I’ve been a reader of Bill Simmons’ work for a very long time. I first knew him as “The Boston Sports Guy” on a website called Digital Boston that I believe was part of AOL back in the '90s, if I remember correctly. I have to admit that I was a little envious of how his career progressed from there, to ESPN, then as a writer for Jimmy Kimmel, and on to founding Grantland and The Ringer. I like his writing. I mean, of course I do, because I’m his exact target audience. We probably have similar styles in some ways because we grew up with a lot of the same experiences—kids in the suburbs of Boston, worshipping Larry Bird and wondering if the Red Sox would ever win a World Series before we died. I admire the path that he took and I won’t go down the emotional rabbit hole of asking myself why I couldn’t or didn’t try to do something similar back then. That’s a different topic for another day.
Anyway…I always loved his mailbag columns for ESPN. He’d simply post emails of questions or discussion topics that he received, and then answer them. This let him cover a variety of topics, in whatever manner or level of depth that he wanted, and he excelled at that. He would also work in some of the weirder emails that he received. He’d often sprinkle in a few of these that would get progressively more strange. Ultimately, he’d wrap up the column with an unhinged reader email followed by a succinct line to cap the entire column off.
“Yup…these are my readers.”
Keep reading with a 7-day free trial
Subscribe to A newsletter by C.C. McCandless to keep reading this post and get 7 days of free access to the full post archives.