PLAYBOY: Speaking of the establishment, what will The New York Times look like in 10 years? Will it exist? Will the Sulzberger family still own it, or will they have sold it, perhaps to Michael Bloomberg?
DENTON: The New York Times will exist. Someone else will own it. Most families, the more generations they are from the original founder, the more fragmented the ownership, and eventually the nephews, grandnieces and great-great-grandchildren want their money now. They’d rather take the purchase price than zero dividends. I think the Times has bottomed out, and now, even though the signs are mixed, it will be able to put on more in digital revenue than it loses in print. Or I hope so, because I like the Times. There should be at least one or two survivors. Even when a major disaster kills most life on earth, usually a few species survive. Dinosaurs survived and became birds. Maybe that’s the future of The New York Times: It will be the survivor of the dinosaurs, the little tweeting thing you see flying around.
PLAYBOY: If you’re Jeff Bezos, what do you do with The Washington Post?
DENTON: Obviously you apply the Amazon recommendation engine. The interesting move would be to see whether you could take an entire newspaper-reading population and wean them off print. The price of Kindles is coming down. How much would it cost to bundle a Kindle with your subscription to The Washington Post? Discontinue the print and, as a gift, give everybody a Washington Post reader that can also buy books for them. That’s what I’d do. That’s what Bezos would do if he were ballsy.
PLAYBOY: Do you know him at all?
DENTON: No, though I had a dream that he had acquired us.
PLAYBOY: What would you do if you picked up the phone and he was on the other end, saying he wanted to buy Gawker Media?
DENTON: Amazon’s the only company…. Well, I also like the idea of News Corp. Buccaneering was a word I always liked to describe Gawker Media.
PLAYBOY: Rupert Murdoch had the same notions about News Corp, to the point that he reportedly considered adopting a pirate ship as the company’s logo. Do you feel a kinship with Murdoch?
DENTON: That sounds arrogant. I think he’s done four amazing things, and most people get only one: Fox Network, Fox News, satellite TV in the U.K. and breaking the print unions. He saved Fleet Street. He saved London’s newspaper industry.
PLAYBOY: What about Tina Brown? Is she done? Have we seen the last of her?
DENTON: I don’t know about that. She has a tough rap. Was her Newsweek really that bad? Her biggest problem has been that she was dependent on the goodwill of media proprietors—Si Newhouse, Harvey Weinstein and then Barry Diller. And a media proprietor, particularly a late-era media proprietor, is a fundamentally dysfunctional businessman. There was a time when media made money and rational businesspeople would go into it. In an era when media basically doesn’t make money, the only businessman who would go into it would be some kind of egomaniac, like me. [laughs] If I were truly into the money, I’d be in waste disposal or something like that. I’d be in some unglamorous profession. Media is way overpopulated. So she’s dependent on the goodwill and the external financial resources of these erratic, aging proprietors.
PLAYBOY: You didn’t always plan to be a media proprietor. You had notions of entering politics at one point.
DENTON: As a 16-year-old political nerd I wrangled myself a research position for the Social Democratic Party, which was a Labour splinter party. I quickly recognized that I wouldn’t be electable. After that I wanted to be one of those shadowy, behind-the-scenes operatives, like a Lee Atwater or a Karl Rove.
PLAYBOY: It’s easy to picture you as a pretty good Karl Rove.
DENTON: Oh, I’d be very good. I’d be so good! [laughs] I’d fight dirty in the interest of good causes. I almost had a whole campaign for a gas tax. Syphilitic Saudi sheiks, American women despoiled—basically taking our money from the gas station to fund their debauched sex lives, their despoiling of our women and terrorist attacks against our country. I don’t frame it as an environmental cause. You’ve won the environmentalists already. You’re trying to win the swing voters, the kind of people who don’t like our money going to our enemies. So you make the campaign about that. No environmentalists—they’re way too prissy to want to win. That’s what I hate about liberals in this country. I hate them so much.
PLAYBOY: You do? You hate them?
