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RE: Double life plus forty for creating a voluntaryist website. Sign the Free Ross clemency petition!
I'm sure he has regreted creating and running this dark side website thousands of times. Being locked up for this crime for life seems like a very harsh sentence.
I dispute that the website was really part of the "dark side". In fact, many see the website as ethical, since it reduced dangers to drug users.
From this article by the Drug Policy Alliance, there were several ways that the Silk Road had a net positive effect on safety:
I'm sure he did not create the silk road, he was probably the last DPR who run the site though. So he had the keys of the building, but he didn't build the building :)