In the case of Ross Ulbricht A/K/A Dread Pirate Roberts (DPR) it seems like a slam dunk case for the prosecution. Ross, by his own admission, founded the Silk Road – an underground marketplace used for online drug sales and other illicit materials. He was caught red-handed at the time of his arrest logged into the Silk Road administrator panel at a public library and, perhaps worst of all, on his laptop a journal and activity log were discovered, which documented all of his activities involving the Silk Road. It would seem like a no-brainer that he did it. Toss him in jail and throw away the key. But there’s more to the story that many don’t know. Information that was intentionally ignored during his trial and ultimately may have impacted the outcome of his case.

Ross Ulbricht

Ross Ulbricht

In Ulbricht’s 170-page appeals document a number of points are brought up, but more or less boil down to the defense not being provided with the opportunity to properly defend their case. Thousands of documents were revealed shortly prior to and while the trial was underway, leaving the defense little time to review the materials they were presented with in order to form a proper rebuttal. Even before Ulbricht’s sentencing the prosecution had declared him guilty within the media and he was denied bail on grounds that he was part of several murder-for-hire plots, which he was never formally charged with.

Was Ross Ulbricht the fall boy for a draconian war on drugs witch hunt as the defense claims?

At the time of Ulbricht’s arrest the government was under extreme pressure to capture the notorious Dread Pirate Roberts and shut down the Silk Road for good. A number of other suspects were under investigation for possibly being DPR, including Mt. Gox founder Mark Karpeles, but two weeks prior to his arrest investigators began zeroing in on Ulbricht being the man behind the DPR persona. This conclusion was reached through the FBI’s ability to track down Silk Road servers in Iceland, but how they were able to trace these servers remains a subject of controversy.

Ulbricht’s landmark trial could set a dangerous legal precedent for generations to come, so when it comes to facts surrounding the case it is important to examine them closely in order to ask ourselves, “Was justice really served here?” Highlighted below are several talking points brought up by the defense.

Insider Corruption


DEA Special Agent Carl Force was part of a Silk Road Task Team set up in Baltimore. It was through this agency that Force familiarized himself with the Silk Road and formed an online relationship with DPR. Posing as “nob,” Force conducted a number of online chats with DPR ranging from business propositions to drug deals, as well as the infamous “murder-for-hire” plots, which were later not pursued in Ulbricht’s case.

Ulbricht motioned to postpone his trial after his defense learned of the secret grand jury indictment against Agent Force, but that motion was denied on grounds that the Baltimore investigation was independent of the other investigations on the Silk Road. It wasn’t until after Ulbricht’s sentencing that the defense learned of the indictment of a second agent, Secret Service Agent Shaun Bridges, who had also infiltrated and stolen funds from the Silk Road marketplace.

It was found that both Force and Bridges, under a number of different aliases known and unknown including “Flush,” “DeathFromAbove,” “French Maid,” and “alpacino,” were able to embezzle nearly $1 million worth of BitCoins through selling insider information on the Silk Road investigation to DPR and funds stolen from users through an administrator account they seized from user “Chronicpain.”

From January 2013 until Ulbricht’s arrest in October of 2013, agents Force and Bridges had administrative access to the Silk Road website through the “Flush” account, used by the Silk Road administrator they arrested. This account allowed them to reset other user accounts and effectively take over these user accounts if they wished. This brings up the question —  since much of the evidence used to convict Ulbricht came in the form of chat logs —  if these chat logs had somehow been altered or contrived by the agents in order to frame Ulbricht. The judge decided to agree to the grand jury’s request and leave out mention of the corrupt agents in the trial, forcing the jury to accept that the chat logs were authentic and in no way fabricated.

Another point the defense brings up is that prior to the investigation on Ulbricht, a number of agencies, including the Chicago branch of Homeland Security, had suspected Mark Kapeles of being the person behind the DPR moniker. When Karpeles was under investigation for charges unrelated to the Silk Road, Karpeles’ lawyer agreed to meet with multiple agencies in order to negotiate what actions would be taken against the BitCoin mogul.

