The biggest and weirdest question left in the Silk Road story is probably never going to get answered.
The biggest and weirdest question left in the Silk Road story is probably never going to get answered. Ross Ulbricht—also known as the Dread Pirate Roberts, operator of the Silk Road marketplace—is appealing his conviction, for which he serving a life sentence, to the Second Circuit. Yet his appeal brief is missing any reference to the mysterious seizure of the Silk Road Icelandic servers.
The appeal brief clocks out at 170 pages, with an additional six appendices—a total of 1,794 pages. Don't worry, it's not just you: that really is kind of a lot.
To be fair, this whole saga is really complicated. Even beyond the fairly technical aspects, it's an extremely twisted case. There are drugs. There are bitcoins. There are corrupt undercover agents making sockpuppet accounts on a Tor-hidden service. There are five faked murders-for-hire.
There's just… a lot. But bizarrely, the brief still leaves something out. Back in 2014, one of the Silk Road defense attorneys, Joshua Horowitz, noted that the FBI's seizure of the Silk Road servers in Iceland was still unexplained, because the government's explanation of how they had found the servers was actually technically impossible.
This turned into fodder for conspiracy theories. Did the government illegally hack Tor in order to get at the Silk Road servers? Did the identification of Ross Ulbricht start with a tip-off from the NSA? It seems wild, but it's no crazier than the rest of this case already is.
But anything regarding the Icelandic servers is curiously missing from the appeal. Most of the appeal brief focuses on two corrupt agents who really made a mess out of the Silk Road investigation in Baltimore.
Two Rotten Apples in a Barrel That Was Totally Separate From This Investigation, We Swear
The appeal brief brings up a total of seven issues—including an argument that Ulbricht's life sentence is unreasonable—but much of the actual space in the quite lengthy document is taken up by the weird, wild, and troubling story of Carl Mark Force and Shaun Bridges.
These two law enforcement agents were recently sentenced to 6 ½ years and 5 years, 11 months respectively. Force and Bridges—separately, apparently without knowing about the others' crimes—orchestrated massive thefts, scams, and blackmail using their privileged positions as law enforcement agents in the Silk Road Task Force. Bridges in particular stole 20,000 bitcoins from the Dread Pirate Roberts, and then set up a cooperating witness for the crime. DPR commissioned a hit on the cooperating witness. The hitman he hired turned out to be the undercover Carl Force. Apparently under the direction of their supervisors, Force and Bridges faked the murder of the cooperating witness, and even sent DPR doctored "proof of death" photos.
None of this made it into the New York trial. The reasons were twofold. First, the New York prosecution against Ross Ulbricht didn't include the conspiracy to murder the cooperating witness. Instead, a separate indictment in Maryland addressed that charge.
Second, a grand jury investigation into Force and Bridges was still under seal—which meant that the Ulbricht defense team couldn't talk about the two corrupt agents at all.
It's important to note that the government had Ross Ulbricht's laptop, which contained a diary, chat transcripts, accounting spreadsheets, and even a complete copy of the Silk Road website. They connected portions of the diary and the chat transcripts to emails on his personal Gmail account (email@example.com) and posts on his Facebook account. They even trotted out a college friend of Ross Ulbricht to testify that he had helped him code the website in the beginning.
It is an understatement to say that the government's case was quite strong.
And the defense's theory of the case at trial came under fire from observers for, well, overall plausibility. Their theory was that Mark Karpeles, a CEO of a bitcoin company, had hacked Ross Ulbricht through a Bittorrent client that was downloading an episode of the Colbert Report. Karpeles then planted the diary, the chat transcripts, and other files onto Ulbricht's computer, thus setting him up as the fall guy.
The jury apparently didn't buy it, and convicted Ulbricht on all counts.
It's not like Force and Bridges were the key to catching Ross Ulbricht—what we know tends to show that they were really good at undermining the investigation, but not very good at uncovering real evidence. When it comes down to it, the big thing about Force and Bridges is that their complete omission from the trial just feels kind of weird and bad.
It's more than possible that the jury would have still convicted Ulbricht, even if they had been able to hear evidence about the horrifying mess inside the Silk Road investigation. The point is, even if justice was served, it still feels really unfair.
Whatever Happened to the Icelandic Servers?
The defense moved to suppress a whole lot of evidence prior to trial, based on the theory that the FBI's seizure of the Icelandic server was illegal. The defense couldn't quite prove it, but something didn't add up, and surely it was worth getting to the bottom of it.
In a way, Ulbricht was going to have to 'fess up to being DPR in order to get acquitted of being DPR.
The government claimed that the Silk Road's CAPTCHA had been misconfigured, and that that had led them the Silk Road's IP address. But traffic logs from the Silk Road servers didn't corroborate the story, and when the defense asked for additional information, like the government's own traffic logs, or exactly what kind of software the FBI had been using, they claimed they didn't have any records.
It was pretty weird.
But here's the problem: a Fourth Amendment inquiry into whether a search is legal or illegal begins with whether or not the defendant has a personal privacy interest in what was searched or seized. Ross Ulbricht would have had to declare a personal privacy interest in the Icelandic servers in order to even go down the Fourth Amendment rabbit hole. In a way, he was going to have to 'fess up to being DPR in order to get acquitted of being DPR.'
Maybe it would have worked out. Declaring a personal privacy interest in something isn't exactly the same as saying you're the dude, but Ulbricht apparently decided not to tempt fate. Legally speaking, the whole issue was extremely thorny. The server was physically abroad, in Iceland, and also rented from a third-party service—facts that complicated Ulbricht's Fourth Amendment rights, if any.
So the defense refused to declare a personal privacy interest in the server. And now, despite devoting 170 pages to other issues, the defense has decided not to appeal the trial court's ruling that they had to declare a personal privacy interest in the first place.
In other words, we're probably never going to find out what actually happened with the Icelandic servers. Regardless of whether the Second Circuit takes up Ross Ulbricht's appeal, the biggest unsolved mystery in the Silk Road case will remain unanswered.