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November 19, 2024 48 mins

The US government took a thumb in the eye with the creation of the Silk Road website. Right there on the internet you could anonymously buy drugs and various other contraband, and for a couple years no one could do a darn thing about it. 

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Episode Transcript

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Speaker 1 (00:01):
Welcome to Stuff you should know, a production of iHeartRadio. Hey,
and welcome to the podcast. I'm Josh, and there's Chuck
and Jerry's here too, and this is stuff you should know,
all about the Dark Web and all the crazy crazy

(00:21):
drugs and him men. You can buy on it.

Speaker 2 (00:25):
Sorry, I was still doing my vocal warm ups.

Speaker 1 (00:31):
I didn't know that that helps. What does that help?

Speaker 2 (00:33):
Why twenty dwarfs took turns doing push ups in the lawn.

Speaker 1 (00:37):
I'm ready, okay, okay, Well, so welcome to the podcast, everybody.

Speaker 2 (00:43):
I figured it should start warming up. You know, seventeen
years into this eighteen? How long you sixteen?

Speaker 1 (00:49):
So yeah, sixteen ish, a little over sixteen coming up
on seventeen.

Speaker 2 (00:53):
Chuck, just wait till you hear the way my lips
move in this episode. They're so loose.

Speaker 1 (01:01):
So did you loosen your lips up? Just specifically, because
the content of this episode is so thrilling.

Speaker 2 (01:06):
I authought you can say something about sinking ships. No,
I didn't, but this is a good one.

Speaker 1 (01:12):
This.

Speaker 2 (01:12):
Yeah, if everyone heard our episode in the Dark Web
from twenty twenty, some of this will be familiar. But
this is just more in depth about the Notoriou. Yeah,
Silk Road itself, Yeah for sure.

Speaker 1 (01:23):
Yeah, And we were talking about Silk Road for those
view history buffs Middle Eastern history buffs who were disappointed. Sorry,
but you should stick around because this is going to
be a pretty interesting episode.

Speaker 2 (01:34):
I didn't think about that. When are they going to
talk about cinnamon?

Speaker 1 (01:39):
We did a whole episode on cinnamon, So relax there, guy.

Speaker 2 (01:41):
Yeah.

Speaker 1 (01:43):
So you know, we're talking about what is widely considered
because I think it is the world's first illicit marketplace
on the Internet that was opened in twenty eleven shut
down in twenty thirteen. It had a very very brief run,
was like the Beatles of illicit drug trading websites, and

(02:05):
it's legend will live on for basically forever because not
only was it just the most audacious thing anyone had
ever done on the Internet as far as anyone knew
up to that point, it created a blueprint for a
bunch of imitators to come, and also the way everything
that law enforcement through at this case and the court

(02:29):
case as well, it was just so nuts that it's
just a heck of a story. How about that Brownie.

Speaker 2 (02:35):
That's great, boy. There were fifteen filthy jokes. I was
going to say, when you said the most outrageous thing
anyone had done on the Internet up and to that point,
I was like I had a rolling terminator, like scroll
about all the early internet nasty memes that would go around.

Speaker 1 (02:53):
You couldn't pick any of them.

Speaker 2 (02:54):
No, I just didn't want to say any of them
out loud because then kids would look them up.

Speaker 1 (02:59):
I gotcha. Yeah, I was wondering, and we probably should
have talked about this before we recorded. Are we gonna
like call out any active sites or anything like that? Nah, okay,
because I know some I looked him up.

Speaker 2 (03:14):
Hey, just Texas.

Speaker 1 (03:15):
To me, it's fine, okay. So let's start from the start, right.
We're gonna start with a guy named Ross Olbricht, And
the reason we're introducing him early on is because he
is the mastermind behind silk Row. It was his idea,
he built it originally, He ran the thing by hand,
almost single handedly, for a very long time, and you

(03:39):
just really can't talk about Silkrow without him, because his
personality was so wrapped up into the ethos of the
site that you can't really extract one from the other.
Despite the fact that while he was sitting in federal court.
He really wished that they would extract one from the other.

Speaker 2 (03:56):
Yeah, big thanks to Kyle, first of all our friend
and can tributing writer from across the Pond for his
work on this. But Kyle's keen to point out just
a little bit about the dark Web. You know, we
have a whole episode from twenty twenty if you want
to go listen to that. But if you don't know
what the dark web is, it's a part of the
web where you can go and do things anonymously. And

(04:16):
that's just a you know, the simplest way to say it.
It's much more complicated than that, obviously if we did
a whole episode, but it's where you can go if
you don't want to be indexed by Google, if you
don't want your traffic monitored, and if you want your
anonymity insured. Doesn't necessarily mean you're some awful person doing
awful things. There's a lot of people there that just

(04:37):
believe in in the freedom and anonymity that you should
have on the Internet.

