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This programme contains some strong language.
My name is Jared Der-Yeghiayan.
I'm a special agent with Homeland Security Investigations Division.
I'm assigned to Chicago O'Hare International Airport.
We have canines that run past the mail and smell for drugs.
The officers noticed an unusual amount of drugs
coming in letter-class mail.
It was ecstasy pills, MDMA in powder form,
cocaine, LSD, heroin.
A few seizures became 50 seizures per month.
And then became 100 seizures per month.
And then a few hundred seizures per month.
I conducted my first interview of a recipient...
..and he told me immediately that it was from a website called Silk Road.
-It has been 40 years since President Nixon
declared a war on drugs.
Now, a high-profile panel says that war is unwinnable and that...
The Silk Road was a new kind of black market
that the internet had never seen before.
-..opiates up 34.5%.
Cocaine use up 27%.
And marijuana use up 8.5%.
That's according to...
Silk Road was the first big "fuck you" to the war on drugs.
-The website sells illegal drugs
to anyone who is willing to pay.
As our team investigator Michael George uncovered,
people who run the site stand by what they're doing.
-Silk Road had 20,000 new users every single month.
-Afghani heroin, ketamine, steroids,
Xanax, Klonopin, Valium...
you could pretty much buy anything.
And you wouldn't have to even leave the comfort of your home
to obtain it.
MAN: It was clear there was one person
at the helm of this organisation.
-He was more than a drug dealer.
-He was a genius, in my opinion.
-The alleged mastermind goes by the nickname Dread Pirate Roberts.
-Dread Pirate Roberts. Dread Pirate Roberts.
MAN: Every transaction was meant to be a blow
against the whole idea of government.
-He made Silk Road.
From that day, you have a target on your back.
MAN: I am the head of the organisation of distributors
that manufactured drugs and ran on Silk Road.
-The first time I had ever heard about Silk Road,
one of my friends came up to me and he was like,
"Hey, man, there's this website where you can buy drugs on
"and you can sell drugs on it." And I was like, "What?!"
There was the menu on the left,
which shows all the drugs that you could purchase by category,
whether it be a dissociative, an upper, a downer.
It was all there.
And it was like going on Amazon or on eBay
and seeing your top recently-looked-at items,
except that this was cocaine and DMT
and all the other elusive drugs,
that you could never have before in your life,
just right in front of you.
All you had to do was click twice
and it'd show up at your doorstep a couple of days later.
To become a vendor was very simple.
All you have to do is click on "become a vendor"
in the bottom right-hand corner
and it would easily make you a vendor.
Marketing and customer service were number one.
Everything was shot in a studio with professional lighting
and you got a product that matched that.
In order to sell LSD,
you'd get some kind of lawyering papers, doctor papers,
any kind of paperwork that,
when somebody sees a lot of, they want to avoid.
And then it would just be a matter of figuring out a way
to conceal it in the envelope in a way that they won't see.
We would get a product, such as Dove chocolates,
open it up, put it into the Dove chocolate packaging,
close it up and then we had shrink-wrap sealers,
so the product looks like it's been factory closed and never opened.
I just don't know what ended up in law enforcement's hands,
how much of it, when.
You can't worry about things like that.
This whole business is built on who's got the balls
to disregard that information and make the money.
MAN: I remember the day I got the call.
In late February 2013...
PHONE BUZZES ..my boss told me that Silk Road
was a website that operated on this dark net
that made it hard to locate where the site was
or track any of the customers.
That it was the Amazon of drugs.
That you could buy any drug you wanted.
And the scale was worldwide.
In cases like this,
IRS Criminal Investigation are a lot of times brought in
because we're financial experts at tracking money
and most crimes are about the money.
I had studied accounting when I was at college.
I worked as an auditor
and then I became a special agent.
I hadn't, up to this point,
done any kind of work in the drug-trafficking field.
My first day on the investigation,
the first thing was introducing myself to say,
"Hey, I'm the new agent and what do you know about this Silk Road?"
For the most part, to a man, they hated the case.
I get the undercover laptop,
we power up the site and I am dumbfounded.
I had heard about it, people had told me about it,
but until you actually got to the site
and just saw how professionally it was done
and how easy it was to get to the site, it really was amazing.
-For a normal person to purchase on Silk Road,
they were first required to download a special browser,
which would allow them access onto the dark web.
-The Silk Road really offered two distinct protections to users.
One was Tor, and that's a tool that anyone can download.
It triple encrypts your traffic as you're browsing the web
and then bounces it through three different servers
all around the globe.
AGENT ALFORD: So you couldn't locate
if you were using it or administering the site.
But that does no good if you have to buy the drugs with a credit card.
Because it wouldn't be too hard for an investigator, like myself,
to track down who made this purchase.
So the site specifically only authorised bitcoin transactions.
The second protection was bitcoin, of course.
Bitcoin is a digital currency.
It's independent of any bank or government,
unlike any currency that otherwise exists in the physical world.
AGENT ALFORD: It works like cash on the internet.
You can move it, but it doesn't have to be associated with any name,
so it was used to make sure that people couldn't trace the money.
-What made the Silk Road unique
was that it had combined Tor with bitcoin,
and I think that that's often how real innovation works.
That combination, I think,
was really the spark that changed the whole game.
AGENT ALFORD: Even though there were numerous vendors...
..there was an overriding force that controlled the site.
That's the person that we want to target.
He would call himself the Captain of the ship.
He originally was just called Silk Road or Silk Road Admin.
But, at that time, he took on a new alias or new name
and it was Dread Pirate Roberts.
I know who you are! Your cruelty reveals everything!
You're the Dread Pirate Roberts, admit it!
