Over the last decade, Bill Simmons has become one of the most important figures in sports. He’s an incredibly popular ESPN columnist and podcaster, the editor-in-chief of his own site at Grantland, a key figure in the 30 for 30 series’ formation, a regular presence on TV and an opinionated personality whose three week suspension for criticizing Roger Goodell has both made him the face of ESPN’s inconsistent discipline policy and perhaps signalled the beginning of the end of his relationship with Bristol. But how did he get here? We examine Simmons’ ESPN tenure in chapters. Here is our complete series written by Andrew Bucholtz in one place for you to enjoy.
Chapter I: Rise Of The Sports Guy
Bill Simmons’ rise at ESPN is reminiscent of one of the key ideas discussed in frequent Simmons collaborator and podcast guest Malcolm Gladwell’s Outliers: external circumstances often play massive roles in who finds the highest levels of success. That certainly would appear to be the case with Simmons; his own significant talent and innovations played an important role in his early days at ESPN, but with slightly different timing, it’s quite possible The Sports Guy never would have hit the fame we see today. In fact, with a few different turns, he may never have made it to Bristol at all, much less become a sports media titan.
While Simmons became known for unconventional fan takes laced with cultural references that were starkly different from most mainstream pieces at the time, that wasn’t his initial career path. Under slightly different circumstances, it’s quite possible that Simmons could have become a local print sports reporter or columnist rather than an ESPN figure. His background certainly seemed to set him up for that; he worked as a sports editor at the Holy Cross student newspaper, then earned a master’s degree in print journalism at Boston University in 1994 and then landed a job as a high school sports reporter at The Boston Herald.
For many people in many places, jobs like that have been the starting point for long, conventional media careers, and it could have been here if the Herald had done more to encourage and nurture Simmons as a writer. He’s said that the menial tasks he was given drove him away, though, and freelancing for The Boston Phoenix almost turned him off the media business entirely, causing him to quit and work as a bartender. If this had happened in an earlier decade, that’s probably the end of the story of Simmons as a sports media figure.
This was the start of the internet age, though, and that’s a huge part of what led to Simmons’ rise. He talked AOL’s Boston site into giving him a column in 1997, initially sent it to his friends, built up a mailing list and gained enough prominence to start his own BostonSportsGuy.com site as a side job while still tending bar for a living. Simmons did a terrific job of building enough of an audience there to attract ESPN’s attention in 2001, but again, the era was crucial; Simmons came to Bristol’s attention precisely at the right time, when they were still in the early stages of figuring out what to do with their web presence and when they were looking for something new and different to draw in different groups of fans. Simmons certainly provided that in spades, starting off his ESPN career with a guest column entitled “Is Clemens The Antichrist?” that proved to be one of the most popular pieces on the entire website.
Location and timing deserve another nod there. Simmons started off as the Boston Sports Guy, and that’s an essential factor in his rise. Would ESPN, at that time, have taken a look at a guy writing about Raleigh sports, or Jacksonville sports, or Memphis (the three smallest non-Green Bay, non-Canadian cities to have major pro franchises) sports? That seems unlikely. Boston’s a great place to pick up a local voice who might resound nationally, though, as it’s a sizeable city with prominent and historic teams that had substantial fanbases in baseball, basketball, football and hockey, plus a built-in rivalry with New York. It’s probably much easier to sell management of a national site on long pieces about Roger Clemens or the Patriots than something on the last days of Mark Brunell’s career in Jacksonville. Still, Simmons’ biggest break may have actually come from ESPN criticism, as he recounts in Those Guys Have All The Fun:
“I did this scathing diary of the 2001 ESPYs, I just killed it. I went after everybody. It was a terrible show. They had Joe Theismann doing comedy, and it was like everything people hate about ESPN. It was perfect for me; I made fun of everything. Well, someone at ESPN read it, and it started getting passed around to the higher-ups, and it landed with John Walsh, who started following me. Then he went back and read all my columns.”
It’s interesting to ponder if ESPN would have noticed Simmons without that piece. He was already a talented writer doing a lot of unique things by that point, and one with a decent audience, but the company wasn’t necessarily scouring the web for aspiring writers then. Bristol noticing criticism is a recurring theme in their history, though, and apparently, it can lead to jobs (although Chris Jones might disagree).
Having a key Bristol figure like Walsh in his corner was critical to Simmons’ rise at ESPN, but even with that, it took the threat of a competitor for them to bring him on board permanently. Jay Lovinger, a key ESPN.com editor, says in Those Guys that Simmons was considering returning to the Herald after a year of freelancing for ESPN. Lovinger had quite the job convincing Walsh to make Simmons an offer, but he eventually did, and the rest is history.
