How The Silk Road Trial Changes the Internet

Katy Levinson
Endless
Published in
10 min readAug 24, 2015
Ross Ulbricht, the man now convicted of 7 felony charges related to running the Silk Road, rendered here in a courtroom sketch. Sketch by Jane Rosenberg.

You can love Ross Ulbricht or you can hate him, but if his story ends here, we as a society will be the poorer for it.

Ulbricht might have broken laws, but we do not want our government empowered to pursue citizens the way they did in this case. The technical evidence used against him was flimsy, internal corruption in the DHS makes it suspect, and some information was collected in a way that may violate our 4th amendment rights. This case also has serious implications for common carrier law, hacking law, and several other areas which become increasingly relevant in a digital world. We must not let this happen.

The Silk Road

Court sketch artist Susie Cagel attempts to recreate a graphic the government created to explain Tor to the jury. Tor is a piece of infrastructure which is used to, among many other things, connect to the silk road.

In early 2011 somebody on the internet calling themselves Dread Pirate Roberts created an online marketplace where you can buy and sell almost any merchandise including heroin and fake drivers licenses. About 70% of the sales were drugs. Only a few goods were banned: Child pornography, assassinations, stolen credit cards or weapons of any type (though they were permitted on other unaffiliated competing sites). You could also buy normal legal wares like books. The site was only accessible via specialized security tools that were by no means idiot-proof, and you could only pay using bitcoin. This payment method, it turned out, was the major differentiator between Silk Road and its predecessors, as illegal merchandise transacted in Bitcoin are far more difficult to legally pursue than those transacted with conventional financial options. Reviews of both products and sellers emphasized quality and reputation in this unique thriving market system. MDMA, a drug in which impurities can kill, was remarkably popular.

The Title of Dread Pirate Roberts

In late 2013 the FBI shut down the site and arrested a man named Ross Ulbricht in the San Francisco Library, alleging that he was The Dread Pirate Roberts, or DPR, and the creator of Silk Road.

The concept of the Dread Pirate Roberts is complicated. Nerds fancy themselves clever people, and we traditionally share the digital equivalent of an ethnic background to make a connection with others in our work. The adoption of a legacy false identity in solidarity with an ideal is powerful and familiar to us. It is the idea that in a broken world a single human can be broken, but we can make ourselves anonymized symbols which the world will first fear, then respect as harbingers of change.

“People need dramatic examples to shake them out of apathy and I can’t do that as Bruce Wayne. As a man, I’m flesh and blood, I can be ignored, I can be destroyed; but as a symbol… as a symbol I can be incorruptible, I can be everlasting.”
Bruce Wayne, Batman Begins (2005)

The Server in Iceland and the Privacy Precedent

One of the defense’s key arguments prior to the trial was the assertion that the US Government had unfairly invaded Ulbricht’s privacy by hacking into his server in Iceland. The judge in his trial rejected this argument before the trial began.

Privacy supporters are worried by this legal precedent of dismissal. Currently we have reason to believe that the US regularly hacks into computers owned by both citizens and non-citizens alike regardless of what country the computers reside. If the computers were treated as the physical objects they are — much like letters, our government would have to obtain the cooperation of the local government in order to gain access.

“The right of the people to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures, shall not be violated, and no Warrants shall issue, but upon probable cause, supported by Oath or affirmation, and particularly describing the place to be searched, and the persons or things to be seized.”
-4th Amendment to the United States Constitution

The Government’s plan was to find Ulbricht’s server, get inside of it, and wait to see what they find.

“The Horowitz Declaration nowhere alleges that the SR Server was either located or searched in a manner that violated the Fourth Amendment. It merely critiques certain aspects of the Tarbell Declaration concerning how the SR Server was location. In any event, even if the FBI had somehow ‘hacked’ into the SR Server in order to identify its IP address, such an investigative measure would not have run afoul of the Fourth Amendment,”
Assistant US Attorney Serrin Turner, Statement October 6th, 2014

It also said that because the servers are not in the US, they are not protected by the 4th amendment.

