There is a lot to take away from ESPN’s flurry of 2012 Upfront announcements. There are some other things we may touch on in the weeks to come, but what stood out most was the overwhelming evidence that the sometimes volatile marriage between Bill Simmons and ESPN is as healthy and productive as ever.

The two major headlines dominating the sports media chatter around the event both tie back to to Simmons with 30 for 30 returning with a vengeance and the continued expansion of Grantland. Even more impressive is the two Simmons creations (with an assist to Connor Schell) now cross pollinating each other. The success of his two babies working together and pioneering through a stodgy obstacle course of red tape is probably a joy that only Richard Williams can relate to in seeing the early success of Serena and Venus. From Richard Sandomir’s writeup:

“As the films roll out, they will be augmented on Grantland by podcasts, feature stories and oral histories. A short digital film — which will be unrelated to the longer ones — will make its debut each month on Grantland.”


Although I’m not a flag waving enthusiast of the growing Grantland empire, the additional content outlined above will certainly increase my frequency of visiting the site. Whenever I watch something I really enjoy, I usually spend a good chunk of time digging deeper for more info about the subject matter. Whether that is Wikipedia, Youtube, IMDB, or whatever, there is a thirst to get a more comprehensive viewpoint of what was condensed down into a more commercially viable piece of media. The augmenting of 30 for 30 coverage on Grantland will allow ESPN to meet that demand of curious follow up interest. 

The power of Grantland’s unique place in the content world can be simply illustrated in doing a Google search for “Friday Night Lights.” Given there is a Pulitzer winning book, a successful movie, and the cult classic television series all with the same name, seeing Grantland’s Oral History 4th in the search results is an indication of just how well read and socially shared Grantland can be. It’s a great article if you’re a fan of the show and you really wouldn’t find it anywhere else.

Would devote an entire article touting an NBC/DTV show? Nope. Where would this go on NBC Sports and would it reach as many people? If an independent media site tried to get access to all of the people quoted in that article, would they be successful? No freaking way. 

Similar to Simmons, Grantland isn’t for everyone. That said, it has carved out a sizable audience that is unique in this fact – content that would struggle elsewhere thrives on Grantland. 


Other “that just happened” announcements in regards to Grantland include a new Youtube channel and podcast network. In a nutshell, Grantland will get bigger, “hipper”, and have more platforms. This bodes well for ESPN, who has found the venture to be commercially successful. The extension of Grantland could allow for ESPN to experiment various initiatives and also serve as a farm system for television and personalities. More importantly it allows them to connect to a younger audience who generally has a mixed opinion of the parent company. 

You couldn’t blame Simmons for wanting to leave ESPN in 2010 when he was rumored to be looking around. There was a massive chip on his shoulder because an older generation of sports media personalities were making more money and being featured more despite not resonating with younger audiences. (The long standing bad blood between Simmons and Chris Berman as well as Rick Reilly has come to light over the past couple of years.)  Simmons even wanted to start his own “underdog competitor” to and maybe do a series with HBO.

Fast forward two years and ESPN is thriving commercially and critically in both of Simmons’ pet projects. More importantly they found a way for Simmons to get an HBO like series and an “underdog competitor” to all under their own umbrella.

Although I am a bigger fan of 30 for 30 compared to Grantland, I find myself more impressed by Grantland’s success. In regards to 30 for 30, Simmons had the vision, cut through the red tape, got corporate buy-in, and got the wheels moving on the project.

Grantland’s success is more impressive given ESPN’s spotty web ventures track record that includes:

– An odd/indecisive strategy of having only a handful of regional ESPN sites.

– The Heat Index where ESPN has a comparable amount of writers covering the Heat than the entire NHL.

– Continued failed forrays into the lucrative college recruiting subscription industry.

Criticism of the current Ombudsmen relationship.

– Murky details surrounding Bruce Feldman’s exit and Sarah Phillips’ hiring.

– A half baked blog network which I contend is exploitative of independent bloggers.

– A criticized social media policy that ruffled a lot of feathers.

In a nutshell, ESPN just hasn’t been able to adapt with the times on the digital front. Worse, a lot of younger folks were migrating away from The Worldwide Leader. Instilling change and infusing a hipper more innovative culture at any massive corporate entity is extremely tough. Lifers who are making six figures and seven figures typically lose their appetite to roll the dice to build something new. Given the outlined questionable moves on the digital front, Simmons’ vision and ability to push Grantland through as well as 30 for 30 should be recognized even if you’re lukewarm on either initiative. 

That chip is on his shoulder that “dinosaurs” Berman and Reilly were making more money, getting featured more, and eroding the coolness of the ESPN brand? You’d imagine that chip can finally be removed in his next contract discussion given Simmons has actually built his own thing, done it his way, and reconnected ESPN to younger fans.  

Simmons and ESPN is beginning to evolve into that obnoxiously cute couple who you tell to get a room but secretly root for an ugly divorce. After a bumpy couple of years, ESPN and Simmons are as frisky as ever.

It’s hard to see Simmons having similar success anywhere else and it’s hard to see ESPN thrive in these endeavors without Simmons.  Just like many marriages, the strength of the relationship is that both parties desperately need each other. 

About Ben Koo

Copying and pasting my Twitter bio. I'm also refusing (for now) to write this in the third person. This is me - EIC and CEO at @comeback_sports and @AwfulAnnouncing, world's greatest chinese jew, proud Buckeye, funny dude, and sports and digital media zealot.