Ross Ulbricht’s Complete Journey To Making Of The Silk Road & Indictment


Ross Ulbricht is one of those personalities that people are still curious to get a good knowledge of him and his deeds. He is a computer science engineer who was the mastermind behind one of the most famous dark web markets, the Silk Road. He had been earning humongous via this self-made online black market when he was in his early twenties. Little did he know that he was soon going to be caught and that he would be serving his worst days of life.

Back in 2011, the FBI became conscious of a darknet market online named Silk Road that lets the users buy and sell goods, weapons, ammunition and illegal drugs. People discussed openly about the hitman-for-hire services or the murder-for-hire services. The FBI had found out that the dark web website was operated by an individual under the alias or username “Dread Pirate Roberts” (DPR), which typically was a character belonging to the Classic film “The Princess Bride”. With just an alias, it is quite hard to tell who or how many individuals are behind the alias.

The cops had busted and seized the Silk Road website in 2013. Ross was arrested and he was aged 29 years. He was sentenced to 40 years along with two life sentences in the prison. Currently he is serving prison terms.

Julia Vie, Ex- Girlfriend of Ross Ulbricht Explains How It All Started

Image: Knowledia News

Julia mentions that they met at an African drumming class after which they fell for each other. In 2008, they met each other at the Penn State after which they started dating. While Julia was a freshman, Ross was a graduate student in materials science and engineering.

In the Summer of 2009, Ross completed his graduation and moved to Austin, his home-place. In a short while, Julia joined him. Both were focused in their respective careers. Julia had opened a photography studio while Ross devoted all of his time creating Silk Road that would surpass the government scrutiny.

In the early 2011, Ross had launched the Silk Road with a stash of homegrown hallucinogenic mushrooms. He started promoting his website in various dark web forums as he knew that merely possessing a website selling illegal drugs would not get him anywhere and that promotion or letting people know about the website became utmost important. With this technique, Silk Road gained immense positive response from people all around the world.

Ross Ulbricht’s Business Got Unveiled

Image: All Things Vice

Soon after in 2011 itself, a Homeland Security Agent named Jared Der-Yeghiayan came to know about the Silk Road deep web market via some seized packages containing small amounts of illegal drugs intercepted at the international mail hub at Chicago’s O’Hare Airport and attributed to the Silk Road. The packages (five or six of the same kind) bore printed labels on them that hinted at a business that distributed them to various people all across the United States.

Initially, it was just a couple of packages a day, say two or three, which suddenly rose to 30 to 50 packages a day. Within just a couple of days, it was a hundred. The drugs were hidden in some unique contents like CD and DVD cases which later got more creative.

These trails of drug packages led the cops to find more about Ross and they ended up reaching him at his residence. Unfortunately (or fortunately) he was out and the cops met his room-mate who informed them that Ross receives international mail packages which Ross had mentioned to be coming from the Silk Road website that has a .onion extension. He also mentioned that all the transactions take place via the cryptocurrency Bitcoin (BTC).

On further scraping the internet, the law enforcement came across a website Gawker. An author wrote a pretty long article on the Silk Road, what it was, what was sold, how people engaged, how easy it was to get illegal things and more in detail. This intrigued the agents to go ahead and get into the website to see if it actually works.

Ross came to know about the cops behind him and he was very nervous. He was sure that anytime soon he would have to go to jail forever.

In September 2012, the New York’s Cyber branch launched a case naming “Operation Onion Peeler” whose mission was to locate the Silk Road server. The agents tried hard to get to the server’s IP but every time it got changed and they missed out on the IP address in just a couple of minutes.

Ross and Julia had already broken up back in 2011 because Julia thought Ross wanted her to keep this insane secret of the darknet site which was posing immense pressure on Julia. Later Ross contacted Julia and said that he wanted to quit the website and move to San Francisco. In reality, Ross had not quit the deep web website and that Silk Road was processing millions of dollars per month and Ross took a cut from each of the transactions. To hide his identity, he also gave an interview on Silk Road in the Forbes magazine.

In the spring of 2013, a vendor had messaged Dread Pirate Roberts where the vendor threatened Ross that he would expose the personal information of thousands of users. At this point, Ross was aggressive and he paid $650,000 from his bitcoin account and opted for hitman service to kill the ones threatening him.

Image: Sophos

The Game Changing Moment

The early summer of 2013 seemed pretty fruitful for the FBI agents who were in continuous search of the Silk Road server’s IP address. At that time, the New York Cyber branch got a break and they detected a vulnerability on the Silk Road website where due to its coding error, the IP address of the server was leaking. The agents in no time detected the location of the server and to their surprise the location was 2,700 miles away in Iceland. The agents followed the server to Iceland but to not distract Ross from what he was doing till then, the cops made a mirror image copy of the server so that they could work with it. They did not take the original server.

