He was also fluent in what boorish men call "locker-room talk" (like when he told a reader that his friends "lost the ability to call themselves guys the moment they allowed a female in their football fantasy league"), but his brazenness about sports usually came off as bravery, and for that he became one of ESPN's most valuable stars.
Simmons is no stranger to a high-profile breakup. In 2015, the popular podcast host and media personality had a contentious exit from ESPN, which is also owned by Disney. He rebounded strongly and sold his sports and culture site, The Ringer, to Spotify for close to $200 million in 2020. Simmons said in the latest episode of his eponymous show, "The Bill Simmons Podcast," that Kimmel could similarly strike out on his own.