Saying that Deadspin isn’t anything near what it was once likely won’t draw much argument. But in its heyday, the site made a significant impact in sports media and was extremely popular with reports like Brett Favre sending explicit texts to Jenn Sterger and revealing that the story of Manti Te’o’s dead girlfriend was a hoax.
Former Deadspin editor Tommy Craggs and writer Drew Magary appeared on Dan Le Batard’s “South Beach Sessions” podcast to reminisce about the site’s legacy and the sequence of events leading up to both leaving Gawker Media. Both discussed Deadspin’s role in disputing ESPN’s dominance of the sports media marketplace and giving voice to fans who felt they weren’t getting the whole story.
Le Batard has his own issues with ESPN, resulting in him leaving the network to start his own venture, and expressed admiration for Deadspin’s fearlessness, anger, and willingness to be brutally honest, perhaps best demonstrated by Magary.
“The thought was we need to be the site that’s referenced instead of the thing doing the referencing,” said Magary. “That’s how you get a bigger, more lasting audience.”
Drew Magary on Deadspin’s evolution as a site: pic.twitter.com/QUcrMnIbdR
— The IC Workstation (@ClippelBoardy) February 11, 2021
(By the way, Magary revealed that he and Craggs talked to Le Batard back in December, but Le Batard didn’t want to post the conversation until he left ESPN.)
But Craggs nearly went to work for ESPN — more specifically, for Bill Simmons’ Grantland site — until it became clear to him that working for a large corporate entity wasn’t for him. Le Batard asked him to recount that experience, which doesn’t include the most flattering portrayal of Simmons.
“He spent the first 10 minutes on a soliloquy about who the hottest woman to come out of Boston was,” Craggs recalled. “I think it was between Maria Menounos and… I can’t remember the other. Obviously, I have very different sensibilities from him.”
Former Deadspin editor Tommy Craggs remembers meeting with ESPN and Grantland about working for them: pic.twitter.com/lKjh423ThI
— Ian Casselberry (@iancass) February 11, 2021
Craggs did go on to praise Simmons’s editorial taste for writers different from him before skewering him for what he’s become in regards to unions and workers’ rights. You can read far more about Craggs meeting with ESPN executive John Walsh here.
That probably sums up what made Deadspin so appealing. Editors like Craggs appreciated good writing — and produced good work himself — but also aimed at big targets that deserved to be taken down for their actions and disingenuous public personas.
Unfortunately, Deadspin’s best days keeping drifting further into the past. Craggs left Deadspin more than six years ago. It’s been more than a year since the remaining staff left. Defector has revived the site’s best traits and sensibilities, but will it ever hit that same sports culture and media criticism sweet spot?
However, the fact that Le Batard felt compelled to look back speaks highly of the site’s legacy and continues to set a bar that other sites — including Awful Announcing — strive to reach. That is certainly worth remembering — and celebrating.