He has become one of the most popular and influential sports writers of this decade, he has an epic, second book hitting stores Tuesday and he is one of the masterminds behind the best thing ESPN has produced since Keith Olbermann sat across from Dan Patrick and first uttered, “Welcome to the Big Show.”
Bill Simmons has forged an incredible and unique journey from working as a frustrated newspaper writer to bartending to running his own Web site to cultivating a massive and loyal audience as one of the two signature properties on ESPN.com. He will be in the District on Monday night at ESPN Zone to launch his whirlwind tour for “The Book of Basketball,” and fans will flock to meet the guy who writes from their perspective - if they were incredibly funny, smart and could write really well.
All Simmons has to do is remember to bring more books this time.
“For some reason D.C. was the best signing of all my book signings the last time,” said Simmons, referencing the tour for “Now I Can Die In Peace,” his first book about his life as a Boston Red Sox fan. “We actually ran out of books, but people were really cool about it. They could have been [terrible], and they could have been mad about it, but it was like this really neat blend of people. I’d meet a Red Sox fan, then the next guy was an Orioles fan, and then I’d meet a Yankees and then a Dodgers fan - it was really a hodgepodge.”
Known to most sports fans as “The Sports Guy,” Simmons grew up wanting to be a columnist for one of the two major papers in his hometown of Boston. After growing increasingly disillusioned by where his newspaper career was heading, he gave it up before eventually deciding he was going to become a columnist on his own terms.
Simmons started his own Web site, “The Boston Sports Guy,” in 1997, and ESPN hired him in 2001. Since then Simmons has rocketed to the top of the sports journalism scene, drawing many of his most faithful fans from younger demographics and gaining tremendous popularity without making the transition to television personality.
His style, which mixes plenty of crude humor and pop culture references, isn’t for everybody. But he is the most famous sports writer in America who doesn’t talk to people through their television sets.
“I think his story is pretty familiar. It is about passion and having a dream and not seeing a clear path and making your own,” said Rob King, ESPN.com’s editor-in-chief. “That is pretty much the American success story. In addition to seemingly coming out of nowhere, it is a testament to the hard work he has put into it.
“He grew up as somebody who was able to express himself through written words. He chose a nonconventional path in terms of embracing the Internet space when not many writers were. His belief in that form of communication probably distanced himself from a large group of people in that generation. I know that there are many writers in the next generation who are starting in that space.”
Being one of the first stars of the Internet generation of sports writers was only the beginning of a common theme throughout Simmons’ career. He hasn’t been afraid to test new forms of media and new technologies to continue the connection with his readers.
He was listening to one of those new forms, an online radio broadcast called a podcast, in 2007 and quickly recognized the benefits. Shortly after that, “The Eye of the Sports Guy” podcast, soon renamed “The B.S. Report,” was born. Since, it has become one of most-downloaded sports podcasts on the Internet.
Simmons always had written about his friends in his columns, but now people like Jacko (Yankees fan John O’Connell) and local resident Joe House have found their own places as featured-guest celebrities on his podcast.
Some of the topics can be silly, but Simmons also will catch up with iconic athletes and writers like Malcolm Gladwell (who wrote the forward for his new book) and Chuck Klosterman.
“[ESPN’s] Chad Ford did a podcast with Danny Ainge in the summer of 2007,” Simmons said. “I listened to the whole thing, and I just thought it was so cool that it was like radio on demand. This was totally different than, ‘Oh, I hope I catch Danny Ainge when I’m in the car while I’m driving.’ This was, ‘Hey, I can listen to Danny Ainge at any time.’ It was a technology that made sense to me. I was looking for a way to kind of augment what I was doing with my columns, and I knew I was going to start working on the book pretty heavily.”
After bristling at the idea at first, Simmons also has cultivated a gigantic audience on Twitter with more than 900,000 followers. Another of his “famous for being buddies with Bill Simmons” friends, Kevin Wildes, turned him onto the social networking platform because it was a way to self-promote and it was a way for him to tell jokes without being censored by ESPN.
Simmons has waged a sometimes tense and public battle with his company about creative freedom and censorship. ESPN has since cracked down on its employees’ use of Twitter, but the site remains a place for him to launch one-liners and tell fans about what he has written - or read - of late.
“I didn’t understand it. I don’t know if I was really late, but I think I jumped in just as everyone was starting to figure out what it really was,” Simmons said. “Initially, it was just this place that Ashton Kutcher went on to tell everyone he just had a Mexican dinner. I thought that was absolutely stupid. Who cares? I don’t care that Ashton Kutcher just had three chicken tacos.
“It is good as a writer to try and figure out what is the most efficient joke I can make in 140 characters. I’ve had fun with it. It is a great way to keep in touch with people.”
His two most recent projects have resulted from his ascent to power in sports journalism - and also have shown off the true zenith of his abilities. Simmons, with the help of his friend Connor Schell, hatched the idea that eventually became “30 for 30,” an ESPN weekly documentary series about 30 people or events to commemorate the network’s 30-year anniversary.
Each film is done by a different filmmaker, and the talent ESPN collected is staggering. Already there have been documentaries by Peter Berg on the Wayne Gretzky trade and by Barry Levinson on the Baltimore Colts band that kept playing even after the team left town.
For years people have criticized ESPN (and Simmons hasn’t been afraid to lead those charges) for some of its “original entertainment” disasters (the movies “3” and “A Season on the Brink” come to mind), but this project has been lauded by critics.
“It is the greatest thing I’ve ever been involved with because it was so collaborative and so many people played a hand and so many people can be proud of it,” Simmons said. “The best part about it is hearing the directors talk about it and how it was such an awesome experience for them and how ESPN really let them pursue their creative vision and didn’t mettle.”
When Simmons wasn’t writing columns for ESPN.com or ESPN the Magazine, producing podcasts or working on “30 for 30” during the past four years, he was working on his new book, which is a 700-page tome about the sport he loves the most.
“The Book of Basketball” is his quest to find out who really are the best players and teams of all time and the answers to some of the greatest “What ifs?” in NBA history. More than that, it is a book that could redefine the way people view individual basketball players and teams.
The right book to compare it to might be “Moneyball,” which is Michael Lewis’ defining take of this generation on baseball. “Moneyball” changed the way people viewed baseball players and updated the language of the sport with new statistics and new methods of evaluating them.
“The Book of Basketball” could become equally as important for how future fans of the sport view and evaluate basketball players.
“I think it is brilliant,” King said. “My favorite part of the book is I think it ultimately explains what Bill is about, which is a real, deep-seeded disgust toward anything that doesn’t represent excellence. He loves the NBA, and the things he really digs into with this book are about excellence, and the things he really dogs out in this book are about coming up short of excellence.
“It is the kind of book that will get people to nod their heads in agreement, and it is also the sort of book that will start 1,000 different arguments, and from that respect I think it is a very important book. It is funny. It is profane, but it is also really heartfelt.”