Ashley Feinberg trolls for all the right reasons

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A couple of days before Thanksgiving, Ashley Feinberg was sitting in a Manhattan bar, nursing a Bud Light and staring at her phone. A few hours earlier, Feinberg had announced she was giving up Twitter for the next six days, but she was getting twitchy as her hiatus from social media set in. One reason: She had just posted a deeply sourced story about an impending—and now published—Times exposé on sexual harassment at Vice. Her piece was beginning to make the rounds among media observers, and Feinberg was monitoring feedback to make sure she hadn’t gotten anything wrong.

But a more pressing concern was also on her mind: As the clock neared 8:15 pm, she was anxiously awaiting a tweet she had no control over, set to go out from her account. Feinberg had recently lost a bet with her editor at HuffPost, Tommy Craggs, who had won free rein to write and schedule a tweet in her name—which meant that, if she hewed to her Twitter hiatus, the tweet would sit, unexplained, at the top of her feed for a week.

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Feinberg, 27, has a kooky sense of humor and isn’t easily embarrassed, but what seemed like a playful wager was suddenly feeling a lot more serious. She cringed helplessly as Craggs’s message materialized online for all to see.

“I want to apologize for my recent tweet, which has been deleted,” read the cryptic note. “The joke was offensive and not at all funny—particularly in our current climate—and I deeply regret any pain I may have caused.”

Though Feinberg had done nothing wrong, she was still worried the message would bring trouble. “Right now, I’m anxious about people thinking I tweeted something super racist,” she told me, taking a swig of her beer. She sighed as a string of notifications began cascading down the screen of her phone, whose background was, somewhat creepily, a photo of Mike Pence and his family at the inaugural parade.

“This fucking tweet,” she murmured.

If Feinberg was nervous the joke apology would give her enemies reason to scrape her digital past for inflammatory pronouncements, it was probably because she’s carved out a beat for herself as one of journalism’s foremost chroniclers of internet fuck-ups. As it turns out, she would be compelled to apologize, for real, a little over a week later for a different tweet mocking an ailing John McCain and his family. But Feinberg’s faux pas was merely a social media blunder, whereas the dirt she’s dug up on others has been far more revealing.

Over the past few years, Feinberg has earned a reputation as a supremely savvy digital sleuth, capable of sniffing out embarrassing personal details left behind by public figures—mostly conservative—who haven’t adequately covered their tracks online.

***

THE VICTIMS OF HER SCRUTINY have included Donald Trump Jr., who likely wrote hundreds of posts as a member of an obscure online hunting forum (“My name is don and I’m a bowaholic,” the user, who goes by DJTJR, says in one message); Blake Farenthold, the Texas congressman whose puerile early-’90s internet message board posts are still online; Sebastian Gorka, whose Amazon wish list may or may not have contained a book called Be the Pack Leader: Use Cesar’s Way to Transform Your Dog…and Your Life; and James Comey, whose once-private Twitter account Feinberg discovered under the alias of Reinhold Niebuhr. (Feinberg currently has a Freedom of Information Act request out to the FBI to see if Comey used direct messages, which should have been filed as government records, in accordance with the Federal Records Act.)

“What she did to Comey she would be doing to Comey if she weren’t a journalist,” says Alex Pareene, the politics editor at Splinter who edited Feinberg when they worked together at Gawker a few years ago. “She’s such a strange sort of journalist who could only exist in this time period.”

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Feinberg isn’t the first reporter to master the art of digital spelunking. Adrian Chen, now a staff writer for The New Yorker, established himself as an estimable force at Gawker when he went lurking around in subreddits to unmask trolls. And the art of sifting through a Twitter timeline to root out gaffes—now a potent if bad-faith maneuver—was perhaps established a couple of years ago by Tom Gara of BuzzFeed, who almost ruined Trevor Noah’s reputation when he went back and found some distasteful tweets from Noah’s past before he took over The Daily Show. Still, Feinberg’s approach—covering the “internet’s funhouse mirror,” as Craggs puts it—places her on her own unique shelf.

“She’s sort of an anti-troll,” says John Cook, who worked with Feinberg at Gawker. “She uses the weapons of the troll for the forces of good.”

Feinberg didn’t set out to do that. Born in Dallas, she got her start in journalism, in 2011, as an intern at The San Antonio Current, a free alternative weekly, where she wrote, among other things, an analysis of Queen’s remastered albums. But she wasn’t long for music criticism. “Reading that now is deeply painful and, like, it is one of my least favorite things,” Feinberg told me, wincing. She moved to New York in 2012 and got a job at Gizmodo, where she started as an intern and worked her way up to a staff writer position, though she longed to move over to Gawker, which she found to be appealingly swashbuckling.

“I never knew anything about tech,” she admitted. “I lied profoundly in my Gizmodo interview. They asked me something about Android, and I tried to pretend that I knew what it was. I think the closest I got was, like, ‘It’s a type of phone.’ ”

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Former editors say they realized what weird potential Feinberg had when she published a surreal story for Gizmodo about the creepiest things you can do on Facebook, such as tagging yourself in someone else’s engagement photo and requesting a relationship status. “That really captures the extent to which she revels in making people uncomfortable,” Cook tells me.