Timing again mattered for Simmons, too, as he started writing for ESPN shortly after they launched Page 2 in 2000. Right from the start (see the site’s launch day page here, from Nov. 6, 2000), Page 2 was much different than your conventional sports coverage; it tried new ways of appealing to fans, threw in more pop culture, and even featured Hunter S. Thompson (whose ESPN work in particular carries plenty of ideas similar to Simmons’ columns). It was a natural home for Simmons, one where his pieces fit right in, and one where his work would eventually become the defining trademark of Page 2, encased in its own “Sports Guy’s World” section. If ESPN had decided to only have a newspaper-like presence online, and if they hadn’t already had a quirky section like Page 2, Simmons might not have been such a good fit for them.
The success of the Patriots and the Red Sox also helped here. National outlet ESPN suddenly had a voice who was already prominent locally on those teams, and having the backing of ESPN helped Simmons establish himself even more as an authority on Boston sports. In fact, an anthology of his columns from 1999-2004 was turned into his first book, Now I Can Die In Peace. There were plenty of massive Red Sox fans who would say that World Series victory changed their lives, but Simmons was one of the few to get to write a nationally-published book about it. That’s a nice little perk of being ESPN’s Sports Guy.
One further often-underdiscussed factor in Simmons’ rise and his early days at ESPN is his appeal to bloggers and other influencers who helped grow his audience. Sports blogs were in their infancy when Simmons started, but the content he (and other Page 2 figures) provided was essential to the development of the medium. Simmons certainly wasn’t the first to unashamedly write from a fan’s perspective, or the first to make pop-culture references, or the first to analyze games well beyond traditional recaps and box scores, but he was an important figure in popularizing those concepts. Moreover, his writing at first was so different from a lot of what was seen in local newspapers that it became a frequent conversation topic amongst early bloggers, and amongst those who would later become bloggers. As discussed by Gladwell, Simmons has a huge and highly-engaged fanbase, and particularly early on, one that was eager to spread his work around and discuss it. That helped make him a valuable presence at ESPN, even when he was still just a regular columnist.
Simmons and Page 2 proved a perfect match, and one that benefited both sides. The relationship wasn’t without bumps (Lovinger says Simmons was “an incredibly pain-in-the-ass guy to work with,” particularly when he’d disagree with edits and complain to Walsh or John Skipper, who was running ESPN.com at the time), but Simmons provided a lot of great content and helped make Page 2 a destination for many digitally-savvy sports fans, while ESPN gave him a national platform and one that would continue to grow. Simmons wanted to do more than just write columns, though, and he did. We’ll get to that in our next installment.
Chapter II: The BS Report Hits the Fan
In 2014, Bill Simmons’ The B.S. Report may not seem all that remarkable. Sure, it’s a hugely-popular podcast, but there are all sorts of podcasts out there today with sports personalities giving opinions and interviewing notable figures and friends, and tons of those podcasts are under the ESPN umbrella. When The B.S. Report first launched in 2007, though, it was a relatively bold leap. The podcast also helped to create and develop some of the tensions that have been building in his relationship with the company. The B.S. Report is an important part of Simmons’ story overall, and it continues to be a key part of his work, but it’s especially essential in understanding how things changed for him from 2007 to 2009.
2007 was only a few years after “podcast” itself was coined as a term and the idea of on-demand radio started to take off. While Simmons’ podcast wasn’t the first sports one out there (or the first ESPN one; the company started podcasting in 2005), his became one of the first really-high profile sports entries into the podcasting arena. Perhaps even more notably, the podcast represented Simmons’ first real venture into other platforms than his ESPN.com columns, and as such, it was a big part of his transformation from an online-only writer into a central figure at the network.
It’s interesting to explore how Simmons got into podcasting. ESPN entered the arena in 2005, but he started The B.S. Report in 2007 as a result of approaching his bosses, according to this 2009 piece from John Ourand of The Sports Business Journal:
Simmons creates three or four new podcasts per week, and says they help him interact with his readers and listeners in a new way.
But that was not the reason why Simmons first approached his ESPN bosses in the spring of 2007 about producing his own podcasts. ESPN began podcasting in the summer of 2005, and Simmons said he was intrigued by the medium.
“I thought it would give me some reps, and help me get rid of vocal tics if I ever wanted to do anything down the road with TV and radio,” he said. “It would keep my options open.”
It didn’t take long for ESPN to agree, and they quickly outfitted Simmons with “a weird machine, two headphones, [and] an ISDN line in my house.” …
Simmons’ podcasts defy traditional rules. Told to keep his podcasts under 20 minutes, Simmons regularly talks for about an hour. Told to break his podcasts into segments, Simmons generally carries one theme throughout.
