Designated: Special Agent on “The Silk Road” with Jared Der-Yeghiayan

Beginning in 2011, the Silk Road was the place to go online for any number of illegal drugs and contraband or other illicit items.  And as long as a buyer had some of this new digital currency called Bitcoin to spend, they could find whatever they wanted for purchase. This illicit activity on the Silk Road really put crypto on the map…. especially for law enforcement.  In  2013, the Silk Road was shut down as part of an intense federal investigation involving multiple law enforcement agencies. Key to the disruption of the Silk Road was an undercover special agent with the Department of Homeland Security.  Jared Der-Yeghiayan spoke with Designated host Yaya Jata Fanusie and explained what happened behind the scenes of the Silk Road and how he and a team of his fellow agents were able to shut it down.

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Episode Transcript

Speaker 1 (00:00):
Today's podcast is supported by Winston and Strong ll Winston
and Strong, a trusted legal advisor and advocate for clients
across virtually every industry designated, is proudly supported by a Hummingbird.
Hummingbird is a modern compliance platform designed to make financial
crime investigations smarter, faster, and more effective because today's financial

(00:23):
criminals are sophisticated, savvy, and agile, meaning the tools used
to fight them should be two. Learn more at Hummingbird
dot Co. I'm Yaya Jata Fanussi and this is designated

(00:44):
on the Illicit edge Network, the silk Road, you know,
the digital one from a few years ago. You may
have heard about it. Beginning in twenty eleven. It was
a dark net market that sold all types of contraband.
But in order to buy illicit items on this silk Road,
you had to use this new thing at the time
called bitcoin. Perhaps you've heard of that, But in twenty eleven,

(01:05):
bitcoin was still in its infancy, and this illicit activity
on the Silk Road really put crypto on the map,
especially for law enforcement. But by twenty thirteen, the silk
Rome was shut down as part of a federal investigation
involving multiple law enforcement agencies. Key to the disruption of
the Silk Road was an undercover special agent with the
Department of Homeland Security. The name of that agent Jared

(01:30):
dear Yagen. His story is not very well publicized, but
he sat down to talk with me about what happened
behind the scenes of the Silk Road and how he
and a team of his fellow agents were able to
gather evidence and conduct a raid that brought down the
creator of the site, Ross Obricht, who went by the
moniker dread pirate Roberts, and is now serving two life

(01:51):
sentences in a federal penitentiary. Now there's a bit of
a free Ross movement in some circles, pushing to commute
his sentence or to even pardon him. This interview with
Jared deer Yegan doesn't aim to take a point of
view about his conviction, but rather to lay out the
facts from the perspective of the agent who went undercover
and worked with Ross on the Silk Road and played

(02:11):
a key part in bringing him to justice. I hope
this conversation will help you decide what you think time
to get designated with Jared dear Yagan. You told me
recently that you had an event I think last week
that I think maybe says a lot about you. What
in the world did you do a few weeks a
few days ago.

Speaker 2 (02:35):
It's hard to talk about, but I ended up finishing
one of my big races for the year. So I
did an ultra race that was in like midwest Virginia
in the mountains, and I did complete it, and so
I'm pretty happy about that. But it took me about

(02:55):
twenty nine hours to complete.

Speaker 1 (02:59):
So what does that ultra marathon? What could you describe
what that was?

Speaker 2 (03:04):
Sure, it was an ultra marathon race. It was They
say it's one hundred miles, but it ended up being
about one hundred and seven, which doesn't really sound like
some more miles is that big of a problem. But
when you're moving as slow as you are, and you're
as tired as you are and hungry as you are,
those extra seven really matter.

Speaker 1 (03:23):
I think that says a lot. Jared, You've got an
amazing story. I think we should start with your own origin.
Could you tell us a bit about your family, your background.

Speaker 2 (03:35):
I'm Armenian, half Armenion, I guess, and other half is
just a good mixture of American different different immigrants that
came in. So my father immigrated here in the seventies
and met my mother and got married in college. And
his background being Armenia and the family had a rough past,

(03:59):
you know, with the genocide, and he ended up actually
being born in Syria because of it, and the family
was I grew up in Syria and then eventually he
moved to Lebanon with his family and grew up there
playing soccer. And that's how he came the United States,
was on a soccer scholarship and where he met my

(04:20):
mother in college and and yeah, the rust was really history.

Speaker 1 (04:26):
And then so where did you end up growing up?

Speaker 2 (04:31):
So he was he ended up getting a job with
Department of Justice as an attorney and with Immigration Naturalization Service,
and he was a trial attorney and ended up getting
assigned to Chicago. And so that's we grew up in
the North side of Chicago, in a suburb about forty
minutes from the city.

Speaker 1 (04:51):
We're going to get into your government career, but I
know it started started way back. Tell me a little
bit about why you went to CPP, Customs and Border Protection.

Speaker 2 (05:06):
I didn't really go to CBP. CP sort of came
to me my father being immigration. I was applying for
different federal jobs. This is right before nine to eleven.
This actually nineteen ninety nine was when I first started applying,
and I was looking at jobs primarily trying to get
into Secret Service. I guess like the whole idea of

(05:30):
like jumping in front of a bullet or something was
appealing when you're nineteen, But at the same time, I
didn't really know what I wanted to do except for
just to get into federal law enforcement. And so I
applied with Secret Service, and I applied with US Marshals,
and I apply with Immigration Naturalization Service as a special Agent.
And the one that came knocking first was was I

(05:53):
ins which is Immigration Nationalization Service, and they ended up
offering me a job as an inspector in Chicago, which
I not traveling internationally hardly at all growing up, I
really had no idea what that was, but my father
convinced me it was the greatest job ever, and and
so I took it, and I found myself then instead

(06:14):
of really jumping in front of bullets, stamping passports.

Speaker 1 (06:18):
So you're stamping passports, your young sense of adventure. So
at this point, were you disillusioned or how did how
did you feel?

