For years after starting Gawker Media, the online publishing network, in 2002, Nick Denton ran the company out of his apartment, in SoHo. “He said, ‘If you run it out of your house, then no one expects anything,’ ” Denton’s friend Fredrik Carlström, the film producer and adman, told me. “ ‘If you have an office, people want stuff. They want cell phones, lunch breaks, beer on Fridays.’ ” Gawker Media was a deliberately fly-by-night operation: incorporated in Budapest, where a small team of programmers still works, and relying on elegantly jaded bloggers who considered themselves outsiders with nothing to lose. Early contributors tell stories about bounced checks, and receiving payment straight from the A.T.M. The arrangement, many assumed, was a convenient hedge against potential libel claims. (Scarcely a week passes without one or more of Denton’s nine sites receiving a cease-and-desist letter.) It also helped bolster Denton’s image as a kind of digital-sweatshop operator—he initially paid his bloggers twenty-four thousand dollars a year—and cultivated a helpful sense among contributors that they were the crew of a rogue “pirate ship,” as Gawker people sometimes say, initiating stealth attacks on the ocean liners in midtown.

“I don’t have a huge amount of time for noble failure,” Denton says. Photograph by Max Vadukul

Nonetheless, two years ago Denton, who is forty-four, set up a permanent base for the operation in a large loft in Nolita, which he increasingly shows off, as if to demonstrate that his bloggers do not wear pajamas all day long. They now make good money, sometimes in excess of eighty thousand dollars, with 401(k)s, and, soon to come, maternity leave (not that many of them yet need it). Roughly sixty of the company’s hundred and twenty staffers work on-site, sitting at three long rows of desks alongside Denton himself—who, in the fashionable mode of modern media executives, declines a corner office. There is also a roof made for hosting parties with bands and Ping-Pong tables.

Denton’s receptionist sits beneath a large digital screen known as the Big Board, which lists the ten best-performing posts across the company network; these are determined by the number of new readers—as opposed to returning obsessives—in the previous hour. Denton says that the primary purpose of the Big Board is to encourage competition among his writers. A few months ago, he told the Times, “Sometimes one sees writers just standing before it, like early hominids in front of a monolith.” But on the day I first visited the office, in late July, there was no one standing before the board, and, in fact, there was nothing on the board. It had gone blank, as a result of a cyber attack on the Gawker server.

“You missed all the excitement,” Denton said, bounding over to greet me. “We were just brought down.” He was dressed in dark jeans, sneakers, and a tight-fitting polo shirt. The office seemed almost eerily quiet and untroubled, a room full of stylish people wearing headphones and instant-messaging one another. The excitement—was it virtual? The Big Board sprang to life. “Are we back up?” Denton asked his chief technology officer, Tom Plunkett, who looked to be the only other middle-aged person on the premises. They were back up, and this is what had caught the attention of Web surfers previously unfamiliar with Denton’s oeuvre: “How a 17-Year-Old Craigslist-Swapped an Old Phone for a Porsche,” “How the Internet Beat Up an 11-Year-Old Girl,” “When Video Games Go Wrong,” “Clueless Secretary Prompts Hilarious Office Email Thread,” “11-Year-Old Viral Video Star Placed Under Police Protection After Death Threats,” “Incredible Physics Engine Yields Some Seriously Jaw-Dropping Dirt,” “4Chan’s Sad War to Silence Gawker,” “Funny, My License Says ‘WHERE2CHRG,’ ” “Glenn Beck Is Going Blind,” and “10 Superhero Buddy Movies We’d Love to See.”

“So that ‘4Chan’s Sad War to Silence Gawker’ was rather unwise,” Denton said, not unhappily, referring to the seventh-ranked post on the board, which was itself a follow-up to the second (“How the Internet Beat Up an 11-Year-Old Girl”) and the fifth (“11-Year-Old Viral Video Star Placed Under Police Protection After Death Threats”). Gawker, Denton’s flagship title, had described 4Chan.org, an anarchic Web forum frequented by teen-agers, as “the Internet’s scariest hive mind,” and detailed its role in terrorizing and exposing the name and address of a young girl who made a YouTube video. 4Chan’s partisans had retaliated, at first unsuccessfully and then, after Gawker taunted them, with sufficient force to bring Denton’s gang offline. You might say that it marked a peculiar moment in the evolution of Gawker, which was once described to Denton at a dinner party as the place where losers talk about winners—a venue for punching upward, with hive-mind tendencies of its own. Now the site that had once been the class cutup (“Lady Gaga’s Vagina Almost Fooled Us Into Forgetting About Her Penis”) was acting the part of digital hall monitor.

