I don't know him personally, but his being top wheel of the FSF has skewed his reality. I cannot remember where I heard it, but I believe he is quoted (heavily paraphrasing here) along the lines of, "I may be fighting a losing fight, but it's all I can do, and I won't stop until I'm dead."
Practicality is the ultimate deciding factor at its core. Practicality decides whether you use a GPL-based license or the Apache license. Practicality decides whether you choose to avoid a website because of non-free Javascript. Practicality decides whether you can eat that muffin and switch gears on the road, and so on. It is a bit like using secure services and utilizing OpSec. Where do you draw the line between convenience and security? Where does it stop being practical and where does it matter to stick to a principle?
Maybe he is just aging, and his brain is in an infinite loop. As I said, I do not know the man myself. But not having a clear focus of how life is for a majority of people can be a huge factor.