Speaker 2 (06:30):
I felt like it was it was not exactly what
I envisioned for law enforcement or for my career, or
really what I was going to do in my life.
And I still really wanted to do something within law
enforcement that was a little more sophisticated and interested in
investigating different crimes and you know, but but I learned

(06:53):
a lot actually through that job, and I learned a
lot about people, and learned a lot about nationalities and
and different types of like trends and patterns and identifying
those and ticketing and the way that you talk an
interview with people was something that I felt if actually,
if I never really had those skill sets, it would

(07:14):
have been really difficult to develop them as as an
agent or anything else that I want to do later
in my career. And so it was it was actually
really beneficial, and I stayed in that job for about
seven years and doing a variety of different things, not
just stamping passports, but also I was on a counter
terrorism response team, so I were actually responding to people

(07:34):
that were high risk for terrorism, interviewing them, and then
at the same time I was also going after narcotic
smugglers and primarily at Chicago OHAA National Airport.

Speaker 1 (07:45):
So I always find it interesting talking to folks who
were in government, you know, going twenty years plus back.
You were, I assumed at CBP. It sounds like during
nine to eleven, So how did that affect you?

Speaker 2 (08:00):
Actually, no, So the typical government set up. I applied
in ninety nine. I didn't get in until two thousand
and three. It took that long. So there was a
hiring freeze, which is what prevented. So nine to eleven
happened essentially right in the middle of all these applications,
and at that point in time, no one really knew

(08:22):
what was going to be happening with the different agencies.
And that was about the same time when we were
talking about Immigration Naturalization Service, which was originally in the
Department of Justice. It was identified as being one of
the failure points for nine to eleven, along with Custom
Service and FBI and the various agencies that just weren't
sharing intelligence or information. There was a really good actual

(08:44):
book from the whole nine to element Commission. There was
actually a separate book that was the Travel and Trends,
which I found to be actually way more interested in
the commission's report because it actually talked about all the
different hijackers and how they came into the country and
where they were at and actually broke down what they
said during their interviews and who was waiting for them
outside the airports. And it's actually a really it's a

(09:08):
it's very very well written. It's a lot of documentation,
and it gives you a lot of insights. And that
was something that pinpointed, you know, the failures and how
Immigration wasn't talking with Customs, and how the different intelligencies
weren't talking together with different law enforcement. And so that
was primarily obviously why Department of Homeland Security was stood

(09:29):
up and why I ins was eventually dissolved and became well,
in typical government fashion, they took Immigration, Naturalization Service and
the Custom Service two different agencies, and to make it
more streamlined, they made three agencies.

Speaker 1 (09:45):
So that typical, yeah, typical US government efficiencies.

Speaker 2 (09:51):
So when I went to the Academy in two thousand
and three, even though I was hired by I in
S and I was hired as an inspector, we had
no idea what agency I was going to be working
for when I left there, because there was ice that
was being created, which is Immigration and Customs Enforcement. There
was CBP, which is Customs and Order Protection, and then

(10:12):
there was CIS, which is Citizenship and Immigration Services. And
they didn't know which one we're going to be a
part of, Like when we're even going through the academy,
they're like, I don't know when you get out of
there and give me part of one of them, or
we think, And so we actually still wore our Department
of Justice badges, and we wore the patches, the Department

(10:33):
of Justice patches for like another two years in two
thousand and four thousand and five, until they started identifying
themselves as being CBP, and we all eventually got like
the same shirts and the same badges. Working at the airport,
you went on to.

Speaker 1 (10:49):
DHS Department of Homeland Security and you joined something called
a HSI, which I don't think a lot of people
know about, especially the idea of there being agents at DHS.
Could you explain your trend your journey.

Speaker 2 (11:03):
There absolutely so they you know, in this confusion of
forming three different agencies, both immigration and Customs Enforcement or sorry,
I guess both in s and at the time Customs Enforcement,
they both had officers and they both had special agents,
so they had criminal investigators and then they had the

(11:24):
regular officers. What they did is they ended up taking
the two officer corps from both agencies and combining them.
That became CBP, and that's what you see today at
the at the airports, and they're the ones who are
wearing the blue shirts with the badges and the uniformed
officers and they're also made up of a Border Patrol
amount too is a part of them too, So that's
all under CBP. The special agents, though, were combined in

(11:46):
into one agency called ICE, which we're familiar with more
for the immigration side of it, because there was also
the enforcement angle of of of the whole I ins
component of going after you know, people that were either
like absconders or people that were in country that were illegal,
and there was a totally separate component of ICE. So anyway,

(12:07):
so there's two different divisions of ICE, and one was
the criminal investigators that investigate all the crimes and another
one was the like sort of immigration enforcement angle, and
HSI is that criminal investigator side of it. They're the
ones who are the special agents that traditionally came from
customs and from Immigration I and S at the time,
and so they're referred to now as Homeland Security investigations.

Speaker 1 (12:32):
So tell us about your role in HSI and maybe
some of the initial work that you did.

Speaker 2 (12:41):
So when I got on, they were they still I mean,
they follow in the umbrella of ICE, so there's a
part of ICE, and and what they do is a
really wide range of different criminal investigations. They do everything
from narcotics to human trafficking, even smuggling, financial crimes, and
they have a cyber component going up to child expectation.

(13:01):
That's a really big aspect of their investigative core. But
they have a lot of statutes that they cover because
beaten to different criminal investigative agencies, they derived both of
their authorities and powers. So the agents that are under
HSI have a lot and they break them down primarily
in their different field offices to those different sort of
core fundamental programmatic areas. And the one that I was

(13:25):
assigned to is actually just a sort of catch all,
and it was the office that was dedicated to supporting
anything criminal really that was coming out of Chicago hair
National Airport, and they called it like a resident Agent
in charge office. So that's where I was assigned to.
Begin with.

Speaker 1 (13:42):
So, what were some of the first cases that you
dealt with?

