The Final Voyage of the Dread Pirate Ulbricht

Nicholas Weaver
Feb 5, 2015 · 4 min read

So with Ross Ulbricht now convicted of operating the Silk Road, and facing the realistic prospect of a lifetime in prison (the mandatory minimums alone are three decades), what lies in store and what should he do? We hear cries of “appeal, appeal”, but they will be as fruitless as Joshua Dratel’s attempted trial by ambush. Why?

An Appeal to Insanity

You can’t just appeal a case and expect things to go your way, you need some grounds, some error in the case that the appeals court can consider. There were four major decisions in the case that might, perhaps, remotely be grounds for appeal: the rejection of the motion to suppress the server, the rejection of the motion to suppress the other searches, the preclusion of the defense’s experts, and the rejection of Dratel’s bleating cries of “mistrial! Mistrial!”. All will fail. And even with success, its still failure.

The server seizure: If the defense didn’t present “what he must certainly understand is a fatally deficient motion to suppress”, there might have been a chance. The defense did catch the FBI red handed in an illegal search and lying to the court about it. Instead the judge notes:

There is no doubt that since defendant was indicted and charged with seven serious crimes resulting from that initial investigation and the searches that followed it, he has a “personal interest” in the Icelandic server in a colloquial sense. But longstanding Supreme Court precedent draws a stark difference between that sort of interest and what the law recognizes as necessary to establish a personal Fourth Amendment right in an object or place. To establish the latter, defendant must show that he has a personal privacy interest in the object (a server) or premises searched, not just that the search of the specific object or premises led to his arrest. Were this or any other court to ignore this requirement in the course of suppressing evidence, the court would undoubtedly have committed clear error.

the court was saying “this won’t work on appeal”. The bell was rung when the defense refused to claim the server as Ulbricht’s. The defense can’t say “the server wasn’t Ulbricht’s” in the trial court and then say “oh, but it was” in appeals. Appeal, denied.

The other search warrants: Dratel spun a lovely tale that the remaining search warrants represented “general warrants”. The judge effectively laughed at him, stating bluntly “Nor are these general warrants”, and only in a footnote added a remark that dude, you never claimed these items either. Calling a legitimate search warrant for a computer or email account a “general warrant” probably helped Dratel get more defense donations, but that was it. This appeal is also doomed.

The preclusion of experts: Just as Dratel willingly threw away the 4th amendment issue, it was Dratel’s preference for “trial by ambush” and a refusal to get his work submitted on time that had the court preclude his experts. The judge spent her Superbowl Sunday shutting down any possible appeal on this issue, including recapping Dratel’s history of gamesmanship, reviewing the proposed Bitcoin “expert’s” qualifications, citing a mountain of caselaw on providing expert declarations on time, and treating Dratel’s replies to the prosecution as serious, shredding them mercilessly for still lacking the necessary specifics. About the only thing she didn’t include was a screencapture of what you see when you search for Andreas Antonopolis.

Mistrial: Although also highly unlikely (it appears Dratel makes a sport of saying “Mistrial”, the five in this case tying his record from the last time he appeared before Judge Forrest), the Gods of the appeal could smile on Ulbricht. So even if he got his mistrial, what then?

Why the prosecution repeats the same exercise: bombarding the defense with evidence until the earth shakes, while the defense can only present a few “but he’s a nice guy” character witnesses. Any properly noticed experts will become prosecution experts by the time the prosecution finishes with them, while there is no evidence to actually support the presence of the mystical hacker-elves. The only differences are the defense attorneys gets to collect another few hundred thousand dollars from Ross’ parents and he prosecution will better phrase certain aspects of the evidence, allowing a new jury to only take two hours instead of three and a half.

So the Final Voyage

So what should Ulbricht do now?

Fire Dratel: Dratel showed his incompetence when he threw away the server seizure issue. He compounded it with a Chewbacca defense. He has already made tens or hundreds of thousands of dollars off donations and Ross Ulbricht’s family. He deserves not a penny more.

Even if the defense does try to appeal, they need a better lawyer, one who isn’t getting paid more to appeal screwups that he made the first time around. Oh, and before you ask, although Dratel seemed incompetent in his tactical decisions, he was not incompetent enough for a ineffective counsel appeal.

Settle in Maryland: Ulbricht is not out of the legal woods yet anyway: there exists another possible trial in Maryland. Although the Maryland trial won’t consider the drug charges (due to double-jeopardy concerns), the Maryland murder for hire plot is still on the table: both soliciting murder for hire and using interstate commerce to do so, another 10 to 20 years. Fighting these charges would cost another few hundred thousand dollars while replaying the spectacle we already witnessed. So he should plead “no contest”, accept the sentence, and be done.

Admit the truth to his mother: One of the biggest victims in the whole sordid affair is Lyn Ulbricht, Ross’s mother. It is almost certain she will never see her son breath free air in her lifetime. Worse, despite the sheer mountain of evidence, she still believes her son’s ridiculous denials. I worry that she will never be able to accept what has happened.

Ross Ulbricht owes his mother the truth. Hopefully then she can start to heal from the damage he’s done.

    Nicholas Weaver

    Written by

    Researcher: International Computer Science Institute & Lecturer @ UC Berkeley