On investigating the mirror server, the cops found out about the jaw-dropping volume of activity that was running on the Silk Road. They found out that in just 2.5 years, the website had conducted 1.2 million transactions with Bitcoin and generated a revenue of approximately $1 billion.

The law enforcement agents were able to see some of the crucial things like the activities of Dread Pirate Roberts, who logs in and out, the time of logins and logouts, who is using the administrative console or who operates the website. The scrutiny of this information led the agents to an internet cafè located in San Francisco from where an alias “Frosty” was logging in.


The Homeland Security agent named Jared Der-Yeghiayan visited the website and had made over 50 undercover purchases. But he received the biggest break in the spring of 2013 when he was successful in locating one of the deputies of Dread Pirate Roberts who had created an alias or screen name “Cirrus”. For an agent to get an administrator of a website who is ready to cooperate with him and the agent being able to take over the account of the administrator would mean that the identity of the administrator is revealed.

Thus, the agent gained control of the administrator account “Cirrus” and gathered trust of the other administrators including the mastermind of Silk Road, Dread Pirate Roberts (aka Ross Ulbricht). Ross at that moment was totally congested with the heavy load of shipments and he immediately gave the agent (posing as Cirrus) assignments.

To get more assignments, the agent had to prove himself which he did and in a short while he became one of the most trusted employees. He learnt how the website operated internally; that was a very valuable step. Simultaneously, he was working with DEA and the Internal Revenue Service on the case.

A special federal agent in the New York field office named Gary Alford had been assigned to trace the money that was financing the illicit activities on the dark web. He was determined to track the person who was working behind the alias “Dread Pirate Roberts”. Thus, Gary used the advanced search feature of Google to find out the previous mentions of Silk Road knowing that the dark web marketplace had existed.

This is when Gary came across an user’s various postings where the alias “Altoid” was used. One of the postings on a website discussed psychedelic sort of drugs and magic mushrooms. Altoid had also advertised the dark net website Silk Road on one of the bitcoin talk forums. On the same talk forum, there were multiple postings of which the final one bore an email account that said Ross Ulbricht at ([email protected]). This was the very first time that Ross Ulbricht’s name was openly exposed in the case. Alford had shared his findings with his colleagues.

Gary did not feel to immediately take any action against Ross but whenever he got some spare time, he used to try in order to get more information on Silk Road. While doing so, he uncovered a second mention of Ross’s name with a new identity in a post that was based on the coding for the dark web. The alias used on the blog post was “Frosty”.

Alford’s determination to find something new on Silk Road and Ross Ulbricht that led to a post from StoryCorps dated 2012. The post contained the conversation of Ross Ulbricht and his friend. From the conversation, Gary learned that Ross had moved from Austin (Texas) to San Francisco. StoryCorps is a national project that records personal stories.

RENÉ PINNELL: So, Ross, how did you come to live in San Francisco?

Ross Ulbricht: You twisted my arm until I said, “Ah, fine, I’ll come.” [laughs]

Combining information from both the posting of Frosty and the interview had convinced Gary to come to a conclusion that Dread Pirate Roberts is Ross Ulbricht.

The Closing?

In July 2013, San Francisco, the U.S. Customs and Border Protection officers who were not at all involved in the Silk Road investigation had intercepted in total nine fake or counterfeit IDs that came from Canada to the United States. Jared mentioned that all of the IDs had been identified to be of Ross Ulbricht. Soon after, the agents of the U.S. District Court for the Southern District of New York had been dispatched to the residence of the ID owner for investigation.

Image: NY Times

The agents found out that the identities on the counterfeit IDs were the same as the person under investigation in his residence. When they asked his name, he was mentioned to be Ross Ulbricht. When the agents counter questioned Ross, he became nervous initially and denied his knowledge about the fake IDs. As the conversation intensified, Ross stated that he has heard of a website named “Silk Road” from where one can buy and sell anything they want and can also acquire fake IDs. Until then the agents were not at all aware of the existence of Silk Road but Ross presented an excellent report and documented it.

Following the investigation, Ross abruptly moved from San Francisco.

ALex Bauer, who used to be Ross’s roommate in San Francisco, had been interrogated. He said that he and his co-mates were in search of another roommate for which they put up an advertisement on Craigslist. Ross had contacted them and informed them that he did stuff with computers but never clarified on what exactly he does with the computers. When he moved to the house, he carried certain possessions like clothes and of course his computer. He used to spend maximum of his time on the computer.

Pieces of “Ross Ulbricht & Silk Road” Puzzle In Law Enforcement’s Possession By Far 

  • FBI had located the server of Silk Road
  • The IRS had identified Ross’s name in a personal email address
  • A Homeland Security (HSI) agent is already in direct contact with the Dread Pirate Roberts.