Speaker 2 (13:46):
Everything from there was a drug called cop at the time,
so khat, and there was a lot being smuggled through
O'Hare in cargo and passengers bringing in their suitcases just
filled with this stuff. If you're not familiar with it,
it's a drug that acts a little bit like amphetamine
or like speed. And if you've seen the movie Black

(14:07):
Hawk Down, this is what people were chewing to like
stay up for like seventy two hours straight and fighting,
you know, without any rest. And so this drug is
smuggled in an abundance into Chicago. And so some of
the very first things that I worked on, and I
worked on primarily as an officer and then when I
became an agent was criminal cases against those they were
responsible for smuggling into the Chicagoland area.

Speaker 1 (14:32):
So one of the things that you know, sort of
came on our radar about your work is undercover work.
And a lot of people would be surprised that there
is an undercover component to HSI. So could you tell
us about some of the undercover experiences that you had.

Speaker 2 (14:53):
Yeah, there's the traditional undercovers that you know, those guys
that you know, are the biker gang of thing, you know,
work really deep undercover. I've seen Donnie Brasco, you know,
those type of things, and you think about that, you're like, wow,
that's really hardcore and being legacy customs and being involved
in the narcotics trade. They did have a lot of

(15:16):
traditional undercovers, a lot of people that would work in
that capacity that we're either trying to infiltrate narcotic you know,
organizations and other people that are involved in like the
smuggling of goods and services, and so there's people that
really go deep undercover, and they have a pretty elaborate
set up with and program that that goes back for

(15:39):
decades on working undercover and in the physical form. But
they really hadn't touched on too much of like the
the undercover online. They were doing it with child expectation,
but it really wasn't something where you it became like
a full fledged sort of undercover role.

Speaker 1 (16:01):
So it sounds like you started to do some different
type of work. How did you get involved in the
cybercrime side?

Speaker 2 (16:10):
Again, that just like sort of this job in finite
MS sort of came to me. This land in my
lap as well, too. I'd never really envisioned myself working
on cyber crimes. And even though I felt like I
had a little bit of an understanding of online activity
and working online, and I was active in different forums online,

(16:34):
you know, before working for Homeland Security, and so I
had some familiarity, but it wasn't really like a tech
savvy type of person. I couldn't code, I didn't really
take any classes in coding or understanding necessarily like anything
too much depth, and so I didn't really think I'd
ever be involved in working cybercrimes. But there was a
there was a trend that we started noticing in the

(16:55):
summer twenty eleven which was coming through the mail unit
of Chicago, and it was small drug parcels that were
coming through in letter class mail, and we were finding
small amounts of ecstasy, small amounts of LSD And it
appeared to us at the time as it was coming
from an online website, because it was coming from packages

(17:17):
that had pre printed labels, and it was all coming
from like the same type of like receiver or sender,
but going to different types of people all across the
United States, and it was all printed labels, which in
our experience typically that's what like an online store would
do because it's more of a business and it's just
an operation. They just print labels out and they put them.

(17:37):
It's not going to be sending there someone writing it
by hand and sending you know, a small amount of
drug from a friend to a friend or something or
so it really appeared like it was an online website.
And the officers pointed out to me, and it was
something that I started investigating, and it led me really
quick in a few different types of interviews to it
being from this website called Silk Road. And and I

(18:00):
learned that this Silk Road operated on this thing called
Tour and it was using this thing called bitcoin, and
and I had no idea what that was at the time.
I actually had to do my own research at the
time and figure it out because I hadn't heard of it.
Even in our our training, I hadn't heard about it,
and you know, through other investigators, and it wasn't something

(18:21):
that was on our radar.

Speaker 1 (18:23):
So explain exactly what is tour.

Speaker 2 (18:26):
So Tour is the Onion Router's It's essentially a like
a program, if you will, or a configuration that you
could do to your computer. When you're on the Internet
to anonymize yourself, and it anonymizes where you're at, and
it basically it's like a protection to not show where
you're being located at or where your computers is basically located.

Speaker 1 (18:53):
So tell us more about how this silk Road operated,
like who's using it, how are they using it, and
what's on the site.

Speaker 2 (19:02):
These are hardcore drugs and you're talking about heroin and
cocaine and MBMA and these are specialized ones, and you
would think a website wouldn't be advertising them openly or blatantly.
And that was something that stood out right away is
that silk Road was essentially like an Amazon where anyone
can become a vendor, anyone could could be a buyer.

(19:22):
You just sign up and you could see all these
drugs and you can see everything that was listed just
in its you know, the pictures of it and the
description of it and the purity levels, and it was
it was really amazing because they weren't hiding anything. They
weren't hiding that they had that they wouldn't weren't hiding
that they had counterfeit goods. They weren't hiding that they
had counterfeit ideas that they had hacking equipment, things of

(19:45):
that nature, just deliberately for sale right on the site.

Speaker 1 (19:48):
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(20:09):
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(20:30):
capabilities at Winston dot com. And So is this basically
what folks call the dark net or a dark net marketplace?
It is.

Speaker 2 (20:42):
So anything that's tour because it's behind this wall protection,
it's typically called a dark net. So anything on tours
is a dark net. Related, there's other types of dark nets.
And when you think of a dark net as is
basically a protection in overlay, and there's other various dark nets,
but tours is one of the easiest to get to

(21:03):
the most abundant I think that are that's out there,
and these marketplaces that exist only exist in this this
world of Tour, So it's it's something where you can
only access it using their program.

Speaker 1 (21:18):
So if I'm a user, uh, exactly, how do I
do the transaction? How do I pay for these goods
and then get them?

