For years, Bill Simmons has made a career out of holding grudges in plain sight. Sometimes it’s the NBA MVP voters. Sometimes it’s NFL owners. And sometimes, it appears, it’s former executives.
Enter John Wildhack.
As Wildhack exits his post at Syracuse University, Simmons has taken not-so-subtle swings at the outgoing AD — most recently in reaction to Syracuse’s coaching moves and broader athletic department decisions. Simmons essentially delivered a “I told ya so,” about Wildhack’s tenure. To the casual fan, it might seem random. Why does a national podcaster care this much about Syracuse’s athletic director?
The answer traces back to Bristol.
Wildhack spent decades as a high-ranking executive at ESPN, overseeing production and helping shape the network’s content strategy during the same era Simmons was building Grantland and becoming one of ESPN’s most powerful voices. But Simmons’ time there didn’t end cleanly. After repeated public criticism of NFL commissioner Roger Goodell, he was suspended in 2014 and eventually left the network in 2015. Officially, it was framed as creative differences. Unofficially? It was a power struggle.
Wildhack was part of the executive structure during that period. He was part of the corporate side of ESPN — the side that reined Simmons in.
Fast forward to 2026. Wildhack is wrapping up his tenure at Syracuse after a turbulent stretch that included football instability and fan frustration. Simmons, meanwhile, is still Simmons — independent, influential and never shy about circling back to old grievances.
Simmons recently reacted to Syracuse’s situation and even referenced Wildhack while discussing UCLA hiring Bob Chesney. Simmons is a Holy Cross grad and Chesney turned around his alma mater’s football program. Simmons is making fun of the fact Syracuse and Wildhack didn’t hire Chesney. The tone wasn’t neutral. It wasn’t detached. It was pointed.
That’s kind of Simmons’ brand.
This will be a one-sided rivalry. Wildhack isn’t going to fire back on podcasts. But there’s clearly residue there. Simmons doesn’t forget who was in the room when his ESPN tenure ended. And Wildhack, as a longtime executive, represents that era of corporate oversight that clashed with Simmons’ freewheeling style.
For Syracuse fans, it’s another subplot in a messy administrative chapter. For media watchers, it’s a reminder: in sports media, nothing ever really disappears. Old tensions just wait for a new headline.
And if there’s one thing Bill Simmons loves, it’s revisiting history — especially his own.
