Are you dating a Fox News spy? Read it at Gawker, as the news site careens toward bankruptcy sale

Nick Denton, founder of Gawker Media, in a Florida courtroom in March.

By Matt Pearce

Aug. 10, 2016 4:25 PM PT

Gather ’round, readers. It is time to soak up Gawker Media’s final days of freedom before the irreverent, influential and financially doomed media company goes up for sale next week.

As of Wednesday morning, tucked between the site’s daily news bulletins, you can find the following headlines at Gawker.com, which you will never, ever find in the Los Angeles Times:

“Please Stop Asking For Shrek Nudes”
“Signs You Are Actually Dating a Fox News Spy”
“It Has Been 17 Months and Counting Since Donald Trump Last Took Off His Jacket, According to My Research”

Gawker has good reason to be extra weird right now. The end is nigh.

They are the loudest and meanest and oftentimes most brilliant, in my opinion, news media outlet on offer.

— Brendan James, journalist who often covers the media

The staffers at New York-based Gawker Media, whose digital properties include Jezebel, Deadspin and Gizmodo, planned to hold a party Wednesday night to mark “14 years of independent journalism” — and their potential end at a bankruptcy auction next Tuesday morning.

Gawker stands out as the Internet’s loudest and most adversarial independent news outlet in an era when the power of publishing extends to everybody, with few limits. The feeling that writers were taking on the topics nobody else wanted to touch—stuff readers would never see in stuffier, more traditional outlets—was the source of Gawker’s popularity and, ultimately, its undoing.

Gawker Media got torpedoed by more than $140 million in legal damages after its flagship site published a sex tape of pro wrestler Terry Bollea, known to the world as Hulk Hogan, and Bollea won a lawsuit in Florida.

The company then filed for bankruptcy protection, as did its British founder, the former Financial Times journalist Nick Denton.

So it could be goodbye for Denton’s reign over an empire that started as a gossip blog about New York media — often small-fry stuff that infuriated its targets but made for great lunchtime reading for people with stuffy office jobs.

Gawker Media offered new writers a chance, and it offered them the opportunity to say almost anything they wanted to say, as long as it was interesting.

“It was like a place that always gave people a shot, who other places would maybe not give a shot to — people who weren’t maybe professional writers by trade, hadn’t gone to J-school, didn’t have a reporting background, but had a funny perspective,” said Erin Gloria Ryan, a former managing editor of Jezebel.

Ryan was working in finance in Chicago when Jezebel hired her — because it liked her comments beneath Jezebel stories.

Some of Ryan’s most popular posts included “How to Tell the Difference Between All the Dudes Running for President,” “What We’re Really Talking About When We Talk About Hillary Clinton Without Makeup,” and a reported story about a college rugby team that had chanted about rape, necrophilia and violence against women.

“When I talk to people who worked there, we had the same lament: that we were spoiled, we didn’t know what we had when we were there,” Ryan said. “Most places are not like that. It was really singular in the amount of freedom that we had.”

Over the years, Gawker grew into a nationally read publication whose alumni can be found everywhere, from such legacy media like the New York Times and the New Yorker to cutting-edge digital operations like Vox Media and the annotation site News Genius.

It influenced the way younger writers now write online. Its predominant literary influence seems to be Slack or Gchat, with posts often written in the voice of an ultrasmart twentysomething trashing a more successful enemy while trying not to come off like too much of a snob.

Gawker has unmasked trolls, brought down congressmen and embarrassed captains of industry in Silicon Valley by publishing the kind of exposes it published about business tycoons in New York. That, in a true tabloid turn, is what led to Gawker’s demise at the hands of tech investor Peter Thiel.

It was recently revealed that Bollea’s suit against Gawker was the culmination of a secret, years-long vendetta by Thiel, cofounder of PayPal, whom Gawker outed as gay back in the 2000s. Thiel later admitted to secretly bankrolling legal action against some of Gawker’s more questionable posts — including Bollea’s.

Thiel was “a malevolent supervillain” who waged “a covert legal war against us for a decade,” Deadspin editor Tim Marchman said.

“We have a lot of heads mounted on the wall that I’m pretty proud of,” said John Cook, executive editor of Gawker Media. “If you’re a Wall Street billionaire, you understand that when you acquire power and you wield it, that there’s people whose job it is to try to check that. … Peter Thiel decided it wasn’t part of the deal.”

Gawker’s willingness to publish seemingly anything made it a long list of enemies, not just Thiel. “If any outlet was going to get in trouble and create this year’s or even this decade’s 1st Amendment freedom-of-the-press case, it was going to be Gawker,” said Brendan James, a New York-based journalist who often covers the media.

“They are the loudest and meanest and oftentimes most brilliant, in my opinion, news media outlet on offer,” he said.

Gawker’s aggression stemmed in part from the fact that Denton’s ownership meant it didn’t have to worry about irritating the powerful.

“You have all these new places popping up like Buzzfeed and Mashable that are funded by Silicon Valley,” James said. “Basically they are doing news and real journalism until their [venture capital] backers say it’s not worth it.” (Buzzfeed’s news operation is going strong, but Mashable recently slashed its corps of news reporters.) “I think that honestly is going to be the largest thing that affects media.”

Some staff at Gawker Media are upbeat about next week’s sale, which could draw a range of interested investors and media companies. Some industry analysts expect that the next owner (or owners) will be interested in maintaining the sites’ nervy and independent perspective on the news, because that’s what had made them successful.

“Next week we’ll probably have some pretty good news about where we’re going, and if we don’t, we don’t. That’s the nature of journalism,” Marchman said.

Either way, “there’s definitely going to be changes, whether we’re going to be bought by awesome new owners or horrible ones,” he said.

Denton may still play some role in the next version of Gawker Media. Publishing company Ziff Davis has expressed interest in buying the company and “has said Nick [Denton] will be a consultant there if they win the auction,” said Gawker spokesman Davidson Goldin.

One thing appears clear. While it may not be the end of the road for Gawker, “it is the conclusion of the ‘independent’ phase of Gawker Media’s life cycle,” Cook said.

“The mood is, I don’t know, stoic,” he said. “There’s a number of different scenarios, and hopefully we’ll end up in the hands of a company that values what we do and wants to help us keep doing it.”

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@mattdpearce