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Since its beginning in 2002, Gawker has been a veritable schadenfreude machine, taking delight in deflating the egos of New York’s cultural elite, among other, perhaps less worthy, targets.

So it made sense that it commemorated its own bankruptcy proceedings and impending sale Wednesday night in Manhattan with a party at its Chelsea offices.

At 7 p.m., a couple of hundred writer types were milling around the offices, where there was a makeshift bar with boxes of pepperoni pies from Joe’s Pizza stacked on top of it. Vodka was served by the caseload.

“I’m looking around realizing how few people I know,” said David Haskell, the deputy editor of New York magazine. “It’s like, did I miss it?”

Actually, no. That’s just how it feels when you find yourself at a reunion of a media company that has become a revolving door for young writers and editors. Most of them served their apprenticeships under the Gawker founder and chief executive, Nick Denton, before moving out of his sphere.

The party, which at times had the feeling of a giddy wake, drew in past and present journalists from its flagship site, as well as those from the offshoots Gizmodo (Gawker for gadgets), Jalopnik (Gawker for car culture), Jezebel (the Gawker “ladyblog”), Lifehacker (Gawker for productivity tips) and Kotaku (Gawker for video games).

Many returned having gone on to substantial success.

Elizabeth Spiers, who established much of the Gawker editorial voice as the namesake site’s founding editor, was there. Since her time with Mr. Denton, she served as the editor of The New York Observer and founded her own research and analytics firm. Nearby — in a navy Prada shirt and gray pleated Valentino trousers — was Choire Sicha, who did two stints at Gawker beginning in 2004, and is now the director of partner platforms at Vox.

Also in attendance was Irin Carmon, a Jezebel alumnus who is now a correspondent for MSNBC and a co-author of the recent critically acclaimed book “Notorious R.B.G.: The Life and Times of Ruth Bader Ginsburg.” She likened the evening (and Gawker’s current troubles) to the “Seinfeld” finale. “Do you remember?” she said. “Where they all go to jail after everyone from their past lives shows up to testify against them?”

But gimlet-eyed humor was not the prevailing sentiment of the evening. Instead, Gawker veterans past and present largely framed the last few years as a David-versus-Goliath struggle between a scrappy group of renegades and a gaggle of 1-percenters intent on bringing them down.

One of its wealthy enemies is Terry Bollea, better known as the WWE titan Hulk Hogan. He successfully sued the site and was awarded $140 million in judgments after it posted a 1-minute-40-second clip of a sex tape of him and Heather Clem, who was the wife of the shock radio host Bubba the Love Sponge. Jurists at the trial in St. Petersburg, Fla., seemed perplexed by Gawker’s take-no-prisoners brand of journalism.

Another is Peter Thiel, the billionaire investor of Facebook who, in 2007, was the subject of a post on Valleywag‚ Gawker’s former site on Silicon Valley, titled “Peter Thiel Is Totally Gay, People.” Mr. Thiel subsequently helped bankroll Mr. Bollea’s suit against Mr. Denton’s company.

Describing that conflict and the role Mr. Thiel played in it, Jessica Coen, a former editor of Jezebel, said it was “like watching a sociopath try to light your family home on fire.”

At 7:45, she and fellow Gawker veterans headed away from the office space and into the adjacent amphitheater.

First to speak, standing before a movie screen, was the company’s founder and chief executive, Mr. Denton, 49, a London-born, Oxford-educated onetime financial journalist who started Gawker in his Manhattan apartment.

“To all the writers who were here in the early years, I’m sorry,” he said. “We were very cheap.”

Mr. Denton, who wore a fitted white shirt from Banana Republic and gray slacks, said the last year was especially hard on staff members who worked hard to increase traffic even as the ax hung over their heads.

“I’m incredibly proud of how they stuck together during this tricky time,” he said, going on to note the punishing economics of the media business and the growing power of Facebook.

Next to speak was Gawker Media’s executive editor, John Cook. He said it was “insane” that Gawker had ended up in bankruptcy proceedings that had ensnared even its former editor in chief, A. J. Daulerio, while Roger Ailes is walking away from Fox News with a $40 million pay package after being accused of sexual harassment.

This got big applause. Less successful was an attempt to invoke Khizr and Ghazala Khan and their recent fight with Donald J. Trump.

“We just had a national conversation out of the D.N.C. when the father of a soldier who was killed in battle said to Donald Trump, ‘What have you sacrificed?’” Mr. Cook said. “Not that the sacrifices here come close to losing a loved one, but it is a sacrifice to be a 23-year-old kid and to find your name on a complaint from Hulk Hogan.”

After that came a toast from Gawker’s president and general counsel, Heather Dietrick, along with more remarks from Mr. Denton, who then made his way back to the bar.

Many openly discussed the court-supervised auction of Gawker scheduled to take place next week. The media publisher Ziff Davis has made an offer of $90 million. Party guests discussed other possible suitors as well.

“At this point, you’ve probably heard more than I,” said Tom Scocca, the features editor of Gawker Media. “Ziff Davis has put their name on it, that’s the only thing I know.”

In the early years of the site’s existence, Mr. Denton was a hard man to read, seemingly emotionless, with a religious devotion to truth and a seeming indifference to humanity.

“This was at the heart of my conflict with Nick,” Mr. Sicha said after watching Mr. Denton speak.

But at the party, it seemed to Mr. Sicha that something had shifted or that he had misjudged his former boss.

“I don’t know if we didn’t get Nick early on, or if he just opened up,” Mr. Sicha said. “People always said that he was this cold, heartless person, and it either wasn’t true then or it isn’t true now.”

Nevertheless, Mr. Denton remained defiant. He stood in a sea of current and former employees, and he was talking about Gawker as if it were the only media entity on earth with guts enough to take on the powers that be.

“The economy’s going to be dominated by a dozen monopolies, and people who have their share of the monopoly profits are going to be able to buy the press and use the court system to their advantage,” he said.

Mr. Denton and others in the fold seemed somewhat less inclined to address the mix of admiration and contempt journalists hold toward Gawker, recognizing it as both a training ground for gifted young writers and a place where too many of the articles published were not only mean but inconsequential.

“I don’t think there’s many people who work at Gawker who think it is beyond reproach,” Mr. Scocca said. “But when you’ve been put through a show trial, there’s not a lot to be gained from adding to that testimony.”

Toward the end of the party, the scent of Parliaments and Camel Lights filled the room, and Mr. Denton walked around basking in the affection of his troupe.

It was hard to see him as the gossipy Julian Assange-like character he had once been. He had tears in his eyes as he made the rounds, and he seemed, finally and completely, human.