That name has significance because it comes from this film and a novel
called The Princess Bride
and the Dread Pirate Roberts is a title that's passed down
from one kind of noble criminal to the next.
You seem a decent fellow. I hate to kill you.
You seem a decent fellow. I hate to die.
DPR COMPUTER VOICE: You may be shocked to find listings here
that are outlawed in your jurisdiction.
That doesn't mean Silk Road is lawless.
Our basic rules are to treat others as you would wish to be treated.
Mind your own business
and don't do anything to hurt or scam anyone else.
There are some things you will never find here.
They include child pornography, stolen goods and assassinations.
As a community...
..if we are going to survive,
we need to adopt a long-term vision.
It is my sincere hope that,
by making drugs available in a secure and predictable way...
..we will eliminate the violence of obtaining drugs
through traditional methods.
-Silk Road users just loved it.
They called DPR a Che Guevara figure,
changing the liberties of man.
DPR really believed, and I think his users did, too,
that they were ushering in this new era of human freedom.
DPR COMPUTER VOICE: I searched long and hard
for the truth about what is right and wrong.
About what is good for humanity.
All of a sudden, it was so clear.
Every action you take outside the scope of government control
strengthens the market and weakens the state.
I saw how quickly the state would crumble
if it didn't have its tax revenues.
No soldiers if you can't pay them.
DPR COMPUTER VOICE CONTINUES:
We are like a little seed in a big jungle
that has just broken the surface of the forest floor.
It's a big, scary jungle with lots of dangerous creatures...
..each honed, by evolution,
to survive in the hostile environment known as human society.
There's two ways to see the Silk Road.
You can see it as just a vast criminal conspiracy,
as it's described by the FBI,
or you can see it as grand experiments
in granting people an almost dangerous level of freedom.
A kind of new anarchy on the internet,
where people can act with impunity from laws.
The first thing you want to know in an investigation
is not what you do know,
you want to know what you don't know.
And I knew I didn't know a lot.
So I had to go all the way back to the beginning.
It was only after a few months of Silk Road getting started
that it came into the public consciousness.
And what happened was there was an article written by Gawker
about, I believe it was,
"You can buy any drug imaginable."
Within days of that press article,
Senator Schumer, from New York, called a press conference
calling for the site to be shut down.
-It's a certifiable one-stop shop for illegal drugs
that represents the most brazen attempt
to peddle drugs online that we have ever seen.
It's more brazen than anything else by light years.
Traffic to the site went through the roof.
Authorities say they are absolutely shocked by a popular new website
brazenly selling illegal drugs to anyone with a computer.
WOMAN REPORTER SPEAKS IN DUTCH
A lot more eyeballs and traffic went to the site
and it became much more profitable.
Drugs were being shipped all around the US.
Drugs were being shipped outside of the US.
Drugs were coming in from outside.
It was going all over the place.
LSD, cocaine and ecstasy are now just a click of a mouse away.
The case was pretty high profile and people wanted results.
MALE REPORTER SPEAKS IN FRENCH
AGENT ALFORD: But they didn't know how to bring it down.
We even found a local customer
who says there's not a lot police can do to stop it.
I am calling on the DEA and the Department of Justice
to immediately shut this site down before more damage is done.
Whoever this person running this site,
you would think, at this point, they'd say,
"Oh, I should get out of this game."
But surprisingly, the person's reaction who run the site was...
The gauntlet has been thrown down. Bring it on.
-Prior to Silk Road, all the customers I had
were almost all face-to-face.
When the Silk Road came along,
it virtually expanded my network
to every single customer in the world.
MAN: The New York cyber branch of the FBI
was the lead technical investigative agency
for this investigation.
There were millions of dollars being transferred back and forth
and it was large-scale purchases.
From casual drug users to hardcore dangerous drugs.
DPR was taking money from every transaction.
He was getting a fee for every time a good was sold on the site.
AUSTIN BERGLAS: Six months into the investigation,
we had limited success.
Clearly, we hadn't identified the hidden service yet,
we hadn't been able to defeat Tor
and we hadn't identified the Dread Pirate Roberts.
We didn't know where he was,
who he was, how old he was,
if he was a male or female.
That creates a huge challenge
to a very aggressive investigative team.
DPR COMPUTER VOICE:
-DPR COMPUTER VOICE:
-I have let fear pass through me
and commit myself fully to the mission outlined in the charter.
What we are doing is more important than my insignificant life.
What we are doing will have rippling effects
for generations to come...
..and could be part of a monumental shift
in how human beings organise and relate to one another.
Silk Road is going to become a phenomenon.
At least one person will tell me about it,
unknowing that I am its creator.
MAN: DPR played the vendors very well and kept them close to him.
And we took care of him, he took care of us.
The site had a commission, somewhere around 3%.
They later increased their percentage to somewhere around 12%.
This further brings my reasoning to DPR only wanting money.
Anybody who says that they're doing this for other than money is a liar.
-DPR COMPUTER VOICE:
-To those of you chalking my actions up
to pure greed,
I say, "Shame on you!"
DPR COMPUTER VOICE:
-DPR COMPUTER VOICE:
-Do you think it runs itself?
Do you have any clue what goes on behind the scenes
to keep this going?
Whether you like it or not, I am the Captain of this ship.
And if you don't like the rules of the game...
..you can get off the boat.
Dread Pirate Roberts could have been anybody.
There was a lot of theories.
-Of course I wondered. But I'd rather mind my manners
and not ask that type of question.
They were different nationalities, different age groups.
The writing of the Silk Road
made us believe that it was someone from Australia
or other English-speaking countries.
I imagined some kind of potbellied guy in his basement
in Silicon Valley.
There were theories that the person had connections to Russia.
-My guess was that he was from the UK.
I thought he was relatively young,
because he would use this term "epic".