Speaker 1 (04:43):
Yeah. Also, yes, for sure, some people are just like,
there's no reason for you to be invading my privacy.
While I'm reading The Guardian or something like that.

Speaker 2 (04:50):
Right, Yeah, just to sell me stuff exactly.

Speaker 1 (04:53):
That's part of it for sure too. And then also
other people are like they have they might be whistleblowers
and they have information that they could very easily get
them thrown in prison. But it's really important to get
out to the public. There's sites like pro Publica and
other journalists that have dark web sites to where you
can submit information, and even Pro public it doesn't know

(05:15):
who you are. And with silk Roads specifically, there were
three things that came together that made Silk Road exists,
and without any of them, I don't think it would
have ever existed. One was who I already introduced, Ross Olbrick.
The second is Tour, the Tour network, which basically when
you go onto the dark web using Tour, the first

(05:38):
thing it does is route you through three different random servers,
and each one encrypts your information and gives you a
new IP address, so no one can figure out who
you are, including the website you visit. And then the
third thing is bitcoin. There's just no way you could
have made transactions on drug deals over the Internet without
untraceable currency that doesn't involved like a central bank or

(06:01):
some other third party like.

Speaker 2 (06:03):
That, Yeah, for sure. And you know, Bitcoin was huge
because it was they were good for each other, Like
Ross Olbricht sort of embraced bitcoin in a big way,
which even though it was on the dark web, and
even though Silk Road was you know, as you'll soon learn,
dabbling and illegal drug trading, they use bitcoin exclusively. So

(06:25):
the rise of bitcoin and the rise of you know,
things on the dark web kind of go hand in hand.

Speaker 1 (06:31):
Yes, for sure. And this is also a time where,
like the early twenty ten, this was in like disruptive
technology was just coming out left and right from Silicon Valley,
whereas like well, say goodbye to newspapers, say goodbye to
printed books, say goodbye to music. And I mean, it

(06:51):
did have disruptive effects, but as we've seen, it still
kind of mellows out. It's not like the original thing
just totally goes away. But this was that same time.
So a lot of people have likened ross Olbricks to
basically a darker version, if there is such a thing
of some of those Silicon Valley bros who started up

(07:13):
a lot of those disruptive tech companies.

Speaker 2 (07:15):
Yeah, and you know what, I think we need to
add a fourth on our Silk Road Mount Rushmore, because
we have to mention Adrian chen who in twenty eleven,
when the Silk Road went live, wrote for Gawker and
wrote this big expose on the Silk Road just a
few months later, including like how to get there, what

(07:37):
you can do there? And it would have been a
thing anyway, but the fact that it was kind of
exploded on Gawker made it bigger quicker than it would have.

Speaker 1 (07:47):
Been, I think, right, And that also brought it to
the attention of the authorities pretty quickly. Chuck Schumer, Yeah, Chucky.
He basically came out against it first, I think so
now the Senate was against it. He said it was
a certifiable one stop shop for illegal drugs that represents
the most brazen attempt to pedal drugs online that we

(08:09):
have ever seen.

Speaker 2 (08:10):
And they went, yeah, exactly, Yeah, you nailed it.

Speaker 1 (08:13):
Yeah right. And so because of that tour network, and
because of just the anonymity of bitcoin and the fact
that people were drug dealers and drug users engaging in
illicit crime over the Internet, like there was a sense
like it doesn't matter, like the government can't find any
of these people. If they do, it's just random luck,

(08:35):
like say intercepting a drug shipment in the mail. But
if you're really trying to track somebody down who's a
user of Silk Road, You're just not going to be
able to do it. There was just a sense of
security and safety that people had when they were using it,
including Ross Olbricht.

Speaker 2 (08:52):
Yeah, and they also were pretty smart early on. Our
guess Olbricht was by making it a familiar shopping online
shopping experience. It I mean I never saw it. I
think I managed to find some like screenshots and stuff,
but it supposedly looked and operated much like any other
e retailer. You would go on there and you would

(09:13):
have your little shopping basket and you would have your
items that you could you know, are all categorize and
listed that you could sip through, and you could look
at customer reviews and uh, you know, I'm sure there
were bad deals that went down, but supposedly it was.
It worked because the people selling the drugs believe that

(09:35):
you should really sell the thing that you're trying to
sell and you'll stay in business.

Speaker 1 (09:40):
Right just like if you're a a like you have
terrible customer service and you're selling like.

Speaker 2 (09:47):
Which it's sure.

Speaker 1 (09:50):
I was thinking like some sort of sown strawberry potholder,
something in the shape of a strawberry, so much better
than a wedget. But you tell all of your customers
who say, like it's the the stitchings coming loose, that
they can go to hell and die. Yeah, you're gonna
get a bad rating and people are gonna stop buying
from you, especially if there's other people selling sewn strawberry potholders. Right,

(10:12):
same thing, if you're selling drugs on Silk Road. There
were a ton of people selling pot and acid and
ecstasy and heroin and cocaine that like, you just didn't
have to rely on just one dealer. So the dealers
were competing with one another, and to compete they just
tried to keep their user rating up as best as
possible and that kept them honest. It's just nuts, Like

(10:34):
this whole thing in theory should have collapsed on day one.
It just should never have worked out because it was
just based on so many faulty assumptions that just happened
to come together and support this site until the FED
shut it down.

