I think I get it, it was a surprise to him and everybody else that he ended up in prison.
You say he wasn't particularly gifted but he was definetly smart no? I mean him graduating from MIT is at least evidence that he is not suffering from brain-damage.
I have to admit that all i know is from the media. I did not know about his powerful family, I always assumed he was just a regular kid who just got lucky.
I definitely fell for the story developed over years.
I just cant believe the complacency and utter lack of paranoia, given the means he had, both monetarily and intellectually.
He was an MIT grad in physics and minor in math, his girlfriend was a mathmatician too. Clearly he must be intelligent. Maybe he wasn't the genius everybody hailed him as. However if you are smart enough to understand topology and other math-related topics, I would assume that he would be smart enough to funnel money out to secret untraceable accounts, buy diamonds and stash them at strategic locations in numerous countries, have an exit strategy.
Why couldn't he just have bought a submarine and flee to russia? Or just make a run for it on a regular boat?
I have a lot of trouble believing that if you have all that money, and you have at least as much smarts as the average math student, that you cannot extracate yourself from the situation he was in.
What you are observing is birds with clipped wings...
...now ask yourself, who would want a birds wings to be clipped in the first place? right. It's those who seek to keep the chickens from regaining their freedom, and who seek to hurt them (slaughtering them/steeling their eggs/offspring).
TPTB don't want an educated, sophisticated, thinking on their feet type of populace. Those would be impossible to rule and to exploit for your own selfish ends. TPTB carefully orchestrated the so called failure of our education.
Maybe one could tweak BitTorrent for this one mega torrent so that you have to seed/leech one of the least popular files along with every popular file?
He thought his wealth would buy his freedom... interesting point of view. He should of known better.