Bill Simmons: Boston Sports’ Most Famous Fan Lands a New Gig

Bill Simmons is a giant in the sports world, a mogul of sorts, with over four million twitter followers, two New York Times best-selling books, and executive producer credits on dozens of documentary films in ESPN’s highly successful 30 for 30 series, which he co-created. He’s appeared on TV as part of the NBA Countdown crew and in 2011 he founded Grantland.com, acting as Editor-in-Chief and recruiting a team of esteemed writers from around the country to cover both sports and pop culture.

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He got his start in Boston, scraping by doing high school sports coverage for the Boston Herald and freelance work for the now-defunct Boston Phoenix after getting a journalism degree from Boston University. He grew up in Marlborough and Brookline and lived in Charlestown post-BU. In 1997, Simmons landed a position at AOL’s Digital City Boston. He dubbed himself “The Boston Sports Guy” and slowly started to build a following.

Four years later, ESPN came calling, and since 2001 he’s been a part of the company. Starting out as a guest columnist for ESPN.com, he quickly became one of the site’s most popular writers and his role in the company has expanded steadily ever since. All that came to a halt this past May, however, when ESPN announced that they would not be renewing Simmons’ contract, which was set to expire in September of this year. He abruptly left the company about a week later, vacating the Editor-in-Chief position at Grantland, a site ESPN owns.

Although ESPN didn’t say outright that Simmons was fired, they clearly wanted their relationship with him to be over. There’s been a ton of speculation as to exactly why, but it’s a pretty good bet ESPN simply grew tired of Simmons’ outspokenness. He’s been brutally critical of NFL commissioner Roger Goodell in recent years. ESPN suspended him for three weeks last September after he called Goodell a liar during a podcast in the wake of Ray Rice’s domestic violence case.

A day before ESPN announced they would not be renewing his contract, Simmons appeared on former ESPN sportscaster Dan Patrick’s radio show and criticized Goodell once again, this time regarding his handling of the Deflategate scandal. ESPN and the NFL have a $15 billion TV contract and Simmons’ repeated attacks of the commissioner may have put a strain on the network and league’s relationship.

Whatever the exact reason, Simmons’ time at ESPN is over and earlier this week his new gig was announced. Beginning in 2016, he will host a weekly talk show for the premium network HBO, covering both sports and pop culture. The deal also includes resources to allow Simmons to produce documentaries for HBO Sports, and it gives him the right to take his written column, the true backbone of all his success, to another media outlet.

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Time Warner owns HBO and they may simply help Simmons build a new site of his own, an interesting prospect given all the effort he put into creating Grantland just four years ago. Wherever his articles end up, Simmons seems poised to continue his success. ESPN certainly gave him a launching pad back in 2001, but he’s become his own brand entirely in the decade and a half since.

Even with a national audience, he remains a relentless homer, never shy about declaring his love for the Patriots or Red Sox. Readers have come to appreciate the fan’s perspective he brings to his writing. Simmons has become so famous that he’s gotten to meet many of his sports heroes (including Larry Legend), but he’s still a relatable, down-to-earth guy, with a unique and often hilarious perspective. Joining a premium network like HBO gives him a chance to be even more outspoken, and he should take this opportunity and run with it. Simmons has gone from Boston’s Sports Guy to the nation’s. With his new post secured, millions await his next word.

Next: Titletown: Ranking Boston's Championship Teams Since 2001