“It’s the most ambitious project in our 15 years,” Greenwell explained, later noting that it would be entered in several film festivals.
Afterward, Will Leitch, who founded Deadspin in 2005 and attended the screening, couldn’t help but chuckle.
“It was very earnest,” he said. “That’s a little different.”
Leitch started the site writing 40 posts per day from his Brooklyn apartment. Deadspin, then part of the Gawker network, quickly grew into the Internet’s most influential sports blog.
And in its early years, Deadspin was an irreverent boys club.
It called out the stuffiness of ESPN’s analysts and exposed network executives for having an extramarital affair; it introduced something called “telestrator dong;” and it paid $12,000 for pictures of Brett Favre’s genitals, posting them against the wishes of the woman who received them.
As its national profile grew exponentially, it also suffered from charges of sexism and homophobia, crossing journalistic lines and moral lines — with few apologies.
Greenwell, 35, was hired last February. She is not just the site’s first female boss, but as a former editor at Esquire, ESPN the Magazine and New York, she comes from the traditional media that Deadspin built its reputation mercilessly mocking.
“I remember sometimes feeling uncomfortable because it felt very specifically not for me,” Greenwell said. Years ago, she wrote a Tumblr post that questioned the site’s lack of female voices. “But the heart of the mission today is the same: to call out hypocrisy in sports wherever it is.”
These days, the most shocking and paid-for scoops in sports typically are found at TMZ, while a coterie of other outlets and reporters thoroughly cover ESPN and provide the media criticism Deadspin made famous. Deadspin has evolved into an unabashedly progressive voice in sports and beyond.
The site, with its more than 20 editorial employees, writes about barriers of entry in an industry dominated by white men; it makes important corrections when sportswriters fumble coverage of domestic violence; and it regularly offers vivid rebukes of President Trump.
Perhaps most differently, Deadspin now critiques other sites around the Internet for their crude behavior. Several writers — Leitch, who now writes for New York Magazine, among them — have apologized for their past writing.
“[Take] a good hard look at the man you’ve been, and ask if that’s really the man you want to be,” wrote longtime columnist Drew Magary, who once drew the ire of GLAAD for his own homophobic insensitivity.
If Deadspin was once the place on the sports Internet where guys went to goof on the establishment, the site now crusades for more inclusive, more evolved sports journalism. And that leaves outlets still courting that same audience pining for the older, bro-ier version of the site — and also wondering exactly what crime they’re committing.
“They’ve gone from irreverent and zany and fun — from speaking for the regular sports fan — to painting themselves into a woke corner,” said Clay Travis, a former Deadspin editor turned Deadspin target as a Fox Sports radio host popular with conservatives. “They said I’m going to hell — for what I say about sports!”
Deadspin is currently for sale by parent company Univision, but even as it wrestles with the uncertain economics of digital media, there is a more fundamental question for the site. The enfant terrible has grown up: Is the new version righteous or self-righteous?
'It's a new voice'
In the beginning, Deadspin had a motto: Sports news without access, favor or discretion. When Leitch founded the site, ESPN singularly dominated sports coverage and conversation, and much of it, he believed, was too self-serious. His conceit was to be the anti-ESPN, reporting on the press-box gossip that never made it to print.
For instance: Deadspin reported on Michael Vick using the pseudonym Ron Mexico when he sought medical treatment for herpes.
Deadspin’s timing was perfect. In the early days of the Internet and camera phones, the site became a clearinghouse for athletes — and media members — behaving badly (or sometimes just hilariously): USC quarterback Matt Leinart drunk and partying, ESPN personalities leaving voice mails for women.
Over time, the reporting turned more pointed and adversarial. Editor A.J. Daulerio, who replaced Leitch, wrote in 2008 about late-night text messages that married ESPN host Stuart Scott sent to a cheerleader; later came a series titled “ESPN: Horndog Dossier.” (Daulerio would go on to edit Gawker when Hulk Hogan successfully sued for invasion of privacy; Univision then bought the site.)
The cash for the Favre photos in 2010 put Deadspin in a new category of notoriety, and in 2013 the site broke the story of how Notre Dame star Manti Te’o’s deceased girlfriend, a story line in several media outlets’ profiles of the player, in fact had been invented by online pranksters. The story was one of the biggest bombshells in sports over the past decade, and a co-author, Jack Dickey, now works for Sports Illustrated, while other Deadspin alumni now work at places such as the New York Times and The Washington Post.
Cruelty, though, was as much a calling card as any Deadspin innovation, and women and minorities were frequently the targets. ESPN’s Bomani Jones worried that the site’s attitude toward race encouraged the racism of the “angry white man.” And there were posts that mocked the weight and appearance of women, from a high school football player to a Fox Sports sideline reporter. “Charissa Thompson continues down suicidal path to frumpyville,” read one headline of the more PG variety.
In 2008, Leitch appeared on a panel on an HBO show hosted by sports commentator Bob Costas about sports writing on the Internet.
“I think blogs are dedicated to cruelty,” said panelist Buzz Bissinger, author of “Friday Night Lights.”
“It’s a new voice,” Leitch said.
“It’s a disgusting voice,” Bissinger replied.
The outlaws go straight
During the summer of 2011, a paparazzi photographer snapped a picture of New England Patriots quarterback Tom Brady’s toddler son naked on the beach. Deadspin didn’t publish the photo, but another site did. “Check Out The Howitzer On Brady’s Kid,” read the headline on Barstool Sports.
For Deadspin, it raised a question: What if there were places on the Internet willing to tell dirtier jokes than it was?
“It was hard for [Daulerio] to say that there was something beneath us, and in that way, there was some ground ceded to Barstool,” former Deadspin editor Tommy Craggs said.
