In early June, Gawker posted a rumor regarding Bill Simmons and Jon Stewart – the biggest media free agent and biggest media free-agent-to-be – joining forces to start an online subscription network.

Wednesday, The Hollywood Reporter (redundant) reporter Lacey Rose wrote about how Simmons could land at HBO.

“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,” Rose wrote.

Buried in Rose’s Simmons-style, 86,739-word post, is an HBO rumor regarding Stewart.

“Though he’s tight-lipped about names on his wish list, [HBO President of Programming Michael Lombardo] acknowledges the soon-to-be available Jon Stewart would hold appeal.”

Lombardo tells Rose that there has already been a “polite conversation” with Stewart.

Simmons and Stewart share the same agent, James “Baby Doll” Dixon.

In another “things-that-make-you-go-hmmm” deal, Simmons and Stewart have both shown up on WWE programming of late. Video: Simmons Video: Stewart 

Likely, it was simply a deal WWE cut with Dixon and his clients who used to like wrestling, but maybe Simmons and Stewart were getting some insider tips on the new world of bypassing cable companies altogether and hosting your own streaming network. The WWE Network, which debuted in February of 2014, now has 1.3 million subscribers and is slowly moving from “flop” to “success.”

Another reason Simmons’ transition to HBO would be benefitial for both parties is that HBO could provide Simmons a platform to run “30 for 30” style documentaries. Simmons created the “30 for 30” venture at ESPN and the documentaries proved to be wildly popular. In fact, Simmons’ docs bumped HBO from its throne as the unquestioned king of the sports documentary.

HBO had scored documentary winners with The Curse of the Bambino (2003), Barbaro (2007), Brooklyn Dodgers: The Ghosts of Flatbush (2007), Ted Williams (2009), Battle for Tobacco Road: Duke vs. North Carolina (2009), Lombardi (2010), Magic & Bird: A courtship of rivals (2010) and Namath (2012).

ESPN’s 30 for 30’s began in 2009. It’s first one, Kings Ransom (on the Wayne Gretzky trade to the Los Angeles Kings), earned modest numbers. Gaining steam, ESPN began putting the docs in key primetime slots. “I Hate Christian Laettner” debuted on Selection Sunday of this year and drew an impressive 2.319 viewers.