Will HBO Stay in the Bill Simmons Business?

Next Tuesday, HBO will air an Andre the Giant documentary that has been receiving rave reviews and is a project that has been years in the making. Bill Simmons’ media group co-produced it with HBO, and it will be interesting to see whether this film is their first and last collaboration along these lines, or whether the relationship endures.

Simmons signed with HBO in July of 2015; a year later, USA Today reported that he had a three-year deal, which Hollywood Reporter pegged at $7-9 million per year. HBO was an investor in The Ringer; last December, when Simmons launched Ringer Films, HBO was said to have first pass rights on all its projects.

Any Given Wednesday, which was canceled after just five months, was a disaster any way you slice it. Simmons took full responsibility for this. “It just didn’t work,” he told Recode. “It was a gamble to some degree, because I’m not a performer. And I was hoping that an interview show would work. And I took a big swing, and it just didn’t work. And you just move on to the next one.”

He continued: “To me, the show — I knew it going in, because I did the interviews, and I said the same thing every time — ‘I’m not a performer. This is a show that if it works, it’s going to have to work because it’s really smart and has good interview content.’ I really believed, heading into the show, that there was a void for a new kind of smart interview show. Because there was Charlie Rose, and Howard Stern’s podcast interviews [and nothing in between]. And I think, you know … I just was wrong.”

The show may not have done better viewership if all it entailed were longform interviews with titans of sports and Hollywood — and we caught a glimpse of this in the Aaron Rodgers episode — but it would have been better received from a critical perspective. Instead, the show was muddled with awkward monologues and unfunny Michael Rapaport sketches.

Simmons was signed to HBO by Michael Lombardo, who stepped down from his role as the network’s head of programming before Any Given Wednesday launched. While Lombardo remained at HBO as a producer, it was a bad sign for Simmons there that the executive who brought him there was no longer in charge.

There have been successes and failures at The Ringer. The podcasts have undoubtedly been a big hit, and programs like the Game of Thrones postgame show resonated on Twitter. Recently, The Ringer’s CEO Eric Weinberger and Simmons made the “mutual” decision for Weinberger to leave the company following an investigation into alleged sexual misconduct that occurred during his time at NFL Network.

Now, the question becomes whether HBO will want to remain affiliated with The Ringer, its podcast network, and its films. With the caveat that this is speculation, my guess would be no.

One thing I would say, though, is never bet against Simmons finding a landing spot. Back in his days at ESPN, there were many years where he was the roadrunner and his detractors in John Skipper’s inner circle were Wile E Coyote. From 30 for 30 to Grantland to NBA Countdown to the Grantland Basketball Hour, he was always a step ahead of them. After his rocky exit from ESPN that was in the end attributable to persistent Roger Goodell criticism, Simmons got a raise and a hefty seed investment at HBO.

What that future landing spot would be is an open question. Eric Jackson at Forbes made the case last April for Simmons to return to ESPN; I’d never say never on that but it still feels a little soon, even if he is close with new president Jimmy Pitaro (when Pitaro got the job, Simmons tweeted, “Good hire by the Mouse”).

There are any number of digital entities Simmons and/or The Ringer could, conceivably, become affiliated with. They moved their publishing platform from Medium to Vox last year; maybe that could become a bigger partnership? Or, perhaps Yahoo/Verizon? Or what about The Athletic, which has shown interest in acquiring FiveThirtyEight from ESPN?

Or, perhaps Simmons could make videos for B/R Live? This is the streaming app that Bleacher Report just announced last week. There will be a lot of resources poured into this venture in the coming months. Bleacher Report’s parent is in the ideal position of being a broadcast partner of the NBA — Simmons’ specialty — and, for the time being at least, not being in bed with the NFL, whose leadership Simmons has an adversarial relationship with. During his HBO deal, Simmons has largely not appeared in The Ringer’s digital videos. There are a number of directions a collaboration with B/R Live could go, either with himself as an individual talent or also inclusionary of other Ringer staffers.

Whatever winds up happening, we are getting to the point where all this bears observing: Will Simmons and HBO part ways in July? If so, what’s next?