He calls podcasting “radio on demand,” and says it has several advantages over traditional radio. “By the time radio guests are getting warmed up, the segment’s over. With this, you’re really having a conversation with somebody,” he said.
Breaking those traditional ideas was key to Simmons’ success, and it’s notable that podcasting in general has evolved much more in the direction he favoured than the one his bosses advocated way back then. However, ESPN was a big help in the rise of Simmons’ podcast too. In fact, his relationship with ESPN has played a vital role in his overall success across a wide range of media arenas, from writing to podcasting to documentaries to running a website to TV. Tons of people have thought of making sports documentaries, or of launching a sports website, but it’s a lot easier to see that turn into end products of the calibre of 30 for 30 or Grantland when you have the self-proclaimed Worldwide Leader In Sports and its vast resources behind you.
Similarly, the early history of The B.S. Report is far different from most podcasts’ path of starting small, gaining credibility and eventually landing distinguished guests. Simmons kicked things off with ESPN basketball writer Marc Stein, had Adam Carolla and Paul Shirley follow him, and did a podcast with NBA commissioner David Stern in just his second month of podcasting. Names like that certainly helped attract an audience, as did the promotion of The B.S. Report on ESPN’s site.
At the same time, Simmons’ efforts turned out to be the anchor of a key new area for the company. In May 2009, ESPN’s podcasts saw 9.6 million downloads, with The B.S. Report listed as their most popular, and it pulled in 10.7 million downloads in the first six months of that year. The advertising revenues and corporate sponsorships weren’t huge, but ESPN’s Traug Keller (senior vice president of production, business divisions) told Sports Business Journal that podcasts were a desirable venture to attract a young audience that wasn’t listening to traditional radio and expose them to ESPN talent. Simmons was the leader on that front, and thus, in theory, it should have made him and Bristol even more closely entangled.
In practice, though, podcasting created tensions. Simmons was already battling with editors over the content of his column, and that perhaps became even more difficult with podcasts, where a problematic reference couldn’t just be stricken. That led to the disclaimer at the start of each episode that the podcast “is a free-flowing conversation that occasionally touches on mature subjects.” Even that didn’t solve everything, though; in Those Guys Have All The Fun, Simmons discusses the trouble he got into for saying people perceive soccer as gay, and how Super Dave Osborne made a joke on his podcast that was cut, but was allowed on Conan O’Brien’s 11:30 NBC show.
Perhaps most importantly, ESPN vetoed a podcast where he’d scheduled Barack Obama (then campaigning for the 2008 Democratic nomination) to talk sports. That created a massive backlash, and it led to Simmons railing against the network’s anti-politics stance over that and a nixed Sarah Palin reference in Those Guys:
“So at some point—as I made the case passionately and repeatedly—are we not reflecting what real life is like? Everyone I know is talking about Sarah Palin’s speech and I’m not even allowed to breathe a mention of that in my column? What kind of alternate universe are we trying to create here?”
One area where Simmons did get away with more was 2009′s The Book Of Basketball, which marked both his first original book (not a collection of columns) and another chance for him to test ESPN’s limits. As he says in Those Guys, he thought it was unusual the company didn’t clamp down on his book’s coarse content more given how they tried to censor his podcast.
“How do you explain my book? It’s a book released by ESPN that has dick jokes and porn jokes in it. It has jokes about how I smoked too much pot in 1995. I compare Shaq to Peter North. Hell, I probably pushed the line too hard. Why was that not a problem for anyone at ESPN? Sometimes I wonder if they’re willing to look the other way unless it ends up in the Sports Business Journal—if it gets in there, they know George [then-ESPN president George Bodenheimer] is going to see it.“
The Book of Basketball only added to Simmons’ increasing notoriety as it became a #1 New York Times bestseller.
As 2009 came to a close, Simmons’ star was still rising. He’d become not just a key online presence for ESPN, but the unquestioned star of Page 2, the company’s most valuable podcaster (and one of their most valuable voices overall, especially at reaching younger readers and listeners) and a best-selling author. Bristol had given him tremendous resources, connections, and exposure, and he’d repaid them by delivering an incredible audience, notable for its size, its demographics and its passion for his work.
More was to come, with Simmons continuing to find new ways to make ESPN a leader in all forms of media. However, the relationship between him and his employer was starting to hit more rocky patches, and some of the issues exposed in this period would turn up again and again later on. In particular, The B.S. Report saw Simmons push some limits he hadn’t really before, and then get upset when the company censored him. There were even greater days ahead for Simmons’ role at ESPN, but also even more significant feuds. We’ll cover that and more in Chapter III.
