Bill Simmons and Colin Cowherd are living proof that leaving ESPN is not a career death sentence, and they wear it proudly.
It’s not uncommon for someone to find success after ESPN, but there was a time where sports media talent feared there may not be life beyond the Worldwide Leader. Simmons and Cowherd weren’t the first to build successful post-ESPN careers, but they are two notable examples.
Monday afternoon, Simmons joined Cowherd’s Fox Sports Radio and FS1 show to discuss his Boston Celtics docuseries that premiered on HBO earlier this month. And before saying goodbye, the founder of The Ringer took a moment to boast about their post-ESPN success.
“Look at this! Two guys who used to work for the Worldwide Leader, still doing well. Funny how that happens, huh?” – Bill Simmons with Colin Cowherd pic.twitter.com/g6kUfRNt3Y
— Awful Announcing (@awfulannouncing) March 24, 2025
“Look at this! Two guys who used to work for the Worldwide Leader, still doing well,” Simmons noted. “Funny how that happens, huh? Everyone says, ‘Oh you can’t leave there! Oh no, can’t leave the Worldwide Leader! Whole life is gonna fall apart!’ Guess what, we’re fine.”
Many sports media personalities have left ESPN and found success on another network or platform. But years and decades ago, there was a bit of a stigma associated with leaving a sports brand big enough to warrant the nickname “Worldwide Leader.”
Cowherd and Simmons both departed ESPN in 2015, with their tenures ending unceremoniously. Simmons exited as ESPN opted not to renew his contract. Cowherd’s ESPN career ended with a suspension, albeit after he already announced plans to leave for Fox Sports.
A decade later, Simmons just re-upped with Spotify, five years after they purchased The Ringer from him for $250 million. Cowherd launched a podcast company in The Volume that he says received a valuation of more than $100 million two years ago, and he recently signed a new contract with Fox Sports. Simmons and Cowherd left ESPN, and they’re both doing better than “fine.”
