Bill Simmons’ 10 Go-To Writing Moves

Getting lost in ESPN.com’s Trade Machine, which allows fans to create mock trades on an easy-to-use interface, is a favorite activity for any basketball nerd, and Simmons in particular loves to burnish his credentials as the "Picasso" of the Trade Machine. He’s good at coming up with interesting scenarios, and it can be doubly fun to watch him spiral off into the wildly hypothetical: One column earlier this year somehow gave Kevin Love and Carmelo Anthony to his Boston Celtics.

House, JackO, J-Bug, The Sports Gal, Gus, and of course, Bill's Dad: Simmons wasn't shy about peppering his early writing with references to his friends and family, and when Grantland got running he continued to showcase them in podcasts and video features, with the occasional guest column. Another frequent co-star is Cousin Sal, a writer Simmons met while working for Jimmy Kimmel Live! He's become fixture on the B.S. Report podcasts and his "prop bet" picks for Grantland are a staple of the site.

Simmons loves to revisit the Ewing Theory, a concept (hit upon by Dave Cirilli) that he popularized in 2001 that pointed to the trend of teams performing better after their so-called stars were lost to injury. (The 0rigin being the 1999 New York Knicks, who made a surprise trip to the Finals after Patrick Ewing sustained an Achilles injury.) The theory doesn’t always come through. When Rajon Rondo went down for the remainder of the 2012-13 season, Simmons wrote a column asking if the Celtics were a candidate to make the Eastern Conference Finals. They lost in the first round.

Larry Bird — aka the Basketball Jesus — is Simmons’ favorite player of all-time, and Bird’s number 33 jersey doubles as his answer to the universe. In honoring David Letterman, Simmons wrote: “He’s leaving after his 33rd year. My favorite number.”

It’s not always easy to come up with original ways to discuss topics that come up multiple times over the years, and Simmons is guilty of reusing some player descriptions. He first likened Steve Nash to "a complicated Italian race car" in 2007, and eagle-eyed fans will have noticed a variation of the comparison a few times since. 

Sometimes the lowest-hanging fruit is the tastiest, and Simmons doesn’t hesitate to repeatedly bring up a team’s bone-headed mistakes. The most recent example might be the James Harden trade, in which the Oklahoma City Thunder traded the aforementioend player, now the league’s best shooting guard, to the Houston Rockets for, essentially, the less glamorous role player platter of Jeremy Lamb and Steve Adams. As he wrote in a recent column, "You know what’s amazing? [Owners] Bennett and McClendon could sell Oklahoma City for $850 million–$900 million right now, if only because they have two of the league’s biggest assets: Jeremy Lamb and Steven Adams. (Sorry, I had to.)" 

Simmons has had his fair share of feuds over the years, whether with online basketball collective Free Darko, the Boston Globe’s Charles Pierce (whom he later hired at Grantland) or former Boston Celtics coach Doc Rivers, who he accused of quitting on the team. Simmons and Rivers went at it on air and over the Internet until patching things up, giving fans the rare thrill of public figures unafraid to poke at each other in full view of the world and providing the writer with new material.

The signoff to Simmons' mailbag is a premeditated act, like the Rock dropping the People’s Elbow or Phish cramming a few more solos into "Halley’s Comet." It’s a contest amongst his readers to get the most outlandish/saddest/weirdest question or comment into the 'bag, so that Simmons can then marvel at the types he attracts. Examples? Try, "Bill, I named my birds after you and Larry Bird and now they won’t stop having sex." To which Simmons, as he always does when he finds his prime mailbag entry, replied, "Yup, these are my readers." 

One of Simmons' most popular columns is his semi-regular mailbag feature, in which he answers questions from readers. Turns out, though, that it’s easy to talk about what you want when you set yourself up, and the sight of a question from "Bill S., Los Angeles" has dotted many a mailbag whenever no one’s raised a subject that Simmons wants to expound upon. 

If you’re ever in the same room as Simmons and don’t know what to talk about, bring up Boogie Nights or The Wire. He’s written columns in which he uses only quotes from Paul Thomas Anderson’s porn opus and David Simon’s cops-and-robbers saga to analyze what’s going on in sports. (A close runner up: The Godfather.)