Speaker 2 (21:28):
The way that Silk Road worked was more on a
scroll level. So when we say it that way, it's
that you would sign up as a user the counter free.
When you get on there, you could see everything that's
for sale and just sort of like Amazon, you would
just scroll through the different listines and then you would
click on something that you want. It goes into your

(21:49):
your you know, your your shopping cart, and and then
you you pay for it. And the way you pay
for it is through this cryptocurrency, primarily through bitcoin. And
the way you do that is you would load your
account with bitcoin and then you'd have a balance and
then you could do these transactions. When you do the transaction,

(22:10):
the funds themselves would transfer internally to the vendor, and
once the vendor received the funds, they'd be notified to
then ship the goods to the recipient and you would
enter in your shipping address. The vendor would receive that
and then they would send you essentially the drugs, and
then the money would be held in escrow, meaning that
the website self, the administrators, the people that running the website,

(22:33):
would hold those funds until you then received them, receive
the goods, and then you would market as being received,
and once your market is being received, that would release
the funds to the vendor. Now, if you didn't receive it,
or you report that you didn't receive it, there was
like a customer service that would then step in and
try to arbitrate the issue and either work with the

(22:57):
vendor or work with the buyer to resolve the transaction.
And you would think that something like that wouldn't work
that well because you're behind this layer of a not
like an anonymous traffic and there's really not a better
business bureau when it comes to buying the legal drugs,
you know, on the internet, So you think that this
wouldn't work, But it did work, and surprisingly it worked

(23:20):
really well because it was it was based on feedback
and so as you see like people get like four
or five stars you know for for whatever. You would
see that on Soilk Road. They had ratings for all
the different vendors, and vendors with really high ratings would survive.
Vendors with really low ratings. So if they scammed a
lot of people and they didn't ship the goods and

(23:41):
they said they shipped it, eventually they get really low
ratings and eventually those no one would buy from a
really low rated vendor. And same thing, if you had
a really low rating as a buyer, a vendor would
would get credit for that transaction even if they ship
the goods, like they get the money or what type
of thing. Like they you couldn't pull off too many scams,

(24:05):
you know, in that that sort of environment, the way
they had it set up, and people would leave comments
like you know, the high was really good and you
know the stealth on the on the products of hiding it,
you know, in the packaging was superb, you know, like
really enjoyed, like the heroin thinks, and it was just
it operated like it would any other regular marketplace, but

(24:26):
just using you know, explicit goods.

Speaker 1 (24:28):
So who was behind this marketplace?

Speaker 2 (24:32):
That's what we didn't know. That's a law enforcement was
trying to get to. It took us two and a
half years investigating it, and it took working undercover, and
took working with a number of different agencies, and it
took a lot of small pieces coming together with a
lot of effort from a lot of people, and it
eventually led to a twenty nine year old US citizen

(24:56):
that was living in San Francisco, a person by the
name of Ross Olbrook was was an individual that was
behind this entire website, operating it under the the moniker
dread Pirate Roberts, which is from The Princess Bride if
you've uh, if you've seen it, But great eighties movie.

Speaker 1 (25:14):
So how did this case unfold? So it seems like
it fell into your lap and you were investigating it
for a while. So take us from you know, once
you've identified who's behind it, and then what you did?

Speaker 2 (25:28):
Yeah, it Uh, it was. It was a lot of error,
a lot a lot of mistakes along the way, learning
you know what you can and can't do with uh,
dealing with tor and dealing with this this online undercover
work and dealing with cryptocurrency and figuring out all the
nuts and bolts and pieces of that, because the agency

(25:49):
wasn't prepared for this, like they they didn't have the
structure in place to really support something of that nature.
I mean, the process for doing undercover purchases just wasn't there,
And so we were really having to write the book
on a lot of the processes in which we were
having to do transactions with, you know, in this investigation.

(26:11):
And you also found yourself sort of paralyzed in the
sense because you had all this authority to send subpoenas out,
and that's pretty much the playbook. You send out subpoenas,
you send out, you do search warrants. You you can
pretty much leverage probable cause and leverage the evidence that
you have to then force other, you know, parties typically

(26:32):
to reveal or to do discovery, and do it through
that that mannerism. In this investigation, there wasn't any of that, Like,
there was no one to subpoena there was there wasn't
an internet service provider to do a warrant on. You
didn't know where the servers were at. So we really
had to get creative in trying to figure this out.

(26:52):
And the way that it eventually wrapped up was one
of the investigators was doing some simple Google searches and
came across, you know, someone that reported Silk Road really
early on that, you know, in combination with other evidence
that we had already where we did eventually find the
server because there was a misconfiguration in the way that

(27:14):
it was being operated and FBI found that, which then
led them to gain a copy of the server. When
they looked at the image of the server, they found
information that pointed to someone that might have been in
San Francisco at the same time. My investigation in Chicago
was working undercover. By that point, I had developed an
account that was an administrator on the website, so I

(27:38):
was operating as one of the support administrators undercover, working
directly for dread Private Robertson. There was evidence that I
was getting from our engagements in chats that also made
me believe that this person was in San Francisco. Essentially,
they were leaking at time zone through one of their programs,
and you know, when we had those small pieces starting
to add up, and then eventually we had this name

(28:00):
through this this individual that was posting about Silk Road
really early on before anyone else, and that led us
right to Ross Olbrich. And by the time that we
started really looking at him in depth and starting to
look at his activity, it really started mirroring and matching
exactly who we thought Power Roberts was, and that led
us again to warrant and doing this arrest. It was

(28:23):
in twenty thirteen in San Francisco.

Speaker 1 (28:27):
So, but before you got to that arrest, I mean
you said you had an account, So what would you
be doing, how would you be interacting with the site
and with with with Ross.

