The Simmons brand

In recent days the big sports media news revolved around ESPN’s Bill Simmons, one of its most popular personalities. Simmons started years ago as the independent Sports Guy, a bro-friendly, pop culture-drenched writer who gained eyeballs handicapping pro tennis’s foxiest female players and interrupting discussions of the NBA to add thousand-word footnotes on Dennis Hopper’s suit coat in Hoosiers. At ESPN, he became a multimedia superstar and the tip of the conglomerate’s spearhead into prestige products like the web site Grantland (founded by Simmons) and the award-winning documentary series 30-for-30 (suggested and exec-produced by Simmons).

Well, now Simmons is out. ESPN canned him late last week and announced that he would no longer contribute to any of the various platforms and properties in his portfolio.

vogan espnWhat did Simmons mean to ESPN’s efforts to cultivate a high-brow, sports-for-smart-people ‘tude that garnered the network plaudits and key advertisers?

Plenty. Travis Vogan’s upcoming book ESPN: The Making of a Sports Media Empire, available this fall, lays out just what the former Sports Guy brought to the table. Below Vogan discusses Simmons’s vision for Grantland, the most high-profile of the properties he developed for the network:

Simmons’s stock had never been higher in the months leading to Grantland’s June 11, 2011, launch. The Book of Basketball was a New York Times best seller, and 30 for 30 gathered ESPN’s fourth Peabody. Furthermore, his contract was set to expire after 2010. The sports media Renaissance man used his rapidly escalating renown to negotiate a freestanding publication organized around his appreciation for the intersections between sports and pop culture.

“I was going to do it whether I was at ESPN or not,” he claims. “I want to do it with you guys. If you guys don’t want to do this, I’m not going to be upset, but I’m going to do it somewhere.” ESPN indulged its superstar writer to retain his services and celebrity.

Simmons said his principal goal in developing Grantland “was to figure out how to capture the spirit and creativity of 30 for 30 and transfer it to a website.” The site, which he claims was modeled after fashionable magazines like Esquire, GQ, Inside Sports, and Spy, would specialize in long-form journalism by recognizable writers—an adaptation of 30 for 30’s engagement with cinema, the documentary genre, and established directors.

To do this, he compiled what the Boston Phoenix’s Matt Parrish describes as an “A-Team-style masthead of nerdy badasses” from print and the Web. Grantland’s original editorial staff included publisher David Cho, New York Magazine’s Lane Brown, GQ’s Dan Fierman, Harper’s Rafe Bartholomew, and the celebrity consulting editors Dave Eggers, Malcolm Gladwell, Chuck Klosterman, and Jane Leavy. Its staff and freelance writers ranged from Esquire’s Chris Jones to Deadspin’s Katie Baker to video game critic Tom Bissell.

The website’s development resembled ESPN the Magazine’s recruitment of Sports Illustrated employees to fuel its launch. The similarly renowned, but far more diverse, collection of talent Simmons culled for his project, however, demonstrated Grantland’s comparatively eclectic scope. The website also adopted 30 for 30’s sponsorship model by recruiting Subway—which was already sponsoring Simmons’s podcast—Google, Lexis, and Unilever. This allowed Grantland to rely less on page clicks and to minimize the presence of ads, much like the ESPN Films documentaries’ frequent presentation with limited commercial interruption, while enabling sponsors to identify with an exalted division of

“It’s the quantity over quality trap,” Simmons explained. “Everyone’s chasing page views and I’m not sure that’s always the way to go. We want to put up longer, more thought out stuff.” Because of its personnel and design, Simmons boasted that Grantland would be “to ESPN what Miramax was to Disney, a boutique division with more room for creativity.”