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Inside the FBI takedown of the mastermind behind website offering drugs, guns and murders for hire

Dangerous Journey on the Silk Road
The FBI Declassified: Dangerous Journey on the Silk Road 43:25

Through never-before-seen footage and in-depth interviews,  "The FBI Declassified" takes you inside the minds of heroic federal agents and analysts as they reveal how they solved some of the biggest cases of their careers.

Produced by Caroline Sommers and Emily Bernstein 

In 2011, the FBI became aware of an online black-market website, Silk Road, where users could buy and sell goods, including illegal drugs and weapons — even murders for hire were discussed. The site was run by an individual known only as the Dread Pirate Roberts, named after a character from the classic film "The Princess Bride." An elite FBI cyber taskforce worked to infiltrate the site and identify its founder: Ross Ulbricht, a 29-year-old computer science engineer.

Ross Ulbricht
Ross Ulbricht Julie Vie/Vivian's Muse

Silk Road, accessed anonymously by users on the dark web, brought in approximately $1 billion in sales, according to investigators, with Ulbricht making millions by taking a cut of each transaction.

"Silk Road was the Amazon of drug sites," says former FBI Special Agent Milan Patel.

The investigation led FBI agents from Iceland to New York to San Francisco in search of the shadowy figure behind the website.

"They trafficked in – anything you could get in the black market – poisons, things like that," says Vincent D'Agostino, an FBI agent with the cyber division.

"Silk Road took drug trafficking into the 21st century," says D'Agostino. "This was so easily accessible that it ended up getting into the hands of people that never really would have touched it." That, D'Agostino says, led to overdoses and deaths.


In 2011 there was a new bad guy in cyberspace behind the website Silk Road. He oversaw more than $200 million in illegal transactions on the dark web, involving the sale of drugs, weapons and illicit services such as computer hacking. Even murders for hire were discussed on the site. 

Austin Berglas: Bad guys will always find a way to use technology for malicious purposes. It's just the way it is.

Austin Berglas: I'm Austin Berglas. I was the assistant special agent in charge of the cyber branch in the FBI's New York office. 

When FBI agents got the case, they only knew the site was run by someone using the alias "Dread Pirate Roberts," a famous movie character.

Milan Patel | Former Special Agent, FBI N.Y. Cyber Branch: I think he had a fascination with the cult classic, "The Princess Bride." Like many of us who grew up in the '80s. Love that movie. 

U.S. District Court for the Southern District of New York

THE PRINCESS BRIDE: I inherited the ship from the previous Dread Pirate Roberts. Just as you will inherit it from me.

Milan Patel: And it was a good way to sort of signal that you would never know who he is.  

Vincent D'Agostino | Former Special Agent, FBI N.Y. Cyber Branch: As a method to throw off law enforcement you had that smokescreen of saying, hey, Dread Pirate Roberts may be one person, maybe 10 people…. So that's the origin behind it. 

It would take multiple law enforcement agencies more than two years of following dead ends and false leads to unmask Dread Pirate Roberts as 29-year-old Ross Ulbricht.

Julia Vie: Ross and I actually met at a African drumming class. And when we first met, I was totally not into him. ...I just didn't really see him for him. And then once I started talking to him more…  that's when I started really liking him

Julia Vie and Ross Ulbricht Julia Vie/Vivian's Muse

In 2008, Julia Vie met Ross Ulbricht at Penn State and began dating. She was a freshman. He was a grad student in materials science and engineering.

Julia Vie: When Ross and I really started to get to know each other, it was intense. … We were always hanging out; we were always doing these amazing things together. 

In the summer of 2009, after getting his master's degree, Ross moved home to Austin. Julia soon joined him.

Both were trying to launch their careers. Julia opened a photography studio. Ross followed an unconventional path, creating a free market website, where users could avoid government scrutiny. the project consumed him. 

Julia Vie: A lotta times I was just angry at him because I wanted to go out, I wanted to have fun, and he was like, "Julia, that's a waste of time." 

Julia says Ross told her he "needed product" to sell on his new website. In early 2011, with a stash of homegrown hallucinogenic mushrooms, he launched Silk Road. 

