To me, the most instructive part is the open web's triumphalism at defeating AOL.
AOL thought they could own the internet by controlling the front door... portal strategy, in the terms of the times. They expected to brute force their way to scale with expensive marketing campaigns. etc
Once the www "won," everyone knew how foolish AOL was. Information wanted to be free. Open protocols will run circles around a closed kludge. etc.
It's very 90s. A sort of peak modernism. Openness wasn't just desirable and effective... it was also inevitable. Maybe we needed to watch for network neutrality, but otherwise things would look after themselves.
Freedom isn't just better. It's so much more effective, more popular and powerful than short sighted alternatives that it is inevitable. This optimism was so powerful, we got completely blindsided a few years later.
In retrospect, AOL's strategic vision was prophetic. Their flaw was not pushing it hard enough, not having enough belief, giving up too early. Maybe they couldn't own everything, but they could have owned a lot. Even if they had just held onto the lest sophisticated users, chatrooms and news they would have been a goog/fb/amzn.