Speaker 2 (10:52):
Yeah, they had a seller's guide where if you're going
to sell your drugs. They would say, hey, here's how
to do that. Here's how you can ship drugs through
the mail, you know, pretty safely, vacuum ceiling and all,
you know, all kinds of tips and tricks, and not
that many packages supposedly were intercepted, a very small percentage
of them. But you mentioned some of the things in

(11:13):
your I thought you were singing that Queens of the
Stone Age song there for a second.

Speaker 1 (11:17):
Which one when you heard that.

Speaker 2 (11:18):
I don't know if they had that one song that
was I thought it was not so great. Cocaine and
ecstasy and blah blah blah blah blah, and they were
just like rattling off drugs or whatever.

Speaker 1 (11:28):
That didn't sound very great.

Speaker 2 (11:29):
No, it wasn't one of their best songs. I was
into them for a minute.

Speaker 1 (11:32):
I'd like that one hit song of theirs. It's really good.
No one knows maybe yes, yes, the one man, I know.

Speaker 2 (11:41):
It's a good song. Uh yeah. So you could buy
anything you want. And it wasn't just like, hey, here's
some cocaine if you're interested in this upper. It was
very very specific stuff like a very specific strain of
Colombian cocaine or a very specific strain of heroin, the
tar heroin that you could find, you know, if you've

(12:04):
ever been to a legal cannabis shop in any of
the states that allow that here in the US, it
was sort of like that. You know, you get very
detailed descriptions of stuff, and you know, you could have
a customer service representative help you find what you wanted,
and it was like, if you were into that kind
of thing, it was probably pretty great for you and

(12:24):
probably much safer than going to some drug dealer's house. Maybe,
I don't know.

Speaker 1 (12:28):
That's a big deal. So one of the things that
was touted by supporters of ross Olbrichton Silk Road was
that it was a site for harm reduction. Yeah, that
it was so vastly safer than buying drugs on the street,
often from some randow you don't even know, or at
a club or something like that. Oh, yeah, I state
that it just yeah, that it was actually providing a

(12:49):
service that actually made the world safer. It didn't fly
very well, as we'll see, but that was that was
a big, a big talking point for them.

Speaker 2 (12:57):
Yeah, And I don't want anyone to misinterpret that. I'm
saying that, like, hey, you should just be able to
buy drugs in the mail and it's totally safe and
you should trust that. But they seem to be setting
up a situation where they were trying to ensure that
there was a lot of trust between buyers, sellers, everybody. Like,
a situation like this doesn't happen if there's not trust

(13:19):
between all the participating parties.

Speaker 1 (13:21):
Precisely, Yeah, for sure. I Yeah, it's just it's just
crazy to me that it ever worked. Should we take
a break, Yeah, let's take a break and we'll come
back and talk about some of the nuts and bolts
of the whole thing.

Speaker 2 (13:33):
All right, we'll be right back. So you've mentioned this guy,

(14:00):
Ross Olbrecht, the founder and creator. We need to talk
a little bit about this dude. He went by the
alias dread Pirate Roberts, even though later in his defense
that would be it would be brought up that there
were like many dread Pirate Roberts over the years, and
that he sold it at one point and wasn't even
involved anymore. If you follow the court case, it gets

(14:23):
really really in the weeds.

Speaker 1 (14:25):
Yes, quote in court was do you not know the
dread Pirate Roberts reference?

Speaker 2 (14:30):
Right? Yeah, they were like, why would you name yourself that?

Speaker 1 (14:33):
Right?

Speaker 2 (14:34):
And he said, have you never seen the Princess Bride?

Speaker 1 (14:37):
Yes, for the people who haven't seen the Prince's Bride,
number one, go see the Prince's Pride, and number two,
dred Pirate Roberts was the name of a well pirate
who was essentially like a character that different people over
the years and generations inhabited. So say, dread Pilot Roberts
was two hundred years old because he was made up
of successive pirates who wore that mask and used that name.

Speaker 2 (15:00):
Yeah, for sure. So Ulbrich had a very very smart guy.
As a very smart guy, he had a Bachelor of
Science in physics, got his master's in material science and engineering,
and was in Austin, Texas in two thousand and nine
when he tried a few different initial companies. Basically he
had a video game company tried. He found the most

(15:21):
success with a second hand book retailer called good Wagon Books,
where he kind of learned how to do web development
and inventory management and e retailing, kind of a starter
kit for what he would need to start Silk Road,
but it still wasn't making the kind of dough he
wanted to make I think they were pulling in maybe

(15:42):
low six figures in a year.

