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Nick Denton, Peter Thiel, and the Plot to Murder Gawker

As if the sudden death of Gawker Media, felled by a Hulk Hogan invasion-of-privacy suit, wasn’t shocking enough when it happened earlier this year, word quickly got out that the whole thing had been bankrolled by one of Silicon Valley’s most successful investors. But Nick Denton, Gawker’s founding rogue, and Peter Thiel, his arch-nemesis, had a more complicated relationship than anyone imagined.
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Illustration by Sean McCabe. Photographs by Bruno Levy/Challenges-REA/Redux (Thiel), Alan Schindler/Courtesy L&L Holding Company (background), Stephen Yang/A.P. Images (Denton)

One day in September 2014 the publisher of Gawker Media, Nick Denton, sent an e-mail to Peter Thiel, the Silicon Valley venture capitalist and billionaire. It could easily have been a message to a friend, or at least a kindred spirit, for, as many people who know them both have noted, the two have so much in common.

They are contemporaries: Denton turned 50 this past August, and Thiel 49 two months later. Both were born in Europe—Denton in England and Thiel in Germany. Both graduated from fancy universities—Denton from Oxford and Thiel from Stanford. Both made their fortunes in the digital world; in fact, it had brought them together in San Francisco a dozen or so years earlier. Both are gay, and both came out relatively late. Both are libertarians, and nonconformists, and visionaries, and science-fiction fans, and workaholics, and wonks. Both have resisted getting old, Denton by attitude, Thiel through human growth hormones. Both have a cultish kind of appeal. Both were wealthy still in 2014, though as winner of one of Silicon Valley’s greatest daily doubles—he co-founded PayPal and was Facebook’s first big investor—Thiel was exponentially more so, a fact that stuck in the ultra-competitive Denton’s craw. “Nauseatingly successful” was how Denton once described him. “Does Nick Denton wish he were Peter Thiel?” a headline on Denton’s own gawker.com once asked.

But, in 2007, Gawker’s Silicon Valley tributary, Valleywag, had outed Thiel, or at least Thiel thought it had. Both before and after that, Valleywag and Gawker had continued to ridicule Thiel, his investment decisions, his ideas, and his friends. It was such stories that had led Thiel, in 2009, to label Valleywag “the Silicon Valley equivalent of Al Qaeda” and to liken its writers to terrorists.

Maybe, Denton hoped, Thiel had moved on since then, or grown a thicker hide. So Denton drafted his note, which he read to me off his iPhone one day this past September. “Hey, Peter, this is a long shot but I’m going to try,” he began. “Would you get together for coffee when I’m next in San Francisco? We obviously have our differences, primarily over the politics of outing, and some of our coverage on Valleywag and Gawker has been needlessly gleeful. But your political views, while mockable, are a breath of fresh air. We have more in common than might meet the eye. I’d like to get some more constructive debate going between the New Left, which is represented rather heavily on New York editorial operations, and the Valley libertarians. The enemy is stagnation, and the vested interests that ensure stagnation, and yes, sometimes also the culture of Internet criticism that stymies original thought.”

“That’s all I got,” he concluded. “Let me know if there’s a conversation to be had.” He closed with “Regards, Nick.” He then read me Thiel’s response: “Nick, I’m not sure that a political conversation would be that constructive, but . . . ” Denton began, only to cut himself off. “I’m not going to share that with you,” he told me, at least not without getting Thiel’s permission. (“Just manners,” he explained.) He did show me what Thiel had written, but would not let me copy it down. I remember only that it was perfectly polite, and that whatever else he may have been thinking, Thiel had agreed to have that cup of coffee. “Nothing came of it,” Denton told me, and this is not surprising. For by the time he received that note Thiel had already begun pouring millions of dollars into a campaign to crush Denton and Gawker Media, using Hulk Hogan, of all people, as his cudgel. And by the time Denton and I spoke, Thiel had annihilated them all more completely than even he could have imagined, thanks to a Florida jury’s awarding Hogan $140 million in his Thiel-funded lawsuit last March, sending Gawker Media and Denton into bankruptcy and then killing off gawker.com altogether. It was the largest invasion of privacy payday ever against a major media company, and perhaps the first ever to bankrupt one. It was far more than Denton could handle, and it led in August to the fire sale of Gawker Media to Univision for $135 million. But Univision swallowed up only six of its seven Web sites; gawker.com, which generated 20 percent of its traffic and revenue and, according to Denton, 80 percent of its tsuris, was left to die. “Good riddance,” Thiel later said of its demise.