“Given that the SR Server was hosting a blatantly criminal website, it would have been reasonable for the FBI to ‘hack’ into it in order to search it, as any such ‘hack’ would simply have constituted a search of foreign property known to contain criminal evidence, for which a warrant was not necessary.”
Assistant US Attorney Serrin Turner, Statement October 6th, 2014

The court provided Ulbricht an opportunity to argue his 4th amendment rights were violated if he claimed in court the servers (and thus Silk Road) were his property.

The defense argued that evidence from hacking overseas computers can not be used against Ulbricht because it was not lawfully obtained, but Judge Katherine Forrest rejected the argument. This is important because it provides legal precedent for using information on computers which is obtained illegally for convictions. This signifies two other important things:

  1. A general warrant to search computer systems is narrow enough to comply with the 4th amendment, and
  2. The government claims the right to attack any computer in the world and lurk there for any amount of time without a warrant.

A lot of people, myself included, are uncomfortable with the legal implications of this precedence.

The Judge, Ulbricht’s Sympathizers, and Hostilities

US District Judge Katherine Forrest of the Ross Ulbricht trial. Sketch by Jane Rosenberg.

This ruling led to increased hostilities from netizens who were unhappy with the ruling. Many of these netizens harassed the judge and threatened further action. The judge’s personal information was posted online, and she began receiving death threats.

Ulbricht’s final sentencing was carried out by judge Forrest. It’s reasonable to assert that the harassment caused Judge Forrest to hand down what many feel is an extraordinarily harsh penalty.

In June, reason.com was subpoenaed to find the real names of those who spoke poorly of Forrest there, under the suspicion that those people might have been the same people who harassed her. This is troubling because expressing criticism of a public figure and threatening harm to them are normally considered two different things.

The Mt. Gox Possibility

Mt. Gox was a bitcoin exchange.It was declared insolvent in 2014 and it was seized by the Department of Homeland Security after the US Government claimed Mt Gox was an unauthorized money transmitter in the US.

The trial began on January 13th 2015 with Ulbricht admitting right away that he had founded the Silk Road, but claiming to have transferred control shortly afterwards to other people, consistent with the Legacy Character idea. His lawyers claimed the CEO of Mt. Gox, Karpeles was actually Dread Pirate Roberts — the mastermind — and had set Ulbricht up as the “fall guy.”

This is particularly interesting because these allegations might actually be true.

The Department of Homeland Security was investigating the CEO of Mt. Gox suspecting he was Dread Pirate Roberts. In fact, Karpeles had a large amount of money seized and criminal charges for unlicensed money transmission appeared imminent. A federal agent swore in an affidavit that he had heard from the U.S. Attorney’s Office in Maryland that Mt. Gox’s attorneys had approached Baltimore law enforcement during the investigation with an offer: the identity of the Dread Pirate Roberts in exchange for dropping all criminal charges on all criminal charges against Karpeles.

Karpeles has still not been charged with anything in the United States. Japan charged him with embezzlement several months after the Ulbricht trial concluded. Japan is where Mt. Gox was based.

Furthermore Judge Katherine Forrest ruled that any speculative statements regarding whether the Mt. Gox CEO or anyone else ran Silk Road would not be allowed, and statements already made would be stricken from the record.

Digital Proof

Digital proof was a big issue in this trial. Most folks miss the most important aspect of digital proof: it is remarkably easy to fake.

Because the only evidence here is in digital format, we must be wary of its veracity. In this case, Ulbricht’s servers were compromised by the government by its own admission long before Ulbricht’s arrest. It is not only entirely technically possible, but would in fact be trivial for the government to place fake incriminating information on Ulbricht’s computer.

Particularly, digital evidence was used to assert that Ross Ulbricht was the Dread Pirate Roberts when the government brought forth journal entries allegedly written by Ulbricht.

The Feds that Plead Guilty

Two of the federal agents who lead the investigation of Ross Ulbricht were recently indicted for corruption: DEA agent Carl Mark Force IV and Secret Service agent Shaun Bridges, who specializes is computer forensics. Two months after Ulbricht was convicted it was revealed that Force and Bridges had both been under investigation during the trial. The investigation focused on, among other crimes, allegedly stealing and extorting funds from Silk Road. Force plead guilty to extortion, money laundering, and obstruction of justice.