Speaker 1 (15:45):
Yeah. Yeah, And he had like five employees sorting like
fifty thousand books and not bad. They were selling them
on Amazon like you do, like you can buy use
books on Amazon. That's just what they did. But his
heart wasn't in it. And after the show elves that
he had built in this warehouse to hold the books
all collapsed.

Speaker 2 (16:04):
He was like, I'm not.

Speaker 1 (16:05):
Going to pick those up. I'm just gonna set this
warehouse on fire and walk away.

Speaker 2 (16:09):
That's really funny. That sounds like something.

Speaker 1 (16:11):
I would do. I would do the same thing.

Speaker 2 (16:14):
I wouldn't say it on fire and walk away, but
I just walk away.

Speaker 1 (16:17):
So he One of the other reasons he was keen
to walk away is he'd been already thinking about Silk
Road for close to a year by now.

Speaker 2 (16:25):
Yeah.

Speaker 1 (16:26):
And one of the things that really kind of spurred
his interest in creating something like an online illicit drug
sale website is that he became interested in libertarian theory,
specifically libertarian economic theory, which is basically that if you
don't have economic freedom in particular, you're going to be

(16:48):
a slave to the grind. They've got you essentially, and
that to you can either get rich and remove yourself
from that game or that rat race, or you can
try to change the rule of the game and make
it much more fair and equitable and get rid of
coercion and all that stuff. And it's all based on
the libertarian philosophy of self ownership, which essentially explains itself.

Speaker 2 (17:11):
Yeah, he I don't know, explain it.

Speaker 1 (17:15):
Oh, well, you own yourself. So any kind of laws
or prohibitions of anything that say you do to yourself, say,
taking drugs, is just completely outrageous and immoral and is illegitimate. Okay,
So drug laws specifically are illegitimate and terrible to libertarians

(17:38):
because you're taking the drugs for yourself, and that's your choice, right,
It's personal choice. So that really kind of explains a
lot why he was like an illicit drug website. It
was a thumb in the eye to the drug laws
that he and other libertarians feel were illegitimate.

Speaker 2 (17:57):
All right, I'm glad asked Yeah, I'm glad.

Speaker 1 (18:00):
You asked too, because I really wanted to get that
off my chest.

Speaker 2 (18:03):
So Silk Road grew. He started. It was not just
a one person operation. It was too big for that,
so he needed some employees. These people all went by
these kind of fun little nicknames, including Variety Jones and
Nigo Oh also from Princess Bride. Yeah, didn't notice that

(18:24):
libertas Smed and then another one chronic pain one word
the first sea's capitalized, and that person's name was Curtis
Green and he was the first person that would be
arrested in the Silk Road operation. And so you'll just
you know, sort of put a pin in that.

Speaker 1 (18:41):
Guy, Yes, for sure. So he gets the website launched
in twenty eleven around the beginning of twenty eleven, and
to get things kicked off, he started growing psilocybin mushrooms
so that there was something somebody was selling on Silk Road,
and pretty soon other people were like, wait, this is

(19:02):
you're really doing this, Like this is for real? I
want to I want to make money selling drugs online,
and it just kind of took off from there. Again,
without cryptocurrency, there just wouldn't have been a Silk Road.
And this is actually pointed to you by some people
as like an early proving ground that showed like yep,

(19:22):
bitcoin works, it does exactly what it says it can
do and it could completely revolutionize global the global economy.
This was the first chance for it to really kind
of show it stuff, and it really did because it worked.
And one of the other reasons it worked too, is
because ross Oldbert was honest. He hand I guess hand

(19:44):
transacted every transaction between seller and buyer on the site
for a while, and at that point he would hold
the money in escrow and then when the whole thing was,
when the deal was done and everybody was satisfied, you
would release the money to the seller. At any point
in that string, he could have been like, thanks for

(20:06):
the money, chumps, Thanks for the money, chumps, Thanks for
the money, chumps, and just taking off with the bitcoin,
and he didn't. And the reputation that that helped give
that site was another reason it started to grow and flourish.

Speaker 2 (20:17):
Yeah, for sure. So as the site is, you know,
kind of going along and it's making all kinds of
money and getting more and more popular or as popular
as something is on the dark web, he started getting
a little more political. Under his moniker DPR dread Pirate,
Roberts started making these big statements about just sort of

(20:38):
his philosophies about politics. He would say things like stop
funding the state with your tax dollars and direct your
productive energies into the black market. So it started sort
of bordering on manifesto kind of stuff. I think they
would have shut it down anyway, just because they were
dealing in illegal drugs. But the US government definitely hates

(21:00):
it when they don't like the word manifesto. So I
think I think all this other political stuff definitely drew
even more attention and ire maybe than it would happen.

Speaker 1 (21:12):
Yeah, No, I think so. Like I said, it was
a thumb in the eye, and I think it kind
of felt like that to the government and the powers
that be, right.