“Totally, totally oblivious!” Denton said of himself, amazed at his own blindness over what Thiel was up to. He laughed—more, it seemed, out of embarrassment than bitterness.

It was fashionable to dismiss him with terms such as “robot,” “nihilist,” “villain,” or “sociopath.”

On November 2, Denton announced that Gawker had settled the Hogan case. The settlement was for $31 million. It was, he confessed, a “hard peace,” one to which he’d reluctantly agreed largely to remove the Gawker editor who’d posted the Hogan video, A. J. Daulerio (whom Hogan had also sued and who, despite his negative net worth, had remained on the hook for $115 million in damages), out of Thiel’s cross-hairs. But Denton, too, has a stake: the as-yet unsigned deal should restore some of his millions to him, and may even allow him to keep his beloved SoHo loft, site of what had once seemed would be an unending series of Gawker soirees.

Denton, though, was not the only one who wanted the case resolved. The papers had picked up much of what the generally circumspect Thiel had said at a press conference two days before the deal was announced, including his support for Donald Trump and his continued attacks on Gawker, which he called a “singularly sociopathic bully.” But it overlooked a thought that Thiel, a lawyer and a chess master, had cribbed from Jose Raul Capablanca, the great Cuban champion. In court as in chess, Thiel had said, “you must begin by studying the endgame.” And the endgame of Hogan’s case may well have been a verdict that was either slashed or overturned on appeal—and a defendant, Denton, who would thereby be at least partly vindicated. In settling, Thiel has shut that process down.

Bitchy, Breezy, and Snarky

At his high-water mark, before the Hogan lawsuit, Denton owned 40 percent of Gawker Media, a company valued at as much as $300 million to $400 million. The outfit, which Denton launched in 2002 with two egregiously underpaid bloggers in his apartment, on Spring Street in Manhattan, had become an Internet innovator, disrupter, and powerhouse—an “octopus with chainsaws,” someone once called it—consisting not just of its eponymous gossip Web site but six others covering everything from design and tech (Gizmodo) to sports (Deadspin) to women’s issues (Jezebel) to cars (Jalopnik) to video games (Kotaku) to self-help tips (Lifehacker). It was also an Internet rarity, a media company that, unlike BuzzFeed or Vox or Vice, had made it without outside financing, which meant it could say whatever it damned well pleased, and did.

Gawker Media was the blogosphere’s version of a floating island—not unlike the man-made, tech-friendly, libertarian ones that Thiel once envisioned and invested in—beyond traditional journalism’s territorial waters. The goal, Denton liked to say, was to reduce “the friction between the thought and the page,” and his journalists, often young, green, smart, and bratty (had Holden Caulfield lived in the mid-2000s, he might have gone to Gawker to expose phonies) were the freest on the planet: free, that is, to trash or humiliate or dish or out with almost no adult supervision, least of all from Denton, a superannuated kid himself. (Denton was, after all, someone who would never call himself a C.E.O., because, as he once put it, all C.E.O.’s were “douches.”) Until relatively late in its life, when it turned to more substantive journalism (and also, at times, to meaner, more punitive, and potentially more defamatory gossip), much of Gawker was spontaneous, unfiltered, improvised—“the ultimate expression,” Denton said, “of the journalistic id.” It reflected what Denton called “iterative” journalism, in which readers would build on, or dismantle, the skeleton Gawker put out there. Click on “publish” first, then worry afterward about what was wrong. Unlike, say, Salon or Slate, Gawker felt like the first journalistic outlet that truly understood, and exploited, the Internet.

And unlike, say, “Page Six” of the New York Post, Gawker played no favorites and made no deals. No one in what Denton called the “celebrity media industrial complex” was off limits. Because Denton had few famous friends—that small fraternity includes South Park co-creator Matt Stone and CNN newsman Don Lemon—no one could really lean on him. One Gawkerite recalls how, on his first day at work, someone shouted to Denton that Harvey Weinstein was on the phone, upset about something. “Tell him to go fuck himself!” Denton shouted back. (“‘Go fuck yourself’ is not my style,” Denton says. “I’m not that aggressive.” Weinstein, he adds, “was used to massaging stories behind the scenes, and we didn’t do that.”) When Brian Williams, the object of one of Denton’s rare celebrity bromances and an inveterate Gawker reader himself—“[I] check your shit 10 times a day by iphone,” he once wrote Denton—e-mailed him to suggest that Gawker write about the singer Lana Del Rey’s bombing the previous evening on Saturday Night Live, gawker.com posted Williams’s e-mail instead. Williams hasn’t spoken to Denton since.

