Breaking up with Bill Simmons

By Sterling Pingree

You never forget your first. First kiss, first car, first trip to Fenway. In more modern times, some of these chestnuts have changed I’m sure. Here’s a fun exercise, if you have Twitter, go into the list of people who you follow, scroll all the way down and see who the first person you followed was. Mine was the reason I got Twitter in the first place, @SportsGuy33 aka Bill Simmons.

I started reading Simmons’ columns in college on ESPN’s Page 2 and his stuff spoke to me. His sense of humor, Boston homerism and voice of the fan was something that all of my friends were reading. It was common for AIM messages to come through proclaiming that Simmons had written a new column, no links included because in the mid-2000’s you had to find things for yourself. It was Simmons’s BS Report podcast that first introduced me to the genre and until probably 2012 was the only podcast I listened to. It wasn’t until Simmon’s Grantland site that I found other shows of which to subscribe, I figured if they were endorsed by the great Bill Simmons that they must be something I’d like.

The podcast was great and I believe that I listened to every episode of the BS Report ever recorded but it was the writing that really had me. I bought his book “Now I Can Die in Peace” a collection of his best Red Sox columns starting in the mid-90’s and running through the 2004 World Series, in paperback and hardcover, each receiving multiple readings. Ditto for his “Book of Basketball” the 700-page tome of seemingly every basketball thought Simmons has ever had, complete with 6 million footnotes. I relished all of it.

When Simmons got his own website, I couldn’t get enough of Grantland. I read his columns of course, but I dove into so many other articles because the long form style was the same and if it was on the site, it had to have Bill Simmons stamp of approval on it. Grantland introduced me to other writers that have become favorites of mine such as Chuck Klosterman, Malcolm Gladwell, Michael Lombardi, Robert Mays and David Shoemaker. I was so entrenched with what Simmons was doing, I even subscribed to Grantland Quarterly, a hardcover book of the best writing from Grantland over that ¼ period of the year. Being the completest that I am, I had to read each volume (12 in all) cover to cover as they came out. Now during these books, I read a lot of stuff I had zero interest in: video games, science fiction, television and movies I had not seen nor wanted to see, but this was the exception not the rule. No matter what was included in this “Best Of” collection, I always knew that Simmons would be featured and that Simmons would deliver sports. Then, like a Lifetime movie, everything changed.

ESPN announced that they weren’t renewing Simmons contract and a short while later pulled a Crazy Joe Davola and put the kibosh on Grantland all together in 2015. Simmons fans didn’t know what to do, where would they get their fix? What would happen to this pirate ship of wordsmith-rebels who were changing internet writing one 3,000 word Breaking Bad column at a time? HBO would come to the rescue and soon, Bill Simmons would return with the podcast, a new tv show, a new website and a whole new feel.

Some of the hallmarks of the podcast remained on the new Ringer edition; Cousin Sal doing NFL picks every Monday, Joe House talking hoops and Simmons’ buddy and resident Yankees fan Jack-O to talk baseball but over the last 3-years there has been a seismic shift in the content of the podcasts. It was slow at first, but has become more and more apparent over the last year or so. Sports took a bit of a back seat, not all sports, the NBA was featured more prominently than ever, but football was covered in season and then put away like wool sweaters in June. Even baseball with Simmons’ beloved Red Sox winning multiple division titles were only a slow news day topic and even then only warranted a section of a podcast. Over the last year, Simmons has done two-hour marathon podcasts with horror movie directors and multiple pod-slogs talking about food and restaurants in California.

To get a hint of the shift that Simmons was going to make after his emancipation from ESPN, one need look no further than his failed HBO show “Any Given Wednesday”. Exhaustively publicized for months and months, the show lasted only 17 episodes. The guest list was star studded with names like Aaron Rodgers, Kevin Durant and rapper Nas. The problem was that he tried to go in too many directions and wound up going nowhere, case in point, Durant and Nas were interviewed at the same time in an incredibly awkward segment. One can draw more parallels from Simmons failed HBO show and his current podcast product than from the hundreds of podcasts that got him here in the first place.

After listening to each Simmons podcast since 2007, last month I broke that streak as Bill approached his 400th podcast with The Ringer. It wasn’t a bad podcast that did it, it was with a guest that I quite like, Chuck Klosterman. It was during the middle section of this podcast, as Simmons slammed baseball for “having a problem” and saying that soccer has far surpassed it was a major draw in America that I realized Bill Simmons and I had grown apart. We had become different people than when the relationship began in college. Simmons had moved out to the west coast by the time I started reading him, but he still felt like “one of us”, but the longer one stays “out there” the more ones interests and perspectives are bound to change. Where once there were columns (there haven’t been in months) and podcasts about sports besides the NBA, now it seems to have morphed into a more mainstream, Cali-culture landing spot featuring young Ringer writers who all sound the same.

I’m sure that I’ve changed too, I don’t want to put this all on Bill Simmons and say that he’s the only one who has changed, I’m sure I like different things too but the core of why I listen and read is still sports, humor and east coast bias. This is a break up of a relationship that is one of the longest I’ve ever had. I broke up with Sports Center years ago, and that one got messy. I’ll still check in from time to time, I plan on continuing to subscribe to Simmons podcast but will only cherry pick interviews that peak my interest. I’ll listen to his NFL over-under podcast every Monday with Cousin Sal, because Sal’s hilarious.

Sal used to joke that Simmons had become an “NBAhole” because as they’d discuss the NFL, Simmons would somehow bring the line of conversation back to the NBA as an example of being superior. It was a running joke, but in this Summer where the Red Sox have been historically great with two MVPs, a Cy Young candidate and sit 50 games over .500, Simmons thought that having his teenage daughter on to talk about “teen culture” was important enough to deserve equal time as talk about the Red Sox sweep of the Yankees. I’m sure there’s some metric or analysis stating that talking about Cardi B or reality show stars drives more traffic than JD Martinez or Mookie Betts, but for someone who made his name as the Boston Sports Guy it runs far afield from what made you great in the first place.

I think we should see other people. We’ve just grown apart. I don’t think we want the same things out of this relationship anymore. It’s bizarre to think of reading a columnists work as a relationship but after more than a decade of following one source, it does begin to feel a lot like one. This one has simply run its course, there’s no hard feelings and we had some good times like back when Adam Carolla was a regular guest. Maybe I’ll try other online sports sites, maybe I’ll read more Barstool.

But we’ll always have Page 2.

Sterling Pingree (@SterlingPingree on Twitter) is a co-host on The Drive, weekdays 4pm to 6pm on 92.9fm The Ticket and streaming live at Follow us on Twitter, @DriveShowMaine and “Like Us” on Facebook, Drive Show Maine.