Julia Vie: Here he had this website, he had designed everything, he'd figured out the system — he was excited. And then no customers. … And then he came up with the idea of posting to these forums, like "Hey, there's this really cool site!"  

Vincent D'Agostino: He understood that in order to make the site successful, you can't — simply couldn't just, you know, hang a shingle in the dark web and hope people are gonna find it because that's not how the dark web operates. 

The postings worked. Soon, Silk Road attracted buyers and sellers from around the world to his illegal drug marketplace.

Jared Der-Yeghiayan | Former Special Agent, Homeland Security Investigations: On the main page it would give you all the different items that sort of pop up, that were featured items. 

In the summer of 2011, Homeland Security Agent Jared Der-Yeghiayan learned about packages containing small quantities of illegal drugs coming through the international mail hub at Chicago's O'Hare Airport.

Jared Der-Yeghiayan: These are the seizures that we got at O'Hare that were attributed to Silk Road. 

Jared Der-Yeghiayan: They were addressed with … printed labels on 'em so it looked like it was more of a business. ... It definitely stuck out because you'd find five or six of the same packages, all addressed to different people, going all across the United States. 

Vincent D'Agostino: So as the government started to intercept these packages, it started to make people ask the question of what is going on that, suddenly, people are starting to mail drugs? 

Packages containing small quantities of illegal drugs coming through the international mail hub at Chicago's O'Hare Airport  were attributed to Silk Road.  United States District Court for the Southern District of New York

Jared Der-Yeghiayan: They started getting a little more brazen …  we went from seeing maybe, like, two or three packages a day to 30 packages a day to 50 packages a day. Within a few weeks, it's a hundred. 

Jared Der-Yeghiayan: You'd see some unique things. … There were CD cases, DVD cases, just people that would … put the actual pill … taped to a piece of paper. … But then other people got a little more creative so you'd see things like cardboard and like even in the little ripples of the cardboard, they would stuff the drugs in those ripples. 

Determined to find the source of the drugs, the agent showed up at a residence where one of the packages was headed – to conduct a "knock-and-talk." 

Jared Der-Yeghiayan: The term's basically used essentially for what it is. It's — we're literally knockin' on the door. And we just want to talk to the person. 

The recipient of the package wasn't home, but his roommate was willing to answer the agent's questions. 

Jared Der-Yeghiayan: "I'm curious, your roommate … does he get any international mail, any packages, anything unusual?" And he looks at me. And he says, "Yeah, he's getting drugs." … and he says, "It's coming from this website called The Silk Road" and, you know, I ask him, "Well, what's the … the website domain? Is it .org? He goes, "No, onion." 

Austin Berglas | Former Asst. Special Agent in charge, FBI N.Y. Cyber Branch: The onion router or Tor, the onion meaning there's multiple layers to get to the center. … And that's the way that the — that Tor works. … There are multiple computers that one has to go through in order to reach that content, the center of the onion. 

Vincent D'Agostino: The Tor network ... was created for the purpose of allowing people to communicate on the Internet without anyone having the ability to know who or where they were. 

Jared Der-Yeghiayan: Then I said, "OK, well, tell me about the way that they're — they're paying for these things." And he says, "Well, they're — paying with — with bitcoin."

Bitcoin – a cryptocurrency.

Jared Der-Yeghiayan: These websites do not accept PayPal or Visa or MasterCard or any other types of credit cards … because all that's traceable. 

Der-Yeghiayan didn't know what he was dealing with. but incredibly, a Google search helped clear things up, when he found an article on the website Gawker. 

Milan Patel: In June of 2011, Gawker wrote this long article on Silk Road and did a great job explaining what it was, what people were doing there, what they were buying, how easy it was to buy drugs and other paraphernalia. 

Vincent D'Agostino: The uptick in traffic was enormous. …  I mean, you have to remember, people are reading this going, this is — sounds incredible. You know, let me try to log on to this thing and see if it actually works. 

But the publicity came with a downside: Silk Road was now on law enforcement's radar. Politicians demanded the site be shut down. In Chicago, Der-Yeghiayan stepped up his investigation, seizing an ever-growing number of packages, and matching them to specific vendors from around the world.  

