Bill Simmons and Colin Cowherd exemplify that leaving ESPN is not a career death sentence, and they embrace it wholeheartedly. While it’s common for individuals to find success after their time at ESPN, there was once a prevailing fear among sports media talent about life beyond the “Worldwide Leader.” Though Simmons and Cowherd weren’t the first to carve out successful post-ESPN careers, they stand out as two significant examples.
On 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. Before signing off, Simmons proudly highlighted their accomplishments after leaving ESPN.
“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 remarked. “Funny how that happens, huh? Everyone says, ‘Oh, you can’t leave there! Oh no, can’t leave the Worldwide Leader! Your whole life is gonna fall apart!’ Guess what, we’re fine.” Many sports media personalities have departed ESPN and thrived on other networks or platforms. However, years ago, there was a stigma attached to leaving such a dominant brand.
Both Cowherd and Simmons exited ESPN in 2015, with their departures marked by little fanfare. Simmons left as ESPN chose not to renew his contract, while Cowherd’s exit was overshadowed by a suspension, despite his plans to transition to Fox Sports.
Fast forward a decade, and Simmons recently re-upped with Spotify five years after selling The Ringer for $250 million. Meanwhile, Cowherd established a podcast company, The Volume, which he claims was valued at over $100 million two years ago, and he has recently signed a new contract with Fox Sports. Both Simmons and Cowherd left ESPN and are flourishing well beyond mere “fine.”
