The Undefeated launched yesterday and first impressions were generally warm spanning the content, the site design, to the general tone of the site.  It’s early and just a like a television show after its pilot episode, I can’t proclaim a definitive affinity for the site but imagine I’ll be a casual reader when I see something in my Twitter feed that sounds interesting.

I really enjoyed Kevin Merida’s welcome note. Those are hard to whiff on but I thought he did an exceptional job setting the tone for the site as he connected the site’s mission and its name to his father’s life as a black man in the very white world of Geology. Give it a read if you can… but I only mention this because the ending left me wondering what’s in the long-term future for the upstart site.

Merida’s uplifting article was on equal footing of any cinematic halftime locker room speech, but what stuck with me was the inclusion of the names of all those involved with the site. Not the names themselves, but the amount of them totaling nearly 50. Presumably there are more behind the scenes folks as well, although I imagine many of the folks involved with The Undefeated may have their overhead expense to ESPN shared with other divisions like television and and many may be part time hires.

Either way, that’s how high the bar is for The Undefeated to turn a profit and find some level of security from the Disney bean counters who suddenly are being heard after decades of being largely ignored in Bristol. By no means am I throwing dirt on The Undefeated (I’m not that guy at all). That said, I intimately know the challenge of running a financially viable content venture and it’s a very tough business and worse, it’s getting increasingly more challenging. While The Undefeated certainly has a path to success, below a look at some of the realities they will face.

The timing went from great to awful

Times have changed in the nearly three years since we first heard about “Black Grantland.”

Grantland was young and growing, cord cutting wasn’t this turbulence-causing-headwind rattling the massive jumbo jet that is ESPN, and in terms of digital readership the bulk of traffic was still coming from destkop computers which yield MUCH better advertising rates and the industry was not fearing an ad blocking apocalypse.

ESPN has done a lot of belt tightening of late, and while this is John Skipper’s pet project, the reality is that The Undefeated probably has two years to either turn a profit or at least show a trajectory to profitability before Disney’s board and its investors begins to put the venture under a microscope similar to Tim Armstrong’s pet project Patch drawing the ire of AOL’s investors. Skipper can likely provide some additional runway beyond two years (perhaps up to four should the site find itself in the red after two years but willing to make some changes), but there is a reality that ESPN is having a hard time right now retaining its sports rights as well as some of its most high profile talent. Skipper can’t shelter the site forever from financial scrutiny (we’ll get to that), so unfortunately the clock is ticking on The Undefeated to carve out a pretty sizable readership in a short matter of time.

Skipper is already out on a limb here and expectations have only gone up

It’s not hard to see why John Skipper would be interested in a site like The Undefeated. Increasingly we find ourselves “exploring the intersections of race, sports and culture” to quote the site’s about page. That said, think how much patience, momentum, bad publicity, and goodwill has been burned with the Jason Whitlock disaster. How far along would the site be at this point in time had this concept been developed internally rather than pushing all-in blind with someone as volatile, obtuse, and high-maintenance as Whitlock?

Skipper had his out when Deadspin’s Greg Howard jumped off the top rope twice on Whitlock’s never launched site. ESPN tried to spin the situation and looked ridiculous doing so. Howard, once a target of the site, is now at the New York Times along with former acclaimed Grantland writer Wesley Morris. Whitlock now writes on a Tumblr site.

Winding down Whitlock was a much needed restart for the site, but you have to wonder given the amount of negative publicity, if Skipper has overextended himself by staying the course. While it’s impressive that The Undefeated is off the ground and with a talented group assembled, you got to wonder if they’re coming to the plate too late in the ballgame and already facing an 0-2 count.

ESPN is risking further alienating fans who believe the company has a liberal agenda

Don’t worry ESPN. This site is too. The “They took our jobs” crowd is quite uppity these days and it’s not that hard to at least see their point of view. Connect the dots of “They just showed Michael Sam kiss another man!” to “They’re giving Caitlyn Jenner an award!” to “Obama should be fighting ISIS instead of doing a damn bracket!” to “They fired Curt Schilling for sharing Facebook memes!” to “Why are all these women talking sports on TV!” and you have the dossier of why a large contingent of sports fans are seething mad. John Skipper himself had to comment on this topic this week and I’m not that confident that Bristol has any idea how passionate and widespread this sentiment has become.