Speaker 2 (28:40):
I was originally so it was an account that we
took over. That was it was a moderator on the forums. Originally,
so soak Road had forms and in the capacity of
that person worked for soak Road and they would respond
to different people who had questions about soak Road. And
that was primarily the job of like a moderator, was

(29:00):
moditoring the forms and you would you would resolve questions issues,
talk about like how to get to log and pages,
things of that nature. And so that was primarily my
job to begin with, and that transformed though pretty rapidly,
where Robert would give me additional tasks. So one of
those tasks would be, I need you to help me
rebuild our wiki page and do a tutorial on how

(29:23):
to do pretty good privacy PGP. And so that was
something like I'd write the procedure on how to use
PGP for the users on soak road and do a
wiki page on it. And in addition to that, then
he had other tasks and things that he was trying
to get me to be a more administrator on and
in the marketplace itself. So there'd be people that would

(29:45):
be advertising falsely, or people that would have that weren't
a paid vendor that we're trying to utilize the website
as a platform that's unauthorized, and so he'd have me
like monitoring that and like trying to resolve those issues.
So it was like a lot of little administered work.
But those are the types of duties and services that
I provided as one of his administrators.

Speaker 1 (30:06):
Did he think you were a specific person and someone
else get like a different identity?

Speaker 2 (30:12):
He did? He he at that point in time, So
this is I took over the account in about early
to mid twenty thirteen, so a few months before we
actually ended up identifying who he was and shutting down
the website, and when I took it over, it was
from someone that was a previous moderator before we identified
that person and ended up getting them to cooperate and

(30:33):
turn over their account to me. So I absorbed that account,
which means that I had to absorb that identity to
everything from the way they wrote, to their knowledge base
to the configurations on the computer. Pretty much had to
absorb all that and absorb all their knowledge too, because
they were involved in a lot of online chats and

(30:53):
different conversations with you know, hundreds of people potentially, and
I had to know those those stories, what they talked about,
and know who they talked to and why they talked
to them, and who knew you by this user name
or that user name, and in order to really fully
take over that account and absorb it, that was it was.
It was a lot of work.

Speaker 1 (31:14):
The site itself was it just drugs.

Speaker 2 (31:18):
No, so it was primarily drugs, but there was counterfeit goods.
There was intellectual property rights type of violations, so that
like the counterfeit stuff like the the Gucci bags, the Uvaton,
you can find counterfeit IDs everything from drivers licenses to
pass ports and the holograms that are being used to
for security measures, which is really difficult to find really

(31:41):
good quality stuff of that nature. You would really have
to know someone to identify half these things, let alone
finals in one spot. They had an addition to that
hacking equipment, so you could find different coding. You can
find services that offered hacking services to get into emails
or to to to get into this account or that account,

(32:02):
tutorials and how to access those as well, so there
was different things you could purchased that way, and for
a little while, they actually did have weapons on the website,
so they had firearms for sale that exposess for sale
that later on got moved out to another website called
the Armory, and then they shut that down because the
whole fast and Furious thing. I guess they didn't want

(32:23):
the type of heat that would come down from the
government with the firearms. The one thing that they were
really against was child pornography and counterfeit money like that
was pretty much the two things that I guess I
was more into, like the libertarian stance of rossol Break
than druphiot Roberts. That prevented those two things from being

(32:44):
on the website, but there were euthanasia drugs on there.
There was organs for sale from time to time, and
those are things that were okay to be sold.

Speaker 1 (32:59):
So you're you've sort of taken over this account now,
dread private Roberts thinks you're just a regular moderator. Walk
us through what you did and what the team did
to get to an actual raid.

Speaker 2 (33:16):
So we we identified him and it was September eleventh
is by the time that they really fell on the
radar of us, when we were law law enforcements coming
together and talking about what little pieces we had, and
it took us about a week and a half to
really be confident that this is our guy. By September

(33:37):
twentieth or so, I remember, we started drafting up and
having our complaint ready to go to filed against you know,
Ross Albert just being drug higher Roberts. And the reason
I'm giving these dates in twenty thirteen is because the
government was also in the process of shutting down and
that was really significant for us, right and when there's
a government shut down, you know, law enforcement still works

(33:58):
if you're considered essential, which we were considered essential, but
we don't get paid and regardless of getting paid or not.
We also don't have half the services that we normally
would have available to us, one of that being travel.
So knowing that we're we are on the cusp of
finally identifying this person who's also become very dangerous by

(34:19):
this point, and it wasn't just what they were selling,
but Jepout Roberts ross Olbrick ended up actually commissioning six
murder for hires as a result of this website and
tried to fulfill one of them earlier in the year,
paid someone off for what they believe they murdered someone
which actually end up being an undercover agent at the time,

(34:40):
and thought they actually didn't murder someone that was one
of his prior admins that was working for him, that
he thought was stealing from him.

Speaker 1 (34:47):
So wait to explain what happens. He thought that he
had commissioned a murder, but it didn't happen.

Speaker 2 (34:54):
So he did so he thought that someone, well someone
did steal from him, and in that stealing from him,
he thought it was this person, this vendor that used
to work for him, and he then tried to go
to pay to have this person murdered. The person he
tried to pay, though ended up being another undercover that
pretended then to murder this other person sent some fake

(35:16):
photos and received money from Ross Albreck, paying them off
for basically killing this person. And then Ross proceeded to
brag about it and use that as like influence against
his other moderators and admins to say, if you steal
from me, I will this is what will happen to you, essentially,
and so he was pretty brazen about that, and he

(35:39):
ended up getting I believe it was threatened again later
on a few months later, where another person that this
ended up being a scam. He didn't know it, but
this person said that they essentially were a vendor and
they were going to release a lot of the buyer's
names out there, you know, and they kept all these
and they weren't supposed to keep them. And Ross decided

(36:02):
that it was like justified to try to murder him
and his family to protect this, so he went after
him by paying out this other person who he thought
was part of a biker gang, but it actually ended
up being the same person that was threatening to release
all the names, and he ended up paying that person,
you know, hundreds of thousands of dollars to kill like

(36:24):
another like five people essentially, and he got fake photos
back and he thought he did those murders too, So
I mean, in his mind, he believed he went ahead
with all these murders, but in reality they didn't result
in anyone dying.

Speaker 1 (36:40):
So at this point, you know, he's basically become a kingpin.
The site has grown, but you all know who he is,
how did you take him down?