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Gawker Media pissed off Steve Jobs by prematurely unveiling a new iPhone; helped to unseat Toronto mayor Rob Ford when it exposed his penchant for smoking crack; revealed the football player Manti Te’o’s long-running relationship with a nonexistent woman; and helped bring down Bill Cosby. More recently, it devoted significant real-estate to the architecture and maintenance of Donald Trump’s hair. And, most fatefully, in 2012 Gawker posted a grainy video of Hulk Hogan with his best friend’s wife, before, after, and, for nine seconds, during sex.

With its signature bitchy, breezy, snarky, chatty style—which one of its shrewdest (and most appreciative) critics, the late David Carr, of The New York Times, likened to mean ninth-grade schoolgirls trashing everyone else in the playground—Gawker became a journalistic landmark, especially, perhaps, for millennials. Less appreciated is the fact that it also represented the greatest incursion ever of a gay sensibility into mainstream American journalism. And the Gawker saga—in which one fabulously successful gay man tried to ruin another—also encapsulates an epoch in gay history, a time when attitudes in both mainstream culture and within the gay community about acceptance and respectability, privacy and duty, changed so fast that it became impossible for journalists, gay or straight, to keep up. Though the stakes were obviously very different, Denton versus Thiel may be the gay version of United States v. Julius and Ethel Rosenberg: a soap opera in which members of a newly empowered but instinctively insecure minority—then Jews in postwar America, now gays—devoured each other in full public view.

For its nearly 14-year run, gawker.com reflected Denton’s ever changing and often conflicting instincts, whims, crushes, and epiphanies. And whomever he’d happened to meet at a party the night before and the state of his love life. The site was bipolar, or maybe schizophrenic, but it was never the same for long; only the chaos, and the contradictions, were continuous. Moments after one of Denton’s periodic pushes for respectability, he might suggest exposés on which public figures had dandruff, or whether the editors of the leading women’s magazines had synchronized menstrual cycles, or whether Peter Thiel was bad in bed.

During their (generally short) tenures, Gawker writers regarded Denton with admiration, bemusement, puzzlement, and, a bit ostentatiously, contempt. It was fashionable to dismiss him with terms such as “robot,” “nihilist,” “villain,” or “sociopath.” “Dark Lord Balthazar,” they called him, after the restaurant across the way from his Spring Street loft, where he hung out. Denton took none of it personally; speculation that he had a dash of Asperger’s even pleased him, since it made him seem more like a Silicon Valley genius. There was something almost extraterrestrial about him. “You get this sense that he’s this life-form that was sent to earth to gather anthropological research and then send it back to the mother ship” is how Gawker reporter J. K. Trotter, whose media beat included Gawker itself, puts it. But when all of Gawker came crashing down, it was gratitude—for launching their careers, for letting them write whatever they wanted, for giving them a home—that these writers generally felt. Most, if not all, was forgiven.

Take A. J. Daulerio, who, as editor of gawker.com, posted the Hogan video and wrote the accompanying story, “Even for a Minute, Watching Hulk Hogan Have Sex in a Canopy Bed Is Not Safe for Work but Watch It Anyway.” As Hogan’s case wended its way through the courts, Daulerio grew angry at Denton, feeling he had distanced himself from the decision to post the sex tape. (“We could not talk about testimony and other things, so he might have felt isolated,” Denton concedes.) Daulerio, who left Gawker in 2013, nonetheless calls Gawker “the best place I will ever work” and Denton a “once-in-a-lifetime” boss. Then there’s Tommy Craggs, executive editor of Gawker Media when, in 2015, it ran the story that nearly tore the place apart, about a married media executive’s alleged aborted assignation with a gay escort. Denton’s decision to remove that story from the Web site after a storm of criticism, much of it from Gawker fans, marked yet another stage in his much-dissected-and-debated evolution from amoral ass to mini-mensch, a process variously attributed to therapy, restlessness, pot, maturity, and marriage. Craggs resigned to protest that decision, mainly because it was made in consultation with a group that Denton had put together that included two people from the business side. He hadn’t spoken to Denton until spotting him at one of Gawker’s numerous wakes in August, when he approached him and shook his hand. “Nick is easily the best boss I’ve ever had. And fuck Nick Denton,” he says.

“Interesting—and scary” is how he describes Thiel.