Speaker 2 (21:19):
Yeah, thought he kind of thought, and he kind of
was leading a revolution in a lot of ways, because,
as we'll see later on, a lot of more sites
like this were born in its wake.

Speaker 1 (21:30):
Right, So it's interesting to see too, the evolution of
him going from a libertarian idealist to what the Fed's
eventually described as like the kingpin of a global drug cartel. Yeah,
really overblown, as we'll see. Yeah, but in the beginning,

(21:51):
he even as a libertarian, said dump there's limits here,
Like this is not just a free for all. You
can't have child pornography. You can't try to sell weapons
of mass destruction, you can't offer hitman services, sell stolen
credit cards or personal information, like, you just can't do that.
And if you scam anybody, we're gonna boot you off
the site and we're gonna hunt you down and sick

(22:12):
dogs on you or something like that. He said, basic
rules are to treat others as you would wish to
be treated, and don't do anything to hurt or scam
someone else. So that was like the whole idea. And
then the fact that his moniker was dread Pirate Roberts
and everybody loves like, there's no one who's seen the
Princess Briden doesn't love it. Prove me wrong. I will
prove you wrong. So all that kind of combined almost

(22:36):
a cult of personality grew up around dread Pirate Roberts
and attracted more and more people to Silk Road. And like,
I think I get the impression, like you were, like
you felt cool to be a user of Silk Road.

Speaker 2 (22:50):
Yeah, he created a kinder, gentler drug trade in a
lot of ways. Yeah, if you're wondering, like, yeah, but
this guy could get shut down in a lot of
ways that don't have anything to do with the government,
like a denial of service attack or something like that.
Supposedly he was paying a lot of money for protection

(23:11):
for this kind of thing, maybe up to fifty thousand
dollars a week. Wire did a really great and I
remember reading this back then. I didn't go back into it,
but a big two part report on this, and they
had it up to fifty grand per week in protection.
But considering they ended up making about a billion dollars
over what two years or so, that's you know, pennies

(23:33):
in the fountain.

Speaker 1 (23:34):
Yeah, for sure. But protection is in quotes like that
was from the very hackers who are like, we're gonna
shut your site down if you don't get it, like
any other protection exactly for sure. Yeah, so yeah, he
would get blackmailed all the time. People were trying to
shut down the site like it was a They're like
criminals were attracted as silk Road, and there's plenty of
criminals who they're like speculators, So blackmailers are you know,

(23:58):
they're not actually doing anything product if they're just making
money off somebody else's work, right, Yeah, So yeah, I
kind of attracted that stuff. So in addition to dealing
with all of that, he was dealing with customer service.
He was trying to keep the site running. Something to
know about ross Oldberg too, He was a self taught coder,
so he was teaching himself how to keep this massive

(24:20):
website going as he went along, and keeping himself totally
anonymous to everybody, including all of the people he worked
with who were de facto employees basically, so it was
a lot of stress after a little.

Speaker 2 (24:34):
While, totally. And besides the drugs, he also had a
team of crocheters making those strawberry elements.

Speaker 1 (24:43):
Lots keep up with for sure.

Speaker 2 (24:46):
So how did it all go bad? Well, it's because
again the government was very very keen on getting this
thing shut down as fast as they could. But like
you mentioned earlier, the very way this thing was built
made it really really hard, almost as impossible but clearly not,

(25:08):
but really really hard to find out any real information
about who these people were, where they were, where those
their computers were. So the FBI got involved initially in
trying to take down tour. It was called Operation Onion
Peeler and I'm pretty sure we talked about that in
the Dark Web app but they in twenty thirteen, there

(25:31):
was an agent named Chris Tarbell that identified secret server
at a data center, a tour data center in Iceland.
And this is really what got the ball rolling.

Speaker 1 (25:43):
Yeah, So this is the official line of the FBI.
The way that they finally discovered the actual IP address
of Silk Road was that Tarbell was sitting there analyzing
the traffic going to and from the site while he
was like sending in bad information at it, like bad

(26:04):
passwords and stuff like that, and then tracking what IP
addresses came back. And then he copied the IP addresses
and he put him into a browser URL and do
that over and over again, and eventually he struck gold
and stumbled onto the real IP address of Silk Road,
which was then traceable to that server data center in Iceland.

(26:24):
And from there they then had a copy of the
Silk Road website including all administration access and privileges, and
they started to set up their case from that point on.

Speaker 2 (26:35):
That's right, That was the FBI's line. If that seems
a little hard to believe that they would just sort
of get lucky, You're not the only person who thinks that.
None other than oh geez is he billed Bill Bill
Alex Winner from Bill and Ted's Excellent Adventure and don't.

Speaker 1 (26:53):
Forget he was a vampire and Lost Boys too.

Speaker 2 (26:56):
Yeah, a good point. He made a film called Deep
Web that jeez, was that out this year?

Speaker 1 (27:03):
I think so or last year? Very recent?

