The Definitive Bill Simmons Interview, By Those Who Know Him Best
This image was lost some time after publication. Well, we covered the 3-2-1 Liftoff! of Our Boy Bill Simmons' Now I Can Die In Peace in our own goofy way, and now, for that whole "perspective" and "intelligent analysis" way, David Scott of Boston Sports Media Watch talks in length with Simmons about his place among the Boston media, his meteoric rise, his influence on sportswriting both online and off, what ESPN has to offer and a TON more. We're going to give you a bunch of highlights after the jump — though the piece itself is a must-read — but here's a teaser:
"There's going to be a point where it will no longer be worthwhile creatively for me to write my column for them, and that point is coming sooner than anyone realizes. Including them."
All kinds of Bill goodness after the jump, though we STRONGLY encourage you to read read the whole thing on BSM.
"I am just hitting my prime: 35-40 (years old)," [Simmons says]. "That's when every writer peaks."
"I hate the word blogger only because I actually wrote 2-3 full-length columns a week back then, unlike just about everyone now, he says. "Was it an early prototype of what's all over the place right now? Probably. But most of this stuff would have happened, anyway I was just the first one. As for the guys floating around now, I can't really comment because I don't have the time or the interest to read them. The only three sports blogs I read are: www.sportsbybrooks.com; www.bostonsportsmedia.com; and www.deadspin.com (all for their links)."
About the cartoon: "They (ESPN) promised me more leeway than I was receiving in my column which, by the way, I don't have a lot of leeway with and I ended up getting less," the Guy says. "That's all I'm saying about that. But it was a good experience for me because I learned, once and forever, to trust my own instincts and not listen to anyone else with decisions about my own life."
"Don't get me wrong, I'm glad I took the chance (with the cartoon), I learned from the experience, and that's really all you can ask for out of life. And sure, that sounds like something Rick Pitino said after he was fired from the Celtics, but I honestly feel that way. At the same time, I'm still pissed that I didn't trust my gut. And just for the record, I quit the cartoon everyone else wanted to keep going. The numbers were actually pretty good."
"I wrote a movie last summer that ended up getting buried by the studio that hired me to do it, even though everyone loved the script and Chris Moore and Live Planet were the producers."
And I feel the same way about ESPN, even though they exposed me to 10 times as many readers as the Globe would have. I just feel like a newspaper column, when it's done correctly, can resonate with an entire region."
Why the WNBA Won't Monetize Sophie Cunningham's Viral Point
What Prediction Markets Are Telling Us About NFL 2026 MVP
The Sacramento Kings Need to Blow It Up Before It's Too Late
Ben Askren Didn't Win the Match—But He Won the Weekend
- UFC Fight Night Best Betting Picks for Du Plessis vs. Usman in OKC
- France vs. England Best Bets: Three Picks for the World Cup Third-Place Match
- Dodgers vs. Yankees Friday July 17 Best Betting Picks and Props
- July 17 White Sox vs. Blue Jays Prediction, Odds and Best Bets
- Three MLB Futures Bets to Make After the All-Star Break
- Three Heisman Trophy Sleepers Worth Betting Before the 2026 Season
- England vs. Argentina Best Bets: Three Picks for the World Cup Semifinal