But till then no one could match the jigsaw puzzle.

When all these happened and he had already moved out from San Francisco, Ross had re-contacted Julia (Ross’s ex-girlfriend) and they began talking again. According to Julia, he had invited her to San Francisco and asked her to purchase her own travel tickets. Julia was excited as she had never been to San Francisco. But she also thought that if Ross quits the website, he would not have money.

That weekend she flew to San Francisco to meet Ross and they spent some time like the good old days. But Julia felt something strange. Ross would spend more time with her except for the time she was out of the room or in the shower. He did not let her see him working on his computer and that when she suddenly entered the room, every time Ross would close his computer. He had also told her that the setting in his computer is different and that if he would close it, all the information would be destroyed and no one would be able to ever get any information out of it.

Julia had a gut feeling that something was not right and something bad is going to happen. But she wanted to rekindle her relationship with Ross. So she had invited him to come with her to Austin. She forced him to speed up his work and visit her in Austin. She asked him to leave his computer at home and visit her real quick. But Ross had said that he had some pending works that needed to be finished before he visits Austin. He said he already has the ticket and he would be there in a couple of weeks.

Joining The Puzzle Pieces

Back in August 2013, Jared Der-Yeghiayan (the agent who was taking assignments from Ross on Silk Road under the alias “Cirrus”) joined forces with the cyber team of FBI New York. While working with them, the FBI agents showed Jared the mirror copy of the Silk Road server. Jared observed a reference to San Francisco after which things started to click.

Jared mentioned that every time he used to chat with Dread Pirate Roberts, the zone of Ross would display that of the Pacific Time Zone.

The FBI felt they started to solve the jigsaw puzzle after agent Gary met Jared and the entire New York cyber team. Gary noticed that the board in the wall of their office was covered with leads. Gary did not intend to get into them until he saw that all the leads were pointing towards a clue – “San Francisco”.

Gary had already read from the StoryCorps interview of Ross and his friend that he used to stay in San Francisco. He informed the FBI that he is looking for a guy who lives in San Francisco. After the meeting, Gary had carried out another search on Ross and found a newly filed report by the Homeland Security that mentioned about nine fake IDs. Gary could now conclude in his mind that it was Ross Ulbricht. So, he in no time got on the phone with the assistant United States attorney and the prosecutor had got others on the phone as well – HSI and FBI.

The watershed moment in the Silk Road came when Gary mentioned the name “Frosty”. The FBI said that the name of the server was also frosty ([email protected]). This was the enormous break and everyone was sure that this probably was it. They believed there was something more to it. Jared felt that they had gotten their man but one more clue had convinced him.

Ross used to use the word “YEA” every time he chatted with “Cirrus” and it was spelt Y-E-A. Jared had found Ross’s YouTube page named “Oh Yea, Ross” and the spelling there was also Y-E-A.

The first thing that the federals did was a subpoena to the Gmail account. They accessed the Google history of Ross and learned that the Silk Road account activity and Gmail lined up. Whenever Ross logged in to the Silk Road account, his Gmail displayed him as online and as he would sign off from the Silk Road account, his status in Gmail showed him to be offline. This tracking went on for a couple of days until the feds were confident that they had got their man.

In just ten days, the U.S. Attorney’s Office had drafted a criminal complaint, the FBI had got an arrest warrant and the team had headed to San Francisco to arrest Ross Ulbricht. But in the bid to make their case, they had to catch him red-handed when he was on his computer. So they had planned to nab Ross Ulbricht with this laptop open and unlocked.

The Final Showdown: Silk Road Comes To An End With Ross Ulbricht’s Arrest

The members of the FBI cyber security team had traveled to San Francisco in October 2013 to arrest Ross Ulbricht, who they believed to be the mastermind behind the Silk Road. FBI agent Austin Berglas said that they were not focussing on the traditional knock on the door, barge in and arrest Ross in his living room. This is because they would not have access to Ross’s laptop, which is what they do not want.

HSI agent Jared was still in contact with the team and simultaneously, he was also logged in as “Cirrus” and was still in contact with Dread Pirate Roberts. He says that he was digitally monitoring Dread Pirate Roberts and he was online. The other cops at the same time were physically keeping a close watch on him at his house in San Francisco. While Der-Yeghiayan went to a local café, ordered a coffee and was waiting for his order to arrive, the surveillance team spotted Ross leave his house.

Jared says, “So, as I was waiting for my coffee … the FBI agent walks in and says, “Our friend is coming down the street.”… I walked outside and … turned to my right. And there’s Ross Ulbricht actually standing next to me — about 10-15 feet away, at a street corner, waiting for the light to change.”

