When Bill Simmons first became the Boston Sports Guy, writing an obscure blog for AOL in the early days of the internets, he gradually cultivated a loyal audience who appreciated his exhaustive essays dissecting Beantown’s sport fandom while sprinkling in Karate Kid and Road House references. He wrote from a fan’s perspective, which is the only perspective he could afford at the time, but that voice ultimately made him famous and influential. He’s been at ESPN now since 2001, and if he doesn’t yet run the network, he certainly is one of the Sports Leaders’ most important assets. In addition to being the editor in chief of Grantland.com, he also is an executive producer of their heralded 30 for 30 documentary film series, the host of the popular B.S. Report podcast, and an occasional guest on Pardon the Interruption.
Beginning tonight, he’ll also be taking a seat next to Magic Johnson, Jalen Rose, and Michael Wilbon as a contributor on the KIA NBA Countdown show, ABC/ESPN’s basketball showcase studio show. The one-time outsider is now the ultimate basketball insider. It didn’t happen overnight or by accident. The best-selling author of The Book of Basketball spoke to EW about conquering the business from the outside-in, why he said no to the show last year, and a hilarious Godfather-like offer he once received from one Mike Francesa.