Bill Simmons and Colin Cowherd have each done okay for themselves in the sports media world. Simmons, 55, is the founder and CEO of The Ringer, a website and podcast network, while Cowherd, 61, hosts his popular show The Herd on Fox Sports 1 and is also the founder of "The Volume" sports media network.
On top of their success, what the two also have in common is a similar career arc, each having worked at ESPN for a time—Simmons from 2001 to '15 and Cowherd from '03 to '15. While the network was certainly paramount to their achievements, Simmons took an appearance on Monday's edition of The Herd with Cowherd to take quite the dig at their former employer:
"Look at this!" he exclaimed. "Two guys that used to work for the Worldwide Leader [ESPN's nickname] still doing well. Funny how that happens, huh?
"Everyone says, 'Oh you can't leave there!'" he continued. "'Oh no! Can't leave the Worldwide Leader! Your whole life's gonna fall apart!' Guess what? We're fine."
"We've done O.K.," Cowherd answered with a wry smile on his face. "We've done O.K."
"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
Seems as though there's still plenty of animosity towards ESPN—at least from Simmons' side.
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This article was originally published on www.si.com as Bill Simmons Takes Pointed Jab at ESPN in Appearance on Colin Cowherd's 'The Herd'.