Deadspin would go on to address the lack of gender and ethnic diversity on its staff — including naming Emma Carmichael managing editor in 2013 — but there was another, more gradual dynamic: In a changing world, the outlaws went straight.
As the #MeToo stories swept journalism, some of the content that made Deadspin popular went from a source of inspiration to a source of embarrassment. The site “has a disgusting past that can never be atoned for,” wrote Diana Moskovitz, a current Deadspin staffer who has reported extensively on domestic violence.
And with it have come mea culpas from Deadspin writers.
Magary: “I did gay jokes. I did rape jokes. . . . I don’t want to make those jokes anymore.”
Longtime deputy editor Barry Petchesky: “There was a fat joke. There was an anorexia joke. . . . Men (cis, straight, white, neurotypical) have it so . . . easy.”
At the same time, Barstool Sports has, if anything, moved in the opposite direction. Founded in the Boston area a few years before Deadspin, Barstool always has trafficked in an aggressive fratiness with none of Deadspin’s hipster smugness. And as Barstool has continued to insist that sports should remain free of all political correctness — one of its slogans is “Saturdays are for the Boys” — the company has grown markedly, netting a $25 million investment from media holding company The Chernin Group. It now produces some of the most popular sports podcasts in the industry, and huge stars such as Cleveland Browns quarterback Baker Mayfield appear as guests.
Barstool also continues to host some of the Internet’s least tasteful jokes. “Is Rihanna Going to Make Being Fat the Hot New Trend?” read a post that was ultimately taken down (and the writer was later fired). Its fans have harassed female journalists, and when ESPN commissioned a Barstool show in 2017, it was canceled after a single episode amid furor over a professional association with a site whose founder, Dave Portnoy, had said an ESPN host should “sex it up and be slutty,” among other degrading comments.
Deadspin has covered Barstool’s travails exhaustively, but Portnoy offers no contrition and considers the criticism hypocritical scolding.
“Can you write one thing that says disregard everything that built me up and made me famous and say none of that counts?” he asked. “And now I can criticize other people for making the same jokes?”
Travis, who worked as a Deadspin senior editor in 2008, has since gone on to found his own site, where he sells T-shirts with the acronym “DBAP,” short for “Don’t Be a P----,” and has made a name for himself accusing ESPN of liberal bias.
“They want to be some kind of moral arbiter, but whose morality?” he said. “They really sound like a parody of being self-serious.”
Greenwell pushes back at that critique, even as she occasionally embodies it. When explaining that she lives in Brooklyn’s Williamsburg neighborhood, she added, “but the part where a lot of Puerto Rican families live.”
“I always want Deadspin to do the fun and silly,” she said. “But percentage-wise, it won’t feel like it did in the old days because the Internet is dramatically less fun.”
She added: “Trump ruined everything. Barstool ruined everything.”
Young, brash and female
On the afternoon of the documentary premiere, Laura Wagner sat on the roof of Deadspin’s office, the Manhattan skyline rising behind her. While Greenwell is in charge, Wagner, 25, has become Deadspin’s biggest lightning rod.
She has written exposés about the labor practices of SB Nation and Fansided — and how they make money off unpaid labor — as well as highlighted hiring barriers that make it more difficult for low-income people to break into sports journalism.
Wagner’s media criticism has rippled through the industry, prompting a Sports Illustrated senior writer to tweet, “you have repeatedly shown a lack of respect for writers who are far more accomplished than you,” a remark that could be seen as elevating her credibility as much as undermining it.
“Deadspin caters to the smartest people,” she said. “It’s the people with the best sense of humor, giving you the smartest takes.”
Wagner was hired by Deadspin in early 2017, and her consistent coverage of Barstool has been particularly noteworthy — “She called me a sniffly raisin and an Adderall pill,” Portnoy complained — and has extended to those who treat the site or its personalities in ways she sees as giving it respectability.
After Charlotte Wilder, a Sports Illustrated writer in her 20s, hosted two popular Barstool personalities on her Web series, Wagner tweeted a link to the video with a message: “sports media advice for women: not this.” She also criticized Wilder in a follow-up piece for offering a friendly venue to joke about the canceled ESPN show.
“It was a strange feeling to be accused of being a bad woman in sports for associating with those guys,” Wilder wrote in an email about the backlash she received around the Internet. “For my whole career I’ve tried [to] be helpful and supportive of other women in the industry . . . [including] successfully advocating for sports media companies to hire more women.”
Wagner has little sympathy. Asked whether there was a goal to her coverage of Barstool, she said, “I want them to be seen for what they are, which is not a legitimate sports site.”
It is difficult to imagine a voice such as Wagner’s in the earliest iterations of Deadspin: young, brash and female. Whether the site can maintain and grow its audience with more progressive content is another question.
Deadspin says it already has, pointing to internal numbers that show monthly average visitors grew 18 percent between 2017 and 2018, reaching an average of 14 million unique monthly visitors. A viral video the site produced last year about the conservative agenda of Sinclair Broadcast Group has been nominated for a National Magazine Award. (According to media analytics company ComScore, average monthly unique visitors were up 7 percent between 2016 and 2018.)
Greenwell said Deadspin always will write funny posts with profanity in the headlines, but she sees growth for the site in the kind of big magazine features she has shepherded in her career. Her wish list, were she to sit down with a potential buyer, includes more reporting on business, women’s sports and sneaker culture.
“There is lots of coverage right now that still speaks to sports as the fun stuff away from the rest of the world,” she said. “Deadspin never does that and will never do that.”
She added: “There is a joke that when every new editor takes over that they ruin the site. I don’t want to be the one who ruins Deadspin.”