The Bill and the Office

Bill Simmons’ move to HBO can lay the groundwork for the service’s ascension to sports broadcasting’s zenith.

Bill Simmons is a man of his words. Unfortunately, those words have recently embroiled him in a confusing and erratic saga between him and ESPN (his former employer). On his BS Report podcast a few months back, an audibly angry Simmons called out NFL Commissoner, Roger Goodell, on his mishandling of several player behavior issues. The NFL and ESPN have partnered for a number of years and Simmons’ scathing words towards Goodell put ESPN in a rough predicament: Should it support one of its prized talents or forsake that talent in the hopes of salvaging the infinitely- more-lucrative deal with the NFL?

Simmons, who came to prominence by writing columns on his own website as the “Boston Sports Guy” in the late 90's, is now heading to HBO in a multi-year deal announced today. Simmons’ departure to a rival network comes on the heels of another of ESPN’s star talents, Colin Cowherd, leaving the Worldwide Leader in Sports for FOX Sports. These departures beg the question: Is there a talent drain occurring at ESPN? Surely not.

ESPN still has a fair share of respected journalists and columnists in its stable. The sports broadcasting giant also has popular spin-offs in Grantland (which Simmons found) and FiveThirtyEight (led by Nate Silver). However, one-by-one, the network’s star power seems to be leaving for its rivals.

“The former ESPN writer and commentator has signed a multi-year deal with HBO to host a new weekly television series for the network that will air on the main HBO service, as well as the HBO digital platforms HBO GO and HBO NOW. HBO said the show, which will debut in 2016, will feature stories and guests from across the sports and cultural landscapes.”
— Richard Deitsch, “Bill Simmons heads to HBO to host weekly television show”

Which leads us to why Simmons felt the need to push-and-shove his way out of ESPN. Since 2001, Simmons has called ESPN home. Why would he leave the place that helped turn him into one of the most revered (and polarizing) personalities in the sports landscape?

The answer lies somewhere in the fulcrum of creativity and failure.

Individuals engaged in creative pursuits tend to succeed only when they are willing to embrace failure. Writing, one of Simmons’ talents, is such an example where one can obsess, persist, and refine to no discernible end and the work will still be nowhere near success. Most writers will fail more than they succeed. A wide majority of their works will go unread; dying quick deaths right in the editing software.

Knowing this impending failure and embracing it is what separates the great, perceptive writers of our time from those who simply don’t make it. Simmons, for all his drawbacks, is unafraid to fail. In a April 3, 2015 BS Report podcast, Simmons outlined his story to ESPN and how he almost didn’t make it.

“You have to understand, I always dreamed of writing a column for one of the Boston papers, and every move I made after college was made with that goal in mind: I’m gonna be the next Ray Fitzgerald, I’m gonna be the next Leigh Montville, I’m gonna be the next Gerry Callahan. And you have this romantic ideal in your head about the way life works, and then you find out that life doesn’t work that way — and it’s just about the most discouraging thing you can imagine.”
— Bill Simmons, “Now I Can Die in Peace”

Almost-not-making-it is what propelled Bill Simmons when he did make it with his ESPN opportunity. And, that same character-building that comes from staring abject failure in the face is what allowed him to stick to his guns when ESPN came bearing down on him for his Goodell comments this year.

Again, a person in a creative field will only succeed when they’re truly unafraid to take risks and, in the process, fail.

So, when I heard news this morning that Simmons had finally found a home at HBO, I could not be happier for him. While ESPN gave Simmons an extensive creative license, it did not allow him enough room to fail (and fail spectacularly at that). When push came to shove, ESPN opted for the profit-maximizing opportunity that the NFL alliance would provide rather than supporting one of its star creative talents in Simmons.

HBO, on the other hand, is all about offering creatives a chance to fail. It’s the network that took a chance on David Simon with The Wire, the place that gave David Benioff and D.B. Weiss the luxurious budget for Game of Thrones, and now HBO will become the place that allows an unafraid creative mind from Boston a chance to make his mark on the sports world once again.

Good luck, Bill Simmons.

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