Well he did sneak into a closet and cause JSTOR to threaten to cut MIT's access. After things settled down, MIT dropped all charges. I think that was pretty reasonable.
MIT dropped trespassing charges. (JSTOR also dropped their charges after Aaron deleted the files and promised not to do it again or something.) The feds got involved with the "hacking" because it crossed state lines, and the district attorney in Boston continued the criminal case after both JSTOR and MIT had settled with Aaron out of court.
You may not know this, but he founded Demand Progress. He was also the keynote speaker at Freedom to Connect 2012 in Washinton, D.C. So yeah, he probably thought about it a lot more than you have.