Jared Der-Yeghiayan: And as we're doing that, we're also taking' our fingerprints that are coming' off the packages. We're running through our international data bases and law enforcement databases, we're sharing it with our international partners but ... That doesn't take us any closer to really identifying who's running Silk Road. 

By the fall of 2011, Der-Yeghiayan convinced the U.S. Attorney's Office in Chicago to take on the case. But even with his identity hidden, Ross was starting to get nervous. 

Julia Vie: He was scared. He was really scared. He was like, "I think I'm gonna go to jail forever for this." 


Milan Patel: You still didn't know who was behind the website. You didn't know where the website was. And you didn't know who was visiting the website. 

By the end of 2011, Silk Road was processing orders worth half a million dollars a month selling drugs and other illicit goods and services. Some drug buyers and sellers were arrested as law enforcement redoubled their efforts to figure out the identity of the site's mastermind: the Dread Pirate Roberts.  

Vincent D'Agostino: Those traditional techniques that an investigator would use were useless in an online drug market — they didn't work. 

On the Silk Road  website, people from around the world could buy and sell illicit drugs, weapons, poisons, and services such as computer hacking. In Silk Road forums, users could even discuss murders-for-hire. U.S. District Court for the Southern District of New York

Looking for a new perspective, prosecutors asked the New York FBI cyber branch to join the hunt. This was an elite team – with experience working inside the dark web and with Tor – also known as the onion router – where Silk Road was hidden.

Milan Patel: We're in New York City where all the big banks are. There's a lot of cybercrime happening. It's our jurisdiction. … and so, we had built this reputation of working these global cases and bringing them to successful prosecution.

But to get involved, the FBI team needed to prove to their bosses this case was about a lot more than drugs.

Austin Berglas:  We had to show that Silk Road was offering hacking services, cybercrime services on the site ... in order to devote the resources.

Milan Patel: We saw murder-for-hire postings, hacking-for-hire postings, which was, "hey, pay me two bitcoin, and I'll hack into your ex-wife or ex-husband's email account." … and I suspect people were using it because it made a lot of sense. It was totally anonymous. And you could never trace it back to the person who asked for it.

In September 2012, the New York cyber branch opened a case under the name "Operation Onion Peeler." The mission: find the Silk Road server. 

Jared Der-Yeghiayan: There's a computer somewhere — that actual website's running off of, and when the internet's trying to direct traffic to the website, it has to know where to go to. And what Tor does is it protects that information, it protects the IP address.

A server's IP address is like a telephone number. Normally, once agents find a potential IP address, they get a subpoena from a judge to request further information from the internet service provider. But Tor protects its users by constantly changing that information. 

Austin Berglas: By the time we got the request back from the internet service provider, the pathway to that content ... had changed. We were always too late. 

Milan Patel: Always one step behind. Sometimes by minutes. … It's painful because you want to get lucky at least once. 

Agents speculated about who was the Dread Pirate Roberts – also known as DPR. 

Milan Patel: My initial guess was he was probably a normal kid that did something that he thought was really cool, and then it spiraled into something huge…. We had arrested folks in the past that were global phenomenons on the internet. ... and when you arrest them, you find that they're totally normal people. I mean, they've got day jobs, they've got families. 

Milan Patel: DPR had a real life. ... I'm sure he had friends that had no idea that he was — probably one of the biggest masterminds on the internet. 

At the time, one of the only people who knew the real identity of DPR was Julia Vie. After several years of dating, she and Ross had ended their relationship in 2011.

Julia Vie: Probably one of the main reasons why we broke up was because I felt like he put this insane pressure on me to keep this insane secret.

In the summer of 2012, Julia got an unexpected visit from Ross, who told her he was moving to San Francisco.

Julia Vie: He just showed up. … I was honestly shocked to see him. 

Julia Vie: Ross and I hung out by the water. ... And then, randomly, he just said, "I'm not doing the site anymore." ... To me, it seemed strange. Like, "why would you bring it up?"

Julia Vie: I didn't know if I fully believed him, but I wanted to.

Ross Ulbricht
Ross Ulbricht Julia Vie/Vivian's Muse

But Ross hadn't quit the site. Silk Road was processing millions of dollars of transactions each month, with Ross taking a cut on each one.

