I think you don't understand the script-kiddee phenomenon. From Scott's limited description, he was just an over-excitable, "regular" kid. He got a hold of some scripts for spoofing mail and DoS'ing a website and tried to use them with no expertise and probably very little inclination to gain any. It is very unlikely that he would have grown up to be the future equivalent of your AS/400 guy. Rather, he's probably got more in common with the stereotypes of fraternity members than he does with the "living in mama's basement professional programmer" type -- you've heard the phrase - young, dumb and full of ... machismo, just like so many other teenage boys.

As for computer (or more generally techincally-oriented) guys with bad interpersonal skills, you really ought to read up on Asperger's Syndrome, particularly the research about people who are even higher-functioning than the average Asperger, but still not what society currently considers normal. As a potential manager of people like that, you'll get a lot more insight into how their brains are functionally wired differently than yours.