We may be facing the final end for Deadspin as we know it, which is a perfect occasion to look back at its beginnings. Deadspin founder Will Leitch recently joined the Log Off podcast and discussed the start of Deadspin at Gawker Media in 2005. In the interview, he revealed that Gawker originally tried to hire a more established voice to run the website with Leitch as a No. 2. That short list included none other than Bill Simmons.
Of course, Simmons turned down the opportunity and Leitch went on to build Deadspin into one of the most revolutionary sports outlets in media history. But the revelation that Simmons could have taken over the site in its infancy is a fascinating what-if.
“They all turned it down, so they came to me and said, ‘OK you’re cheap, if this thing doesn’t work, no one knows who you are anyway,” Leitch explained on Log Off. “It really felt like this was my chance to finally … do this exactly how I’d like to do it and not let anyone in the world stop me.”
But it could have been exactly how Simmons wanted to do it. Or, Leitch also revealed, fellow ESPN Page 2 writer Dan Shanoff or even the disgraced former baseball writer Jonah Keri.
At that time, Simmons had just returned full-time to ESPN after a pit stop writing for Jimmy Kimmel Live! He had not yet launched 30 for 30 and was years away from starting Grantland. He would admittedly have been a risky hire to run an entire website for Gawker.
But so was Leitch. And in the end, Leitch’s inexperience may have been his ultimate strength. Deadspin made its bones as outsiders critiquing and contrasting stodgy old sports media.
In the end, writers like Drew Magary and David Roth at Deadspin ended up turning Simmons himself into a target of the site. So it’s safe to say Deadspin probably would have turned into something entirely different with Simmons at the helm.