Speaker 2 (27:06):
Yeah, pretty recent film I think twenty four where he
you know, he doesn't he didn't like create this contention,
but he basically brought to light like, hey, a lot
of people say that, no, no, no, that's not how
you found out. What you did was trampled on Oldbrick's
Fourth Amendment rights and that you hacked Silk Road, you
didn't have a warrant to do so, and you had

(27:27):
some sort of you know, mass scanning going on on
the Internet for passwords, and you lied about all this.

Speaker 1 (27:34):
Yeah. The idea is that the NSA was involved helping
in this investigation, using their crazy, terrible powers to basically
find passwords to that site and they used it to
hack in and there. Well you were like, okay, whatever,
they're trying to take it on the site. It's the FBI. Well,
the gist of that is is that they did that first,

(27:55):
then got the evidence that they then went and got
a search warrant for and then everything started to get
legitimate from that point on. So that's the contention about
his Fourth Amendment rights to against search, illegal search, and
seizure were violated.

Speaker 2 (28:10):
Yeah, and if it's all just sounds like weird and
screwy because it's online, it would be no different than
if they broke into someone's house, took some evidence and
then said, now that we have the evidence, we're going
to get a search warrant to go legally back into
that house.

Speaker 1 (28:25):
Right. Yeah, And you mentioned Tarbell, he was an FBI agent.
He and the FBI were just one of multiple agencies
from Department of Homeland Security to the DEA to the IRS.
Oh yeah, all working like each one had a task
force trying to take down this website, competing with one

(28:45):
another in a lot of cases to take down this
website and catch this big fish that Chuck Schumer didn't like.
And like, finally, Tarbell was the one who gets the
credit not just for finding the actual life addressed and
then the server for Silk Road and all of the
evidence that that yielded, but he was there on the

(29:07):
day and helped orchestrate this guy was a cyber crime
FBI agent. So again this is the official line, and
it's very thrilling in the Wired article how they describe it.
But he helped orchestrate, or oversaw the actual arrest of
Ross olbrit which in and of itself was just fantastically amazing.

Speaker 2 (29:25):
Yeah, for sure. All right, So the FBI gets that
copy of the server contents from Iceland. They look at
all the traffic and they found traffic to the administrator's
log in and then narrowed that down to the most
recent traffic was in San Francisco at a place called
Cafe Luna on Sacramento Street. They did some more investigation

(29:50):
through the IRS chipping in this time, Like you said,
so many agencies involved, and they matched the San Francisco lead.
So they are like, this is all up, you guys.
There was an IRS agent named Gary Alford who saw
post about Silk Road on forums in I think a
couple of years twenty eleven and twenty thirteen from a

(30:10):
user name altoid, and the email in the post history
said ross Olbricht at gmail dot com. They found out
that he lived near that cafe, and all roads all
of a sudden, we're pointing to Ross Olbrecht.

Speaker 1 (30:25):
And then supposedly on the really damning piece of evidence
was that that user altoid quickly changed their user name
to Frosty, and Frosty was the main user account that
ran silk Road. Yeah, that was the name of the
main central user account. Right. So, like all of these
things just falling into place, it was just almost almost

(30:47):
too good to believe.

Speaker 2 (30:49):
Yeah, and then it went down like a movie. And
you know what, maybe that's a great time for a
little cliffhanger. Huh oh boy, all right, we're gonna see
what movie we're talking about right after.

Speaker 1 (30:59):
This, Chuck, I'm gonna guess the movie is Old Yeller?

(31:29):
Is it? Am? I right?

Speaker 2 (31:31):
You nailed it?

Speaker 1 (31:32):
Okay, poor Old Yeller. I hate how this goes.

Speaker 2 (31:36):
I was gonna spoil Old Yeller, but I decided not
to watch it that that dog may live. You never know.

Speaker 1 (31:41):
Good for you for not spoiling a sixty year old film.

Speaker 2 (31:46):
Yeah, in the book, I think.

Speaker 1 (31:47):
Too, right. Yes, although there was a sequel, it wasn't
very well.

Speaker 2 (31:51):
Received Old Yeller two.

Speaker 1 (31:54):
Really, it turns out the little kid missed the first
time he did this in the second can film.

Speaker 2 (32:00):
Them and now hold Eller's back for revenge? Yeah, write
that down. That's a good one.

Speaker 1 (32:07):
Okay. So okay, what movie are we talking about that?
How about what type of movie are we talking about?

Speaker 2 (32:13):
Well, we're talking about probably some sort of a courtroom thriller,
because what happened was they went to a library and literally,
and this is what the prosecution said, literally caught him
with his fingers at the keyboard running Silk Road. They
were in the library, they had an agent, you know,

(32:34):
chatting with him and obviously surreptitiously undercover. And while this
was happening, they drew his attention away by starting a
little like quarrel among some other people also, you know,
FBI actors or whatever. And there was a woman, another
FBI agent, sitting across from Olbrich at the time when
this happened, and Olbrich turns around, it is like, what's
going on over there? She grabs that laptop. And because

(32:57):
he could probably in a single swipe of a key
stroke or something like encrypt everything on his laptop if
he saw somebody coming at him, so they knew that
could happen, they diverted his attention just long enough for
this agent to grab his computer and that was it.