Speaker 2 (36:50):
So with the government shutdown and made it like we
were flying out literally on like one way tickets, and
we ended up going out to San Francisco September thirtieth.
It was twenty thirteen. Governments shutting down October first, that's
the new fiscal year, and that's when we had no funds,
so we had like a skeleton crew. We had a
few surveillance agents that were in San Francisco that were

(37:12):
monitoring russ Olberg. Myself, another agent from FBI called Chris
Tarbell ended up going out there with our computer scientists,
which is Tom Kiernan, and you know, the three of
us were pretty much the team that went out to
San Francisco. We had another team that was going out
to Iceland, which is where the server was located, and

(37:33):
the goal was that we're going to do this type
of arrest if it was going to be this house
or somewhere else, that would be followed by a shutdown
of the server and capturing the server and getting all
the contents off of it. Not really knowing how it
was going to play out, we ended up working with
the local teams there who were insistent that we're going
to do this like really elaborate, like swap arrest type

(37:55):
of style thing at the house and they're going to
send this massive team in and you know, and try
to arrest him like in the home where he was living.
The only prompt with that is that he was living
in this three flat and he's living up on the
upper floor and there's multiple people at the house that
are living there as well, And we want the laptop.
You know, we have a lot of good evidence, but

(38:15):
we really want that laptop and we need the evidence.
Its gonna be out there, and it'd be really good
if we had more proof to show that he was
exactly dry prior Roberts, so there'd be like no doubt
in the minds of anyone else that ever see the
evidence that we have that this is the operator of
the website. So using my account, you know, we're in
a unique position as one of the administrators that I

(38:36):
could communicate with him. And that was a goal that
I'd be communicating with him during this arrest and that
we'd be able to show that either there'd be communication
or drop off the communication once he was arrested, similar
to that effect. And it ended up leading us to
pretty much winged arrest that we didn't really plan for,
because he ended up leaving his house the following day

(38:58):
after we arrived, and as monitoring him, he walked into
a It was a library that was actually just right
across the street from where we were staged away from
his home, and when we saw him go into the library,
he ended up having a shoulder bag and he went
inside the library, opened up a laptop, and on my
computer I could see when drub how Roberts is online,

(39:19):
and he popped up online right as you know, Russ
Alberick went there and turned his computer on and I
ended up initiated a chat with him as his administrator,
asking him to go to an administrative panel that was
on Silk Road and asking basically to look at something
for me and what that did is that caused him
to then log into his drub Hiot Roberts, which is
what we wanted, and then to look at the screen

(39:42):
of what I'm trying to point out to him, and
in that he ended up once he was on there,
We're pretty confident we had him literally in the library
with a keyboard and had a team that was inside
there affect the rest. And what led to it was
some surveillance agents just did a great job of faking
to fight in the library and it got Albrook's attention,

(40:05):
and when he turned to go watch his fight, another
agent walked up and grabbed his laptop and walked it
over to our guy, Tom Kernan, and he ended up
starting to copy over the directory right there on the spot,
like a few feet away from Olbrick. Then Albrick turns
around and sees no laptop and then sees this other
guy sitting in there within his lap and tried to

(40:27):
lunch for it and ended up getting bear hug from
behind and arrested in the library. And so that was
pretty much it. But we caught him literally logged in
to the website as Jubhart robertson his chat Mirrord in
my chat, which I was doing from outside the library
at the time.

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(41:28):
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Hummingbird dot Co. So he's I mean, this is in
a library, you're nearby, you're online communicating with him, he's
being monitored. I kind of want to know what was
the fight? How did they actually stage this? I mean,

(41:49):
you don't have too many fights in the libraries. How
did they set that up?

Speaker 2 (41:52):
I mean it was brilliant. I mean, we didn't talk
about this. I mean, it was pretty much just U
We really did wing this. I mean in the sense
we know we had the warrant, we were hoping that
he'd have his laptop. We didn't really know what was
going to happen the next a few minutes, but we
did have a plan for generally what we wanted to
do for trying to lure him online and get him chatting,
and that was sort of the goal for what I

(42:12):
was asking him to do in the chat. But once
he was there, and he was in the library, like
it was pretty brilliant of those people inside, and what
I heard is it was a female that pushed another
male in his back right corner and basically screened some
expletives and and it was really allowed. And I'm pretty sure, yeah,
no one really sees fights in libraries. So it was

(42:35):
a great way to get his attention. I mean, I'd
be watching it too, if I mean, I was staying
in the library, so that that got his attention long
enough for another agent to come up behind him on
his on his blind side, grab the laptop and walk
it over to our computer scientists.

Speaker 1 (42:52):
Wow, So what happened to Ross Olbricht.

Speaker 2 (42:57):
Following the rest, he didn't talk, he cooperate or sorry,
he didn't cooperate. He lawyered up right away. He ended
up evoking his rights, which is perfectly okay. But then
in the months following, there really was no attempt to profer.
There was no attempt to own up or admit to
anything that he did, even though we literally had him
logged in, you know, to the administrative panel as Dray

(43:19):
Pilot Roberts, and in his computer, there was just an
enormous amount of evidence. I mean everything from journals to notes,
to every single like server password that we needed to
like get into, every single thing that we need to
get into. We identified the other support administrators that were
working on the website because he had their photos any

(43:40):
other identification. And the reason he had that is because
he wanted to use that to try to murder them
too if they ever stole from him. And so those
are things that we found all in his laptop, and
so there really was no reason for him to not
cooperate or try to get something over. But he really
believed that he could he could pull this off, so

(44:01):
he tried to fight it and he tried to go
to court, and he he resisted any attempt to try
to do any types of please if anything else. He
ended up getting a superseded indictment after the initial indictment
for the Kingpin statute, which is the Continuing Criminal Enterprise
statute under twenty one USC, which is the narcotics statutes

(44:26):
of the United States, And that was something that is
a massive charged to not just prove, but also you
know the impact of that. You know, is a twenty
year minimum in the federal system, which is which is huge.
It could come up to a life imprisonment. And they
also come with the death sentence if there's anything that

(44:46):
shows that anything you did in operating this continued criminal
enterprise which is aka the Kingpin statute, if you're doing
anything in that capacity that actually led to any type
of murders, then you could get the death sentence too.
So he was looking at some very serious charges, not
not just the continuing criminal enterprise charge.