Milan Patel: If you take away the technology, it's like any other enterprise, organized crime or otherwise.

Vincent D'Agostino Ross was the boss and below Ross was … like the consigliere would be — in a traditional organized crime family. … then he had his captains, right? His top moderators that would handle the business of the site day to day. … And then, below that, his soldiers, which were his lower-level employees that didn't know too much but were doing the mop-up duty.

Milan Patel: in this world, the person giving you direction to commit crimes, you don't know who he is. You don't know what he looks like. You don't know where he lives. But you trust him because you talk to him on the internet every day. 

Vincent D'Agostino: Ross was the captain of the ship and said as much ... you know, "I make the rules. I'm the captain of this ship. and if you don't like the rules, get off the boat."  

Ross was proud of what he'd created and even did an interview with Forbes magazine – careful to hide his identity.

Austin Berglas: He was …  touting that he was going to remain anonymous. …  he was so confident that he was — never going to be found.

Vincent D'Agostino: … says they would literally have to come up behind you and watch you on your computer screen in order to catch you doing this.

Silk Road special agents
From left, Vincent D'Agostino, Milan Patel and Austin Berglas, former special agents with the FBI's New York cyber branch. CBS News

While Ross believed his identity was protected – the Silk Road site began to show vulnerabilities.

Vincent D'Agostino: The site began to get attacked. ... a lot of the extortion started coming in, the blackmail. 

In the spring of 2013, a vendor messaged Dread Pirate Roberts threatening to expose the personal information of thousands of users.

Vincent D'Agostino: This was a major problem because the whole basis of the site was the anonymity. if the site gets hacked and it gets published ... here's — names and addresses for people selling and buying drugs, the site's done.

So, Ross decided to hire someone he believed was a member of a Hell's Angels biker gang to find and kill the blackmailer and his associates. He paid $650,000 from his bitcoin account to get the job done.

Vincent D'Agostino: At this point … the idea of someone fixing this for, what was a for him, a small amount of money was a very appealing option rather than face the reality — that the site just might close up.

Vincent D'Agostino: Now, thankfully, this is something that we at the FBI believe was a scam. …  but in his mind … it wasn't a scam. He actually paid for these murders. 

Julia Vie: The murder-for-hires are still so hard for me to believe — like, that side of Ross, I never saw. …  I think in his chase for success … he was willing to do anything for it. And a lot of people on that site convinced him to do things I don't think he otherwise would have done.

Jared Der-Yeghiayan: He became dangerous to the point that he was gonna protect it at any cost.

Austin Berglas: I never had a doubt that the team was — going to be successful and ultimately find DPR. … I knew that even the most confident of criminals made errors. 


Vincent D'Agostino | Former Special Agent, FBI N.Y. Cyber Branch: There were a lot of mistakes that could be made in setting up a site like this that someone who wasn't very street smart could easily make.

Milan Patel | Former Special Agent, FBI N.Y. Cyber Branch: You will eventually make a mistake because you feel invincible.

Early in the summer of 2013, after nearly a year of trying to crack the inner workings of the Silk Road website, agents in the FBI's New York Cyber Branch finally got a break. They noticed a coding error on the site.

Jared Der-Yeghiayan | Former Special Agent, Homeland Security Investigations: They were able to actually — find vulnerabilities in the website, where they saw it actually leaking its IP address. 

It would be a game changer — investigators discovered the location of the server hosting the website 2,700 miles away in Iceland.

Austin Berglas | Former Asst. Special Agent in charge, FBI N.Y. Cyber Branch: It was pretty monumental. ... we had been working on this diligently for months. And to get a win like this … was just huge.

Agents flew to Iceland, but didn't take the actual server, not wanting to raise the suspicions of Dread Pirate Roberts. Instead, they made a mirror-image copy they could work from.

Austin Berglas: Once we got that server … now we could really dig in and do the investigative type of work that the FBI is known to do.  … the biggest thing that we got — was just an understanding of the volume of activity that was happening on Silk Road. It was just immense. 

Agents learned that in just two-and-a-half years, around 1.2 million transactions had been processed on the Silk Road site with bitcoin, generating the equivalent of approximately $1 billion in revenue. The agents also found information and communications Dread Pirate Roberts believed would never be discovered.