Chapter III: Sports Guy to Sports Czar
While Bill Simmons was incredibly popular by the start of 2009 as both a columnist and a podcaster, and while his popularity was paying great dividends for ESPN, he was largely seen as off in his own corner. Simmons was viewed as one of Bristol’s biggest web stars, but that didn’t necessarily make him an important player within the company in the grand scheme of things; in fact, there were plenty of others at ESPN, including rival Rick Reilly, who publicly looked down on him. That was about to change.
It’s notable that Simmons’ pre-2009 success was in arenas that were rather new to Bristol, and ones that not everyone inside the company valued. Yes, he was the unquestioned star of Page 2 by that point, but it was only a small part of the company’s overall web presence. Yes, his podcasts were by far the most popular ESPN ones, but that was a qualified success; John Ourand’s June 2009 Sports Business Journal piece on ESPN’s decision to strongly back podcasts started with “It’s not a big business, and it may never be a big moneymaker.” The 2009-2011 years would see Simmons expand that success to new realms, though, becoming even more versatile and even more important to ESPN. One of the most notable? The 30 for 30 series.
Exactly how much credit should Simmons get for 30 for 30? That’s debated in some quarters, but it’s notable that the well-researched section on the series in James Andrew Miller and Tom Shales’ ESPN history Those Guys Have All The Fun gives him a substantial role:
“One of the most ambitious and auspicious original projects in ESPN’s history—second only to SportsCentury—began as a brief memo e-mailed to John Skipper and John Walsh in 2007 from dot-com columnist Bill Simmons. He saw ESPN’s thirtieth anniversary looming and envisioned a massive and promising venture: 30 for 30…”
The authors go on to credit Simmons with much more than just the idea of 30 sports documentaries, including the idea of making these “independent cinematic essays,” focusing on key sports stories that have been forgotten, having the director appear on-camera in each one to discuss the film, and (together with fellow 30 for 30 executive producer Connor Schell) going to well-known filmmakers outside ESPN. Even Skipper’s comments to them about how there’s no “singular paternity” gives Simmons a substantial role, mentioning several of the other key figures (Walsh, John Dahl, Keith Clinkscales, Joan Lynch and Mike Tomlin), but saying “without Bill Simmons, 30 for 30 could not have happened the same way.”
Thus, there’s a pretty strong case that Simmons’ involvement in the initial process at least was rather important. Moreover, some later Simmons interviews (such as this 2011 The Hollywood Reporter one by Lacey Rose) talk about him pitching filmmakers, working on the series, and encouraging ESPN to do a second batch of films, further evidence he was more than just an idea man. Those comments do come from him, and others might emphasize their own role and diminish his, but it sounds like he was involved far beyond the initial memo.
The first 30 for 30 series was a tremendous success on many levels, but it particularly showed that Simmons couldn’t be neatly pencilled into a corner of Bristol. On the face of it, it was a project you’d never expect a columnist or podcaster to come up with, much less play an important role in executing. It’s something he proved very good at, though, and something that wound up boosting ESPN’s overall reputation significantly. Along the way, it increased Simmons’ value to the company and boosted his internal significance.
Of course, there are a few factors to consider here beyond Simmons’ own talent. This only worked because of Skipper’s desire to take on an ambitious project for ESPN’s 30th anniversary, because of HBO’s success in the sports documentary realm irking Skipper, because of Bristol’s resources, because of renowned filmmakers wanting to tell sports stories (and generally doing a very good job with them) and because of the talent of the other key 30 for 30 figures. It’s highly unlikely Simmons could have executed anything close to 30 for 30 on his own. Still, he played a valuable role in the significant success it became.
In some ways, 30 for 30 paved the way for Grantland. It illustrated that Simmons wasn’t just a writer or podcaster, but also someone with an eye for good sports stories, good talent to tell them, and good potential projects for ESPN. Moreover, it gave him some experience on the editorial, content-management side, and it gave him a taste of what it was like to be involved in the production of highly-praised content. All of that likely played a role when he campaigned to start Grantland in 2011. In fact, he directly made the connection in the above-mentioned THR piece:
I had spent three years working on this book, and I was hitting 40, and I was like, “What do I want to do long-term?” I always wanted to create a site that was sports and pop culture. 30 for 30 had a big impact because I loved how that was about finding, empowering and working with these incredible directors, and I thought the same thing could work for writers. I researched different sites and looked through all of my favorite magazines and tried to find people who were on their way up.
What’s perhaps most notable about Grantland’s beginnings is that Simmons included it as essentially a contract demand, as he goes on to say in that piece:
THR: How did you convince ESPN to fund it?
Simmons: Simple — I would have done it with somebody else. My contract still had 10 months to go, and we started talking about it, and I said: “I want to figure this out, and I want to do it here. But once we get to the end of those 10 months, I’m still going to do it.”
