I remember some of Steve Jobs' backstory, where he devised a gizmo to let you hot-wire your telephone to get free long distance; "phreakers" was the nickname for those lower-tech hackers. One of Job's contemporaries found that a Cap'n Crunch toy whistle would give the tones to bypass the fee gauges, giving him the nom-de-guerre of Captain Crunch.
Crunch got busted and served five years probation for his dark-side hacks, but Jobs went on to Apple and Pixar fame.
I was thinking of them in the context of Aaron Swartz, who helped developed RSS and Reddit and hacked federal and academic databases for fun and infosocialism; Swartz committed suicide after fighting off depression most of his 26-year life. The federales were on his case for the gray-side hacks, including doing Wikileaks-esque data dumps of JSTOR and federal court case databases and putting them into free public domain.
Cory Doctorow of Boing Boing and Larry Lessig have moving, if occasionally bleepable, eulogies for the young man. They both worked with him, with Lessig helping him fight off the criminal charges for the data-dumps. Swartz had his emotional issues in spades, but a lot of especially high-level geniuses have had their issues on that front.
Unlike Wikileaks, which put a lot of national-security secrets into the public eye for better and worse, Swartz's hacks were of relatively low value documents; the legal database was charging a whopping eight cents a case. Swartz wanted that rounded down to zero for the greater good, but went around intellectual property law to do it.
There's a Robin Hood aspect to Swartz, but robbing from the power that be and giving to the public at large (he wasn't profiting from the hacks; he's been big on open-source communalism in software) is still robbing. Robin of Locksley would be up on charges for his highwayman act even today, and low-impact gray-side hacks are still assaults on IP.
Great mind, twisty ethics. As someone who has had a lower-grade fight with depression, I can relate to his struggles. As someone who has been around computers for almost four decades, I can relate and appreciate a creative genius, but he used it in some left-handed ways.