Speaker 1 (33:13):
And boy, Oh boy, did they find some just damning evidence.

Speaker 2 (33:20):
Yeah.

Speaker 1 (33:20):
It turns out Ross Olbrich kept a diary of his
like ideas and growth and like administration and all the
problems he had to deal with for Silk Road. Those
were found diary chronic pain. Really hurt my feelings today.

(33:40):
Those were found on his laptop, logs of chat logs
that he had between him and other administrators about running
the site. He was logged in as the main user Frosty,
the person who was actually running the show when they
stole it or grabbed his lap book. No, stole it.

(34:00):
He had spreadsheets like tracking silk Road. I mean just yeah.
It's if a prosecutor could be like, I want this, this,
and this for evidence. It couldn't get any better than
what they found on Ross Holbrick's laptop.

Speaker 2 (34:16):
Yeah. What so they also traced about eighty million dollars
in profit to him. This is a dumb question that
I'm just now thinking of. But what did he just
take a cut from every transaction? Was it that simple? Yes, Okay,
that's what I figured. I just didn't know for sure, and.

Speaker 1 (34:32):
I think it was a reasonable cut. I don't think
it was some massive take or anything like that, and
he would only he would just transfer it like once
a week, like his his accumulated cuts from that week.
He was very honest in that sense.

Speaker 2 (34:47):
So he would get his small percentage, a bottle of
Delauded and a strawberry even met yeah, for every transaction.

Speaker 1 (34:56):
Every Saturday night.

Speaker 2 (34:58):
So we mentioned early that as part of his defense.
They were like, you know what, he may have started
silk Road, but he sold it, and there were many
dread pirate Roberts and one of the other ones framed him.
All of this stuff was just a small part of
his defense. It was not an easy cell. It did
not work. He was convicted for creating an operating silk

(35:21):
Road and got five sentences, got a twenty year sentence,
a fifteen year sentence, a five year sentence, two life
sentences with no chance of parole. And the judge said
it was your opus. You wanted it to be your legacy,
and it is.

Speaker 1 (35:38):
Yeah. The judge mentioned harming the fabric of it was
very destructive to the fabric of society. And when your
judge is pulling out fabric of society and your sentencing,
you're screwed. You're in big trouble. And so he was
effectively handed a death sentence, like you don't outlive a
sentence like that, and it was just totally out of

(36:00):
portion to the charges he was facing, like conspiracy to
commit like drug trafficking and fraud and just I mean,
it was some hardcore offenses, but non violent offenses, and
he was given the kind of sentence that you would
give like a multiple killer or a mass killer or
something like that, right, And the reason why is because

(36:23):
he was there was evidence found of five to six
murder for higher schemes that he had ordered or agreed
to as dread pirate Roberts to kill like a blackmailer,
a witness, some other people. And even though he was
never charged in federal court for this, even though they

(36:48):
couldn't prove any of those cases, and the prosecutors in
this case even said to the jury like, we're not
saying like this is not part of his his his charges,
we're not prosecuting him for that, but seriously, let me,
let us just tell you about that. And so they're
like they he was tainted by the media. He had

(37:09):
a bad reputation from that point, because that's totally different
from setting up a libertarian illicit drug marketplace. Now you're
ordering hits on people to keep your drug enterprise going.
That is a whole different kettle of fish in the
public's mind. So his reputation was smeared from the outset.
The jury was tainted with this information and the idea.

(37:31):
Oh and the judge referenced it in explaining why the
sentence was so harsh. And so all of that is
generally considered illegal, like in illegitimate, And he tried to
appeal all the way to the Supreme Court. They wouldn't
hear it, and that was that. So his last chance
is some president coming along at some point and saying, like,
you know what, you're not so bad, presto change, Oh,

(37:53):
you're no longer a felon.

Speaker 2 (37:54):
Yeah. He was actually would likely have been indicted for
a murder in Maryland. It was dropped because he got convicted,
you know, for whatever life and beyond. It was dropped
because he was, you know, convicted on the other charges
for you know, a gazillion years or whatever with no
chance in parole. But it was a pretty interesting situation

(38:18):
with what ended up being a corrupt dea agent and
a secret service agent and a in a sting operation basically, right, Yeah.