In person, Denton—soft-spoken and with a closely cropped salt-and-pepper beard on what is habitually described as an outsize pumpkin head—seems as stoic and detached about his fate as one might expect a veteran journalist, to whom even one’s own life is but another story, to be. Whatever he did to forestall it, he has now convinced himself that Gawker’s demise was preordained and, in the end, the greatest tribute it could have been given: anything that pissed off so many people for so long was doomed. In fact, he now says, it’s amazing it held on as long as it did; had Thiel not come along, some other thin-skinned billionaire (or “comic-book villain”) would have. Mostly, he is relieved. Restless, increasingly estranged from his own creation, and starved for cash to pay his lawyers, he’d discussed unloading the company even before the Hogan trial. And, thank God, with Univision taking on all of his employees, the only person to lose his job was he.

Denton remains convinced that Thiel came after Gawker not because it outed him but because he resented Gawker’s coverage of Silicon Valley generally. Still, he admires Thiel—or, at least, says he does, having learned that flattering Thiel makes more sense than pissing him off. Denton sees in him those traits, notably ruthlessness, that Denton and other successful gay men of their generation needed to survive. He thinks Thiel is just insecure, that he needs to be a genius and hates ridicule. Denton even admires his stagecraft—how he managed to present as a blow for privacy rights something Denton sees as an act of petty revenge. “Canny positioning,” he calls it. Meanwhile, Thiel has single-handedly turned the much-vilified Denton, whom even the mainstream press largely abandoned in his moment of need, into something he’d never previously been: a martyr.

Though Denton steadfastly won’t confirm it, sources at Gawker and also a person with knowledge of the meeting say that, two months after the Hogan verdict, Denton reached out to Thiel yet again, and, with the help of two high-level Silicon Valley intermediaries, got Thiel to agree to see him in San Francisco. Asked, prior to the settlement, for details on the meeting, Denton, who built Gawker on the gospel that everybody has the right to know everything, clammed up. “I’m constrained” is all, at long last, he finally said. And therein lies perhaps the most humiliating part of Denton’s defeat: a man who labored to expose Silicon Valley had ended up submitting to its rules. Eventually, though, he supplied corroboration of a kind. When he volunteered, almost giddily, how socially maladroit Thiel was—“He’s almost bashful. Doesn’t even really seem to make eye contact”—he was obviously speaking from very recent experience. (Thiel declined to participate in this story.)

A 10-Year Vendetta

Denton grew up in North London. Young Nick identified intellectually with his father, a professor of economics, but was closer to his mother, a psychotherapist born in Budapest who’d survived both the Nazis and the communists. A childhood spent amid disputatious Hungarian Jews like her would one day help make polyglot New York feel more like home to him than anywhere else he’d ever been. A picture from his adolescence shows a nerdy boy reading a book by Isaac Asimov in his backyard.

Following Oxford, he became a stringer at several newspapers, including the Financial Times, in Budapest, from which he covered the Iron Curtain’s collapse. He’d escape regularly to Vienna, where he’d buy porn, sushi, and the latest issues of Macworld and Wired. In 1998 he persuaded the F.T. to send him to San Francisco. During the next two years, while shuttling between London and the Bay Area, he founded two start-ups, a news aggregator and a social-events business. The success of the second, along with some real estate investments, provided seed money for something else. It was in San Francisco that he (briefly) met Thiel, whose ideas—like a system of money that transcended governments—he found interesting.

Denton found San Francisco surprisingly boring. “I loved the idea of San Francisco, but it’s not a sexy place,” he says. “I love cosmopolitan big cities and it’s just not that.” Worse, it had few black men—a problem because they were the only men he dated. “They’re just more real,” he explains. (This is why, when false rumors arose in the wake of Thiel’s emergence as Hogan’s funder that he and Denton had once been lovers, Denton’s denials rang true.) And Silicon Valley, overwhelmingly white or Asian and straight and stilted, was still more unappealing, whatever secrets it held. So he came to New York in 2002, and, almost as a hobby—until some tech thing came along—he launched his blogs. Gizmodo came first, in mid-2002, and several months later there was Gawker. (“It sounded like how somebody putting on a New York accent would say ‘New Yawk.’ ”) Denton was unapologetic about its focus: to him gossip, at least about people of consequence, is a social emetic, flushing out privilege and mendacity, mediocrity, and hypocrisy. And, besides, it’s fun.

Other Web sites, some that stuck and many that did not, quickly followed. But, still interested in tech, Denton commuted to San Francisco in late 2006 to run his Silicon Valley blog, Valleywag. Looming large on his beat was Thiel, who, Denton learned from colleagues—“It was all over the journalistic grapevine,” he says—was not just one of the Valley’s biggest stars but one of its few gay ones.