Cos that's a term the younger generation would say.
We really didn't know where the person was located.
He could be located in any country in the world.
He was a, erm...
It was a Friday night.
I was frustrated with the case.
I wasn't getting the results that I thought I should be getting.
So what I decided is, I'm going to go over everything I did.
I was going to redo everything.
My dad was a math teacher
and I think I've kind of got that from him,
in the way he approached things.
Very methodically. Two plus two is four.
And he always raised me to believe I can overcome anything.
So I was going to go over every last bit of evidence,
cos I figured I had missed something.
I was in bed.
I was having a hard time sleeping,
because I just cannot sleep with, erm...
like, something that I should be doing.
My fiancee, she would be upset at me sometimes,
"Why are you up late at night? Why don't you go to sleep?"
So I'd go to where my couch is and that's where I'd do most of my work.
And I just started plugging away.
The Silk Road site was hosted on this Tor hidden service.
But that is no good if someone's just on the regular internet.
So I figured whoever was running this site
had to first advertise it.
I just started putting search terms in, like Silk Road.
Unfortunately, a lot of stuff came back.
So I started putting in limiting searches.
Silk Road started in early 2011.
So I eliminated to before, let's say, February 2011,
to see if there was any mentions of a Silk Road site before then.
And I would start there.
And by doing that search I came across a posting
on the bitcoin forum from an avatar named Altoid.
I click on it, and it brings me to this discussion thread...
..about how someone could have a drug enterprise online
and how would they do it.
And he's advertising for a Silk Road site.
So it predates all other mentions.
So it was kind of eye-opening.
So, how does this person, Altoid, know about this site
before the site was launched?
On his final posting, in October 2011,
Altoid says he's going to start a bitcoin company
and is looking for programming help.
And he asks for people to reach out to him.
And in the posting,
he lists his Gmail account for them to contact him.
And the Gmail account that he lists
And I was like, "Wow!
"Yeah, I have to look into who this Ross Ulbricht is."
-I actually didn't really talk to him the first time I met him.
And then after that, we were inseparable.
I honestly don't think there's anything we didn't do together,
from going to parks and going on hikes, to going to art museums.
He was really into yoga and exercise.
He was also into qigong and breathing.
There was a period of time when he was always in his room,
was always working on stuff.
You know, he really always had his computer in tow
and he was very kind of secretive about it.
Before the internet?
Ask me a question.
What are you most excited about for the 2011 year?
I'm excited to see... how things play out.
I think it's going to be a year of change.
On a broad scale, you know?
Yeah, it's exciting.
-He was known on campus as being, just, you know,
a really cool, awesome dude.
People would just get drawn to him.
He would always try and make sure everybody was having a good time,
you know, that nobody was off in their own little corner
doing their own thing.
He was definitely my first love.
We had great sex.
Hanging out, going to parties, going out to eat
and cuddling in the freezing cold, you know, just perfect.
He kind of made me think about a lot of things,
a lot of different perspectives on life
that I had never even considered before.
ROSS ULBRICHT: What are you most looking forward to?
Erm, I guess I'm looking forward to
the possibility of turning my passion into a viable business.
Awesome. Well, I wish you the best of luck.
I mean, he was a genius, in my opinion.
He was all about entrepreneurship, and his parents were entrepreneurs.
They had owned condos in Costa Rica and rented them out.
He genuinely loved his family.
And Ross genuinely looked up to his dad and he loved his mother.
So I think...
Yeah, I definitely think they had an influence on him.
-Ross would dress in as little as possible.
I knew him for a big chunk of freshman year,
before I ever knew his name - he was No Shirt Guy.
And he was No Shirt Guy to literally hundreds of other people,
who I'm sure never even bothered to learn his name.
I remember, one time, we were going camping.
And to Ross, since he was No Shirt Guy,
you know, wearing a bunch of clothes was, you know,
something that you had to do, because other people made you do it.
And once we got to our campsite, right by this lake,
it was like, "OK, clothes come off.
"I'm going to spend as much time as I can out in nature.
"You know, just completely butt-ass naked, doing my own thing."
-I didn't really have a lot of friends at that point,
so I just hung out with Ross.
When I was working, I don't know what he was doing, to be honest.
AGENT ALFORD: So, on Monday morning,
I went to tell the other guys and girls in the group
about what I'd found.
I have a very expressive face.
So when I get in, I'm pretty excited.
And I was like, "Hey, we've got something new.
"We've got something that we can really sink our teeth into
"and look into this person, Ross Ulbricht."
The case had been going on for about two years,
and they said, "Well, how did you find it?"
And I told them, "Google."
They were like, "Really? That's what you did?"
And I'm like, "Yes."
I mean, you come into this big case
and tell people you've cracked it over a weekend
doing Google searches.
You should expect some, you know, quizzical looks.
I was just this total outsider.
You know, people dismissed it.
-I was working at Forbes magazine
when I saw the first press come out about the Silk Road.
I was pretty much obsessed with the Silk Road
as this new phenomenon on the internet,
especially with the Dread Pirate Roberts,
this mysterious figure behind it all.
Of course I wanted to figure out who he was.
That would be the ultimate scoop.
On the forums you can private message anyone,
and, anonymous as he was, he was still available,
you know, for anybody to reach out to.
And I was shocked to see that he actually was super responsive.
He wrote back to me immediately,
which was not what you would expect from
the kingpin of a massive drug operation.
He said that he wanted to share this vision he had with the world
but that he was waiting for what he considered to be the right moment.
He wanted to wait for some new phase of Silk Road that he alluded to,
but never fully explained.
Very polite and professional.
Espoused these political ideals that seemed very noble.
He was funny at times.
I proceeded to pester him to give me a full interview.