That’s gutsy from Simmons, and it shows perhaps the same sort of management-challenging attitude that’s long been a part of his ESPN history and has him in trouble this time. It worked out, though, for both parties. Even if Grantland had failed, ESPN was still able to keep Simmons and benefit from the popularity of his columns and podcasts (plus his 30 for 30 work). Grantland didn’t fail, though, and has grown into a home for solid writing and a pretty nice asset for ESPN, not to mention an idea mimicked in many other places. It’s also helped boost Simmons’ profile, making him a successful editor-in-chief as well as a columnist, podcaster and documentary producer.
30 for 30 and Grantland may have been two of the biggest keys to Simmons becoming much more influential at ESPN than Reilly, and the importance of Simmons winning that battle is something that shouldn’t be understated. It’s not surprising that the two clashed after ESPN’s 2008 move to bring Reilly in; they were the two most prominent columnists on ESPN.com (and ones with rather different approaches), plenty of journalists asked Reilly about Simmons and vice-versa, and even the Worldwide Leader may not have been big enough for both of them.
In the traditional journalism world, you’d expect Reilly to triumph in that fight. He was an experienced and big-name columnist who had just been brought in from Sports Illustrated in a very high-profile (and high-money) move, while Simmons was someone who went from nobody to big figure just inside ESPN, and did so in an unconventional way. Simmons wound up being far more important to Bristol, though, and in a variety of ways; his columns and podcasts continued to draw huge traffic (and often without anywhere near as favourable promotion on the main page as Reilly’s), but Reilly remained just a columnist (and one often reusing material at that), while Simmons was innovating and exploring new realms for the Worldwide Leader to conquer. The fight wound up as a massacre, but with an unexpected winner, as Will Leitch explored in this 2012 Sports On Earth piece on Simmons’ rise and Reilly’s fall:
At first, the story was “will Reilly and Bill Simmons get along?” a question that seemed especially vital considering how many digs Reilly had taken at Simmons in the past. Simmons briefly fought back but eventually got his revenge the old-fashioned way: He demolished Reilly, not just in page views but in television presence and power at the company. Simmons has become one of the signature faces of the network’s NBA coverage — it’s sort of amazing that Bill Simmons, former anti-establishment figure, is going to be the primary pregame and halftime guy on ABC during The NBA Finals — but even started, in Grantland, an influential and well-written sports/culture site that features some of the most talented young writers in the business. (Albeit on a site that desperately tries to pretend it’s not funded by, you know, ESPN.) The idea that Rick Reilly and Bill Simmons could be competing is as aged and over as a good dental joke. That fight is over, and Simmons won in a knockout.
We’ll discuss Simmons’ TV career more in our next installments, but the points Leitch makes in that piece are good and lasting ones.
Simmons unquestionably beat Reilly in the long run (Reilly still does stuff for ESPN on the TV side, but officially retired from column-writing in June), and he did so not just by putting in more effort, outwriting Reilly, and drawing more readers, but also by building a multimedia empire.
In addition to his columns and podcasts, he became a bigger part of ESPN’s overall plans with his involvement in 30 for 30 and Grantland. By the end of 2011, Simmons was by far the biggest face of ESPN in the online realm, and more was yet to come. ESPN.com editor Jay Lovinger says in Those Guys that “Only ‘Bill World’ will ever satisfy Bill.” Heading into 2012, “Bill World” was far more reality than figure of speech.
Chapter IV: Top Of The Pyramid
As discussed in Chapter III, things were looking pretty good for Simmons by the end of 2011. He’d expanded his role at ESPN well beyond just columns, branching out with great success into podcasting and the 30 for 30 series. He had reached #1 New York Times best-seller status with The Book Of Basketball, and he had become much more influential than rival Rick Reilly both inside and outside Bristol. He was sufficiently important to the Worldwide Leader that he managed to make getting his own personality-driven site, Grantland, a condition of his contract renewal. While Simmons had carved out his own ESPN empire across many different mediums, though, his TV presence on the main network (and the respect, both external and internal, that comes with that) was still quite limited. Within a year, that was about to change; Simmons was set to move from being just the top player in his own empire to performing under the brightest spotlight at ESPN, a regular role on the main TV network.