Denton dates his own coming out to the mid- to late 1990s, but others put it later, and say he remains ambivalent about embracing gay culture generally. Perhaps because he had been slow to come out himself, Denton was emphatic about outing others, at least well-known others. Long forced to remain in hiding and then, in some instances, staying there even after they’d been free to leave, gays had been tragically marginalized, he felt. “The erasure of gay people from the historical record, I think, has been a crime, and it’s a crime that continued until really very recently,” he says. “People led lives that were invisible.” Since gays had so few role models, those who had made it spectacularly in the straight world should come forward, or have it done for them. And what cost was there if it was already common knowledge among the cognoscenti? Journalists, he believed, had no business keeping open secrets. Journalistically and emotionally, Denton was always a libertarian: it was for others to determine “appropriateness.”

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Denton wrote periodically (and suggestively) on Thiel and friends, including “As Decadent as Silicon Valley Gets,” a June 2007 post detailing the “young playboys” of Thiel’s Founders Fund—a venture-capital firm he co-founded in 2005—cavorting, largely among other men, at a Playboy Club–style mansion in San Francisco. “For all the financier’s social awkwardness, teetotal aversion to alcohol and obsession with immortality,” Denton wrote of Thiel, he “always had a weakness for libertines.” The next month, Thiel confessed to a German paper that he checked the site “quite often.” Denton proceeded to tackle Thiel’s gayness more explicitly, only to encounter opposition. Max Levchin, a PayPal colleague of Thiel’s whom Denton also knew, pleaded with Denton to lay off, in part, says Denton, because Levchin feared Thiel might suspect that his girlfriend, who worked for Thiel, had been a source. (Levchin wouldn’t comment.) “I got a series of messages relaying the destruction that would rain down on me, and various innocent civilians caught in the crossfire,” Denton later posted. Running out of time and unable to find some non-gossipy way to write the story, Denton says, he shelved it.

Owen Thomas, the technology journalist to whom Denton had passed the Valleywag job in July 2007, was more persistent, and ingenious. Thomas, gay but more militant than Denton, also knew about Thiel’s sexual orientation and was itching to write about it. In fact, for anyone paying any attention, he already had. In a blog from October 2007, he described how a smitten young woman had asked Thiel to sign something for her after he had given a talk at a college in Tennessee. “If that girl was hoping to score more than just an autograph from Thiel, she’s due for a double-dip of disappointment,” Thomas wrote. Then, in “Peter Thiel Crush Alert!,” a month later, he reported that a local (male) real-estate agent had called Thiel “dreamy.” “We hate to break it to you . . . but Thiel’s taken,” Thomas wrote. “If he weren’t though, you’d have a better shot than that Tennessee girl who lined up to get his autograph.”

Ordinarily, the post Thomas proceeded to write that December would have been considered a puff piece: Thiel, it said, was the smartest venture capitalist “in the world” and “more power to him” for pulling that off as a gay man in Silicon Valley, which, for all its purported tolerance, was, in fact, homophobic. But, for most readers—and, presumably, for Thiel himself—the takeaway was the headline: “Peter Thiel is Totally Gay, People.” The New Yorker once said Thiel had a “pronounced aversion to conflict.” And for the time being, he did nothing to strike back. But with Gawker, at least, Thiel wasn’t so much non-confrontational as deliberate. “Peter figured out that Gawker would get so out of control that eventually they’d do something so stupid that no one would defend them and he’d just wait,” says Keith Rabois, a Silicon Valley executive and PayPal alum whose friendship with Thiel dates back to their law-school days at Stanford. “He correctly forecast that they would get worse in their behavior—that, inevitably, that crowd would massively screw up and no one would want to defend them.” (Thomas, now the business editor at the San Francisco Chronicle, says Thiel’s real beef with the piece was that it turned off potential investors from Saudi Arabia.)

Denton returned to New York, but Valleywag, and Gawker, remained, incessantly, on Thiel’s case, as a few additional headlines attest: “Peter Thiel’s Richer Than You, but Not as Rich as He’d Like You to Think”; “A Facebook Billionaire’s Big Dumb Failure”; “Facebook Backer Wishes Women Couldn’t Vote.” But Thiel indeed bided his time until Gawker made the wrong move. So what is one to make of that polite e-mail exchange with Denton? Or the wine-bar meeting Thiel had with Gawker editor Ryan Tate in 2009 during which Thiel—“a little sweaty and difficult to talk to, kind of like Nick, hard to read his emotions,” Tate recalls—even joked that it seemed he did negotiate with terrorists? A year earlier, Thiel had even enlisted both a New York lawyer and Choire Sicha, the former Gawker editor widely credited with devising its distinctive style, to help him make nice with the press in general and Gawker in particular. “I never felt this was the beginning of a 10-year vendetta,” says Sicha; Thiel struck him as “quiet, thoughtful, perfectly sane.” Perhaps these were feints with pawns as Thiel lined up his knights and bishops.

