It started with the push to be more entertainment driven and the idea of embrace debate under Shapiro - it gave us Playmakers which was great for what it was, but having a fictional dramatic series was a bit off brand, just like the wacky Hustle and Season on the Brink produced reenactments of Rose and Knight with actors, it was goofy. It also drove the opposing point of view programming shift - it was like Point/Counterpoint ripped from early 60 Minutes and forced into the Sport realm.
Long form programming like 30 for 30 is much more true to what ESPN was originally and it makes sense to have that stuff, you've got to fill the shoulder periods between games to keep folks engaged. Skipper was, maybe he still is, all about getting rights almost at all cost, he's always said it's about games (he's given you UEFA and the like) - the issue is that what the heck do you do with all the shoulder programming between the games - analysis can only go so far because at some point even the most ardent sports fan doesn't care about so much deep analysis and you can't drive tune-in in any meaningful numbers and at some point running the Sportscenter wheel is not an option (hence the live SC in the AM). Sure people are NFL fans, but if I'm a Giants fan do I really care that Phillip Rivers has an ingrown hair on his nut sack? No, unless you're a fantasy dufus and if you are it's likely you're not getting that info from ESPN because the local guy will have that info and likely drop it out there on Twitter.
The inability to understand to how platforms (new at the time) were going to fundamentally change how folks got their sports information and how quickly they received it is pretty surprising simply because the company wants to be thought of as a technology company, not just a news and information company.
Company has always know about cord cutting and feared it because they know how many or really how few would pay that for ESPN if given the option, especially in the new media landscape.
Once someone has the $ to complete with ESPN on the next major rights negotiation it will be interesting because without the robust dual revenue stream like the one they've enjoyed they'll have to make some hard decisions.
Oy sorry.
