Bill Simmons, also known as “The Sports Guy,” has been perhaps the most prolific and polarizing figure in US sports journalism since joining ESPN, the “worldwide leader in sports,” in 2001. Simmons is the most visible representative of a huge contemporary shift in sports journalism, which is increasingly leaving behind the traditional, serious-minded “reporterly” mode associated with print media and turning toward the growing influence of a free-form aesthetic, derived from the writing style of non-professional bloggers. This style treats sports as a component of pop culture, rather than a sanctified space apart from it. I argue that the astounding popularity of Simmons’ work, which includes columns for ESPN.com, audio podcasts, television documentaries, a Twitter feed, two New York Times-bestselling books, and until recently a monthly column in ESPN: The Magazine, is a result of his particular style of mobilizing his intersectional identity as an upper-middle class white male sports fanatic. Simmons’ journalistic work is more comprehensible and legible as the demonstration of a particular identity that he models and offers to his fans than as a literary exercise or as a means to deliver information and analysis. The Simmons phenomenon models a new mode of sports journalism production and consumption that is not built on insider information or authority but on the construction of a unique, immersive identity projected by the writer and shared in by his or her fans. Following on this point, I suggest that Simmons’ particular identity is attractive to sports fans because it offers a palatable way for them to define and experience themselves as white and white-collar, both of which are fraught positions in the sports world and the media complex that surrounds it.