DENTON: I hate liberals in this country so much because they’re so fucking prissy. Did you ever see that documentary about Lee Atwater, Boogie Man? Lee Atwater was a terrible man. The Willie Horton campaign is a stain on the Republican Party, on the Bush family—let that all be stipulated. But you see in this movie that he has such joy in the battle, in the struggle, in the game, you know? He loves it. There are interviews with Michael Dukakis 20 years later, and Dukakis still cannot understand what happened. He still doesn’t know how he got beat. This whiny, prissy—who would you want to work with? Who would you want to have beside you in the foxhole? Atwater is way more fun, probably a way better colleague, with way more appetite to win.
PLAYBOY: Isn’t that a stereotype, the wimpy liberal? What about Barack Obama and his gang of tough Chicago politicos?
DENTON: In his own slightly bloodless way, he has competitive people. Obama himself is pretty competitive, and there are different ways of playing the game, right? It doesn’t all need to be dirty South Carolina politics. That said, my political hero is Lyndon Johnson. I love people who are prepared to do what it takes, who aren’t squeamish. If you want to stay pure, never break a story and never fuck anyone.
PLAYBOY: You got engaged recently. Have you always wanted to get married?
DENTON: No. My personal narrative was that I didn’t want to get married in general; I just wanted to get married to Derrence. I’m marrying an individual. I’m not endorsing an institution. But two years ago, we had a party to benefit gay marriage—I think it was right around the date when it passed in New York—and apparently I said there that I wanted to get married because gay relationships ended too easily. I hadn’t remembered saying that; someone reminded me recently. [laughs] I was just coming off a breakup that had taken all of three days to implement—no kids, no jobs, no pets, no nothing. Relationships are hard enough and likely enough to fray, so one needs some kind of glue, some ritual in front of friends and family and the state to ensure that at least there’s a cooling-off period before you actually break up.
PLAYBOY: Is that part of why you want to get married now?
DENTON: No. It’s that this is as good as it’s going to get. Isn’t that the key? It doesn’t sound very romantic, but when I saw my apartment, I knew it was much better than anything else. It was maybe 30 percent more than I wanted to pay, but it was 200 percent better than anything else I’d seen. I had to contain the expression on my face, because what I was thinking was, Yes, this is the one. That’s how I felt with Derrence.
PLAYBOY: That’s not a very romantic metaphor.
DENTON: I think it’s actually a very real metaphor when you’re with somebody in a better relationship than you ever expected or hoped for in your life and by far better than anything you could ever imagine with anybody else. Yeah, hypothetically, theoretically, there might be somebody else out there for me, but I don’t have 100 lifetimes to go find him. So this is the best person I could be with in this lifetime.
PLAYBOY: How did you meet?
DENTON: How did we meet? [laughs]
DENTON: [laughs] I think you can say on the record that I knew his boyfriend.
PLAYBOY: The New York Post’s gossip column reported at the time that the boyfriend you’re referring to threw a brick through your window.
DENTON: It was a stone, not a brick. I actually gave them the whole backstory. I knew they couldn’t do anything with it.
PLAYBOY: Why couldn’t they?
DENTON: Too complicated. The mainstream press doesn’t really want gay gossip. They can’t even deal with closet cases. It’s a mixture of lingering distaste for the homosexual act and a modern version of correctness. They don’t even know whether outings are politically correct or not. So they’re completely paralyzed. They do not know how to deal with gay guys. They’re just about getting to be able to deal with, say, a gay engagement being news. But the true pansexual messiness of most gay sexual histories is not something they or their readers are ready for.
PLAYBOY: Which is funny, because “pansexual messiness” sounds more interesting than most of what you read in the gossip pages.
DENTON: Well, I think everybody is more interesting than how they’re portrayed.
PLAYBOY: Do you ever have misgivings about exposing people’s private lives, their sex lives?
DENTON: If there’s a gap between your private behavior and your public status, that’s what makes the story for us. To my mind, the only real modern sin is hypocrisy.