Enter The Undefeated,  which will tackle complex and delicate issues via a staff you’d largely presume skews progressive and tailored for an audience of similar left leaning beliefs. With Fox’s growing portfolio of live sports rights including NASCAR, baseball, golf, and soon Big Ten rights (all of which skew a bit towards a conservative audience) as well as their conservative tilted news network, it’s not hard to see ESPN bleeding some audience as momentum builds behind the ESPN=liberal narrative that has been gaining traction of late, aided by the noisy backdrop of a presidential election.

Regardless of my opinion on The Undefeated‘s politics now or after they’ve established more of a track record, the reality is that should ESPN and Disney be able to track any notable loss of viewers and readers to a presumed political agenda, then right or wrong you’re probably going to see ESPN look to quell that presumption.

Is ESPN/Disney a fit for The Undefeated?

Hard to say. ESPN and Disney are so big that there are advantages to having that type of corporate backing. However you wonder if a more humble launch within a more modest and less scrutinized company would better serve the long term viability of the site. Vice and Vox come to mind.

It’s not just that those companies may have a better grasp of launching successful online verticals, but culturally I’d say there is an advantage of being attached to a scrappy upstart backed by VC money which is pretty lenient on turning a profit opposed to a media conglomerate who is under a Wall Street microscope.  More importantly, should The Undefeated find itself in any type of editorial controversies (which I’d argue is to be expected given the subject matter) I’m not sure Disney and ESPN would be as supportive as other companies who don’t face the pressure of preserving the long term legacy of the company the consumer relationships that go along with them.

We can’t ignore Grantland’s success was still ultimately a failure

Back in November I penned an article titled “Shutting of Grantland hints at corroding ESPN culture, competency, and gumption.” I was not kind to ESPN and was particularly dismissive of The Undefeated at that point in time. I’ve warmed up a bit since as the post-Whitlock stench has worn off and momentum built up to the point where the site has finally gotten off the launch pad.

That said Grantland had the cord pulled out despite almost a million social media follows between Facebook and Twitter. Grantland had the star power of Simmons to drive traffic and inhibited a much larger content space and audience segment than The Undefeated aims to.

My column really bemoaned the fact that Grantland had achieved a lot of success and yet ESPN didn’t really make an effort to adjust the economics or strategy to make it viable. You’re not going to find many content brands fold up shop with the amount of audience they had as well as the social audience, which are valuable assets that ESPN opted to decommission and collect dust instead.

I mention Grantland’s history because it gives us some data-points of what in most universes would be considered a success or at least “a good start” or “something we can work with” but ultimately was killed off in the name of cost cutting and petty personal politics.

The Undefeated will be initially shielded given Skipper’s involvement with the project but you can bet that if and when the site beings to hit a ceiling or plateau in traffic that falls below profitability (it will), the same lazy and stodgy decision makers may begin to lobby Skipper to give up on the concept rather than attaching their reputation to the site as well. Basically it’s hard to see people fighting for The Undefeated should it have a shallower trajectory than Grantland, which I think many anticipate will be the case.  For those who don’t have access to traffic data, I’d keep a close eye on the site’s social accounts to get a feel of how the site is trending.

Deadspin’s story on Whitlock

Will readers stay away because of the bad taste of the doomed Whitlock era?

Back in 2015, I spoke with a lot of people who had the sentiment that the brand would never shake the Whitlock debacle. Fast forward to now and maybe a lot of that has worn off.

Given the fact the site got so much bad press and missed so many relevant stories while failing to get any substantive momentum needed for a launch, I do wonder how much of the intended audience just lost faith that ESPN could deliver the type of site that intrigued many when hearing about its initial conception. Despite the tremendous staff in place, I think some will look at the fact that the site failed miserably to recruit Howard and Ta-Nehisi Coates along with the failure to retain Morris and make the snap judgement that the site has already swung and missed.

With that said…..

I am rooting for The Undefeated and hope anyone who reads this involved with the venture has an understanding for the challenges ahead both internally and externally. It’s not just you I’m worried about. The Ringer faces a lot of these same challenges, and who knows what will happen to 538 when we hit midnight on election night. The Undefeated is a noble and unique concept and its failure will only mean that ESPN’s original content ambitions and future risk taking will continue to regress digitally. Unless you find yourself content with the portal experience on or Whitlock’s Tumblr, despite its messy past and the ham handed demise of Grantland, The Undefeated likely serves as ESPN’s last stand at niche digital experimentation and thus is something that warrants a rooting interest regardless if it’s not your cup of tea.

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