ESPN’s October 2012 decision to add Simmons and Jalen Rose to their primary NBA pre-game show, NBA Countdown, was notable for both what it said about the network and what it said about Simmons’ status within Bristol. For starters, it made Simmons one of an exceptionally rare breed on sports television; a guy in a primarily-analytical role on a pre-game show who wasn’t a former professional athlete, and a guy who wasn’t even a long-time print columnist. That showed that ESPN was willing to try some new things on-air, and that boded well for Simmons and others without professional playing experience; it suggested there was less of a hard ceiling on what their on-air roles could be. Beyond that, it allowed Simmons to finally get a regular on-air presence on the main network. That may seem like a small distinction given how big Simmons’ empire had already grown, but it certainly mattered within ESPN. Consider what Chris Berman said about Simmons in the 2011 ESPN history Those Guys Have All The Fun:
“I don’t know Bill Simmons. I wouldn’t know him if he sat here right next to me. I’m not knocking him, because I know he’s important to the company, but that’s some other limb of the tree that I don’t touch.”
Berman’s attitude towards and lack of knowledge of Simmons likely wasn’t universal amongst on-air talent, but there’s plenty to suggest that there’s still a significant divide between ESPN’s TV operations and other corners of the Bristol empire. Simmons had boldly carved out new swathes of empire for ESPN, helping to make them a worldwide leader on the dot-com, podcasting and documentary fronts, but that wasn’t enough to win everyone over. Now, he was being given a more established, high-profile position within the main network, one that was much harder to downplay as “some other limb of the tree.”
It’s notable that ESPN management had tried to make this happen earlier. Richard Deitsch reported when the move was announced that Bristol leadership had made Simmons Countdown offers before, but that the timing wasn’t right with his Grantland launch and other activities. Thus, even though Berman and his ilk weren’t high on Simmons, that opinion wasn’t reflected at the top levels of management, and the desire to have him as part of the TV empire was strong. Given Simmons’ love for and knowledge of the NBA, Countdown seemed like a logical place to put him, and it seemed like a way to expand the joint empires of The Worldwide Leader and The Sports Guy.
Empires don’t expand forever, though, and the issues that arose with Countdown illustrated some of the problems that were to come between ESPN and Simmons. Some of these weren’t his fault; the show was still trying a “hostless” approach in 2012-13, and that led to discussions that often flowed poorly. There were also major chemistry issues, which we’ll get to later. It’s interesting that despite the 2012-13 struggles, though, management still believed in Simmons as a Countdown figure; in fact, they doubled down on him. Deadspin’s John Koblin reported that the changes to the show ahead of the 2013-14 NBA season (the addition of Doris Burke, Magic Johnson’s abrupt exit and a lessened role for Michael Wilbon) were to make it more Simmons-centric:
So, why did Magic make his sudden announcement that he’s leaving ESPN, less than three weeks before the NBA season begins? An announcement so sudden that the newest addition to NBA Countdown, Doris Burke, appears to have had no idea it was going down?
ESPN sources tell us that Johnson’s departure was the result of an old-fashioned power war, with one very clear winner: Bill Simmons. “It’s Simmons’s show now,” said one source.
Magic apparently was not at all happy when ESPN told his buddy Michael Wilbon that his role on NBA Countdown would be diminished. He was “booted,” according to one source. Another ESPN insider also said that Magic was “privately seething over the Wilbon thing and in general did not like that Simmons held all the power and influence.” Magic didn’t necessarily need the power, our sources explained; he just didn’t feel like kowtowing to Simmons when he’s, well, Magic Johnson.
“The bottom line is they turned that show over to Simmons,” said our source. “That’s why Doug Collins got hired and why Wilbon was out.”
And that’s a very large part of why Johnson decided to bolt the show at the 11th hour. …
Now, the show belongs entirely to Simmons. He’s losing star power with Magic Johnson’s departure, but he’s not necessarily losing a key component of a studio show that had a much-improved but still uneven 2012-2013 season. ESPN said it’s still “determining our NBA commentator roles for the upcoming season.” Simmons will be able to get a proper host in for the show. He’ll be able to shape it however he wants.
Such is his power now at ESPN. “The shadow president,” a source called him.
Whether that’s an accurate reflection of what went down is disputed (Simmons vociferously denied any involvement in Johnson’s exit in an interview with Deitsch), but it certainly indicates the power Simmons was at least perceived to have and the desire of ESPN management to feature him on the main network. It also shows ESPN didn’t mind courting some controversy, as this was after Simmons’ run-ins with Doc Rivers surrounding the 2013 NBA Draft.
Rebuilding the show around Simmons also had some potential; the chemistry of the previous group was lacking, and creating something with at least some overarching vision seemed like a step up. Simmons himself built a whole book around the thesis that basketball is about chemistry and teamwork more than individual talent, and the 2012 iteration of Countdown didn’t have that chemistry. As 2013 was ending, ESPN was trying to find that chemistry with a new show more focused around their franchise player.