Denton acknowledged “the irony of us lecturing,” as he put it, and asked, “Is there Gawker ethics? I mean, I guess there’s Gawker ethics. It’s a dangerous thing to talk about.”

“Picking on 4Chan was genius,” Foster Kamer, a former Gawker writer who now works for the Village Voice, told me. “But you’re scooping the muck from the sewer and holding it up in your hand and saying, ‘Look at this. Smell this.’ ”

Denton used to tell people who asked what he did for a living that he was a pornographer. This was true, in a limited way: he publishes Fleshbot, a blog that boasts of its devotion to “Pure Filth,” and features a great many explicit anatomical images. But Fleshbot, which receives about a million unique domestic visitors each month, is now the worst-performing of the nine titles that Denton puts out, and you won’t find any mention of it on the mastheads of the other eight; it’s a drag on the reputable kind of advertising that Denton now covets. Denton’s best-performing site, Gizmodo, reaches nearly six million Americans a month. It’s a punchy consumer guide to gadgets: cell phones, camcorders, turntables. Denton is a kind of gadget fetishist, but you’d be unlikely to hear him telling a stranger that he is a technology watchdog or a trade publisher. That would be boring, and insufficiently mysterious. Also, it could be interpreted as an attempt at a whitewash, which is something that Denton scorns in others with the ferocity of Mencken and Winchell. On his Twitter feed, Denton identifies himself as a “gossip merchant.”

Like all gossip merchants, Denton fancies himself a truth-teller who relishes flouting the conventions of good taste and privilege. He grew up in London, where the Fleet Street tabloid culture is cutthroat, and he shares the Murdochian view of American journalism as effete, earnest, and uncompetitive. “The staples of old yellow journalism are the staples of the new yellow journalism: sex; crime; and, even better, sex crime,” he wrote in a memo to his staff. “Remember how Pulitzer got his start.” To that old game he brings the conviction of a futurist, someone who is engaging with the world as it must soon be, and speaking with the assured perspective of having experienced success in all its antiquated forms. He was a newspaperman. He has written a book. He taught at Berkeley. But Denton was also an early believer in the transformative nature of the Internet, the kind of guy who, if you’d known him back then, would probably have sent you your first e-mail, and set you up with your first blog. He made his millions in a couple of dot-com-era ventures.

Gawker began as a media-gossip site devoted to “radical Manhattanism,” and has since morphed into a world view for the blogging generation. (Ninety-three per cent of its audience is under the age of forty-five.) One of its early recurring features, Gawker Stalker, invited readers to participate in the modern culture of celebrity obsession by submitting personal sightings on the fly (“Ashley Olsen making her way downstairs to the Pharmacy at the 6th ave & waverly duane reade . . . one very large bodyguard in tow”). Among the implied jokes was that New Yorkers, unlike their counterparts in Los Angeles, pride themselves on being unimpressed by fame, to the point of feigning obliviousness. In this way the site could be read as offering a meta commentary on the vapidity of celebrity journalism, without ever explicitly holding itself above it. This was gossip for smart people—discerning people, who had seen enough “Saturday Night Live” sketches to know that the difference between a trope and a parody can be a simple matter of tone. Another item was “Where Are They Now? Douchebag Edition.” Gawker was never above its genre, but it was certainly against things—“asshats,” the Times, old people—because no intelligent person would deny that the impulse to gossip is fundamentally judgmental.