Gawker reporters knew how obsessed Denton was with outing household names, and catered to his wishes. For instance, after the New York Post described an unnamed gay star beating and raping his former boyfriend, Gawker asked readers to guess the culprit, then named the winner and the runners-up—a stunt that later led the Gawker reporter who supervised the contest to apologize, one of the periodic ex post facto mea culpas that Denton’s minions have felt compelled to issue over the years. When Tracy Moore, of Jezebel, advised readers, “Don’t out someone who doesn’t want to be out,” Denton pounced. “She’s working at the wrong place,” he wrote. “We’re truth absolutists. Or rather, I am. And I choose to work with fellow spirits.” When Thiel told an interviewer earlier this year that “radical transparency” was a policy that East Germany’s Stasi would have favored, he may well have had Gawker, and Denton, in mind.

If, as one Gawkerite says, Denton developed crushes on straight male editors whose fortunes waxed and waned with the state of his infatuation (a suggestion Denton laughingly dismisses), his fiercest and most durable crush was on Daulerio, a rough-hewn throwback to the Five Star Final era of journalism, fueled by sex, controlled substances, and a passion for great and gritty stories. Denton favored Daulerio for the same reason he admired Andrew Breitbart, Lee Atwater (“a joyful warrior”), Rupert Murdoch (“one of the world’s great gossips”), Roger Ailes, and various right-wing enemies of the traditionally liberal journalistic establishment: all were “buccaneers.” It was Daulerio who’d posted Brian Williams’s note to Denton, who upon learning about it stormed up to him shouting, “What the fuck are you doing?,” only to realize that what Daulerio was doing was his job. And it was Daulerio who, in early October 2012, posted the Hogan video and his accompanying story, a rumination on how obsessed ordinary people were with boring celebrity sex. To him, it was no big deal—TMZ had written about the video (and a Web site called the Dirty had posted screen shots from it) months earlier. And, to Denton, who cared so little about sports that he thought March Madness lasted into June, it mattered even less. But to Thiel and Hogan’s lead lawyer on the anti-Gawker crusade, Charles Harder, of Beverly Hills, it proved the long-awaited casus belli.

Blithely unaware that his world was under attack, and with their therapist officiating, Denton married the 31-year-old actor Derrence Washington in New York’s American Museum of Natural History in May 2014. For Denton and his friends it was a joyous affair—“like watching Pinocchio turn into a real boy,” Daulerio later said. As one of Hogan’s lawyers gleefully told jurors, this great avatar of openness had all cell phones confiscated at the door. (It was to ensure attentiveness rather than to protect his privacy, Denton insists.) The affair was covered in the Vows column of The New York Times, a feature that, naturally, Gawker had often skewered. Denton banned Gawker’s Gawker reporter, J. K. Trotter, from the proceedings; pictures of Trotter were posted to keep him from infiltrating.

Smackdown Time

The more the Hogan case ground on, the more precarious Gawker grew: under Florida law, whatever Hogan won, Gawker had to post up to $50 million toward the total damages, even pending an appeal. Making matters worse, its insurance coverage didn’t apply, forcing it to turn to a Russian oligarch for funds. Meanwhile, weary of Internet nastiness and preoccupied with his next thing—an interactive, comment-based Web site called Kinja—Denton found himself ever more aligned with Gawker’s critics. Two stories in particular offended him; it was probably no coincidence that each concerned children, for Denton and Washington were contemplating a family of their own. First came “Zoe Saldana Gives Birth to Hipster Scum,” lambasting the actress for the names (Cy, Bowie) she’d given her twins. Even worse was “Bristol Palin Makes Great Argument for Abortion in Baby Announcement.” “Gawker is out of control,” Denton, who is pro-life, complained to a colleague. He’d stopped reading the full Gawker feed, he added, for fear of what he might find: he was “ashamed of the callow viciousness” and “dull intellectual orthodoxy.” Denton rarely read anything posted on Gawker before it went up; he deferred to his editors, and anyway, there was just too much of it.