It also hints at the obscure techniques Feinberg uses to locate incriminating information—on anyone. At Gizmodo, Feinberg became intimately acquainted with the advanced search functions of Google, Twitter, and Facebook—which she later put to use on more formidable targets—as she sought to embarrass her coworkers, in a playful way. Feinberg enjoys messing with her colleagues. She archives Slack conversations and—trigger warning—often sends nude photos of Shrek, via text message, to those she is close with. “That’s how Ashley says ‘hi,’ ” Craggs tells me affectionately. “With a Shrek dick.”

She’s sort of an anti-troll. She uses the weapons of the troll for the forces of good.

Feinberg’s highly ironized persona gives her the air of a digital-era Andy Kaufman, but she also has the capacity for earnestness. Cook drew my attention to one of his favorite pieces by her, a personal essay in which she describes, in heartrending detail, the difficulty of living through Father’s Day every year while having a dad who committed suicide when she was 14. For the most part, though, Feinberg excels at exposing hypocrisy through the digital crumbs most reporters overlook or can’t find—and while her scoops aren’t always earth-shattering, they do perform an important service at a time when our online selves can, at times, reveal more about our pasts than the things we’ve done away from the internet.

After much cajoling, Feinberg switched over to Gawker in 2015, where she worked for nearly two years before it went bankrupt as a result of Hulk Hogan’s now-infamous sex tape lawsuit, funded by the billionaire venture capitalist Peter Thiel. Feinberg still managed to file a number of worthwhile stories in her time there, like her investigation of Josh Duggar, the family values activist who was also, we now know because of Feinberg’s sleuthing, a paid member of Ashley Madison, “a web site,” Feinberg wrote, “created for the express purpose of cheating on your spouse.”

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“Finding that kind of stuff about conservatives is ideal to me,” says Feinberg, whose reporting tools include Nexis as well as an extension that can pull email addresses from LinkedIn, which makes it easier for her to dredge up hidden information because, she says, people typically use the same usernames across accounts. “I believe in my heart that they are all just driven by these suppressed neuroses they’re carrying with them, and so that stuff manifests itself online.”

After Gawker was shut down, Feinberg moved over to Deadspin and then worked for a bit on Gizmodo Media Group’s investigative desk. But the slow pace didn’t suit her iterative reporting style, and she found the environment depressing. “It felt like working on top of the remains of what I used to care very deeply for,” Feinberg tells me. She did a short stint at Wired, but wanted to write more about politicians, so she jumped to HuffPost, where she’s worked as a senior reporter on the enterprise team since October.

When she got the job, HuffPost Editor Lydia Polgreen announced on Twitter, in a message that got at the heart of her sui generis style, that Feinberg would be covering “the Ashley Feinberg beat: grotesques of the Trump era, weird stuff on the internet, Ted Cruz.”

In her short time at HuffPost, Feinberg has managed to file some stories that typify her absurdist approach. In one of her first pieces, she wrote about Ivanka Trump, whose recent romantically themed anniversary playlist on Spotify, Feinberg credibly surmised, may have been intended for coitus with her husband. In another piece, she published an eye-opening leaked copy of the 17-page style guide used by The Daily Stormer, the neo-Nazi website founded by Andrew Anglin.

***

FEINBERG’S IDEAL REPORTING GOAL, she tells me, is to uncover the seemingly apocryphal “pee tape” described in the Steele dossier on Donald Trump. If that doesn’t show up, Feinberg says that she would love, above all else, to “catch Donald Trump Jr. stealing valor,” the act in which a civilian poses fraudulently as a member or veteran of the armed forces. “Don Jr. humiliating himself in general is a good story,” she deadpans. Feinberg has also been scraping the internet, in vain, for the digital slime trail of Stephen Miller and Jared Kushner, who, she says, don’t have any sort of online presence, “which seems impossible given their age,” she tells me. “It’s driven me nuts.”

Feinberg says she misses Gawker’s buccaneer spirit—as do a number of journalists who make up the Gawker diaspora—but appreciates Polgreen’s “antagonistic” inclinations. She admits, though, that the Hogan suit has made her a little more cautious about hitting publish. Craggs told me that Feinberg was, ultimately, brought on to HuffPost to help expand the definition of what the media organization can be, as Polgreen works to reshape it in the wake of Arianna Huffington’s recent departure.

“It doesn’t really exist elsewhere, that kind of beat,” Craggs says of Feinberg’s coverage area.

Back at the Manhattan bar, in the East Village, Feinberg was on her second beer and still staring intensely at Twitter, despite the promise she had made to herself—and her more than 100,000 followers—that she wouldn’t be checking the site. As the fake apology began to get noticed, a string of replies was forming beneath her tweet—some concerned, others sarcastic, some sympathetic, a few just nutty.

When we’d parted ways, I checked Twitter to see if she’d broken her hiatus to clarify that the note wasn’t hers. She had. “I KNOW I said I was gone but I can’t take this anymore,” Feinberg wrote in response to the tweet, posting a screenshot of a text exchange revealing that Craggs had written it, thus violating the terms of the bet, which stipulated that the loser could make no allusion to the fact that the tweet was written by someone else. Then she gave her Twitter password over to a former colleague, who changed it so she would be effectively locked out for the remainder of her break.

If Feinberg appeared to be more flustered than usual, it also seemed she had gotten some perverse pleasure out of the prank—even though she was its target. “Making people mad or uncomfortable,” she told me, “is always a best case scenario.”

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Matthew Kassel is a freelance writer whose work has been published by The New York Times, The Wall Street Journal, and Slate.