Technically, Bill Simmons is a sportswriter. He writes about sports, after all, in his Sports Guy columns for ESPN.com and ESPN the Magazine. But these are the days of sports columnists as shouting, goateed agitators angling for airtime, or beat writers too complacent to ask tough questions. Lumping Simmons with these hacks is like mentioning befuddled Phillies skipper Charlie Manuel in the same breath as a two-moves-ahead tactician like Cardinals manager Tony LaRussa. The Boston-bred Simmons is more a superfan who happens to have a forum, where he writes with the soul of a poet that The White Shadow was a groundbreaking show, and compares early '80s WWF palookas like Frank Williams to a beleaguered utility player. Even if you don't agree with him, you're usually laughing too hard to notice. Like many a Boston sports fan, the Red Sox are his passion, and his first book, Now I Can Die in Peace (ESPN Books, 368 pp., $24.95) is an annotated look back at nearly seven years of columns leading up to the improbable: the Sahwx winning the 2004 World Series. The format can be distracting, but it allows Simmons the opportunity to do something his "peers" almost never do: admit they were wrong.

City Paper: Boston and Philly sports fans are extremely passionate. I sense with the Boston fans I know—and I get this from you—there's hope beneath it all. With us it can be a lot of misdirected bitching mistaken for passion.

Bill Simmons: Yeah, I saw it when I was at the [2005] Super Bowl. You could see it in the second half, the Eagles fans were angry and they got all quiet. Leaving the stadium, there was a real sense of anger in the air. I took my Patriots cap off. Everyone was drunk and angry. They'll be fine when they win a title.

CP: Which is worse: the Red Sox going 86 years without a championship and enduring all the curse nonsense, or none of the four major sports teams in Philadelphia winning a title for 22 years and counting?

BS: I really don't know. Boston's had the more famous heartbreaks but Philly's been more frustrating. They haven't had as many good teams. You think they would because they have all four major sports. They've had a lot of high-profile guys, and they've come close a few times. One of the reasons I named the book Now I Can Die in Peace was because I thought it would be different now that the Red Sox had won. But that stuff's in your DNA. Once things went wrong [during the 2005] season, the Red Sox fans went right back to their old stuff. Though after we got knocked out [of the playoffs] this year there was a sense of calm, like, "Ah, we won last year."

CP: T.O.: Asshole for the ages? Misunderstood? Just T.O. being T.O.?

BS: I'm not as crazed by him as some other people. There have been a lot of assholes. At least the guy showed up for every game. To me, an asshole is someone like [NBA player] Shawn Kemp, who signs a huge contract and then just gets drunk every night and legitimately kills his franchise because they don't have money to replace him.

CP: Where do you think Owens goes from here?

BS: I like the whole Dallas idea. [2006] will be [head coach Bill] Parcells' last year anyway—he's not going to care. They'll get so much attention and publicity for it. It'll be a good team. I think he can rein himself in for one year and say, "Oh, I'm reborn." I can't think of anyone else that's crazy enough to take a chance on him.

CP: I can absolutely see him involved in the WWE at some point.

BS: That'd be interesting. The only problem is he's actually a very laid-back dude. We had him on Jimmy Kimmel's show [Simmons was a writer for Jimmy Kimmel Live] and he's very shy. A lot of these guys who are very bombastic, in private, are very different people. He was nervous before the show. All of us were pretty shocked. This was the same guy that ran to midfield in Dallas and danced on the star?

Bill Simmons signs Wed., Dec. 7, 5 p.m., Borders, 1 S. Broad St., 215-568-7400.