Milan Patel: It gave us insight as to how many people were on the site, what kinds of private messages were being shared.

Vincent D'Agostino: Everything was out in the open. …  it was almost like someone saying … the odds of anyone getting in here are low. But if they get in here — I'm done. 

Agents could even see records of some of Dread Pirate Roberts' own activities. 

Austin Berglas: Who's logging in and who's logging out, who's using the administrative console, meaning who is actually operating the site. 

That led them to an internet café in San Francisco.

Jared Der-Yeghiayan: The person that was signing in ... the — name was frosty.

By now Homeland Security agent Jared Der-Yeghiayan had made 3,600 drug seizures. He even went on the site and made more than 50 undercover purchases. but his biggest "get" came in the spring of 2013, when he located one of Dread Pirate Roberts' deputies who created the screen name "Cirrus."

Jared Der-Yeghiayan: We got a Silk Road administrator ... to cooperate with us. 

Vincent D'Agostino: If — a person — cooperates, that law enforcement agent can take over that account … you're able to assume the identity of that person. 

Austin Berglas: It's no different from being an undercover in the — kind of the Donnie Brasco sense of the word, where you're … at the table with mob bosses. 

Former Homeland Security Special Agent Jared Der-Yeghiayan, impersonating "Cirrus," was able to gain the trust of other administrators and eventually the Silk Road boss: Dread Pirate Roberts. CBS News

Der-Yeghiayan, impersonating "Cirrus," was able to gain the trust of other administrators and eventually the boss:  Dread Pirate Roberts.

Jared Der-Yeghiayan: He was running a pretty tight ship. … He gave me assignments right away. And — you really wanted to excel and do well so then he would give you more assignments.

Vincent D'Agostino: Jared … became a very trusted employee during his undercover work, learning the inner workings of how the site operated, which was very, very valuable. 

Also working the case was the DEA and the Internal Revenue Service.

Gary Alford: My name is Gary Alford and I was a special agent in the New York field office.

Gary Alford | Supervisory Special Agent, IRS: While they're investigating public corruption and drug trafficking, we'll be tracking the money that's financing these illegal activities.

Like all of the investigators, Alford was determined to find the person behind Dread Pirate Roberts – so he used Google's advanced search option for the earliest mentions of Silk Road. 

Jared Der-Yeghiayan: He was looking to see did anyone really mention Silk Road … prior to us knowing that it existed?

Gary:Alford: … and I come across postings by a user named Altoid. … One was on … a web site that — discussed magic mushrooms and other psychedelic type drugs.

Then, another mention of Altoid.

Gary Alford: And also, one on the bitcoin talk forum. … And what it appeared the user was doing — was advertising the site. 

Digging deeper, the IRS sleuth found another clue.

Gary Alford: On the bitcoin talk forum, it had multiple postings. ... and in the final posting the individual listed an email account, Ross Ulbricht at

It was the first time Ross Ulbricht's name had come up in the case. Alford shared his findings with his colleagues.

Gary Alford: They thought it was interesting, but — it didn't appear they felt it was compelling or enough to take significant action against Mr. Ulbricht. … But I never put it to the side. … in every free moment, afterhours on the weekends, I would try to get information about Silk Road.

He found a second mention of Ulbricht's name in a post about coding for the dark web, with a new identity.

Austin Berglas: On that blog post, he quickly changed his username to "frosty."

Gary Alford: So, I wrote that down, frosty. 

In every spare moment, Alford kept searching Ross Ulbricht's name. That led to a 2012 post from StoryCorps, a national project to record personal stories. It was a conversation between Ross Ulbricht and a friend:

StoryCorps video:

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] 

Gary Alford: I learned that Mr. Ulbricht moved from Austin, Texas, to San Francisco. 

StoryCorps video:

RENÉ PINNELL: You think you're going to live forever?

ROSS ULBRICHT: I think it's a possibility. 

Gary Alford: That posting from frosty and that interview convinced me in my heart, this is Dread Pirate Roberts.


San Francisco, July 2013: U.S. Customs and Border Protection officers who were not involved in the Silk Road investigation intercepted nine fake IDs coming into the U.S. from Canada.

