While there are lots of potential landing spots for Bill Simmons, there hasn’t been much talk yet about which companies have actually made solid pitches to him. It looks like HBO has entered that camp, though, and it sounds like acquiring Simmons might be a big part of the network’s strategy going forward. Lacey Rose of The Hollywood Reporter wrote a big cover story on HBO that went live online Wednesday, and Simmons was important enough to be mentioned on the cover and make the online title, “HBO’s Real-Life Game of Thrones: The Fight to Stay Rich, on Top and Score Bill Simmons.” Most of the piece is more aimed at those curious about HBO’s changing business model (particularly with their new over-the-top HBO Now service that doesn’t require a cable subscription) and their various programming strategies, but the part on Simmons will definitely interest sports fans:

On June 21, HBO will add a pair of testosterone-fueled new editions — Dwayne Johnson’s sports dramedy Ballers and the Jack Black-Tim Robbins political half-hour The Brink — along with a second installment of the drama juggernaut True Detective. And the network will ramp up from there, with plans for more of the addictive Robert Durst docuseries, a not-yet-announced 1970s porn drama from The Wire’s David Simon and, if all goes as planned, a platform for ESPN cast-off Bill Simmons. While HBO executives are staying mum, multiple sources tell The Hollywood Reporter that the network is in talks for a major multipart deal with the biggest media personality in sports (more on that later). …

[HBO programming chief Michael] Lombardo won’t rule out other talk shows, too, particularly if the right personality comes along. Though he’s tight-lipped about names on his wish list, he acknowledges the soon-to-be available Jon Stewart would hold appeal. “Trust me,” he says, “I’ve already had a very polite conversation.” Considerably more likely is Simmons, whom the network is said to have made a big play for after his unceremonious booting from the more corporate ESPN. Such a move would be straight out of the HBO playbook, which famously provided a creative reprieve for former ABC flameout Bill Maher many years earlier. Though Simmons is said to have several suitors, insiders say con­versations at HBO have focused on a TV show — something Simmons is believed to want — along with heavy digital extensions that make the prolific personality tailor-made for the HBO Now era.

A talk show for Simmons would certainly be an interesting step. At first glance, that seems a little outside the box, but it’s not really that different from the televised podcasts he did at Grantland or the more recent Grantland Basketball Hour on ESPN. That also might fit with Simmons’ apparent desire to have a big TV presence, and it might be free-form enough to work well for him. It might turn into important content for HBO, too; as we’ve discussed before, Simmons has an incredibly loyal fanbase, and that’s largely a young fanbase who might well follow him to HBO, especially in an era where HBO Now is available without a cable subscription. It’s notable as well that HBO is much better than many of its competitors at allowing you to watch programming whenever, through services like HBO Go and HBO Now. That might be a good fit for someone who’s coming in from a column/podcast world where his audience engages with his content when it works for them.

Given Simmons’ involvement with ESPN’s 30 for 30 documentaries, work on HBO’s sports documentaries also might be a natural fit for him. HBO Sports president Ken Hershman wouldn’t comment on Simmons when AA’s Ben Koo asked about him earlier this month, and HBO’s 2011 decision to close its in-house unit might make it more difficult to find a role on that side for Simmons, but HBO regularly features content from filmmakers like Peter Berg who have worked with Simmons before, and involving Simmons in analyzing outside pitches, deciding which ones to pursue and potentially even working with the filmmakers would only seem logical. It’s notable that Simmons has made several comments in the past about how HBO’s dominance of the documentary space inspired his work with 30 for 30 and convinced him to challenge them. Simmons is strongly opinionated, and his past criticisms of HBO’s recent documentary direction might not go over well with everyone, but he might also be able to bring a fresh perspective and some of what he learned from 30 for 30 to help HBO recapture a larger slice of the sports documentary market.

The biggest question about a potential Simmons to HBO move may be what happens to his written and podcast content. If he has a regular talk show and is involved in documentary production, perhaps that’s enough work for him, and perhaps it means he doesn’t feel the need to crank out columns or podcasts. If he did want to keep doing those, though, there doesn’t seem to be a natural fit for them at HBO, and that might work against them compared to a company like Turner that could use written and podcast content as well as TV content. Something to keep in mind here is that HBO doesn’t always need to have talent work with them and only them, though; it’s possible to imagine a deal where Simmons does work for HBO and someone else, or where he runs his own website on the side with perhaps some venture capital funding. There are lots of questions still to be answered about any potential Simmons-to-HBO deal, but this is certainly an interesting possibility, and it sounds like one that not only might work out for both him and the network, but one that’s also being actively explored by both. We’ll see if anything comes of this, but it’s definitely something to keep an eye on.

About Andrew Bucholtz

Andrew Bucholtz has been covering sports media for Awful Announcing since 2012. He is also a staff writer for The Comeback. His previous work includes time at Yahoo! Sports Canada and Black Press.

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