On one hand, I think the law tried to make an example of him and exaggerated the damage he did (they said he stole millions of dollars of software, which he never released or used). It's also _not_ cool that they held him for so long without bail or a trial.
On the other hand, he brought all this on himself.
As I recall, he got busted once but couldn't stop breaking into systems. He wasn't doing it to make a pollitical statement (like those guys who keep hacking RIAA).
He sounds like a highly intelligent screw-up who pissed off the wrong people.
I wish him luck in his new legitimate career. Unfortunately, it's an uphill battle since he (rightly so) has had no computer access for many years.