Then, in July 2015, came the story about the married media executive. After 18 hours’ worth of angry tweets, many from Gawker’s friends, Denton pulled it down. “We let that idea gain roots, that freedom is the freedom to do whatever the fuck you want,” he said at one of the several near-insurrectionary all-hands meetings that ensued. “Actually it’s not. I don’t want some guy blowing his brains out and that being on our hands.” Most of his writers disagreed with his decision. The resignations of Craggs and other staffers, including gawker.com editor Max Read, followed.

Under normal circumstances, Hogan, who is not a wealthy man, would probably have settled. (His lawyers had even warned the court that their client could “not afford an endless litigation.”) Gawker offered Hogan millions to go away, even though it insisted it did nothing wrong. In fact, both a federal judge and a state appellate court had ruled prior to trial that, because Hogan was a public personality who made his sex life a matter of public interest, the post was protected by the First Amendment. But, mystifyingly, Hogan never bit. Far from it—an attorney for Gawker says that Hogan’s multiple lawyers dug in and cast their nets. Clearly, Hogan had someone else on his tag team. But who? To Denton, the prime suspects were all in Silicon Valley, where Gawker’s impertinence was an ongoing affront. Thiel not only topped the list; everyone else was tied for 10th.

Already, the trial judge, a Jeb Bush appointee named Patricia A. M. Campbell, had proved unrelentingly hostile to Gawker, Gawker’s team believed. She excluded a raft of evidence from an earlier F.B.I. investigation suggesting, said Gawker’s lawyers, that the wrestler (a) may have known he was being taped; (b) seemed more concerned about the exposure of a racist rant than of his private parts; and (c) was inconsistent in his testimony. Instead, according to Gawker’s attorneys, it was Daulerio and Denton who were demonized by Hogan’s team. Denton’s impolitic utterances—“Every infringement of privacy is sort of liberating”; “We don’t seek to do good. We may inadvertently do good. We may inadvertently commit journalism”; “I don’t think most people give a fuck [about privacy], actually”—were projected on a screen, while Denton himself was depicted as a bully, sadist, and pornographer. The high, or low, point came when he was made to read Daulerio’s Hogan post aloud, reciting graphic descriptions of oral sex and Hogan’s penis (“the size of a thermos you’d find in a child’s lunchbox”) in his Oxford-inflected English.

Hogan’s lawyers tossed out New York references like confetti, the better to make Denton—“this guy . . . up there in New York sitting behind a computer, playing God with other people’s lives,” as one of them, Kenneth Turkel, of Tampa, described him—appear even more alien to jurors in Pinellas County, Florida, than a gay half-Hungarian Jew already was. So completely did the jurors not get Denton that, in a question submitted to the judge, one of them asked Emma Carmichael, editor of Jezebel, whether she’d ever slept with Denton. The verdict was anticipated, but the award—$115 million in compensatory damages and another $25 million as punishment, totaling $40 million more than Hogan sought—was not. It was a great victory for Thiel, but, according to a friend of his, he wasn’t gloating; the friend told me Thiel worried that the ruling might not survive an appeal. Barring a settlement, that was where the history of the case would be written, and Thiel recognized, his friend said, that the case was hardly “a slam, slam, slam dunk.”

“We’re truth absolutists. Or rather, I am. And I choose to work with fellow spirits.”

Two months after the March 2016 verdict, Thiel was outed a second time, when Forbes identified him as Hogan’s sugar daddy. That night, Denton again e-mailed Thiel, but, thinking an intermediary was called for, sent it via Keith Rabois. “If Peter or anybody representing him wants to talk, my line is open,” Denton wrote Rabois. “It’s still not too late to resolve this without further damage to everyone’s reputation.” He said he was sorry for any embarrassment Thiel had suffered from the outing story, but that it had been written “when gay people were invisible or marginal in Silicon Valley, and some of us refused to go along with the omerta.” Far from being moved, the next day Thiel described Gawker to Andrew Ross Sorkin of The New York Times as a “singularly terrible bully,” and called helping Hogan and other Gawker “victims” one of the “greater philanthropic things” he’d ever done.

Denton quickly posted an “open letter” to Thiel on Gawker. “I thought we had all moved on,” he wrote, “not realizing that, for someone who aspires to immortality, nine years may not be such a long time as it seems to most of us.” He then called for a “brief truce,” during which the two might hold a public debate or something similar. Thiel never responded. But with Jeremy Stoppelman, the C.E.O. of Yelp, acting as go-between, Denton and Thiel finally had their secret tête-à-tête. It appears to have accomplished nothing.