It’s worth mentioning that Simmons was finding success in other areas while Countdown drama was playing out. Grantland grew from humble beginnings to an important and influential site, and it brought in some top talent, including SI’s Zach Lowe. The 30 for 30 series continued to shine after the initial run of 30 documentaries, first under the label of ESPN Films Presents (which created a major branding issue), and then as a “second season” of 30 for 30-labeled films once they realized viewership and critical reception was dropping without that label. Meanwhile, Simmons’ own columns and podcasts remained vastly popular.
Thus, betting on Simmons as a television star as well made sense; everything else he’d done at ESPN had worked out. With 2013 ending, he looked like perhaps the biggest face of the network going forward, certainly online but also with podcasts, documentaries and now regular TV appearances.
How did he go from there to a suspension that could prove the tipping point in his relationship with ESPN and potentially pave the way for an exit? We’ll discuss that in our final installment.
Chapter V: Welcome To The Trade Machine
While Simmons’ history with ESPN has had plenty of ups and downs over the years, the general theme from 2001-2013 was one of his ascension in importance at the network. He first started writing for ESPN.com in 2001, came on board full-time a year later as a dot-com columnist, had his columns from 1999-2004 turned into an ESPN-published book in 2006, expanded his brand to podcasts in 2007, helped get the 30 for 30 documentaries off the ground (and played an important role in their ongoing development) in 2009, got his contract renewed and launched Grantland in 2011, and gained a regular TV role on NBA Countdown in 2012. There were rough patches along the way, but Simmons generally continued to become a more notable media figure in general and a bigger and bigger part of ESPN’s operations in particular.
2014 has been different, though. While Simmons has still found some notable successes (particularly with Grantland’s continued growth and work on the next wave of 30 for 30 films), he’s also seen setbacks. While his overall importance and influence in the sports media world hasn’t dropped (and has in fact perhaps risen), his relationship with ESPN has gotten rocky enough that his suspension over criticizing Goodell (and daring his bosses to come at him for it) has been seen as a potential tipping point that could lead to him leaving the network.
This chapter isn’t The Decline And Fall Of Bill Simmons by any stretch, as it seems apparent that Simmons will be an influential media figure for years to come. The debate is more if those future years are going to be inside ESPN, or if the self-proclaimed “Picasso of the Trade Machine” is eager to take his talents elsewhere.
One of the most fascinating developments of 2014 saw Simmons leave his prominent role on NBA Countdown for a new Grantland Basketball Show. Some will argue that’s a demotion; Simmons will no longer be a face of ESPN’s regular NBA pre- and post-game coverage. Some will say it’s a promotion, as he now gets a show that’s much more focused on him and his efforts, rather than one that includes him as just one voice. Regardless of the stance there, it seems like a smart move for both him and the network.
While Simmons’ Countdown stint had great potential, especially considering that he wasn’t your typical ex-jock analyst, it proved to be an awkward relationship in many respects. He sometimes clashed with other analysts on air, was rumoured to be the prime mover behind Magic Johnson’s exit and Michael Wilbon’s lessened presence just ahead of the 2013 season (although he fervently denied that), and even got into a feud with Clippers’ coach Doc Rivers.
His on-air complaints about his own airtime (and Sage Steele’s head-shaking reaction) on a postgame show during the NBA Finals in June 2014 were particularly indicative that the Simmons-Countdown era was on the rocks, and August saw the announcement that he was headed to his own show. It was a rare uncomfortable moment that broke the fourth wall and gave a window into the dissension on set.
That departure probably caused some relief for both Simmons and ESPN leadership. He got a show centred on him and his thoughts (which has been a successful recipe for his columns and podcasts), and they eliminated the most visible tensions on Countdown. However, the way the Countdown drama played out may have exacerbated some of Simmons’ previously-expressed frustrations with the company, and may have led towards him publicly daring Bristol to suspend him.
That element of the suspension saga shouldn’t be understated. Jim Miller said on the AA podcast that Simmons’ three-week suspension (two unpaid weeks, one paid week) was two weeks for insubordination and one week for calling Goodell a liar. That makes sense given both the oft-discussed ESPN desire to prevent any individual talent from getting too powerful and their lack of suspensions for other hard-hitting commentary on Goodell, such as what Keith Olbermann’s been doing (which he told Richard Deitsch has been approved by Bristol with very few changes).
Simmons’ comments on Goodell were incendiary, certainly, and perhaps problematic at an NFL rightsholder (something that’s come up before with ESPN). They might have led to a suspension even without his public challenge to his bosses to go after him. It seems highly probable that the dare to management may have been viewed as more troubling inside Bristol than any of Simmons’ comments on Goodell, though, and ESPN ombudsman Robert Lipsyte’s comments on the suspension seem to endorse that view:
In Simmons’ case, the “dare” was widely interpreted as a challenge to ESPN President John Skipper, who just happens to be Simmons’ most important booster at the company. When asked, Simmons refused to comment on whether it was directed at Skipper.