Speaker 1 (45:04):
How long was that sentence?

Speaker 2 (45:06):
It didn't take the jury very long. I mean we
went to trial. It was four weeks that we the
government put on pretty much their evidence, and there just
was so much evidence, I mean, like we had to
limit it down. I testified in that trial and took
the jury all of about thirty minutes to find him
guilty of all those charges, and he ended up with

(45:27):
the sentencing. We were looking at something looking at twenty
or minimum, you know, with that continuing criminal enterprise charge,
and we didn't really know where it was going to
line with the judge. We did show that there was
also some wrongful deaths and a few parents that came
and testified about kids that overdosed because one of the
arguments that Oliver tried to make was like it made
it safer for people to get drugs, you know, versus

(45:48):
like buying on the streets, and that no one was
harmed as a result of this, you know, And so
we show that there was people harmed. There was at
least six wrongful debts and those were kids, and we
had the parents testify and they came in and talked
about their kids. I mean, it's there's real there was
real pain there, there was real you know loss, and
it was highly reckless and the judge acknowledged that. And

(46:09):
the judge also saw what Silk Road in the model,
what it was, as being a much larger problem because
there was a number of other websites that mirrored that,
and so the judge ended up finding guilty or sorry
sentenced into a life in prison actually two terms life
in prison, which in the court system, based upon the

(46:30):
number of offenses that he was looking at, he was
well over the life sentencing guidelines, especially with that continuing
criminal price charge.

Speaker 1 (46:37):
Well, Jared, there's you know, I know, you know this
right that there's a bit of a free ross movement
out there. There's you know a lot of people that
have made him a rallying cry, I think, especially for
folks in sort of libertarian circles. I mean, you were there,
you were in the midst of the case. What do

(46:58):
you think about all of that?

Speaker 2 (47:01):
If you saw what he did, you actually see the evidence,
and you see how he orchestrated himself, and you see
what has resulted since then. Just look at the evidence
that was presented, you're going to see the true side
of him, which he was getting exceptionally dangerous. He was
contradicted to everything that he stood for. You know, if
you talk about the lilitary movements and free market enterprises, well,
he was controlling just as much as any government, every

(47:23):
single transaction. He was controlling all the activity there he
dictated what his percentages were that he was taking off
of everything. Anything that he would say that he stood
behind that was a limitarian like type of mentality he violated.
I mean things such as like he would he'd say
that he couldn't be bought and he couldn't be paid

(47:45):
off what he could be And he absolutely did take bribes.
He did take money, and he took people that you know,
would provide influence, and he was playing god on the website.
And you're talking about also trying to commission murder for
hires and paying for them. You know, this isn't just
something about like hey, you could get you know, something,
anything you want. It's your choice to put in your body.
There was even an example of a youth in Asia

(48:05):
drug that was being advertised on there, which really upset
me at the time. And it was something that was
like like it was like a few dollars too, this
is something that could stop your heart in an instance,
but it was only listed under the chemical name and
it was this really long chemical name and you didn't
know what it was. But it was also listed only
under stimulants at the time. And what I was afraid
of is some kid or someone else that'd be buying

(48:28):
off of there, that had, you know, a dollar left
on their Bitcoin account and they're looking to buy some
type of stimulant. They don't know what's there, and they
buy this drug not knowing this is going to stop
their heart, you know, And there's no description over what
this is. There's there's no details on the website, there's
no minimum standard on that. And so, as one of
the miministrators, I pointed out to Ross at the time

(48:50):
and I was like, this is this this needs like
a label flag on it and needs something to say like, hey,
this is this is what this drug is at the
very very least, Like I'm not even telling you to
pull it down. I'm telling you put a big warning
label on it or recategorize it. It's not a stimulant.
And he's like, well, how does this fall under our charter?
I'm like our charter. I'm like, like, well, our charter

(49:11):
meaning like like having a choice of what you put
in your body. I think it falls against the charter,
right And he's like, well, I don't know. At the
end of the day, it's really just about money, and
he wants to make the money and he didn't care
about putting a warning label up. I'm there. He didn't
care about, you know, the one kid that might overdose
or die. I even brought that up as an example
to him. And so those are things that you know,

(49:31):
when when you look at the true ross and you
look at who that person was, and you look at
everything he did to protect himself. Ultimately, even at the
very end, he was only just trying to protect himself.
And he still is only just trying to protect himself.
He's not doing any good for anyone. I think you
see a totally different side of what this storyline is
when you just look at the evidence that was presented.

Speaker 1 (49:52):
Did you did your eyes meet during the during the
trial when you were testifying and he acknowledged or any
interaction between the two of you, you know, when.

Speaker 2 (50:03):
It came to sentencing, you know, I think you might
have saw my reaction, even though I was staying right
in front of him when he was trying to save himself,
even though the parents just got done testifying and they
just got done showing pictures of their kids, and you know,
these deaths results of his website and result of money
that he made, and he started the Audacity to stand

(50:26):
up in court and be like, I'm really sorry that
didn't happen, But I don't think there's been enough talk
about me in my life. And it was probably one
of the most horrific things I ever heard come out
of anyone's mouth. And I think I turned around and
looked right at him at the time and and just
couldn't believe what he said. But you know, that's again
that just goes to his character and what he was,

(50:47):
which is he was someone just trying to save himself.

Speaker 1 (50:50):
Wow, Jared, you know, I don't want to take up
too much more of your time. I mean, but you've had, really,
you know, a stellar career. You've done a lot. You know,
anything you can tell us about some of the other
cases that that you'd like to share.

