[mordechai9000]

I first encountered "asshat" in the context of network security: there are white hats, who are motivated by ethics and social responsibility. There are black hats, who are motivated by personal gain and seem to lack a sense of morality. Then there are asshats, who don't care about anything other than amusing themselves at other people's expense.

I have absolutely no idea of this is the origin of the term, or if it just fit there perfectly.

[neltnerb]

And I first encountered it (2004?), exclusively verbally, as a way to soften asshole. As far as I could tell and assumed to this day, it was taken up primarily aesthetically (sounds nicer than asshole and looks nicer in text, literally aesthetics here).

Still, it had the same implication of someone who is sort of oblivious to other people (asshole) but in a somewhat endearing or amusing or not all that serious a way.

[datavirtue]

You describe the BOFH. Total asshat.