Of Pirate's Penance

   
     A black market is a kind of shadow free market. It's a shadow free market that persists in spite of the best efforts of law enforcement to eradicate it.
     Whatever you may think of it, there's a black market for recreational drugs in the United States. In fact, it's the world's largest such market, and its existence exerts a strong influence on the political economies of many nations.
     However, aside from the risks of drug abuse per se, deals concluded in a black market can be dangerous. It was the bright idea of a bright young thing named Ross William Ulbricht to create a website which he called "Silk Road" whose purpose would be to bring together sellers and buyers of contraband goods of all kinds in a safe and trustworthy environment using such recent innovations as untraceable digital currency, anonymous access to internet sites, email encryption, etc. Silk Road was a great success.
     Ulbricht operated clandestinely under a pseudonym; "Dread Pirate Roberts." Nevertheless, in October, 2014, he was arrested by an alphabet soup of government agents who caught him while he was logged into an administrative page of Silk Road at a public library.
     Since Ulbricht was operating pseudonymously, how had the g-men gotten on to him?

     Basically, what happened is he gave himself away. When he was astroturfing (a well-known online technique he used to drum up business for Silk Road), he used the same alias as when he requested technical help with a "venture-backed bitcoin startup company" and gave his gmail address as the contact. Or at least, that was the prosecution's explanation of how they found him.
     So, to summarize, one could say that, though the g-men did exhibit a certain level of familiarity with internet conventions and usages and were able to put two and two together in a moderately clever way, the crucial giveaway was provided by Ulbricht himself.
     Furthermore, although g-men were able to infiltrate Silk Road itself and even attain trusted positions in the administrative hierarchy, that wasn't how they were able to catch Ulbricht. He was indiscreet!

     In any case, the evidence on Ulbricht's logged-in laptop provided enough material for numerous trumped-up charges (all victimless crimes), and he was evidently concerned about his future prospects. The maximum sentence would be life. Accordingly, he wrote an abject letter to the judge prior to sentencing in which he stated (in part):

“Silk Road was supposed to be about giving people the freedom to make their own choices, to pursue their own happiness,” he said. “I learned from Silk Road that when you give people freedom, you don’t know what they’ll do with it . . . If I do make it out of prison, decades from now, I won’t be the same man, and the world won’t be the same place. I certainly won’t be the rebellious risk taker I was when I created Silk Road. In fact, I’ll be an old man, at least 50, with the additional wear and tear prison life brings. I will know firsthand the heavy price of breaking the law and will know better than anyone that it is not worth it. Even now I understand what a terrible mistake I made. I’ve had my youth, and I know you must take away my middle years, but please leave me my old age."

     Later, at his sentencing, he said "I wish I could go back and convince myself to take a different path. If given the chance, I would never break the law again."
     Some commenters have compared his remarks to the following passage:

"He gazed up at the enormous face. Forty years it had taken him to learn what kind of smile was hidden beneath the dark moustache. O cruel, needless misunderstanding! O stubborn, self-willed exile from the loving breast! Two gin-scented tears trickled down the sides of his nose. But it was all right, everything was all right, the struggle was finished. He had won the victory over himself. He loved Big Brother."

     Ross Ulbricht was sentenced to life in prison. But never fear, he'll undoubtedly come to understand that it was all for the best.