Bill Simmons was re-apexing, but he’s now experiencing one of the top seven falloffs of all time. The sports columnist turned media empire empresario has had a hell of a week, catching flak first from his own colleagues for his adoption of artificial intelligence—first as a bit and then as a sponsor—and from regulators for openly discussing proxy betting. But all of Bill’s problems stem from the same starting place: his uncritical allyship with tech companies.
Simmons has, to his credit and certainly to his benefit, always been ahead of the curve on tech adoption. People call him the Podfather because he was one of the earliest people to…
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