Bill Simmons Rick Reilly

Bill Simmons has had a long and storied rivalry with Rick Reilly, so it’s interesting that the comparisons between them are getting easier and easier. Reilly became a star at Sports Illustrated, then left for ESPN for a big contract (reportedly $3 million annually) and a chance to be a cross-platform presence. Simmons became a star at ESPN, and while he didn’t particularly choose to leave (they opted not to renew his contract following a bunch of controversies), he also landed a massive contract (reportedly $7 to 9 million annually over three years) and a chance to be a cross-platform presence at HBO.

Reilly’s time at ESPN didn’t go well at all, though, and while it’s still early in Simmons’ HBO tenure, the cancellation of his Any Given Wednesday show Friday is troubling. That cancellation came after lousy ratings, an identity crisis, just five months and only 17 of a planned initial 37 episodes, and it may be a bad sign for his fit there. HBO certainly still has the chance to have Simmons’ tenure be much beneficial for them than Reilly’s was for ESPN, but if his other projects find Any Given Wednesday‘s lack of success, the comparison may get more and more accurate.

It’s worth noting that Reilly’s failure at ESPN also started with a cancelled interview show, as Jim Weber discussed at AA back in July:

When he left SI for ESPN for a reported $3 million per year, Reilly was very open about his eagerness to be on television.

“I’ve always wanted to see if a well-written piece could work on TV,” said Reilly at the time. “I’ve been itching to do something different. It’s such a perfect job, I figured I’d try it. I hope I’m not Shelley Long leaving ‘Cheers.’”

Reilly was literally everywhere at ESPN. He wrote for ESPN.com and the magazine, contributed to “SportsCenter” and the network’s golf coverage and even had his own show, “Homecoming,” which was supposed to be the second coming of Roy Firestone’s critically-acclaimed “Up Close.” Instead, it was yanked off the air after 13 episodes in a sign of things to come.

It became clear very quickly that Reilly no longer had interest in being a journalist; he wanted to be a talking head. He’s not alone. Plenty of sports journalists have abolished writing for TV gigs on ESPN. But unlike Tony Kornheiser or Skip Bayless, Reilly was neither funny nor polarizing; everyone agreed that his comedic shtick was predictable and tired.

His back-page column for ESPN the Magazine was terrible and my coworkers wondered aloud, “Can you believe he’s making $3 million per year for this?” Reilly’s work for ESPN.com and the network wasn’t much better, as one-liners were more likely to induce groans than guffaws.

Again, just because Reilly’s tenure at ESPN was a failure doesn’t mean that Simmons’ tenure at HBO will be a failure. Reilly had one particular skillset, writing humorous back-page columns for Sports Illustrated, and he proved utterly unable to go beyond that during his tenure at ESPN. Simmons has already proven that he has multiple skillsets, from columns to podcasts to documentaries to personality-driven sites and TV appearances (although the latter came with mixed results), and so he should be able to provide some value for HBO in other arenas. His documentary value in particular may be important; if Simmons can help HBO regain some traction against ESPN in that space, he may be worth all the money they’re paying him. HBO certainly still sounds high on him from their comments Friday, and that’s a good sign for him.

It’s worth noting that nothing Simmons has done at HBO yet has been a great success, though. The Ringer has had some successes, but hasn’t caught on quite in the way that Grantland did, and it’s only partially an HBO project. Any Given Wednesday turned out to be a spectacular failure, which led to its cancellation this early. HBO Now show After The Thrones has worked out decently, but that’s about it to this point. Can Simmons turn it around? That’s certainly possible, and he definitely hasn’t hit Reilly’s level of repeated failures yet. However, if his next projects at HBO don’t meet with more success, comparisons between Simmons and the man he used to mock may become more and more apt.

[Photo from The Big Lead]

About Andrew Bucholtz

Andrew Bucholtz is a staff writer for Awful Announcing.