I, at one point, just launched into a series of questions
about who he was, how old he was,
if he was male or female, even.
And he was so freaked out that he cut off all contact.
-Ross and I would talk about politics for hours and hours.
He thought that people were their own best judges
of what was right for them
and that it was a bad idea to have somebody, essentially,
standing over their shoulder,
telling them what was OK and what wasn't OK.
Drugs are menacing our society.
They are threatening our values and undercutting our institutions.
They're killing our children.
Ross agreed with the libertarian idea
that people have the natural desire to do stuff like drugs
and that, when you have a legal set-up,
where access to drugs is prohibited...
Drugs take away the dream from every child's heart
and replace it with a nightmare.
..you don't stop people from doing drugs.
You've just made it more likely that they'll get injured,
or they'll get ripped off,
or they'll get into an uncomfortable relationship
with some shady drug dealer.
But if we face this evil...
..as a nation united,
this will be nothing but a handful of useless chemicals.
I'm sure, in his mind, he was thinking,
"There's got to be a better way," you know?
-So Ross and I, we started off as neighbours down a hall.
Eventually, I needed to find a new place
and he and his girlfriend were also looking for a new place,
so we ended up moving in together.
-We got a two-bedroom apartment, just a really cute place.
It had a hot tub and everything, it was really fun.
ULBRICHT: Have you ever been to Big Bend?
-Yeah, national park? Yeah.
And looking up at the sky.
Man, looking up at, you know, so many stars.
Yeah, fuck, man.
I was just chilling at these hot springs
and a blue fireball, I kid you not,
streaked, probably, you know, like an arc like this, across the sky.
That was a weather balloon filled with methane gas!
Right! Some kind of, like, space junk.
I think it was, like, human trash, honestly.
-Wait! Wait! We have trash in space?
I had no idea.
-Ross was always working on a new project.
He was always telling me
you can accomplish more than you think you can.
But, as far as I can tell, it never really clicked for him
with sort of the nine-to-five type of work.
DPR COMPUTER VOICE: I hate having to lie to people.
Friends will tell me, "Why don't you do this or that?"
Like I have all this free time.
-One time, he made me these steaks
and, at some point, he was like, "I can't really talk about it.
"I have this project, I'm working on it, I'm really excited about it.
And I thought, "You know what, this is his new project.
"He's working on it, we'll see where it goes."
I was honestly, like, "OK, great, that's awesome."
The problem is, for Ross, he would work on a new project
and then it would just not pan out.
And that was sort of the way I knew him.
Being an entrepreneur is very hard.
Most people fail.
DPR COMPUTER VOICE: I just want to scream...
.."I'm running a multimillion-dollar criminal enterprise!"
-Growing up, everyone knew I was a drug dealer.
When I went onto Silk Road, I completely went dark.
Everyone just thought that I was doing a normal job.
99% of the time I dressed up in suits.
-That's not how you look today.
I'm wearing 3,000 pants.
-I had all the money I wanted to.
I could do anything I really hadn't even imagined.
The most baller thing we did, we went to party in Thailand.
It was during the Festival of Colour.
We paid a whole bunch of people to ride us around on elephants.
We were on top of the elephants, smoking fucking heroin
and all sorts of crazy things, throwing 100 bills out of the air.
It was like one of those fucking painted elephants, and everything.
And they have, like, the wooden little house on top.
DPR COMPUTER VOICE:
-I've done a bunch of other stupid shit with my money,
but that was, like, one of the most...
That was, like, the happiest point in my life.
DPR COMPUTER VOICE: Thank you for being here.
Thank you for being my comrades.
DPR COMPUTER VOICE:
So I grew up with my family in the projects in Brooklyn, New York.
And we could see first-hand the devastation
that drugs brought to the community.
You'd walk the streets and you'll see people high on drugs
and, you know, it was always something that you was afraid of,
because, you know, if someone was addicted to some of these drugs,
you don't know what they would do. These people were desperate.
People throwing babies out the window.
And people jumping out of windows and...
I mean, crack doesn't care about who you are.
It devastates whoever uses it.
It is frustrating when you think you've found something
and you don't think other people are as enthusiastic as you are.
But, in those times, you just have to remain professional.
Say, "Well, listen, just keep working your case.
"It doesn't really matter what they think.
"If it's the truth, then they are going to have to deal with me."
I continued to look through all the public records
of what Mr Ulbricht had put out there.
And he had somewhat of a public footprint.
He was in his late 20s.
He had a masters degree.
He had a background in finance.
The strange thing was, whatever DPR was into,
Ulbricht was into.
DPR loved Ron Paul.
Ulbricht loved Ron Paul.
And some brand of Austrian economics that I had not heard about
until in this case.
But DPR loved that brand of economics.
And so did Ulbricht.
So...everything I found, I said,
"Wow, everything is matching up to this DPR."
My husband's real name is Curtis Green.
He got into Silk Road, in the beginning,
because he does take a lot
of prescription pain medication for some injuries he's had.
That's why he used the handle Chronic Pain.
As Curtis became more involved in Silk Road,
he would go and post on the forums.
He has knowledge of a lot of prescription medications.
And people found it very helpful.
DPR started to take notice.
Curtis actually called me and said, "Come home, I have good news."
So I hurried home and went in and he said,
"Guess what? DPR offered me a job on Silk Road.
"Just changing passwords
"and settling disputes between vendors and buyers."
And I said, "That's all? He's not asking you to sell?
"Correct?" And he says, "No. Oh, no. It's not that."
You know, 800 a week is not chump change.
I mean, that's more than I make, working full time.
But there was one catch.
He had to send a copy of his driver's licence,
so DPR would know where he was at and who he was.
Looking back now, yeah, that was a big mistake.