Thiel and Harder continued to go after Denton and Daulerio, seeking to track down and tie up their assets. Hogan’s lawyers, and some embittered Gawker alums, suspected that Denton stashed away funds in Budapest or the Cayman Islands, but he says it isn’t so. (Two other Gawker journalists, Sam Biddle and John Cook, faced allegations in a pair of other lawsuits being handled by Charles Harder, which Thiel may or may not have also funded. Those cases, too, are covered by the proposed settlement, with the plaintiffs collecting damages in exchange for dropping their cases.)

Denton and Daulerio vowed to fight on, and the prospects for an appeal—funded by proceeds from the Univision sale—looked good. Apart from strong First Amendment arguments, it was hard to believe that anyone who boasted to Howard Stern, as well as to others, about his sexual habits, about the size of his penis and where he likes to ejaculate and how he uses his mustache during oral sex, as Hogan did, should have elicited much sympathy in claiming invasion of privacy. (By discussing his sexuality ad nauseam, the argument goes, Hogan made it a matter of public interest.) Then there is all of that evidence that Judge Campbell—the most reversed trial judge in her district—excluded. It’s also hard to agree, with respect to calculating damages, that all 7,057,214 people who viewed nine seconds of Hogan sex for free would have plopped down $4.95 for the privilege.

But with the settlement, none of this will matter.

If it goes through, and Denton is sprung from bankruptcy, he stands to collect roughly one-third of what remains after Hogan, Denton’s investors, and those former Gawker employees with equity stakes in the company, are paid off. One reasonable estimate is around $15 million—vastly lower than what he was once worth, but still within striking distance of what Arianna Huffington got when she sold her eponymous Web site. It should be enough to spare Denton having to sell his loft (on the market for $4.25 million), followed by Soviet-style internal exile to New York’s Upper West Side. By year’s end, he should be able once more to pick up restaurant checks, and his plans to start a family, shelved during the Hogan imbroglio, presumably can be revived.

Not once since the Gawker sale has he returned to Gawker’s old office, nor did he read any of the postmortems. Nor, he insists, will he read this story. He did, however, read, and react to, some of what Thiel said at his press conference on October 31: that Gawker’s reporters were “not journalists” (“No one person, no matter how rich, should get to decide who’s a journalist”); that Gawker was a “flimsy” business (it had made money until Thiel came along); that it went after “small fry” (“Thiel is not ‘small fry.’ Nor is Hulk Hogan”); and that Daulerio was an “aspiring child pornographer”—a reference to an ill-advised but clearly flippant remark that Daulerio had made during his deposition. “Despicable,” Denton says, “remarkably tabloid for someone who sets himself up as a guardian of journalistic integrity.”

“Interesting—and scary” is how he describes Thiel. Still, Denton maintains that his differences with him are more philosophical than personal, and bigger than either of them. They reflect, he says, a battle between two groups of people—the control freaks of Silicon Valley and the buccaneering bloggers that their technology unleashed—and two notions of freedom: one in which you can be free only when you’re yourself in public, and another in which you’re free only when you can protect yourself from, well, gawkers.

Gawker, Denton says, “emitted vast quantities of truth into the ether,” and redefined journalism in the Internet age. He even takes partial credit for another kind of outing—of a presidential candidate. “When I see the forthrightness with which mainstream newspapers called Trump out for lying, I see echoes of the blogs—the realization that ‘Hey, this thing is so obvious, it’s in front of us, we can’t pretend this doesn’t exist,’” he says. “You can’t be so constrained by convention that you fail in your central obligation to say what you see. And Gawker was the fiercest of the blogs.” He’s proudest not of the marquee stories everyone rattles off—not so many, to be honest, given the hundreds of thousands that it did—but all the unmemorable ones, with their “humdrum honesty.” He’s also proud of what Gawker didn’t do, and, despite the criticism that leaves it unmourned in many quarters, defiant about its achievements and methods. “We didn’t get anyone into any wars, we didn’t ruin anyone’s life, we didn’t get taken in by fabrication or plagiarism,” he says. “With hundreds of young, talented, but sometimes inexperienced writers, you’d have expected some major journalistic malpractice. Never happened.”

His Zen attitude is at the core of what comes next for him: building Kinja, a community of commentators through which Denton hopes to redefine journalism yet again. “I’ve always wanted news just to be a conversation, where the interactions between journalists and sources and subjects and tipsters play out in a more symmetrical fashion, so that the journalist doesn’t have a complete monopoly on what gets included and what not,” he explains. “I’ve done the truth. Now I want to do the reconciliation.”

[UPDATE: This story has been updated to accurately reflect the nature of a Gawker Media story on the architecture of Donald Trump's hair.]