Well, sorry, I read it like you were the one injecting politics about 'government hostility' into it, regardless of Tor or SSL, ssh keys or whatever methods are involved. You seemed to be attributing motives to the previous poster with comments about "maybe you prefer it that way" which seem to place him on the side of surveilling fascists, and I thought that was unjustified but maybe I misread it. If you're not getting political about it, then neither am I, and sorry.
On a technical level.. I don't see how Tor could have performed better here. It's physically impossible for them to mask the fact that this guy connected, through the harvard network, to the tor network. The rest of it is between the police and the guy. If they had gotten proof that it was his specific machine that sent the emails through some weakness in Tor, then I'd lay some blame with Tor.
I disagree that I have to root for this kid not to get caught. Tor didn't fall down, and I'm not rooting for Tor to fall down. He could have stonewalled the cops, or he could have taken the most basic precaution on earth of not doing it from his frickin dorm room, Tor or no
EDIT: Actually, maybe they'd be able to correlate his mac address if they subpoena'd whatever coffee shop the email came from. That's a much bigger fishing expedition for "any coffee shop that connected to a tor node that day", though. But anyways, my point is that Tor can't be held responsible for things it will physically never be able to mask.