I have been an avid follower of sports pundit Bill Simmons for years. I read every single one of his columns, listen to a majority of his podcasts and try to keep up with each of his other ventures. He was a huge part of the reason I decided to begin writing about sports, and his influence has shaped the way I think about both sports and popular culture.
It was very disappointing to find out last week that Simmons’ relatively new HBO talk show “Any Given Wednesday” was canceled, but it was also unsurprising. Simmons has made many wrong moves over the past few years, and the decisions made in putting together the show were some of his biggest.
It pains me to say it, but it is time to ask a question Simmons himself loves to break out when the timing is right: are we sure that Bill Simmons is good?
Although he broke out at the turn of the millennium as a writer, Simmons doesn’t do much writing these days. After he split with ESPN in 2015, and the media giant chose to shut down his excellent culture site Grantland, he’s bounced around.
Simmons signed a lucrative multi-platform deal with HBO later that year, giving him his own television show among other benefits and responsibilities. He also launched a media group that includes a website similar to Grantland, called the Ringer. For him and his fans, it was an exciting rebirth, although the way he continued to burn bridges at ESPN on the way out was childish and unprofessional.
Now, I was just as excited for the Ringer as anybody else. Grantland was simply a dream come true for sports and pop culture fans that were looking for more nuanced takes, and bursting at the seams with talented and intelligent writers like Zach Lowe, Bill Barnwell and Wesley Morris.
The Ringer has taken a similar approach, but in my opinion, does not come close to the same level of success. The site’s articles land right in the murky spot between clickbait and substance, which isn’t satisfying for anyone, and its writers, while certainly more talented than I am, write with a frustrating pretension that really hurts the strength of the arguments they are trying to make. There is some great content coming from the site, but not nearly as often as it came from Grantland.
On top of that, Simmons barely writes for it. He’s written just two articles since it launched in June, with the most recent one being a languorous NBA piece about LeBron James that only really became about LeBron at the article’s halfway point.
The piece highlighted many of the bad characteristics that have creeped into his writing recently and cannibalized all of the fun parts: needless self-complimenting, contextualizing things he says within things he’s said in the past and stories about his brushes with fame that the average fan he once represented will never be able to relate to.
Now, I still enjoyed that piece, because once Simmons finally reached his LeBron angle, it was a unique and refreshing one. But comparing his writing at the Ringer and his writing during the late stages of Grantland to his old ESPN archives is no contest. He’s fallen off.
Why? It may be that he is spreading himself too thin. After signing his HBO deal, he found himself the leader of an online media network, a talk show host, a bi-weekly podcaster and when he felt like it, a writer. Simmons has shown great skill in many of these arenas, but there’s only so much time in the day. To perform all of these roles and also consume the content to be suited to perform these roles is an impossible task. You can only keep so many plates spinning before they begin to tumble.
Unfortunately, it’s not just his writing that has suffered. The Ringer seems directionless. His podcast has lacked the diverse suite of guests it once had. And most of all, his television show has been a resounding failure.
“Any Given Wednesday” had a bevy of red flags right out of the gate. Simmons has never been more than a passable on-screen presence, and the premiere episode displayed his stilted delivery and posture in front of the camera. The written material was weak, and the guest interviews never quite became anything more than a televised podcast segment.
Worst of all, the show brought to the forefront his fanaticism for Boston sports teams, which has always been a rewarding and integral part of his personality, but has threatened to overwhelm everything else recently. Every discussion about the Cubs’ remarkable playoff run somehow comes back to the Red Sox in 1986, and every NBA conversation lasts about five minutes before the topic becomes the Celtics. I am a devout fan of New York teams, including the Yankees and the Nets, so of course I have a little extra salt running through my veins, but nonetheless it’s exhausting.
“Any Given Wednesday” made it about ten minutes before Ben Affleck was drunkenly ranting about Deflategate, and even staged a full Deflategate trial in just its fifth episode. No real evidence here, but I’m pretty sure no one cares about Deflategate these days.
I enjoyed the show at times, but after a few weeks I was no longer watching. I’m still listening to Simmons’ podcasts, but with the guest list thinning, they have become less entertaining. His columns, when they do come, are decreasing in quality.
For the first time, it feels like Bill Simmons is behind the curve, and following trends instead of setting them. Hopefully he turns that around, and I’m behind him every step of the way. But right now, he’s on a cold streak, and there’s a lot at stake for both him and HBO. His next step in this changing sports media landscape will be fascinating.