Ross Ulbricht fake IDs
"These are the nine fake IDs that were identified as— belonging to Russ Ulbricht," said Jared Der-Yeghiayan. U.S. District Court for the Southern District of New York

Agents were dispatched to the intended recipient's residence to investigate.

Vincent D'Agostino: And out comes this man who was pictured in the identification, they can see it's the same person. ...They ask what his name is and he says, "My name is Ross Ulbricht." … And they say, "OK, well, Ross, you had these ID's mailed to you and you're in the picture — you're the man in the photograph."

Jared Der-Yeghiayan: Ross was nervous at first. And says, you know, "I don't know anything about them." 

Vincent D'Agostino: And as the agents continued their conversation with him … his response was, "Well, I heard of this website called Silk Road where you can buy and sell anything, including fake IDs." 

Jared Der-Yeghiayan: The agent didn't know anything about Silk Road at the time. … But he did a good report and documented it. 

Soon after the visit about those fake IDs, Ross Ulbricht abruptly moved. 

Alex Bauer: My name is Alex Bauer and I was Ross's roommate in San Francisco. … My housemates and I were looking for another roommate and so we put an ad up on Craigslist. … And Ross said he did stuff with computers. He was sort of vague about what exactly he did. 

Ross brought very few possessions with him. 

Alex Bauer: Ross came … with some clothing and like his computer, of course. … Ross was definitely on his computer a lot. 

By now, law enforcement agencies investigating Silk Road had several pieces of the puzzle: the FBI had found the server, the IRS had identified Ross Ulbricht's name in a personal email address, and Homeland Security had an undercover agent in direct contact with Dread Pirate Roberts. But no one was seeing the whole picture … yet. 

It was around this time Ross and his ex, Julia, started talking again. 

Julia Vie: He basically just invited me to San Francisco. ...I had never been before, so I said, "Why not?" But then he told me I had to buy my own ticket. ... I was like, "Oh, well, I guess if he quit the site, then he doesn't have money." 

Julia Vie: I just was, like, really into Ross that weekend. Everything was very similar to how we were in college together.

But something seemed strange to Julia.

Julia Vie: He didn't let me see him on the computer at all. That's when I knew something was up. He specifically was not on the computer except when I would leave to maybe go take a shower. And then I'd pop in the room and he'd close his computer.

Julie Vie
Julia Vie CBS News

Julia Vie: You know, the way he told me his computer was set up was that, if he closed it, all the information would be destroyed if anyone ever tried to get it. 

Despite her suspicion that Ross was still involved in Silk Road, Julia was interested in rekindling the relationship. She invited Ross to visit her back in Austin.

Julia Vie: I was begging him to hurry up and come to me 'cause I just had a very bad feeling. I kept telling him, I said, "push your trip up. … Leave your computer at home. Just come to Austin." … And he just, he was like, "no, I've got to do some more things here and I'll see you in a few weeks. I got my ticket."

In August 2013, Jared Der-Yeghiayan joined forces with the FBI New York cyber team. They showed him the mirror copy of the Silk Road server. When he saw a reference to San Francisco, things started to click.

Jared Der-Yeghiayan: Every time that I would actually chat with Dread Pirate Roberts, something would happen to his account where I would see that his time zone … was … Pacific Time Zone. 

More puzzle pieces fell into place when IRS Special Agent Gary Alford met with Der-Yeghiayan and the FBI New York cyber team. On the wall of their office, Alford saw a board covered with leads.

Gary Alford: So, I tried not to look at the board because this is their house, this is their office, and this is their investigation. But I couldn't help to see the arrows are pointing to one thing on the board that said San Francisco — 

Alford knew from that StoryCorps piece that Ross Ulbricht lived in San Francisco. 

Gary Alford — and I say, "Hey, I have a guy I'm looking at — who lives in San Francisco." 

More puzzle pieces fell into place when IRS Special Agent Gary Alford met with Homeland Security's Jared Der-Yeghiayan and the FBI New York cyber team. CBS News

After leaving that meeting, Alford ran another search on Ross Ulbricht and found the newly filed Homeland Security report about those nine fake IDs.

