The Saga of Silk Road’s Dead Pirate Roberts, Ross William Ulbricht


The downfall of Silk Road and the capture of the alleged Dread Pirate Roberts has made digital newsreels and much digital ink has been spilled over the issue, and the saga is far from over. The presence and persistence of the Silk Road as a part of the dark web, hidden from prying eyes within the confines of the Tor network (a technology the NSA has complained about because they couldn’t easily break it) shows how successful the confluence of anonymity, security, and Bitcoin can be when put to use together.

Recently, we even learned that the FBI has failed to confiscate the bulk of DPR’s Bitcoin stash (estimated at nearly 600,000 BTC or approaching $80 million) and has only gotten their hands on about 26,000 BTC. The current thought is that the 26k BTC represents the digitally stored wallet of Silk Road customers, wallets, transactions, escrow—but DPR himself kept his pirate booty elsewhere, outside of the range of the Silk Road servers.

With those Bitcoins in his lawyers possession, Ulbricht could have quite a nest egg to mount a legal defense. This is especially true because often justice entities freeze the assets of potential targets to make them easier to prosecute; but since it’s difficult to impossible to freeze a BTC wallet that you don’t have access to, those 600k BTC (or some fraction thereof) could be turned surreptitiously into cash.

The legacy of Ross William Ulbricht

As the alleged proprietor of The Silk Road, Ulbricht is known by the moniker of the Dread Pirate Roberts—a brilliant-yet-fanciful name that hearkens to William Goldman’s novel The Princess Bride and it’s subsequent comedy movie. In the movie a pirate exists who is the source of the seas, dreaded in fact and known as the Dread Pirate Roberts. However, as it is revealed the Dread Pirate Roberts is really not the original, but instead a man who took up the mantle and name of his previous boss each time the previous DPR retires. A perfect name for the shadowy master of an anonymous black marketplace.

SiliconANGLE sought out one of Ulbricht’s roommates, Aaron Arnold, from the University of Texas where Ulbricht went to study physics.

According to Arnold, Ulbricht wasn’t a Computer Science major nor a software engineer, but he had some libertarian political leanings that put him well in the sights of what Silk Road was trying to do. During a visit they’d had before Ulbricht eventually moved to San Francisco, Arnold says that they’d had a discussion about Neal Stephenson’s novel The Cryptonomion, a book about cryptography, anonymity, and the search for a truly free (as in from interference) form of currency.

“He’s [Ulbricht] always had an interest in alternative currency, political libertarian, a little anti-government;” Arnold said to SiliconANGLE. “Silk Road does fit nicely, but putting out a hit doesn’t make sense for him. He was always upbeat, a happy guy, opposed to use of force and violence.”

Arnold refers, of course, to the parts of the complaint by Maryland that Ulbricht had become involved in a murder-for-hire scheme.

From what we learned from Arnold, Ulbricht sounds precisely like the sort of person who might seek a business in founding an anonymous black marketplace to enable people to use a crpyographicly-secured currency to do deals a dimly lit cybercafé. In fact, it fits that he was eventually caught by detective footwork because he had sought programmer-related advise and help accidentally using his own real name.

However, what we know makes it sound unlikely that he would actually have been involved in hiring a hitman.

The Legal Saga of the Dread Pirate Roberts

What is Ulbricht charged with? For this we defer to Ken “Popehat” White, an ex-federal prosecutor, who knows a great deal about how the criminal justice system works from that side of the fence. He’s written a long and helpful blog post entitled “The Silk Road to Federal Prosecution: The Charges Against Ross Ulbricht.”

In the New York complaint, Ulbricht is charged with conspiracy to traffic narcotics, computer hacking conspiracy, and a conspiracy to launder money—all of these things seem to arise directly out of running Silk Road, a place where the “criminal element” would have come to roost and do exactly these things. The Maryland complaint, however, looks more grim with another narcotics trafficking charge, but the addition of attempted murder of a federal witness and attempting to procure murder-for-hire.

According to Popehat:

The Maryland indictment also asserts that Ulbricht paid an undercover agent to kill a former Silk Road employee who had stolen from Ulbricht and was cooperating with federal authorities after an arrest. The agent staged a death picture and sent it to Ulbricht. The New York complaint doesn’t charge Ulbricht with murder for hire, but does detail a long correspondence in which Ulbricht allegedly tried to hire a killer to murder a Canadian extortionist. There’s no indication that the murder occurred or that the murderer was an undercover, so it may have been a scam by the purported murderer.

Ulbricht’s bail hearing has been moved to October 9th in a San Francisco court. As a result, he’s still in police custody and has not granted much to the press about the current state of his case. So far we only know that his lawyer has denied the veracity of all the charges.

“We deny all charges and that is the end of the discussion at this point,” Ulbricht’s lawyer told reporters.

Meanwhile, a donation site has been set up for Ross Ulbricht that accepts Bitcoins by Mike Gogulski, who also founded the Private Manning Support Network to raise money for Chelsea Manning’s legal defense.