ESPN never adjusted to the digital era. Sportscenter used to be cool because you'd be seeing the highlights for the first time and the anchors were always very charismatic and likeable. Then we started being able to just watch it on our computers and phones and SC had to start bringing in all sorts of "analysts" to break down what had happened during such and such play during such and such game. Some of those guys were pretty good, some sucked.
ESPN then decided that they needed to boost ratings by having more "debate" style shows. At first, shows like Around the Horn and PTI were good shows, because these were good sports writers from around the country giving their takes on whatever was going on in the world of sports. I used to love ATH.
Then Stephen A and Skip started their little show, and although they were saying things that turned a lot of people off, the formula of "you be 100% this way and i'll be 100% that way on every single issue" got views and got people talking about whatever crazy thing they'd said that day.
During the same time, Disney ruined Monday Night Football by moving from ABC to ESPN. They overloaded the set with too many analysts and it got to be a bunch of dudes shouting at each other rather than football breakdown.
Also, ESPN would let left-leaning people like SAS, Jemele and Michael express polutical views, but when a guy like Curt Schilling(whom i don't agree with btw) tried to do the same thing he was reprimanded and eventually fired. The difference being, he was actually a great baseball analyst, while the other 3 i mentioned have trash ass sports takes.
Long post, but kinda sums up how ESPN fell off in my view.