Unprompted by investigators, Karpeles’ lawyer brought up the Silk Road and claimed that Karpeles would be willing to name names in connection to the underground marketplace in exchange for the agencies to drop the investigation against him. Karpeles has failed to see any sort of prosecution from the U.S. Government, though he has been prosecuted in other countries for crimes related to running unlicensed financial institutions and money laundering. This information was later ordered to be stricken from the record and the jury was instructed to disregard any information discussed on Karpeles’ possible involvement.

This proves that the investigation conducted by Force and Bridges was not independent, but rather a multi-agency effort to take down the Silk Road, in which they shared information with one another. It is unknown how much of this information could have been contaminated by the efforts of Force and Bridges. Additionally, the prosecution later admitted that the DEA had been assisting in collecting information from Ulbricht’s computer, seized at the time of his arrest.

The Inability to Defend Their Case

A photo of Ulbricht's laptop, still open at the time of his arrest.

A photo of Ulbricht’s laptop, still open at the time of his arrest.

Most the prosecution’s case rested heavily upon digital evidence obtained from Ross Ulbricht’s laptop at the time of his arrest. As previously mentioned, thousands upon thousands of documents were released to the defense shortly prior to or mid-trial, successfully preventing the defense from properly reviewing the information contained within the documents in order to form a proper rebuttal.

In addition to the unrealistic time constraints placed on the defense, when Ulbricht’s lawyer attempted to call in his own experts on both BitCoins and computer science, respectively, in order to refute claims made by Ilhwan Yum – an agent working with the FBI who had been tasked with compiling spreadsheets related to the Silk Road and didn’t complete that task until two days into Ulbricht’s trial – their motion was denied and some of the inaccurate statements Yum made during his testimony went unrefuted.

Warrantless Searches

Within Ulbricht’s appeals documents, the defense argues that many of the methods used to pin Ulbricht to the Silk Road’s DPR character violated his 4th amendment rights. They claim that the unlimited searches done to Ulbricht’s computer and access to personal accounts, including his Facebook and Gmail, were not done so lawfully as the warrant failed to list files the investigators were searching for specifically. This resulted in what the defense called “rummaging” through Ulbricht’s personal files in order to find anything and everything that could potentially tie him to the Silk Road and violating Ulbricht’s right to privacy in the process.

In addition to this illegal free-for-all prosecutors had on Ulbricht’s computer and cellphone, investigators had Ulbricht’s ISP provider place a wiretap on his computer. Under normal circumstances this would not require a warrant as typically it is used to track a suspect’s location, but in this instance it was used to correlate Ulbricht’s activities, including activities conducted within his own home, with activities occurring on the Silk Road servers. Under these circumstances the defense argues that a warrant was necessary and probable cause needed to be fully establish before a wiretap could be ordered.

Questions About Chris Tarbell

Chris Tarbell, the FBI agent credited with tracking down the Silk Road servers to a datacenter in Iceland.

Chris Tarbell, the FBI agent credited with tracking down the Silk Road servers to a data center in Iceland.

There were other points not brought up in the appeals document, but are equally perplexing on their legality. Throughout the investigation on Ulbricht, Chris Tarbell headed the FBI’s cybercrimes division and served as one of Ulbricht’s arresting officers. It was Tarbell’s team who was able to track the Silk Road servers to Iceland and subsequently mirror the site in order to gain superuser access, allowing the team oversee all activities including chat logs, user accounts, and more.

The official explanation Tarbell had was that through a reddit post the team was able to discover that there was a flaw in the site’s captcha and that the server hosting the captcha was leaking the IP address of the Silk Road’s servers, which up until then was unknown due to the anonymous protection of the Tor service. This is technologically impossible, since the captcha was hosted on the same server the Silk Road website was hosted on and therefore under the same level of anonymity as the site was.

