. Sullivan didn’t pay himself a salary last year, although now that things are looking a little better, he hopes to in the future.

He’s also expanded the site with a new, subscriber-only platform called Deep Dish, which offers long-form journalism, e-books, and podcasts he hosts himself. And now his model is starting to be modeled. Slate, for instance, recently launched Slate Plus, a subscriber-only site with personality-driven content like “A day in the life of Slate’s Supreme Court reporter” for Slate superfans.

In recent years, Sullivan has had a lot of help with his workload. The Dish has a full-time, paid staff of ten, including interns. “Before I came on, every post was by Andrew,” says Appel, an executive editor. “I remember when I first started drafting things for him, it was like magic, because for seven years nothing had appeared on its own. He reviewed everything at first, and then he learned to trust us and became exhausted enough trying to write 35 or 40 posts a day that we came up with our current system.”

The Dish has no bylines, the exception being when Sullivan is on vacation, so it’s impossible to know exactly which pieces he writes himself and which are a team effort. Still, his hand is noticeable: Longer posts and the use of first person usually signify it.

Plenty of writers would be plenty pleased with his perch. “He really does have an enviable independence,” media critic Jack Shafer says. “No one can fire him. He’s no one’s slave. That’s not true of very many of us.”

The problem Shafer sees comes back to, well, the future: “There is no without Andrew Sullivan. He’s a king without an heir.”

To imagine a future instead of remaining firmly in the all-consuming present might be to contemplate change, and change has never been something Sullivan craves.

“One of the reasons I’m a conservative is I like the status quo,” he says. “I’ve lived in the same neighborhood my whole adult life. I’ve only had one vacation spot for the last 20 years. I go every summer and I stay in the same f—ing house. I’ve been with the same guy for ten years. If I’m happy, why change anything? It’s only sometimes when you go away and you realize what the actual alternatives are as opposed to the Elysian alternatives, you realize this is a pretty goddamn good mix.”

Even so, he acknowledges that blogging has a shelf life and that, given his health, he has no idea how much longer he can keep it up. He’s working on a book about religion, which he hopes will fulfill the lesser-known side of him that has apparently always yearned for a monastic life. “There comes a point where you just don’t want to think about the world,” he says. “You just want to curl up in a ball and live.”

We leave the diner, and he stops to greet almost everyone, saying hello, thanking the servers, and mentioning that he’ll be back for dinner with his husband later. Out in the street, we head toward his gym. On the way, he waves at a handful of people walking past, having to remind one of them who he is.

Sophie Gilbert last wrote about her weird year as a member of Mensa. Find her on Twitter @sophiegg. This article appears in the June 2014 issue of Washingtonian.