-Ross and I, actually, at that time,
started to kind of get a little rocky.
Just a lot of arguing.
Just a lot of fighting.
He had mentioned his desire to make a website, much like Amazon,
that was anonymous,
where people didn't have to worry about the government
getting in on their sales and their money.
The idea of making money outside of the government
is very, very scary to me.
Maybe it was selfish of me, but I said,
"Do I really want my boyfriend to go to jail?"
He didn't listen to me.
DPR COMPUTER VOICE:
I couldn't believe it. I mean, I thought
I was going to end up with Ross
and we were possibly going to get married.
DPR COMPUTER VOICE: It's living with the possibility
and keeping your work a secret.
I just think a lot of those things
kind of made us naturally drift apart.
So we broke up.
So I don't really know what happened after that.
AGENT ALFORD: Regardless of what other people
thought about my investigation, the lead, I have a job to do.
I started looking into him fully.
So I saw his travel records.
I saw that he had travelled to Dominica.
I know Dominica is one of the places that you possibly can get
a second passport from.
And I knew that from previous tax investigations.
I also was able to get IP information from Google,
saying where he logged in.
And I saw that he was logging in from San Francisco, California.
A couple of weeks after I found the name Ross Ulbricht,
I was using Google to do tons of internet searches,
as you can imagine.
I was amazed.
The last thing I thought I would find is a 35-minute video of him
on the internet, talking.
-Today is December 6th, 2012.
I'm here in San Francisco.
I'm 28 years old
and a friend of the guy who's about to introduce himself to you.
It was a very long video. It was, like, 35 minutes
with him and his friend.
And I guess they did it for some sort of documentary.
And it was eye-opening for me
cos this is the first time I got to see Mr Ulbricht speaking.
..what do you want to talk about today?
They talked about them just growing up.
I remember you being very, like, erm...
quirky and witty.
And, like...just cooler than me.
Oh, how things have changed!
It was such a brutally honest,
what appeared to be such a brutally honest conversation
between two friends.
They talked about their sexual interactions,
even losing their virginity.
First thing I noticed about her was her tits, which were very nice.
She was dating a guy named Chad at the time, who...
Chad, I don't like him already.
Chad is a...was a total prick.
Chad was a kind of small-time pot dealer.
His best friend had asked Ross to move out to San Francisco with him.
You twisted my arm until I said,
"Argh! Fine, I'll come!"
And in this conversation he asked him,
"Well, what were you doing in Austin, Texas
"before I asked you to move?"
I was, erm...
I was living in Austin, Texas. The meh of start-ups.
But when his friend asked him that, he had no answer.
He was stumbling around his answers and he was, "Erm, erm, erm..."
When I looked at, on YouTube, how many views it had,
I believe it had one, maybe two views.
And there were two people in the video.
And I am the third person watching it.
That was when it hit me.
Like, "Wow! I might be the only one looking at this guy
"as being Dread Pirate Roberts."
The Silk Road had obviously grown into a real phenomenon.
In fact, a phenomenon unlike anything I'd ever seen before
on the internet.
So after eight months of badgering him on the Silk Road forums,
DPR finally agreed to a real on-the-record interview.
He made me an honorary drug dealer on the Silk Road,
just for a few hours,
so that we could communicate anonymously.
He was funny at times.
But also arrogant, to a certain degree.
He definitely took credit for creating something new
in the history of mankind and that's how he wanted to be seen.
He preferred to talk about himself
and to see himself as a political figure,
the leader of this philosophical and political movement,
and took offence to this idea that he might just be a mere drug dealer.
But he wasn't ashamed of the fact also that he was making
enormous amounts of money from this.
At one point, he told me that he wouldn't sell the Silk Road
for less than ten or 11 figures.
That's tens of billions of dollars.
And he also told me that, someday, we would have to put him
on the Forbes rich list of the world's wealthiest people.
-Can you imagine being
one of the most famous anonymous people in the world,
just dying for that bit of recognition
that you can't ask for anyone?
That Forbes article is his recognition.
He got it.
But that's not how you run an organisation like this.
I have to say that I did think he was overconfident from that moment.
You know, I asked him...
It was a very short answer.
He seemed completely confident
that he was invincible, an invisible character on the dark web.
-They should've just maintained a site to sell drugs.
It was a quiet community, we were all doing our own thing,
we were being happy.
Then politics started getting brought into it.
It was no longer a marketplace for drugs, like it was.
Now it was the new libertarian front for freedom.
The vendors like myself saw it as "Dude, you're fucking up our,
"like, our thing we got going on here.
"Just shut up and, like, let us operate."
-One day in January,
Curtis and I were on the phone, cos I was out of state in Kentucky.
And he saw that the mailman was delivering a package,
but he was not in a normal mail truck.
My first thoughts were,
"Something's going on with Silk Road."
Curtis opened the door and, by then, the mailperson was already gone.
He grabbed the package, he brought it in, opened it,
and a big plume of cocaine went into his face.
And then the door busted open.
There was the DEA, Homeland Security, Postal Inspectors.
And they told him, if he did not co-operate with them,
they would get him for 40 years' prison time.
They wanted his usernames, his passwords,
his access into Silk Road.
That was their goal. They were after DPR.
And also, it was revealed that 350,000 worth of bitcoins
were stolen and it was put in Curtis' account.
That just made the Feds come down harder on Curtis.
They kept accusing him of stealing this money
and Curtis had no idea what they were talking about.
-He didn't start out as some kind of Pablo Escobar.
He tried to build something that would do away
with the violence of the government and of the drug war.
-I'm pretty sure he was in over his head.
He didn't really know how to control it once it was that big.
That kind of stress and that kind of power that you have
can change who you are.
