The Sports Guy, also known as Bill Simmons, got his start in journalism online, reporting on his beloved Boston teams from the perspective of an unabashed fan at Digital City Boston before coming into his own on ESPN.com’s ‘Page 2’ and ‘The B.S. Report’ podcast.  While he’s written two books, his primary mode of engagement is throughly rooted in new media: he blogs, chats, podcasts, and tweets religiously.

He’s a sportswriter, but unlike, the melodramatic musings of, say, Rick Reilly, Simmons is actually a pop intellectual masquerading as a sports writer.  He simply views the enormous sphere of American popular culture through the lens of sports and its attendant structures, emotions, reception, gossip, and metaphors.  Sometimes this unification is manifested overtly; at others, he eschews explicit sports talk altogether, opting instead to spend an entire poll, column, or podcast detailing the Blackberry for cheaters (trademark: ‘The Infidel’), the merits of Friday Night Lights, or the best ‘first boobs’ film moments.

To facilitate the process, Simmons has amassed a vast network of regular pop culture guests, including Chuck Klosterman, Jon Hamm, Adam Carolla, TV critic Alan Sepinwall, and SNL’s Seth Meyers; he also calls on longtime friends and colleagues (Jack-O; ESPN producer and ‘reality TV czar’ Dave Jacoby) to discuss specific shows, sports rivalries, and scandals.

But why does Simmons matter — and is his style really anything new?  Crucially, he rose to fame by writing in a blog-style before blogs even existed, gaining a tremendous (albeit niche) readership, then parlaying that popularity into a national readership.  He’s basically the journalistic version of the YouTube musician.  He cares little for long-form investigative journalism or even interviews with the players.  He’s a fan, and wants to stay that way — thereby increasing reader identification and loyalty exponentially.

And don’t forget the fact that he’s a.) funny and b.) totally a Beta-dude.  In other words, he’s a guy’s guy, but by no means an Alpha jock; his very existence validates your cerebral, thoroughly armchair-based sports obsession.  For while his beloved Red Sox are historically a working man’s team, Simmons and his fan base represent the new brand of white collar, fantasy-league-centric sports fan — the only fans still wealthy enough to buy seats outside of the nosebleeds.  These fans — male or female — can engage in the sort of pop culture puzzles and analogies favored by Simmons, writing into his Mailbag and participating in chat sessions, because they work at sort of desk jobs that create space, both intellectually and technologically, to do so.

Finally, Simmons is theoretically a conglomerate’s dream — albeit an imperfect, glitchy one.  He increases the loyalty of pre-exisiting ESPN while pulling in those, such as myself, outside its expected reach, simultaneously consolidating and expanding the ESPN brand.  And while he’s quick to chide the ESPN powers-that-be, he also deftly promotes ESPN products, including the recent 30 for 30 series for which he served as an executive producer.

But Simmons’ intrinsic conglomerate value lies most explicitly in his potential to create non-traditional lines of synergy, promoting media products within his home conglomerate’s galaxy.  ESPN is owned by Disney, creating any number of possible connections.  But for now, at least, Simmons has succeeded in resisting whatever pressure Disney may or may not have leveled.  He appears to interview people and talk about shows that he likes, including those, such as The Wire, that are about as far from a Disney product as possible, regardless of network or studio.  Nevertheless, Simmons’ style of commentary — niche but broad in both audience and in topic, complimented by a diversified means of distribution — seems to be a potential model of journalism, sports or otherwise, for the future.