Bill Simmons is many, many things, but perhaps more than anything else, he is incredibly savvy about career management and navigating the rocky, constantly shifting terrain of the media landscape. You don't rise to the level he did at ESPN over 15 years after starting as an occasional freelancer simply by writing really long columns. I'd guessed some other places he'd land when ESPN stealthily ended his tenure there back in May, but in retrospect, of course it was going to be HBO. (I am always wrong about Bill Simmons' career choices.) In this afternoon's press release announcing that he will be hosting a talk show on the network starting in 2016, Simmons said, "It's no secret that HBO is the single best place for creative people in the entire media landscape." And he's not wrong.
If I had to work one place in media -- other than Sports On Earth and MLB Advanced Media, of course! -- I think it would be at HBO. This is not necessarily because HBO offers the most money, or the most job security, or even has an unerring eye for how sports television works. (Never forget "Joe Buck Live.") It's just that if you're a "creative person," as Simmons puts it, there's no place you have more rope than HBO. If Simmons had gone to NBC, every story would have been about ratings. If he had gone to Yahoo! (or started his own site somewhere), every story would have been about pageviews. At HBO, all that stuff is far less important. It matters, sure, but it's not the primary way of keeping score. HBO wants prestige. HBO is premium. If you pay for HBO, they already have you. They just need to make sure you keep paying. (Or keep using someone else's HBO Now password, anyway.)
This is no small matter. Simmons, for all his power and his mostly unerring eye for talent, has a secret flaw of not bringing in the massive ratings equal to his influence on the media jungle. Grantland is a terrific site, but its pageview numbers have never quite been as huge as one might expect for a site with the ESPN frontpage traffic firehose turned on every day. The "Grantland Basketball Hour" television show Simmons hosted was smart and funny, but its ratings were average. Simmons obviously had a lot of success with "30 for 30," but that's a series he helped shepherd into existence and was ultimately run by others while he concentrated on Grantland. All of things Simmons put together were excellent. But all of them paled, eyeball-wise, in comparison to, say, Skip Bayless screaming epithets into a camera.
Now, one of the reasons those sites and shows garnered lower ratings and pageviews is, well … they're really good: The reason Bayless and Stephen A. Smith do so well is because they inherently appeal to the basest, lowest common denominator viewer. Simmons could have made his show, and his site, dumber just to fit in with a lot of ESPN's other, more "successful" programming, but he didn't. And that's why everybody likes Bill Simmons. But the problems (if you want to call them that) he had with those ventures would have followed him had he gone anywhere else besides HBO.
He doesn't have to worry about those problems now, at least not too much. At HBO, Simmons can do his talk show and his video podcasts the way he wants, and while executives will of course keep an eye on ratings, they won't be obsessing over every point they way they do at ESPN (and would at NBC or Yahoo! or Fox or wherever). There are tons of other factors involved. This is why HBO is worth the money you pay for it. What matters most -- not only, but most -- at HBO is that the programming is of a high quality: What matters is that HBO looks like a place where talented people go to do their best work. "Girls" has never earned particularly high ratings for HBO, but it's worth every penny HBO pays for it, because every time Lena Dunham so much as makes an armpit noise, everybody on the eastern seaboard scrambles to their laptops for the ALL CAPS. Dunham would find the environment far less welcoming if she went the non-pay TV route.
Simmons will be given more leeway at HBO than he would have anywhere else … including ESPN. (Which is as much as sign of ESPN's shifting priorities than anything Simmons has or has not done.) At HBO, you can just concentrate on the work. It's still not known if Simmons is going to start another site -- HBO is simply the "exclusive television home," according to John Koblin's New York Times story -- and the fate of Grantland, sadly, still seems to be up in the air. There are a lot of questions to be answered, about Simmons, about Grantland, about the future of all of this. But as far as Simmons' television presence goes, he couldn't have picked a better place to go. It should have been obvious to us all along.