These agents had the means to create fake information. Both agents gained high-level access to the administrative function of Silk Road through an arrested informant. This gave them the power to change aspects of the site including access to administrator platforms and passwords, the ability to change PINs, and the ability to commandeer accounts — including the account of Dread Pirate Roberts. The agents also were capable of manipulating logs, chats, private messages, keys, posts, account information and bank accounts.

Why would the agents change information to implicate Ulbricht? Among a huge horde of other illegal activities they were stealing money from Silk Road.

The defense was expressly blocked from referring to it during the trial as the investigation of the Rogue Agents [Force & Bridges] was under seal pending completion of the investigation.

“Despite the attention given to the Rogue Agents issue in defendant’s brief, this Court remains unclear (as it always was) as to how any information relating to that investigation is material or exculpatory vis-à-vis Ulbricht. Either the defense assumes the answer is so obvious that it need not explain, or its omission is purposeful.”
- Judge Katherine Forrest

The Legality of Government Hacking

We are not exactly sure how the FBI got into the Silk Road website. There are a lot of technical issues with the official story of the government hack and the FBI is unwilling to reveal its methods. This implies that the documents, even if nobody can explain where they came from and their sources are highly suspect, are now considered acceptable proof. At best, the situation suggests that the FBI hacked the server then found its IP, and considering they aren’t willing to say that, it probably means that the feds are uncomfortable defending their hacking in court. By permitting this to slide, we are making it easier for them to do this behavior more often. The lack of interest on the part of the courts, with respect to the protection of the 4th amendment, is a chilling harbinger of things to come in our increasingly digital future.

The Alleged, not the Charged

Assistant U.S. Attorney Timothy T. Howard speaks during closing arguments in the trial of Ross Ulbricht. Sketch by Josh Dratel.

Ulbricht was indicted and faces a separate trial in Baltimore, for contracting a hitman to commit a series of murders. However, in the case where he was supposedly successful, no record of the victim’s life or death exists. Even the government has admitted that there is no evidence anybody was harmed in this murder-for-hire scheme.

Ulbricht then allegedly attempted to hire another hit in retaliation for a large amount of money which was stolen. The man Ulbricht allegedly attempted to kill did not actually steal the money, Agent Force did using a hijacked account. As luck would have it, Agent Force also controlled the account of the fake hitman Ulbricht allegedly attempted to hire to kill the suspected thief. Agent Force has now been indicted for forgery. This means the chat logs are at best, suspect.

Since the theft, the fall guy, and the fake hit-man who offered to kill him were all run by federal agents, some could argue that this was entrapment.

According to the Indictment, the defendant “pursued violent means, including soliciting the murder-for-hire of several individuals he felt were a threat to his enterprise.”
US v Ulbricht, Order July 9th 2014

In a bizarre and apparent perversion of due process, the judge permitted the details around this indictment for murder charge to be presented as evidence in the New York trial. In fact, the judge argued that evidence Ulbricht tried to kill people did not require proof to be admitted into the proceedings:

“Evidence that defendant sought to protect this sprawling enterprise by soliciting murders for hire is, in this overall context, not unduly prejudicial.”
- Judge Katherine Forrest

There is no doubt that criminal activity was facilitated by Silk Road. But, what’s getting lost in the hyperbole of the internet as a bastion for criminals is the precedent setting processes and rulings which attach our right to privacy and even a fair trial. It’s as if the digital frontier has become a free pass for the government to suspend rights that were set down nearly 1,000 years ago in the Magna Carta and updated in the US Constitution just 200 years ago.

Will the government keep us in a state of ignorance by highlighting the salacious or will we wake up to defend our rights — digital and otherwise?

You may love Ulbricht or you may hate him, but it is time to fight for him.

(Hopefully Not) The End

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Katy Levinson
Endless

I like looking at things from a systemic perspective. On good days I fix things. Most days I also like people. I make stuff.