-One of the agents, Carl Force, a DEA undercover agent,
sat him down and told him that he had been undercover on Silk Road
and that he was using the handle Nob.
And he told them that he had got a message from DPR that night
that stated that he wanted him tortured
so they could get the money back.
The DEA agent told Curtis that, in order to keep his cover,
because DPR believed him to be a drug vendor
and an all-around "bad guy",
he would have to pretend to torture Curtis...
..and make it very believable,
so DPR would think that he had done his job.
They took him to a hotel in downtown Salt Lake City
and they walked him up to the room.
They asked him to take off his jacket.
They made him get down on his knees
and they filled up the bathtub full of water.
They pushed his head down in the water
and held it there for quite some time.
Curtis was panicking.
His arms were flailing, you know, he was trying to get up.
And they still held him down as they snapped pictures.
And he said it felt like it went on for ever,
like it was never going to stop.
-Whatever Ross Ulbricht eventually became,
I think that he started the project...
and his primary motive for the whole thing
was about creating a kind of political movement
in this little anarchic corner of the internet.
And at some point, also,
I think he felt that he was responsible
to the Silk Road community, that he was protecting these people.
And was willing to resort to violence
to protect the community that he created.
-A spokesman for Hazelden, that operates
treatment centres for drug and alcohol addiction,
agrees the war on drugs has been a failure...
-Curtis came home from the second day
of these interrogations
and he took me by the hand
and he said that the order had been switched
from torture to kill.
And I was so upset and so was Curtis.
I mean, tears were streaming down his face.
He's like, "What did I do to our family?"
The DEA agent asked me to take some photographs of Curtis
since, when they were in Salt Lake that weekend,
they only took torture photos.
They didn't take any death photos.
So they asked me to stage it as best as I could that Curtis was dead.
I took some Campbell's Chicken & Stars soup
and had Curtis kind of chew it and smear it all over his face
and had some kind of dribbling down
and kind of on his shirt
so it looked like he had vomited.
And then I just had him lay very still so it looked like he was dead.
It seemed really crazy that I was going to have to do this.
I was shocked.
Like, "Don't you want a professional doing this?"
Taking these pictures was basically life or death.
It was, it really was.
If I didn't do a good enough job,
then the gig was up and they would come after him
and we wouldn't have any protection.
-Silk Road not only consumes your normal drug-dealing life,
it consumes all your life.
Even though it sounds very easy, the stress just, like, ramps up.
"Is there going to be a tomorrow?
"What am I going to be doing tomorrow?
"Am I going to be OK tomorrow or am I going to be in jail?
"Am I going to be dead tomorrow?"
-Most bad guys make a mistake
and the FBI is usually there when they make that mistake.
We decided to just throw anything and everything
at the Silk Road server.
The goal was to try to, you know, poke the server
to see if we can get information that shouldn't be given out.
And all the while, we're using a very simple tool,
a network packet sniffer,
which basically captures the communication
between our computer in the FBI that we were using
and the computer that it ultimately communicates with.
Eventually, we saw an IP address that really stood out.
We took and copied that IP address.
He throws it in a clean browser, a browser not related to Tor...
..a traditional browser, and then hit "enter".
And when we did that...
..the Silk Road login page popped up.
This was a huge moment for the investigation.
It just proved that we'd found the true IP address
for the location of the Silk Road server...
..located in Iceland.
The thing opens up and, sure enough, it's the server.
It has the famous camel image of the Silk Road logo.
When we were reviewing the server we learned that, behind the scenes,
when DPR would log into the Silk Road server
as an administrator, he wouldn't use his name DPR,
he came up with another name.
He came up with the name Frosty.
And one of the things we were able to identify
was a last known login from the administrator.
An IP address that resolved back,
that comes back to an actual internet cafe in San Francisco.
AGENT ALFORD: So after continuing investigating Ross Ulbricht,
I learn more about these technical terms about some of the programming
that would go into running a site.
As I learned these technical terms,
I would continue doing these Google searches
to see if something come up.
So one of the terms was "code igniter",
which is some programming language.
So when I put that in with his name,
I got a response back about a post on a website,
tech Qs about programming.
So when you click the link, it took me to another site - Stack Overflow.
But the question on Stack Overflow
was under his other avatar, called Frosty.
A lot of people were looking into Silk Road,
so there was an idea that there should be a meeting
to get all interested parties to see if we can get all on the same page.
You know, people having a case is like people and their babies.
Everyone thinks their baby's beautiful,
but there are some ugly babies out there.
The Bureau had obtained a copy of the Silk Road server.
It was just sitting on this computer.
I believe it was an Apple and it was this big screen.
On the board they had, like, these big diagrams,
a picture of Dread Pirate Roberts from the movie,
and I saw all these arrows.
But I tried not to look at it
because I'm there just to look at the server.
Gary Alford, the IRS agent, he came in and he was, you know,
as a new agent, as a new agent would, wanted to move things along.
While I was there...
..I heard in the background that someone said,
"We had gone on some San Francisco address."
So I mentioned, "Hey, I have a guy, a guy I'm looking at.
"He lives in San Francisco."
And he was like, "Really?" And I was like, "Yeah, yeah."
I can't speak for them, but it didn't seem like I had dropped,
like, the big key to the case on them.
They were somewhat dismissive.
So I immediately get on the phone and tell the prosecutor.
I'm talking real fast, all excited, I'm so excited I had to slow down.
He says, "Well, what's the address of this individual - Mr Ulbricht?"
He runs it against an IP location the FBI had found,
where there was some DPR activity...
and he sees that they're around the corner from each other.
So then he says, "We have to have a conference call between you,
"the FBI and HSI immediately."
At the time, I was in Chicago
and that's where I called into the conference call.
All it really was is that he had a target in San Francisco
and he saw that we had San Francisco logins.
