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Yup, These Are His Leaders: Bill Simmons’ Best Columns

Our picks for the Sports Guy’s greatest writing

Bill Simmons

Bill Simmons

Joe Murphy/NBAE via Getty Images

Bill Simmons has written hundreds upon hundreds of columns over the years, and due to the intangibility of the Internet’s archives and the serpentine nature of search functions, it’s not that easy to comb through his work. (Besides, no one probably needs to know that much about the 1999 Boston Red Sox). But for the sake of Simmons’ acolytes and neophytes — and in honor of our new feature on the Grantland writer — we’ve culled a few of his most notable columns, with an explanation of why they mattered.

Patriots win Super Bowl XXXVI
This was Simmons at his most exuberant, as he celebrated the New England Patriots’ upset of the St. Louis Rams in Super Bowl XXXVI, the first time a Boston team won a championship during his rise as a columnist. It’s the alluring mix of earnestness and self-awareness which made his early writing so easy to empathize with: 

I don’t think I’ve ever felt that way before. I mean, have you ever felt totally dumbfounded by something? Have you ever felt totally overwhelmed? I’m telling you, keep the faith, keep believing, keep supporting your team — there’s a slight chance that it might be worth it some day. Just trust me.

Red Sox win the World Series
To commemorate the first Red Sox World Series win in nearly a century, a running diary to chronicle every stray thought was a must — and Simmons didn’t fail to produce a snapshot of how it felt to be a beleaguered Bostonite witnessing a dream come true:

Outsiders made up fake curses, called us losers, pointed to a legacy of failure, questioned our sanity. We kept hoping. We kept the faith. We kept passing this team down from generation to generation, hoping it would be worth it. And it was. The last 11 days were the greatest sports ride of our lives: Eight games, eight wins, one championship, a boatload of memories. We crawled through 500 yards of (expletive)-smelling foulness and came out smelling like roses on the other side.

The re-evaluation of Elgin Baylor
Whatever sarcasm found in Simmons’ writing is built on a foundation of deep love for his subject material, and in analyzing and re-evaluating the career of Elgin Baylor — who in the late aughts was known more for his disastrous run as Los Angeles Clippers general manager than for his innovations as a basketball player — Simmons provided an empathetic, nuanced understanding of one of the underappreciated legends of NBA history:

We might elect our first black president in four weeks; this wouldn’t have a chance of happening without the strength of people like Elgin once upon a time. If you’re younger than 40, when you think of Elgin, you probably remember him wearing one of those Bill Cosby sweaters and wincing because the Clippers’ lottery number came too soon. That’s the wrong memory. You should think about him creating hang time from scratch in 1958. Think of him putting up a 38-19 in his spare time in 1962. Think of him dropping 71 on the Dipper. Think of his eyes narrowing as they passed along his owner’s condescending message during that snowy day in Boston. Think of him retiring with dignity because he didn’t want to hang on for a ring.

Kobe scores 81 points
Written when the novelty of Kobe’s point total was still strong, Simmons contextualizes it as an impressive and slightly empty achievement, secured during a meaningless season on a mediocre team against a crummy opponent. He’s able to appreciate the moment without being overwhelmed by it, as many a columnist did when looking at the big 81 in the stat sheet:

There’s a joylessness about it. Like watching someone crank 15 straight bombs in the Home Run Derby without breaking a smile. For two guys watching history unfold, my father and I weren’t exactly high-fiving in the living room or anything. The game made me feel the same way I felt while watching “March of the Penguins.” I had always wondered what a penguin’s life was like; once I knew how depressing it was, I wanted to sit in my garage with the car running. Sometimes it’s almost better not to know these things. And Kobe’s 81-point game was a little like that. For a perimeter player to score that many points, you have to hog the ball to a degree that’s almost disarming to watch; it almost stops resembling a basketball game.

Save the Sonics mailbag
The longest piece Simmons ever filed, it contains the emails of dozens of Seattle Supersonics fans aggrieved that their team was about to be stolen away by Oklahoma City. It was the perfect convergence of the stand-in fan’s voice allowing the fans to have an outlet when it seemed like only mass incredulity might stop the inevitable:

That’s what this Seattle thing is about. It’s about caring, and joy, and memories, and what a franchise can and should mean to a city and a fan base. It’s about the infantile and ignoble joy that causes people to drown out the PA announcer before Game 3 of the ’96 Finals. It’s also about naivete, for better and worse, and it’s about greed and ego above everything else. I’m an innocent bystander with this whole thing, but still, I can’t shake one simple point: How could David Stern allow a team that won a championship while he was working for the league to move? How could he claim to care about the league and let that happen? How could he allow one of the 30 NBA fan bases to be extorted? How is this OK?

The Annual Trade Value column
This is one of Simmons’ patented concepts, which contextually ranks every NBA player by value, taking into account factors like age and salary. (For instant: Would you rather have Dwight Howard for 4 years at $80 million or Andre Drummond at 3 years for $15 million?) The concept has since been adapted by sites like Fangraphs and writers like Grantland’s Bill Barnwell. The very first one, written in 2001, isn’t available online, but they’re all available after that. Here’s the top ranking from 2002, which would prove oddly prophetic:

If the Lakers ever traded him, Shaq is competitive enough and vindictive enough that he would postpone his eventual retirement plans, then devote the next decade of his life to winning championships, haunting the Lakers and making them rue the day. And the Lakers know this. When motivated and hungry, he’s the most dominant player in the league. Nobody can stop him. Nobody. Not even Duncan. And that’s why the Lakers would never, ever, ever, ever, ever, ever, EVER trade Shaq, not under any circumstances … which makes him the undisputed No. 1 player on this list.

The Levels of Losing
An amusing look at the many horrible ways there are to lose, written when Simmons — as a Boston fan — had experienced enough of it to remain credible on the subject. He would revisit the concept a few years later, but the original remains the best:  

Level VI: The Full-Fledged Butt-Kicking: Sometimes you can tell right away when it isn’t your team’s day … and that’s the worst part, not just the epiphany but everything that follows — every botched play, every turnover, every instance where someone on your team quits, every “deer in the headlights” look, every time an announcer says, “They can’t get anything going,” every shot of the opponents celebrating, every time you look at the score and think to yourself, “Well, if we score here and force a turnover, maybe we’ll get some momentum,” but you know it’s not going to happen, because you’re already 30 points down … you just want it to end, and it won’t end … but you can’t look away … it’s the sports fan’s equivalent to a three-hour torture session.

Death of his dog
When Simmons wrote openly and sentimentally about the death of his dog, Daisy, he received loads of mail from fans who could deeply relate. Even his critics couldn’t deny the potency of the subject:

The day after The Dooze left us, our little boy woke up and my wife carried him downstairs to feed him like she always does. I was still half asleep and could hear her footsteps. Then I heard this: “Day-zee. Day-zee.” That part didn’t make me sad. The part that made me sad happened three mornings later … when my wife was carrying him downstairs again and he didn’t say anything. 


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