Possibly, though AOL had video as well in the late 90s and early 2000s. It doesn't mean having 30 sec. to a few minutes of video was anything remotely like today or back then. That and the only instance of ESPN being mentioned is a radio broadcast over the internet.I remember we were writing code to stream ESPN when 9/11 happened, and I'm pretty sure it took less than a year. So 2009 seems very late to me. You might be thinking of a later ESPN streaming product, not the first one.
https://en.wikipedia.org/wiki/Timeline_of_online_video
I'm sure I could find something if I dug deep into Google. I remember radio broadcasts and what was a graphic you'd open up and it would show players on a field with a delay. It was very cartoon-like.
I also remember questioning whether or not people would be willing to pay for sports highlights. This seems humorously naive today, but keep in mind that back then, content on the Internet was free and nobody knew how to make money on it yet. Management had the idea that sports fans were a serious enough crowd that they would pony up, and sure enough they did. For us that was the foot in the door to putting content behind a paywall.
This general business theory was applied to everything, not just sports. A lot of expanded cable used to be on basic; when companies realized they could make money off these, too, they began moving it into a separate package aside from base. And some took it one step further to remove them from a carrier and offer it as a la carte.
I generally agree with your post--I wouldn't expect Disney to be able to out-Netflix Netflix either. But they'll make an adequate streaming service.
I don't know. I have serious doubts about how serious they are. Netflix has invested enough in itself to design their own tech to crunch down video without sacrificing quality visually noticeable to the naked eye.