I thought, at the time, that it was almost too easy,
that a guy wouldn't be as open as using his name in an e-mail account
and he had videos of himself on YouTube
and just open stuff to the public.
AGENT ALFORD: But in his summary,
the prosecutor forgot to mention the link to Frosty.
So then, when he finished, I said,
"Well, there's one other link I found.
"I found that Ross Ulbricht was linked to this avatar Frosty."
The FBI agent started coming in, like, "What? What was that?
"What is this Frosty? What is the significance of Frosty?"
So I explained to him that's just the avatar he used.
You know, I thought it was kind of strange
he was asking this question, but then he says,
"Well, the reason I keep asking this is because
"whoever's running Silk Road, DPR,
"that is the name of the user that operates the site - Frosty."
It started becoming apparent
that this was a very, very likely target for us.
AGENT ALFORD: I actually felt more pressure than I had felt before.
We started gathering all the information
to get an arrest warrant for Mr Ulbricht.
Ross responded to a Craigslist ad that we had posted online,
renting out the room directly above mine in the house.
Ross lived a really simple life, a very modest life.
He did buy some furniture from a garage sale down the street.
I never got the sense that Ross was really well off.
He was kind of doing whatever he was on his computer
just to pay rent and get by.
Ross said he worked on websites and, at one point, I remember he said
he worked in trading currency, as well,
and I remember asking him, I was like, "Oh, like bitcoin?"
Kind of jokingly, because it was something I'd read about
that I thought was just this far-fetched idea.
And, you know, he kind of was just like,
"Oh, there's a little bit of that."
DPR COMPUTER VOICE: I'm so stupid.
Everyone knows I'm working on a bitcoin exchange.
It felt wrong to lie completely,
so I tried to tell the truth
without revealing the bad part.
-So I started messaging Ross.
You know, "How have you been? What have you been up to?"
And then he started telling me how he was in San Francisco
and how San Francisco was super beautiful,
but it was kind of cold right then.
So I just booked a trip and flew out to come see him.
Honestly, I knew he was working on something and that was it
and I don't think it was really working out that well.
So he was just living, you know, within his means,
which was at that three-bedroom house.
DPR COMPUTER VOICE:
I didn't go into it with that intention,
but I definitely hoped that Ross and I would end up back together.
He was always the one that got away, kind of thing.
-I'm pretty sure I want to start a family
in the next five years.
And, er, just...
Yeah, make more friends and close people I love.
Yeah, I want to focus on...
..erm...being more connected to people.
September 30th, 2013,
is when I took my flight into San Francisco.
At that time I was monitoring DPR Roberts 24/7 with my account.
It was important to really become that identity
and what I did is I sat down with Scout
for the next three or four days
and fully debriefed that person on everything.
There is different lingo that I had to become accustomed to,
every single way that they wrote things to what they were thinking.
We needed to know the full history of that account.
Even when I left, I had another agent
monitor the account while I was in the air.
I was really still trying to take in the whole thought
that we were potentially on the cusp of arresting this person
that we'd been pursuing for so long.
We wanted to get him in a spot where we can grab him,
machine open, without trying to force our way in.
It was critical for us to get Mr Ulbricht on the laptop
for a couple of reasons.
Number one, what better evidence to show that he is Dread Pirate Roberts
than he is typing away as Dread Pirate Roberts
at the time of arrest?
Secondly, there could be valuable information on the laptop.
He's aware of encryption,
so he may do something to the laptop to encrypt it
to put it in a state that we can't get access to the information.
He lived in a three-flat and he was up on the top of it
and we would have to get through a very large steel door
and try to get to him before he would do anything to his laptop.
So our plan was to take the chance of having Ross leave his residence,
open his laptop, log in,
and actually grab him in the middle of either chatting with Jared
or being on the site.
-Surveillance still had him at his home
and so we waited in one of the neighbourhoods really close by.
I had put in my request to travel out
because I was to be on the interview team
because I knew the most about Mr Ulbricht.
But I couldn't get the approval to fly out in time for the arrest.
It was affecting investigations
probably in almost every state and globally,
and it all was coming down to this identification that I had made
of Mr Ulbricht.
Was there doubt? Yes.
There's... There's no certainty in this job.
All too often in investigations, it's about 20 hours of pure boredom
followed by five minutes of sheer terror.
Jared's a young agent.
At this point, he was tense. You could tell he was tense at the time.
Later on in the day, he signed off from being online
and I took that opportunity to go order a coffee.
That's when the call comes in from the SO team
that Ross is leaving his apartment
and he's got his laptop bag with him.
All I was thinking, really, at the time was,
"I'm not going to get this coffee out in time
"and I'm going to have to leave it."
Because you've got to do what you've got to do to accomplish a mission,
but I'm like, "I really want that coffee, too!"
I exited the cafe
and I saw one of the FBI specialists that was from New York,
Thomas Kiernan, sitting on a bench across the street.
And so I went over there and I joined him and I put my computer up.
I looked over to my right
and there I saw Ulbricht standing on the street corner,
about 40 feet away from me.
This was the man that was running this global drug empire.
He looked like a San Francisco techie kid
that you'd expect to have a start-up company somewhere in San Fran,
getting ready to launch his site.
Light turns green and he crosses the street...
..where he went to the Glen Park Library.
-It was a Tuesday afternoon, it was after three o'clock.
Glen Park is a small branch of the San Francisco public library system.
It tends to be that not much happens there.
The library has Wi-Fi, and the Wi-Fi is thought to be best in the corner,
where the young man was sitting - the science-fiction section.
At that time, the FBI agent came and met me back at the bench
with Thomas Kiernan,
trying to get the rest of the agents that were on site at the time
into the library.
