I know a lot of Philadelphians don’t like him because he’s such a Boston homer, but I am a huge fan of the writer Bill Simmons. I often disagree with him, but I think his approach to sportswriting basically reinvented the genre, and while some of the folks who’ve followed in his rhetorical footsteps can be extremely annoying, overall I think he’s played a big role in massively improving the quality of sports and pop culture essays.
As an editor at Grantland and The Ringer he’s brought a number of terrific new voices to national attention, e.g. Shea Serrano.