It’s not that I root for Bill Simmons to fail. Quite the contrary, I want him to do well with the seemingly limitless resources, chances and time he’s been given over and over and over… because if that guy can’t make it, nobody will.

By Andrew J. Pridgen

Bill Simmons is burning through his Nine Media Lives like a teenager hammering down some sick Cap’n Crunch-flavored vapes (aka Cap’n Crunk in case you thought I was making that shit up) on break behind the Subway.

A recap of his two decades in the biz:

Life 1: Boston Herald: Prep sports reporter/weekend score sheet coordinator and bartender.

Life 2: AOL’s “Boston Sports Guy”/early days sports blogger.

Life 3: ESPN guest columnist/ESPN The Magazine columnist.

Life 4: Early podcast adopter/founder Grantland, a long-form sports and pop-culture vertical for ESPN/Host, NBA Countdown.

Life 5: ESPN expat (no contract renewal) HBO host, Any Given Wednesday (cancelled after less than four months.)

Life 6: CEO: The Ringer—Grantland 2.0 long-form sports and pop-culture blog with no revenue stream—also bankrolled by HBO.

Life 7: After a year in the making, The Ringer debuted in July 2016 with 1.2 million/mo. unique visitors. By May, 2017, those visitors were fewer than 300k and falling according to comScore.

Life 8: In March, The Ringer announced it would move away from Medium. Medium, the brainchild of Twitter co-founder Evan (Ev) Williams, let one-third of its workforce go in January. Launched in 2012, the platform was supposed to be journalism’s final egalitarian frontier as a blogging and networking site bolstered by name brands like Simmons. Didn’t happen for either side.

…So, we’ll pause right there, as Bill Simmons’ media life no. 9 begins with the acquisition of The Ringer by Vox which will direct traffic to the site from SB Nation, its Shasta Cola version of ESPN (19 million uniques in May.) Vox’s ad network/connectivity to a readership should give The Ringer and its 70-person-for-no-reason staff a boost in both eyes and revenue.

For his part, Simmons still throws out interesting content from time to time. He loves to take down the N.F.L. and he has a staff of cleverish writers who all kind of come out of the post-Gen X put pre-full bird Millennial Chuck Klosterman school of aww-shucks-self-effacing I-know-I’m-not-Hunter-Thompson-or-Joan-Didion-unless-you-think-I-sound-like-them school of winks and nudges.

He’s also pocketing about $9 million/year through 2019 from HBO (a $20 million-plus contract in total.)

…That on top of the $5 million/year he made at ESPN.

Simmons is also majority stakeholder in the eponymous Bill Simmons Media group, formed after he inked the deal with HBO.

Former NFL Network executive producer Eric Weinberger is president of the group and was an executive producer of Any Given Wednesday. Weinberger is still on staff helping with podcasts and developing scripted and non-scripted projects, short-form digital content and other creative projects as part of Simmons’ deal with HBO. An Andre the Giant doc announced in February being one, perhaps the only one.

So, basically both of those boys are making millions fulfilling their 12-year-old selves’ WWF fantasies and spending lots of coin in the roller room at Caesars whenever they desire. Good on them, I guess.

There is some speculation that if the Vox deal makes The Ringer viable, the Bill Simmons Media Group could sell for upwards of nine figures to that company. Right now they are overstaffed, still don’t have an ad revenue model, don’t have a juggernaut pipeline for viewership like Grantland did and are heavy on the editorial and light on the data science, digital newsroom coordinators/oversight, multi-platform editors, rapid-response team, social analytics and SEO Dungeon Masters and wonky analysts/bloggers for each of the professional sports leagues and franchises they aim to cover.

Right now, it’s just a long-form grab bag.

Not saying that’s a bad thing… if you’re a staff of two working for free.

But if you’re a multi-million-dollar man who owns an aspirational $100 million/year media empire and all you have to show for it is a cancelled pay cable show, some dusty podcasts, think pieces about stuff we already knew about Charlie Murphy and a doc in the can about a man who could crush 119 beers in one sitting… well, maybe it’s time to put the Brentwood compound on the market, dust off that Southie accent and Sox Starter jacket and start pulling Harps in the old neighborhood pontificating about how Boggs should’ve never been in pinstripes while referring to everyone as “Kid.”

Andrew J. Pridgen helps run sister site Goner Party and is the author of the novella “Burgundy Upholstery Sky”. His first full-length novel will be released in late-2017.

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