Gary Alford: And I almost hit the roof. I was like, "this is him. This is him." I went running into my supervisor's office. … Immediately we got on the phone with the assistant United States attorney. … The prosecutor gets us all on the phone, the FBI, HSI and myself. 

In any investigation there's a watershed moment — and in the Silk Road case it came when Alford mentioned the word "frosty." One of the FBI cyber team agents was floored. 

Gary Alford: He's like, "Are you sure frosty? Frosty?" And I was like, "Yes, frosty." And then he said … "Well, that is the username" … and the name of the server: frosty @ frosty. … And then, there was quiet on the phone. And so, everyone kind of took in that, oh, this might be it. 

Jared Der-Yeghiayan: That was a big — big break for us. That was that moment where we said, "OK, there's — there's something more to this." 

Jared Der-Yeghiayan felt they had their man, but one more clue convinced him. 

Jared Der-Yeghiayan: There was one big thing for me, and it had to do with the writing. … So almost every single time I'd chat with him as Cirrus …  he would say the word "yea" at least once during the chat. … And it was spelled Y-E-A. … Then I found Ross Ulbricht's YouTube page. … Oh Yea, Ross. And so that was the name of his YouTube page and it was spelled Y-E-A.

Austin Berglas: Investigative wheels start spinning. … One of the first things that's done is a subpoena to Gmail. 

With access to Ulbricht's Google history, FBI agents discovered that his Gmail and Silk Road account activity did line up. 

Jared Der-Yeghiayan: Every single time Dread Pirate Roberts would sign onto the forums or sign onto the marketplace … you'd also see Ross Ulbricht sign onto his Google account or sign off of his Google account. … And that gave us a lot of confidence — after a few days of it being very consistent, that this is our guy. 

In the span of just 10 days, the U.S. Attorney's Office drafted a criminal complaint, the FBI got an arrest warrant, and the team headed to San Francisco to take down Ross Ulbricht. But to make their case, they needed to catch him — with his fingers literally on the keyboard.

Austin Berglas: So, the plan was to make sure to arrest Ross with the laptop open and unlocked …  much harder than it sounds.


In October 2013, members of the FBI cyber security team traveled to San Francisco to arrest the man they believed was the mastermind behind Silk Road, Ross Ulbricht.

Austin Berglas: We didn't want to do a traditional FBI knock on the door, go in and arrest him in his living room, because we knew that we wouldn't have access … to the laptop. … We needed to make something happen. 

Homeland security agent Jared Der-Yeghiayan was with the team. Logging on undercover as "Cirrus," he was still in contact with Ulbricht's alias, Dread Pirate Roberts.

Jared Der-Yeghiayan: I'm digitally watching Dread Pirate Roberts online. And then physical eyes on Ross Ulbricht had him still at his house in San Francisco. 

Der-Yeghiayan went into a local café and ordered a coffee. Meanwhile, the surveillance team saw Ross leave his house. 

Jared Der-Yeghiayan: So, as I was waiting for my coffee … the FBI agent walks in and says, "Our friend is coming down the street." … I walk 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 walked into the same café Der-Yeghiayan had just left. 

Jared Der-Yeghiayan: I think he's — he's gonna, you know, probably walk right out because there wasn't any open seats when I went in there. And sure enough, he turns right around and then he goes right next door into the Glen Park Library. 

Undercover FBI agents quickly took their places inside the library. 

Vincent D'Agostino: Ross Ulbricht heads upstairs and is observed entering the science fiction section, where he sits down on- at a table there. … At this point, Dread Pirate Roberts is not online. 

Jared Der-Yeghiayan: We're sitting on a park bench across the street from the Glen Park Library … and I have my computer. And we're just waiting hopefully for Dread Pirate Roberts to sign online. 

Austin Berglas: He sat at a table, opened up his laptop.

Jared Der-Yeghiayan: We saw within a few minutes Dread Pirate Roberts ping on my computer. He does sign on the staff chat. And so that— that's my cue to pretty much start up my chat. 

Vincent D'Agostino: The agents in the library can see Ross typing. … A couple hundred feet just outside of the library, unbeknownst to Ross Ulbricht, is the person he's speaking to. …  Jared directs him to go look at this message, knowing that he has to log in in order to actually access it. Once I Ross Ulbricht gets to the post … At that moment, the order to execute the arrest is given. 