But Skipper certainly thought it was, and that insubordination was one of the main two reasons for the severity of the suspension. Particularly on podcasts, Skipper said, Simmons has a tendency to slip back into his “bad boy, let’s-go-to-Vegas” persona. Simmons, Skipper believes, is transitioning into an important influence and mentor at Grantland and needs to leave his well-worn punkishness behind.
Lipsyte goes on to write that “The more important reason for the suspension, Skipper said, had to do with fairness and the difference between commentary and reporting,” so take that for what it’s worth. However, the challenge to ESPN management certainly did not go unnoticed inside Bristol, and for them to cite it publicly as a reason for his suspension indicates it was taken very seriously indeed.
One theory floating around is that this was an intentional move from Simmons, a way to boost his public support and profile and an attempt to gauge other companies’ interest in him ahead of his potentially-pending free agency. That might make it the sports media equivalent of Carmelo Anthony or Dwight Howard publicly lobbying for trades to specific cities while still under contract. There’s some logic here; it would be hard to find a less popular public sports figure right now to align yourself against than Roger Goodell, and ESPN’s suspension inconsistency has brought them lots of criticism. This started a massive #FreeSimmons movement and a bombardment of e-mails to Lipsyte in support of him, and it’s made Simmons even more of a conversation topic than normal (and a much less polarizing and more universally-backed presence than normal). Keep in mind that Simmons is a huge wrestling fan; if anyone’s going to try a public face turn ahead of free agency, it might as well be him.
What are the chances Simmons winds up elsewhere? Miller, the co-author of ESPN history Those Guys Have All The Fun and a regular contributor to The New York Times, typically has his finger on the pulse of Bristol, and his comments on the AA podcast on Simmons are instructive. In particular, Miller says (6:23) that on the ESPN side, president John Skipper won’t pose a problem in patching up the company’s relationship with Simmons, but some of those under him might:
“John Skipper’s DNA is such, he is the least Nixonian person. There are many people who have kind of gone out of the ESPN orbit who have been brought back in. He believes in mending fences. Keith Olbermann returned to ESPN on Skipper’s watch. Skipper doesn’t hold grudges, he doesn’t believe in that kind of psychology, so I believe there’s a great opportunity for Bill Simmons and John Skipper to continue. That’s not the problem. The problem is the layers underneath Skipper, where I do think that there is some tension that exists between Simmons and, you know, others at the network. Again, it comes down to this issue of power, and people who think that Simmons is trying to be more important than the network.”
Miller goes on to say (10:22) that an interesting Simmons possibility apart from the idea of him jumping to a competitor like Turner could be him starting his own site, and perhaps taking Grantland writers with him:
“The nature of technology and the media landscape today is that you don’t need to have a big place behind you. He could create his own ecosystem that has, you know, a web presence, podcasts, anything he would want to do and he doesn’t have to be tied to a network. That’s totally true. He could also go and create his own version of Grantland.
My understanding, by the way, is that if Bill Simmons leaves ESPN, Grantland stays at ESPN, but the whole thing is… you’ve got to think about something: Grantland is just a word. The people who work for Grantland and the relationships that they have and the reasons people write for them, work for them, whatever, is probably inextricably linked with Bill and his team.
The bigger question isn’t whether the word Grantland would stay with ESPN. The bigger question is could Simmons, if he left, basically take the Grantland staff with him and call it something else? If I’m in Vegas, I would be betting that he’d be able to do that if he decided to leave, because I think a lot of people who work there would basically walk through fire for him. It might be a Pyrrhic victory for Bristol in the sense that they get to keep Grantland, but how many people would actually stay?”
With Simmons’ contract up next year, his return from suspension today begins the most pivotal time in his tenure at ESPN. While many believe he’ll be able to repair relationships and stay with Bristol, the lengthy three-week suspension represents a time of great volatility. The platform and reach the worldwide leader in sports offers Simmons could not be found elsewhere and leaving that behind would be a significant risk. However, Simmons is one of the few people with the personality and the profile to take that risk. As the New York Times lays out, Simmons could follow the personal brand path of others like Glenn Beck who have left network jobs to start their own ventures.
It’s clear that while Simmons’ internal popularity at ESPN may have taken a hit following this suspension saga, his external popularity remains huge. With his success as a columnist, podcaster, documentary producer, website editor-in-chief and even (to a degree) TV analyst, there are plenty of options out there for him, from sticking with ESPN to joining an established competitor to starting his own operation (perhaps with some substantial venture capital funding). Thus, regardless of what happens from here on out, The Sports Guy is likely to be a prominent figure on the sports media landscape going forward. The question’s just who he’ll be that prominent figure for.
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