Through Gawker, Denton wages war on self-regard—or presumed self-regard, as his cast of mind is both abstract and deeply tribal, inclining him to sort nearly all people into one or another category that could be judged full of itself. There is a well-travelled image of Denton on the Web, in which he is wearing a tuxedo and tilting a wineglass to his lips. The image bothers him, because it suggests a level of comfort and formality in his presentation that doesn’t accord with his self-image. Denton is tall and rangy, and has a famously large head that sits precariously on a thin neck and narrow shoulders, leaving the impression of an evolved brain that is perhaps a little too conscious of its pedestrian context. He looks perpetually unshaven, with gray stubble complementing his close-cropped, receding hair, which he teases casually forward. He is someone who likes and knows how to have fun—“Nick has a fairly strong hedonic streak,” his friend Matt Wells, of the BBC, says—but who doesn’t wish to be seen enjoying himself overly. “Hypocrisy is the only modern sin,” he likes to say.

A few months ago, at a party, Denton ran into Sheila McClear, a features writer for the New York Post whom he had fired from Gawker. (She learned of her termination when a reporter e-mailed her.) “He went out of his way to talk to me,” McClear said. “I felt kind of honored. He was, like, ‘I have some gossip for you,’ and told me some juicy info about one of my colleagues. Then he mentioned that he thought my job was super-easy, compared with blogging. And then the weirdest part was he claimed he knew someone I work with and said, ‘You know, it’s funny, when you first started, people hated you, and now they love working with you.’ ”

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It was not an atypical exchange. Denton is good but unnerving company. He often prefers to communicate via instant message, where the self, as expressed through a keyboard, is easier to regard, and therefore to keep in check. (His employees have internalized a kind of Morse code for deciphering his moods and intentions: “Hey hey” prefigures good news, for instance, whereas a lone “Hey” means business.) In live conversation, his intelligence is evident, as is his penchant for rational contrarianism. He once announced to his dinner companions that he was in favor of gay marriage (Denton is himself gay) but against abortion, on the ground that, if you’ve got to draw a line somewhere, it might as well be at conception. He speaks quickly, in a soft, clipped baritone that one former colleague of his likens to “whale sonar.” He also bores easily, having been proved right often enough to dismiss most attempts at debate with an insensitivity that is commonly mistaken for meanness. His smiles fade a little too quickly, and can leave you with the nagging suspicion that he views it all as a lark—the high-school-cafeteria metaphor taken too literally. The first time McClear had lunch with Denton, she returned to the office afterward and threw up. She attributed this to food poisoning, but it happened again the second time they had lunch.

This past summer, Gawker published a big “exclusive,” titled “Mark Zuckerberg’s Age of Privacy Is Over.” It featured two dozen paparazzi images of the young Facebook C.E.O., his Mandarin tutor, his sister, and his “comely” girlfriend. They were unremarkable images, and the accompanying text said as much: “His car is nothing you’d blink at on a Bay Area freeway. . . . Zuckerberg’s house is modest, even humdrum. . . . He wears nearly identical faded gray t-shirts day after day.” Its winking conceit was that Zuckerberg had become a billionaire by encouraging people to share more of their private lives with one another.

“Zuckerberg is the Angelina Jolie of the Internet,” Denton explained, in response to a critic who charged him with aspiring to “no higher principles whatsoever,” noting with particular disapproval the exposure of the girlfriend. “His lovers, friends, and acquaintances—like those of any other celebrity—are caught up in the vortex,” Denton went on. “He has to make a choice; and they have to make a choice. And none of the choices—retreat from the public eye, abandonment of friendship—are palatable.”

Denton told me about an afternoon he once spent with Zuckerberg, at a News Corp. retreat in Monterey, where they served on a panel together, performing for Rupert Murdoch. “I actually like the guy,” he said. “Apparently, his original idea for Facebook was this dark Facebook. Like, the idea was that it was going to be a place for people to bitch about each other, and then it evolved. It was interesting how agnostic he was about which approach to take.”

There exists in the collective media mind a caricature of Denton as an evil, soulless, Machiavellian puppeteer: the Wizard of Blogs. It is fed in part by some of the familiar pejoratives associated with tech geekery (Denton as anti-social robot, for example), and also by his own publications, which, in the interest of his vaunted transparency, occasionally turn their pitiless gaze on the boss himself, for comic effect. From reading Gawker, I had learned that Denton is not just a terrible employer but one of “New York’s worst,” as well as an unapologetic liar and the kind of person who leaves his own party early in search of a better one. The caricature was not much diminished by speaking to people about their experiences with the man.

“He’s not, like, a sociopath, but you kind of have to watch what you’re doing around him,” Ricky Van Veen, the C.E.O. of the Web site College Humor, told me.

