Is Bill Simmons 4.0 On Shaky Ground?

To start this out – I will admit I am a Bill Simmons Fan Boy. I am one of those turds who will tell you that I was with him in his Digital City Days. I might have had a few beers in the past (125 times or so) and told you the story of how I emailed his old AOL address and told him my Rick Pitino / Jerome Moiso theory – only to get a reply of “this is really dumb.”

I will admit I am a tad concerned about Bill Simmons 4.0. I was on board with his HBO venture from the start – even after he dropped the F-bomb like a bad boy in his introductory HBO spot. But the minute the above photo came out I started getting an uneasy feeling. For starters, this is the type of photo that SHOULD make him cringe. It’s like he checked every box: Diversity, Yankee Fan (see we get along), MACS, PCs, Smart Phones (the Ringer will work across all devices and platforms), Untuckit Shirt (one of his podcast sponsors), Stickers on laptops (that is what young kids do right?), Casually leaning on a Callaway Putter (another one of his podcast sponsors),  crappy drop ceiling in frame (he’s gritty), and a Bro in an ironic LA t-shirt.

Is this Rick Reilly to ESPN on steroids (with a budget)? I hope not. In my opinion – I think Bill is at his best on his Podcast with a long time guest like House or the guy from Complex Litigation – talking about Karl Anthony Towns defense or Didi Gregorius stepping into Derek Jeter’s shoes. He gets cringe-worthy when he reaches for guests like Lena Dunham or some LA Chef.

And now I am starting to wonder what he has in store for a show on HBO. Who will he be jamming down our throats on a weekly basis? Will he be speaking off camera to his 20 something man-crush, Tate? Is he going make Rembert references? Will HBO execs pass around emails asking who J-Bug is while bookmarking the Wikipedia episode page for 90210 (here I found it for you)?

The good thing is that if all this fails and we are looking at the Magic Hour, I think Simmons can obviously fall back on writing (unlike the most recent incarnation of Rick Reilly). He has built a large stable of writers/podcasters for the Ringer – and time will tell if it will generate the traffic and sponsors to support the team financially. I am confident he can still “own the corner” (you hate me) for the long-form-fan-boy-passion piece like this one. I still think he “has his 98 mph fastball” (have you stopped reading?) when he pulls a randomly great podcast guest out of nowhere like Robert Smigel.

But make no mistake: he is taking a pretty big risk here by putting his brand on HBO. He gets away with saying/writing a ton of stuff in the sports world bubble even if it was supported by the ESPN war machine. What happens if we get a Simmons throw-away comment about a Hollywood actress gaining weight and a prominent “digital influencer” throws his name into the 24-hour-whiteknight-safe-space-fake-outrage cycle? Will he be devoured?  Will they forget that he once told Lena Dunham that he miraculously transcended his own chauvinism?

Now if you excuse me, I have to re-read this post and consider if I even like Bill Simmons anymore. But before you go, can I tell you about the time he posted my “Brushes With Greatness” story about getting a lap dance from Jarret Wright’s girlfriend?