Two undercover agents stationed near Ross created a diversion by staging a fight.

Jared Der-Yeghiayan So, he turns over his shoulder to see this actual fight occur. As he does that, another surveillance agent walks over, picks up the laptop, walks it over to our computer tech, hands it to him. … And as that happens, Ross Ulbricht … lunges towards the laptop. And another agent walks up behind him — bear hugs him — 

Austin Berglas: And then the investigative team then placed Ross under arrest.

Surveillance of Ross Ulbricht's October 2013 arrest in San Francisco. U.S. District Court for the Southern District of New York

Vincent D'Agostino: So, the concern at that point is, you know, we have to keep this laptop alive. 

Austin Berglas: And don't let it go to sleep, don't let it encrypt, don't let it close. 

The cyber team made sure the laptop stayed open. They found a treasure trove of evidence: fake identities, chats, even Ross's personal journal. Most damning, the computer's username  was "frosty."

Vincent D'Agostino: I've never seen more incriminating information in one spot ever in the 11 years I was with the FBI. 

Ross Ulbricht was charged with seven counts, including narcotics trafficking, computer hacking, money laundering, and a kingpin statute usually reserved for mafia dons and cartel leaders. 

Vincent D'Agostino: When you're looking at a site doing the volume that Silk Road was doing, nothing else would really fit charge-wise other than to charge him as a kingpin.

Julia Vie: My good friend called me … she didn't even want to tell me herself. She just said, "Google Ross Ulbricht." And then I did and obviously found Ross Ulbricht arrested, all the whole thing and then I just started bawling and falling on the ground. Like, I was so upset. 

Julia says authorities spoke with her after Ross's arrest.

Julia Vie: I mean, I was just like, I knew he was doing something shady, but I … had no idea it was as big as it was.

In January 2015, four years after Silk Road started, Ross Ulbricht's trial began. The defense admitted while he had created Silk Road, he handed it off to others, who then lured him back in to take the fall.

After a 12-day trial and less than four hours of deliberations, a jury found Ross Ulbricht guilty on all counts.

Jared Der-Yeghiayan: There's a lot of attempts to try to throw in alternate perpetrators and other things that would try to make it seem like there was some injustice done. But the evidence was overwhelming. The jury found it overwhelming. 

Silk Road mastermind Ross Ulbricht sentenced to life in prison 03:13

At his sentencing, family members of individuals who died while using drugs purchased on Silk Road delivered victim impact statements. 

Jared Der-Yeghiayan: So, the mother, you know, gets up and talks about her son Preston … took drugs from Silk Road and fell off a balcony. And — and she talked about the last day she held him. And so, there was a photo that she provided to the court about — you know, the last day she saw him and the last day she was with him.

Jared Der-Yeghiayan: Pretty much, like, the whole courtroom's in tears, you know, hearing this. And it's something that as a parent that, for me, it was— enormously impactful. And so, then it — it came down to the point that Ross had— a chance to then address the court.

Vincent D'Agostino: You know, as far as the half-hearted apology that he presented and, you know, the kind of general … never meant it to go this direction- it was sort of expected understanding that this person was clearly thinking about his appeal at that point.

Jared Der-Yeghiayan: The judge took a little bit extended break and comes back and … She's like, "You had all these things going for you, but you're no different than any other criminal on the street."

Vincent D'Agostino: Ultimately, he received two life sentences plus 40 years. 

And the federal system does not allow parole.

Julia Vie: I don't think he deserves to be in jail for the rest of his life, you know? I mean, maybe take the best years of his life … but leave him with the last part of his life. 

Vincent D'Agostino: Here is a person that, by all accounts, had every opportunity to do something great. … Ross was someone that myself or anyone on our squad could have easily been friends with in a parallel universe. 

At one point, Ross Ulbricht was a multimillionaire. The government was able to recover about $70 million. Silk Road was a lucrative and dangerous venture. Until the FBI cyber team shut it down.

Austin Berglas: If it wasn't for the FBI's technical capability … we would still be investigating Silk Road.

Vincent D'Agostino: That's something as, you know, an alumni of the FBI New York office, I'm really, really proud of.

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