“The villain public persona is not a hundred-per-cent true,” A. J. Daulerio, the editor-in-chief of Deadspin, Gawker Media’s sports blog, said. “It’s probably eighty-per-cent true.”

“He has fun when people say horrible things about him,” the blog guru Anil Dash said.

“I can’t lie to make him worse than he is, but he’s pretty bad,” Ian Spiegelman, a former Gawker writer, said.

“Other people’s emotions are alien to him,” Choire Sicha, another Gawker alumnus, said.

“He’s got a strong carapace of not really thinking other people’s opinions are that important,” John Gapper, a columnist at the Financial Times, said.

“He’s right,” Matt Welch, the editor of the libertarian magazine Reason, said. “He’s never right about me, of course. But people are lazy and not very good.”

“He almost sees people as Legos moving around,” Sheila McClear said.

“He’s not a fully human person,” Spiegelman said.

“I mean, maybe he thinks he’s the one truly advanced human,” Anna Holmes, the founding editor of Jezebel, a.k.a. Girlie Gawker, said.

“Does he have parents?” Daulerio asked.

“I always imagine that he came fully formed out of British finishing school,” Holmes said.

“Part of getting to know Nick is accepting that there are things you’ll never know,” Jeff Jarvis, the new-media critic and author, said.

“What can you do with a person like that?” Spiegelman said. “He’s a character out of Dr. Seuss, frankly.”

“Nick is a bit of a sphinx on purpose,” Joel Johnson, the longest-serving Gizmodo writer, said. “He has some of the attributes of the dork who wraps his Asperger’s around him like a cloak.”

“There’s no point in writing about Nick if you can’t get to the fundamental problem of his nihilism,” Moe Tkacik, who has worked at both Gawker and Jezebel, said.

“He likes pretty things,” Daulerio said.

“He takes cancer very seriously,” Sicha said.

“He wants to be Warhol,” McClear said.

“He’s always wanted to be a magazine editor,” Welch said. “He’ll deny it to his grave.”

“What he really wants is to be the editor of the New York Times,” Spiegelman said.

None of these people really dislike Denton, and some of them are quite fond of him. With old friends, particularly those outside the blogging world, he is “curiously loyal,” as Gapper says, even if he is also “ruthless, actually, in lots of ways.” Several people mentioned that they’d sought Denton’s approval before agreeing to talk about him. “Be interesting,” he invariably responded. Denton once chided his boyhood friend David Galbraith for marvelling to a reporter that at the age of thirteen Nick was already reading The Economist. Galbraith’s crime was to come off sounding “too suburban.” Denton preferred that I not talk to his sister, Rebecca, because “she’s going to give you empty nothings,” as he put it. He also seems uncharacteristically protective of her privacy. Rebecca is three years younger than Nick, and lives in London. “She looks after her kids and writes children’s books,” he said. She used to call him Tricky Nicky, or so he says.

Denton grew up in Hampstead, in a milieu that he described to me as “bourgeois, arch-Jewish, metropolitan, forward-looking, international.” His father, Geoffrey, a product of working-class Yorkshire, is an economist who served in the nineteen-eighties and early nineties as the director of Wilton Park, a conference series not unlike the Aspen Institute. He writes serious books with serious titles: “A New Transatlantic Partnership: A European Perspective on the Transatlantic Partnership for Trade, Monetary, and Security Relations.”

Denton’s mother, Marika, died of cancer the year before he moved to New York and started Gawker. She was a Hungarian Jew, and a psychotherapist, an irony not lost on those who have known Denton a long time and have never thought of him as being especially in touch with his feelings. Last year, in a rare instance of familial disclosure, Denton posted to his Facebook wall a newspaper clipping about her. It was an account of a visit she made to the United States as a university student, several years after fleeing her home country, in the revolution of 1956 (“Hungarian Girl Recalls Life Under Communists”). Beneath it, he added, “For a refugee, she manages to be quite remarkably patronizing—both about the ‘clean-living’ families of Pennsylvania that she met and the ‘emotional’ American press. She preferred the ‘just the facts’ approach of the Brits: facts that merely get in the way of modern Fleet Street.” Of his parents, he now says, “They were both probably journalistic snobs.”