Speaker 2 (51:08):
Yeah, I mean I ended up fallowing Silk Road. I
mean I didn't get any rest, so I ended up
getting lued right into Silk Road too, which stood up
within three days of us shutting down that marketplace, and
my account at the time that was undercovered didn't get exposed.
So I ended up being brought into that that that
next website, and ended up working for that administrator who

(51:32):
also absorbed a drug high Robert's name for a little
while and worked for them for a whole another year
until they identified who they were and we identified that
person who was also living in San Francisco, uh and
arrested that person and shut down silk Row two in
the following year. But that was a whole another year
staying undercover, working you know, every single night, doing customer support,

(51:53):
vendor support on that marketplace, and ended up hopefully, like
we thought, we got to that and shut down. It
was six other markets at the same time, and what
we called Operation Aonymous we did that through Europol, and
soak Row two was one of them, and we got
a few other black markets at the same time.

Speaker 1 (52:12):
So that amount of time undercover, what's that like.

Speaker 2 (52:17):
Uh, it's it's pretty terrible, you know. It's uh, you're
still working full time. You you're you're I'm still running
cases out of the RACC. Ohare the Resignation Charge office,
and I'm I'm I'm still balancing sixteen seventeen other cases
on top of Soak Road and the discover that's going
to Soak Road one and you're working undercover still and it's, uh,

(52:40):
it's a full time job. It's it's more than a
full time job. It's I'm online pretty much from six
am until three am or four am, and I'm doing
all the different customer support, vendor support and engaging and
document all this evidence while also still working, you know,
physically going into work and physically going up and doing
other things, and pretty much just having a laptop tied

(53:02):
to me, you know, for a better of a year
and a half everwhere where I went. And so it
became so draining by the end of soak Row too.
And I was also working at Europol in twenty fourteen
towards the end of it all that I actually had
walking pneumonia. I was like almost on my like deathbed
at the sense because I was just not sleeping in

(53:24):
just under so much stress.

Speaker 1 (53:27):
So what did you do to deal with that stress
over that amount of time? How do you cope?

Speaker 2 (53:34):
I think you do what you see on top of
my head right now, which is just grow a lot
of grays. Like there really wasn't any structure set up
for that. I mean, Homeland Security wasn't really set up
to handle something like that in nature. I mean I
was being paid in bitcoin from soak rod one into
soak Row two, and it was it was really a
full time job, and it was taking up this identity

(53:55):
and living this identity every single day while at the
same time I'm trying to do your regular your job.

Speaker 1 (54:01):
And so.

Speaker 2 (54:03):
It was a lot of stress during that time frame.
It took a lot of a lot of time to
unwind following the silk Row two takedown and then Silkrow
two happened in November twenty fourteen. We went to trial
with Ross Olibrit in January tenty fifteen, and so, and
trial didn't really wrap up, you know, and the sentencing
wasn't until you know, later in twenty fifteen, and so
I was still just trying to recover from everything when

(54:27):
I also was approached on another investigation called kick Ass
Torrents and working that. So I put all my effort
right back into that for a whole other year. And
that was a nice shift because I haven't I didn't
have to work undercover and ended up just focusing on
that website.

Speaker 1 (54:44):
All the stress. I mean, looking back, was it was
it worth it?

Speaker 2 (54:48):
One hundred percent? One hundred percent? I mean I think
the I mean the day that we identified Olburt and
when we got there, like we still couldn't really believe
even though we're super confident this is who we had,
and we had the criminal complaint, and this is where
we're sure we you know, this is the right person.
And then when you rest them and you see it
is the right person a hundred percent, and you're like,
this is amazing, And we got the seizure banner up

(55:10):
and we have this laptop that's being worked on, you know,
from an evidence standard. But taking that that sitting down
and finally just taking that first breath, you know, because
it felt like we were holding our breath for about
two years. And you know that that amount of relief
was was enormous because at the time that website, what
it was is it was something that you could see
and that you get touch, but you really couldn't do

(55:32):
anything with. And we felt powerless, you know, looking at it.
And it was something that kept me up because it
had you know, with the weapons on there, you had
school shootings going on, and you had other things going
on at the same time too. Newtown happened in the
middle of all that, and just being petrified that you know,
there's something like that that's out there that just makes
everything so simple. To get and you know, you're you

(55:55):
feel responsible for shutting this thing down. I mean even
to the point that one of the one of the
parents that testified, I didn't even know this till sentencing
when I was sitting there listening to him. One of
the parents had testified, testified about their son, Brian, that
died on the website and he ended up buying drugs
that like the day that we shut down the website
and his heroin and ended up dying, you know, three

(56:16):
days later from an overdose on it. And for me,
that was enormous. I was still devastated to this day
knowing that, you know, two and a half years of
working down this thing like tire Sley, and how fast
we went at the very end to try to you know,
get to him and arrest him, and we were literally
just one day short of preventing the life running that
pain that you know, you hear that father's out of

(56:38):
that father's voice, and so you know, the whole thing
was really impactful and it actually was worth it.

Speaker 1 (56:45):
This interview with Jared dear Jaegen makes me think about
a quote from one of the favorite rap groups for
my youth, Boogie Down Productions, real bad boys move in silence. Jared,
as you can tell, is not boisterous about his accomplishments.
I mean, the guy runs one hundred mile marathons and
speaks about them humbly, almost reluctantly. He takes a similar

(57:06):
approach about his time as an agent, but the effort,
the precision and tenacity that was required for him to
aid in taking down the Silk Road should certainly be acknowledged.
It's that quality of humility that you'll find in the
most dedicated fighters of financial crime, because they are the
heroes who don't get headlines. To do that sort of work,

(57:27):
and to do it well, one can't be in it
for the exposure or the publicity. I'm thankful that Jared
took the time to tell me his story so we
could share it with you. Please share this with those
you know. I'm Yaya Jata Finussi and this is designated

(57:48):
on the Illicit Edge Network.