How Does ESPN Move Forward?

30 for 30 will be fine. Simmons pushed for that initiative and (along with Connor Schell) was able to extend the series into becoming a mainstay for the network. Simmons wasn’t overly involved the past few seasons other than pushing for particular projects to be done. Outside of that, his departure will not be a big blow here (although we should certainly tip our hats to his pivotal role in the creation of the series).

On the topic of Schell and shifting to Grantland, ESPN should be proactive in keeping all the talent that was close to Simmons. It’s to be determined what he’ll do next and you can bet whatever his next move is, he’d want to add some familiar faces. Anyone with an expiring contract in the next year who ESPN values may find themselves getting some unexpected, lucrative, and time sensitive extension offers over the next few months.

What really bears watching is how Skipper and ESPN will steer Grantland without Captain Simmons at the wheel. There has been much fodder on Grantland’s financial viability, which is rumored to run at a loss. Losing Simmons, whose sporadic contributions and social media promoting drives a significant amount of the traffic, will put further strain on the site.

It’s unknown how much Simmons’ status in the company shielded Grantland from adoption of more advertising units and more newsier/clickier content that would help the site’s financial standing at the cost of potentially going back on the site’s original vision.

Given the stern gaze of many Simmons fans at Skipper and ESPN for their role in his departure, I imagine Skipper and ESPN will be motivated in keeping Grantland healthy and influential regardless of the costs. ESPN does have Simmons’ former salary to potentially redistribute to reinforce the site’s talent base.

As a fan of much of Grantland’s content, I hope that’s the case. When the most ambitious sports sites in terms of quality fail, it makes it so much easier for those with lesser ambitions to blend into the rest of the unambitious noise that is out there. If ESPN can’t make a site like Grantland work with a focus on high quality content and not diving into the lowest common denominator, very few others will even make the attempt.

Keeping Grantland on-course puts further strain on Skipper, who has raised the eyebrows of many by staying the course of launching another personality driven niche site centered around the controversial Jason Whitlock. Skipper now has the fate of two high profile sites tied to key decisions he made with one of them seemingly venting columns of smoke on the launchpad, let alone the questionable pilot at the helm. ESPN can certainly survive some setbacks on the web front, but Skipper personally could find himself on the hot seat if worst case scenarios play out with Grantland and The Undefeated while Simmons opens shop elsewhere with great success.

What Will Simmons Do?

Our own Dan Levy put forth some very good ideas ranking the potential suitors for Bill Simmons here, which is definitely a recommended read if you’re interested in the topic.

To add another voice and examine the situation from a big picture perspective, there are several factors worth noting in the biggest free agent sports media sweepstakes in years:

– Simmons is likely going to want to go somewhere that is “on the way up” to quote Michael Ginsberg.

– Some companies just won’t have the ambition or risk tolerance to whole-heartedly make a run at Simmons.

– Where does Simmons’ true passion lie? Does he want to continue to float between his many roles of producing documentaries, writing, editing, podcasting, and being a television analyst? Not all media companies offer snug fits for all of these outlets. More specifically, does Simmons want to stay active in the documentary game and can he find an equally ambitious dance partner to back the launch of something to compete with Grantland?

First, let’s go through the options that aren’t legitimate players.  There are points in time where a deal could have made sense but I don’t think either company has prioritized their sports verticals the past few years to the point where Simmons would consider them.  AOL didn’t have any sports coverage for a two year plus span recently and is probably too early in a new sports strategy as well as financially a bit more constrained to be a serious contender. Yahoo has been doing some interesting media deals with big personalities and popular shows and the content operations are in LA, but outside of that this just seems highly unlikely as Yahoo has been focused elsewhere for quite some time.

What about digital giants like Twitter, Google, Facebook, Apple, or Netflix? These companies get tossed out as viable destinations for sports media rights all the time. I live in Silicon Valley and would love to see it, but it’s people looking way too far in the future thinking the media landscape as we know it is on the brink of imploding when really there is probably a decade left of mostly the status quo. These options are more like provocative ideas or suggestions that get people talking but almost never materialize.

Established brand names like Sports Illustrated and The Sporting News are not realistic candidates. Comcast and NBC does not seem like a possibility as they don’t really offer anything in Simmons’ areas of interest either.  The same goes for CBS and CBS Sports Network.  Perhaps there’s a 5% chance that Simmons could go to Showtime with some presence on CBS Sports properties a la Jim Rome, but it’s very slim.

New media companies like Vice, Vox, and Medium have the money and are on the upswing, but I’m skeptical any of these companies could create an attractive enough opportunity for Simmons to bypass a more comprehensive and potentially lucrative deal with a television network.

Turner Sports and Fox Sports have emerged as the top two consensus favorites for Simmons’ services. If this was before Jamie Horowitz was hired, I’d say 95% no for Fox as FS1 would still be rudderless, albeit over the hump financially. Simmons can essentially piggyback off of that restart/pivot and work with Horowitz to pick off ESPN talent as they see fit. More importantly – Fox is in LA as is Simmons, they don’t like ESPN, they have money to spend, have a tolerance for talent being outspoken and controversial, and quite frankly could use someone like Simmons to serve as a de facto ombudsman and snipe back at some of the dumber ideas we’ve seen Fox trot out the past few years.

Turner is a bit crowded in terms of Inside The NBA but it’s the most comprehensive and natural fit. Would Bleacher Report allow Simmons to launch something similar to Grantland? Could they find a spot for him in terms of basketball coverage? Would Turner allow him to produce a couple of documentaries a year?  In my opinion, now that ESPN is not an option I could see Simmons and his agent warming up to this over time if Turner really stroked his ego as needed.

Personally, HBO is my favorite option for Simmons, but I’d place the likelihood at only about 10%. Simmons was very outspoken that ESPN shouldn’t kowtow to HBO’s storied sports documentary output. HBO has since parted ways with their in-house production team and it’s been mostly crickets in terms of new projects. The word is that HBO wants to go in the 30 for 30 direction (famous established directors with a wider scope of stories) but hasn’t delivered much yet. Simmons could really pump new life into that operation and it is interesting to think what Simmons could do without beholding to advertisers and relationships with pro leagues with some type of regular show. I documented how Real Sports has gone in a new, broader, and younger direction since 2014 and perhaps Simmons extends that strategy for HBO Sports in a much more ambitious way.

And then there’s the venture capital route. Some VCs have already make public overtures. I could see Simmons putting some of his work under some flashy new startup, but I don’t think his camp wants to go all in with an entirely new endeavor. That’s more risk, more work, and a longer and steeper climb for the ultimate “fuck you, I told you so” revenge on ESPN. That said, it could present a digital option if he were to partner elsewhere on the television side.

I think there is a good chance Simmons may split his various roles between two companies so that his wide array of initiatives are across the board put in a position to succeed and compete rather than having some Simmons projects fizzle out without the proper support or expertise from a media company. Ultimately it really boils down to what Simmons is most enthusiastic about moving forward and who can nurture those initiatives to the point where they has similar or greater success to ESPN. Either way, for the first time potentially in the history of ESPN, Bristol will be keeping a close eye on the competition with a sense of genuine concern.

About Ben Koo

Owner and editor of @AwfulAnnouncing. Recovering Silicon Valley startup guy. Fan of Buckeyes, A's, dogs, naps, tacos. and the old AOL dialup sounds

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