Exactly how Tarbell was able to obtain this information is mostly unknown. During Ulbricht’s trial tech lawyer Joshua Horowitz was called in to question the FBI’s ability to located the Silk Road servers. Horowitz was able to determine that Tarbell was not able to obtain the IP address of the servers through the method he described, but rather, could have been attributed to a hacking technique where pieces of code are input into login fields in order to execute the commands.

The prosecution did not attempt to deny that the methods used by the FBI were hacking techniques, but concluded that even if the methods were hacking techniques, the agency was perfectly within their legal limits to hack into foreign servers without a warrant when conducting a criminal investigation.

Ulbricht Did Not Act Alone

Throughout the trial the defense’s biggest hurdle were the accusations of Ulbricht of being the “kingpin” of a site facilitating international drug trade. A point that was mostly overlooked was that Ulbricht did not act alone in running the Silk Road website. In addition to Ulbricht, the website had two other key players – a mentor of Ulbricht’s known as “Variety Jones” (later “Cimon”) and a programmer known as “Smedley” or “Smed.” Without these two accomplices, it is doubtful that Ulbricht would have been able to maintain the website on his own.

Variety Jones,” A/K/A Cimon had advised Ulbricht on everything from site design, branding, marketing, financial decisions and more. Ulbricht wrote of Variety Jones often in the journal found on his computer and in many ways directed Ulbricht on how the site was run.

The other character, “Smedley”, was the site’s main programmer. Chatlogs used as evidence in the trial clearly demonstrate that without Smedley’s talent for web development the website would have been a sitting duck for hackers and would have been forced offline years prior to Ulbricht’s arrest.

Completely disregarding the defense’s claim that DPR was an moniker assumed by a number of different people throughout the life of Silk Road, it is clear that Ulbricht didn’t have the technological knowledge nor the business sense to act alone in running the site. Neither of these two entities were brought into Ulbricht’s trial. Since Ulbricht’s sentencing Variety Jones, identified as Roger Thomas Clark, has been arrested in Thailand, but is not facing “kingpin” charges as Ulbricht had, in spite of being Ubricht’s top adviser and played a major role in day-to-day site operations.

Unfair Sentencing


Prior to his sentencing, Ulbricht stood by his initial claims that he had founded the Silk Road as a platform for people to sell what they wished. The defense attempted to liken his running of the Silk Road to a landlord renting a home to drug dealers. Even under established “crack house” laws, landlords found allowing tenants to run homes facilitating drug use face a 20-year maximum penalty. Ross Ulbricht was facing a life sentence for providing a digital version of a crack house.

To ensure that Ulbricht received the maximum penalty for all of the charges against him, emphasis was placed on the deaths of six individuals, who prosecutors claimed had purchased drugs on the Silk Road and died as a result. In order to refute this, the defense hired forensic pathologist, Dr. Mark Taff to examine the cases. Taff was able to concluded that there was no way, in his opinion, that the deaths could be attributed as direct result of drugs purchased from the Silk Road. Most importantly, Ulbricht had not been charged for any deaths, intentional or otherwise, and clearly demonstrates the prosecution’s desperation to emotionally manipulate the jury.

99 letters from friends, family and former colleagues of Ulbricht’s were submitted to the courts in order to demonstrate that Ulbricht was otherwise an upstanding citizen and would be able to be rehabilitated if given the opportunity. These letters were mostly overlooked in the judge’s decision to apply maximum sentencing for all of Ulbricht’s charges.

The defense also was able to produce studies which showed that websites such as the Silk Road may be able to reduce the amount of violence attributed to drugs, by taking out the social interactions associated with drug purchases. Additionally, studies were produced showing how the Silk Road promoted harm reduction within the drug community and had people working with the site who were licensed doctors and advised users on how to safely administer drugs, as well as advising users on other necessary precautions.

All of this information did little to sway the Honorable Judge Katherine B. Forrest’s decision to punish Ulbricht to the full extent of the law once the jury found him guilty on all charges. Ulbricht’s seven non-violent offenses resulted in a double life sentence, more time than many rapists and pedophiles serve.