Bill Simmons was a Celtics fan before he became a media mogul. While Simmons became very famous, the Celtics weren’t doing so well. It was coach Doc Rivers who oversaw the not-so-good things. So Bill’s problem becomes Doc’s problem and vice versa.
This is what happens when one of sports media’s biggest stars cares deeply and openly about a particular team, and the person running that team isn’t trying to handle it all. It was awkward and chunky:
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