We waited and, after a few minutes,
Dread Pirate Roberts did come online and on the staff chat.
And I immediately sent him a message...
Jared and I are sitting on the bench across the street from the library,
waiting for DPR to log in and start chatting.
-Recording right now?
I don't know what to say. Ask me a question or something, interview me.
I asked him to do me a favour and to look at one of these messages
that I had control over.
And what that would do is it would require him
to log into the marketplace.
He ends up telling me, "OK, which post?"
And once he did that,
that let me know that he was on that page I asked him to go to
and that's the time that I gave the cue to the FBI agent
to do the arrest.
I'm already on my way across the street into the library
and I guess that's when the case agents start...
Their communications are, "This is about to go."
It's hard to describe. The adrenaline is flowing.
It's a good energy, basically.
We got into this little huddle in the middle of the library.
I'm sure it looked odd to some people, but it was very quick.
And that's when we came up with this plan for a diversion.
Two agents come right behind where Ross was sitting, if I was Ross,
sitting right behind me, and they start yelling,
they start getting into a fight, a verbal fight.
Ross turns around to go look what's going on
and during that time,
that's when the third agent grabs the laptop from him.
That's when I come out of my positioning and grab the laptop
from the third agent at the time.
This was so unusual, for someone to be arrested in the Glen Park Library,
that I actually did run back and text my son on my phone, saying,
"Just to let you know, a bunch of FBI agents just came in
"and busted a guy and took him out in handcuffs!"
Because he always thinks my job is so boring.
The most disturbing thing, to me, about it
was that my son knew exactly what Silk Road was!
But I don't know why he knew that.
There's no way to really describe it but everything, everything is there.
Everything is on that machine and it's all laid out, it's organised,
It's the smoking gun.
A secret website that played host to a massive black-market drug ring
is offline this morning.
The alleged mastermind goes by the nickname Dread Pirate Roberts.
AGENT ALFORD: I got an e-mail from Jared when he got him and he said,
"Gary, you were right."
And that was a great moment.
I had done my job well, so there was a sense,
I felt a sense of satisfaction.
He was supposed to fly down and come see me
and we were going to get back together
and he was probably going to move in with me and then he got arrested.
Two days before he was supposed to fly in and come see me.
I had my friend call me and say, "Oh, my God, did you hear?"
And I said, "What are you talking about?"
She said, "Google Ross's name right now."
After having, you know, had enough time to digest it, it's like,
"Well, can I see Ross being involved in something,
"you know, online? Yes.
"Can I see Ross being involved in something to do with bitcoins? Yes.
"Can I see Ross being involved in something to do with drugs? Yes."
But the idea that the alleged owner and operator of the Silk Road,
this mastermind character, was Ross,
that would've been, you know, beyond unbelievable.
MALE REPORTER: Perhaps the most intriguing charge
against the 29-year-old
is that he was engaged in a murder-for-hire conspiracy,
trying to enlist the help of one of the site's users to execute another.
DPR always talked about taking away violence off the streets.
But then, hearing about the attempted murder-for-hire,
it just cut against everything that he was saying on the site.
Ross was very non-violent. He didn't believe in force.
So a lot of the stuff in the media about how he tried to kill someone
through a hit man and all this stuff, it's just not Ross.
The idea that he would ever have made the leap
from "the best way to implement my vision
"of a more market-based
"and less compulsion and violence-oriented society
"is to have people murdered" is...
I mean, it's absurd on its face.
To me, it wasn't surprising, because this is the drug business
and that's what goes on in the drug business.
Eventually, you do these illegal things
and, you know, even if you have good intentions,
you're around a bunch of criminal actors.
The creator of a hugely successful
and potentially dangerous tech start-up
learnt just moments ago
that he will spend the rest of his life in prison.
So it's life in prison,
that's what a judge handed down to Ross Ulbricht,
the founder of the online black-market site
known as Silk Road.
Prior to the sentencing, Ross Ulbricht addressed the courtroom
and he said that if he is ever to see the light of day,
he's now a completely changed man
and he will live in full accordance with the law.
The judge came back and said,
-"No, you wanted this to be your legacy, right?"
She said, "You wanted this to be your legacy,
"you wanted it to be your legacy and now it is."
The result of taking down the Silk Road has been that,
you know, dozens of dark web drug markets have taken its place,
some of which are doing far more business, far more revenue,
far more narcotics than the Silk Road ever did in sales.
And many of them lack the...
the ideals that the Silk Road did have.
The dark web has only gotten darker.
The biggest struggle for me
is kind of reconciling the two, the two people.
So, like, Dread Pirate Roberts and Ross Ulbricht.
But I think the internet kind of enables people
to act in a way they might not normally,
just cos there's a very big disconnect between
what you do online and what you do in your physical life.
Have you got any more questions or should we wrap it up?
Yeah, future outlook.
What are you going to do over the next 20 years?
I want to have had a...
..a substantial, positive impact on the future of humanity by that time.
-Do you think you're going to live forever?
-I think it's a possibility.
Documentary looking at the black market website known as the Silk Road, which emerged on the darknet in 2011. This 'Amazon of illegal drugs' was the brainchild of a mysterious, libertarian intellectual operating under the avatar The Dread Pirate Roberts. Promising its users complete anonymity and total freedom from government regulation or scrutiny, Silk Road became a million-dollar digital drugs cartel.
Homeland Security, the DEA, the FBI and even the Secret Service mounted multiple investigations in the largest online manhunt the world had ever seen. But it would be a young tax inspector from the IRS, who had grown up in the projects of Brooklyn, who would finally crack the case and unmask 'DPR'.
With unparalleled access, Silk Road is a thrilling cat-and-mouse crime story for the digital age, bristling with intrigue, mayhem... and murder.