Ross had entered the same café where Jared had had his coffee after he left. But he did not get an open seat there. So he left the café and went to the Glen Park Library, which is right next door. The undercover agents followed him to the library. They found out that Ross entered the science fiction section where he sat down on a table. Dread Pirate Roberts was offline at this point. Jared was sitting on a park bench and waiting for Dread Pirate Roberts to come online.

Soon after the surveillance team informed that Ross is on his laptop and in a couple of minutes, Dread Pirate Roberts pinged “Cirrus” and signed on the staff chat. That is when Jared thought of replying back and continuing the conversation.

The agents in the library saw Ross was typing while Jared was speaking to Ross virtually some few hundred feet outside of the library which he was completely unaware of. Jared asked Ross to check the message as he knew that to see the message, Ross had to log in. Jared and the surveillance team had planned that as soon as Ross gets into the post, the arrest execution order will be given.

Two undercover agents who were following Ross, started a fight intentionally to draw the attention of Ross. As soon as the fight began, Ross turned his shoulder to see the fight. Meanwhile, another surveillance agent picked up his laptop and handed it to the FBI computer tech. As that happened, Ross lunged towards the laptop while another surveillance agent walked up behind him and bear hugged him. After this, the investigative team arrested Ross.


The main challenge, at this point, is to keep the computer open and not let it sleep or encrypt. On accessing the laptop, they had found a treasure chest of evidence that consisted of fake identities, Ross’s personal journal and chats. What was most striking was the computer’s username “Frosty”.

Agent Vincent was awestruck with the amount of incriminating information that could be gathered from one spot.

Ross was charged with seven counts that included –

  • Narcotics Trafficking
  • Computer Hacking
  • Money Laundering
  • Kingpin statue reserved for cartel leaders and mafia dons.

Ross’s ex-girlfriend Julia Vie came to know about Ross’s arrest when one of her good friends had asked her to Google “Ross Ulbricht”. Julia was very upset with the news. She has also informed that the authorities had spoken with her after the arrest. Julia knew Ross was up to something shady but she could not imagine that it would be this big.

Situation After Ross Ulbricht’s Arrest

Ross Ulbricht’s trial began back in January 2015, four years after the Silk Road had started. The defence had admitted that Ross had created the Silk Road, handed some of the responsibilities to others. It took a 12-day trial and less than four hours of deliberations for the jury to find Ross guilty on all the charges he had been booked for.

Jared mentions that there were a lot of attempts to make feel that some injustice was going on for Ross. But the judge finds the evidence to be very overwhelming. The family members of the individuals who died due to drug overdose caused by Silk Road had delivered some impactful victim statements.

It was clear that Ross was thinking about his appeal in the court. But the judge said that he was no different from the other criminals on the street. So she sentenced him two life sentences along with forty years behind the bars. Julia Vie mentions that she does not think Ross deserves to be in jail throughout his life. She says it was okay to imprison him in his best years and at least leave him for the rest of his life.

“Silk Road turned out to be a very naive and costly idea that I deeply regret…It was supposed to be about giving people the freedom to make their own choices, to pursue their own happiness however they individually saw fit…I do not, and never have, advocated the abuse of drugs…I understand what a terrible mistake I made.”

– Ross in a letter to the Court

Ross Ulbricht was a multimillionaire and the government was able to recover nearly $70 million. Silk Road was pretty lucrative and dangerous at the same time until the FBI seized it. If the FBI was not capable of taking Ross into custody and solving the Silk Road case, then the Silk Road case would have still been going on.

Other’s Opinion On The Silk Road Case

“…such a sentence should, at the very least, be reserved for the worst crimes committed by repeat offenders. Needless to say, Ross’s crime is nowhere near that category and his sentence was grossly excessive.”

– Shon Hopwood. Appellate Lawyer, Professor of Law at Georgetown University

Ross Ulbricht did not have any other criminal charges prior to the Silk Road Case. Many states that he did not intend to cause any sort of bodily harm or injury and even no victim was named on trial. There were other criminals who had been charged less or even did not receive any jail sentence for crimes they did which is far more worse and violent than Ross’s. There is also clear discrimination between the other defendants who were related to the case, the original drug sellers and the men behind Silk Road 2.0.

Image: Free Ross

It was heard that the judge who passed Ross’s sentencing used the uncharged allegations that never were submitted to or even ruled on by a jury for justifying her sentence in regard to the violation of the Sixth Amendment right to a jury trial. In this context, she had violated the First amendment as well by basing her sentence partly on what she had believed was Ross’s political philosophy.

“The government did not produce a single witness to testify firsthand that Ross authored any of the communications attributable to DPR.”

– Joshua Dratel, Criminal Defense Attorney

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