Speaker 1 (38:28):
One of the guys who was really pursuing him from
the outset was a guy named Carl Force, a DEA
agent and posed. Yeah, he posed as a gangster named
nob who basically became a confidant of dread Pirate Roberts,
and it went so far out of undercover that he
became a criminal himself. He posed as another user to

(38:50):
sell tips and stuff about the investigation against Silk Road
to dread Pirate Roberts for like one hundred grand. He
stole three hundred and fifty grand and bitcoin, which was
one of the reasons why dred Pirate Roberts ordered to
hit on one of the people because he thought that
other person had stolen it. This guy was dirty as
the day is long. And they say in part because

(39:14):
a lot of the charges, including that extra murder for
hire that was in Maryland, was arranged by this crooked
Dea agent. They're like, we're we're not even gonna try
this one.

Speaker 2 (39:24):
Yeah, Yeah, I guess there's no point at that point,
especially because it's not like it was carried out. If
there was like a you know, if it had been
carried out and there was a murder victim or something
like that. They probably would have, but right, yeah, there
were never any just to be clear, you know, no
murder for hires ever took place, But it was just
the hint that that was going on really influenced the

(39:45):
judge and the sentencing and everything he was, I believe.
In Alex Winner's documentary, he points out that a lot
of the people that were also brought to trial for
this got very including some of the drug sellers, people
that ran Silk Road two point zero after this. Yeah,
they got sentences of like six years on average, and

(40:06):
so there's been a lot of calls for clemency that
it was, you know, it was too stiff of a sentence.

Speaker 1 (40:11):
Yeah, and they were clearly. I think the judge also referenced,
like this is a huge like everybody's watching this case.
Everybody's following this, you know, and I want to send
a message to anybody who would follow in your footsteps
that we're going to basically give you a death sentence
if you if you try it. They just didn't follow
through on that, which makes his sense all the more unfair. Yeah,

(40:33):
Like had they handed down sentences similar to his for people,
you know, like setting up illicit drug marketplaces. There's some
sort of like legitimacy to it just because of the
precedent and then the custom that developed. Yeah, just doing
that to one person and then not following up, that's

(40:53):
just that's just wholly unfair and again possibly a violation
of his sixth Amendment rights to a fair trial.

Speaker 2 (40:59):
Yeah, I mean, the idea may have been to send
a message like, hey, this will never be tolerated. This
is the first example of this, and we're gonna throw
you know, ten books at them. But it you know,
it didn't stop anything. Like I just mentioned, there was
a silk Row two point zero that was closed in
twenty fourteen, along with twenty six other sites doing similar things.

(41:22):
So silk Row definitely opened that whole door. And it's
it's I don't know if they can shut them down
as fast as they can be born. At this point, probably.

Speaker 1 (41:32):
It seems like the kind of thing like mushrooms just
cropping up, like you pluck one and two more bow
in its place, essentially, like there's just nothing. I mean,
it's not just American kids doing this. They're like the
Russians are like I'm sure the North Koreans are doing
it like everybody's doing it, like you just can't. It's
impossible to stop now so much so that almost makes

(41:53):
you wonder if somebody else would have come up with
this concept head.

Speaker 2 (41:56):
Oh sure first, you know, yeah, yeah, I'm sure someone
would have come along.

Speaker 1 (42:01):
There's a free raws dot org website which his supporters
created that's still around. And if you're asking, like, we
wait a minute, how can everybody support him if he's
ordered like five or six murders for hire, their position
is that like that was the other dread pirate Roberts
who set him up, whoever that was, that ross Olbrich
did not order those hits. That he's a good guy,

(42:22):
a humane guy. He would never do something like that.
But he's still in prison. I saw a tweet from him,
I don't remember when, but he was saying the thing
he misses the most is not being able to see
the night sky anymore, which is somehow like the saddest
thing you could say as a prisoner. But yeah, there's
a lot of people out there here like that kid

(42:43):
is never getting out. He just puts such a thumb
in the eye of the US government and law enforcement
that I don't know, I don't know if he'll ever
get clemency.

Speaker 2 (42:52):
Yeah, the night sky thing, it's definitely better than saying
olive garden get more sympathy.

Speaker 1 (42:58):
Oh no, man, never any breadsticks.

Speaker 2 (43:01):
That's true. I think that. Uh oh never mind.

Speaker 1 (43:04):
Okay, let's go get some breadsticks after this.

Speaker 2 (43:08):
Okay, that'd be great. Oh boy, remember that time we
went to Red Lobster and yeah, and Silver Spring. Yeah,
and I had never really eaten their much. And that
was one of your special things as a kid, right,
eating those cheddar biscuits or whatever.

Speaker 1 (43:21):
Yeah, kid, an adult, I love those things. Yes, I
introduced you to them, is what you're saying, right.

Speaker 2 (43:29):
I think so. I may have had one when I
was a kid, but we just didn't go out to
eat a whole lot, and Red Lobster was like far
fancier than we could even afford on special occasions. So, yeah, you.

Speaker 1 (43:39):
Always make me feel so bad about my upbringing, which
was not wealthy or well produced.

Speaker 2 (43:44):
Silver spoons Are you kidding.

Speaker 1 (43:46):
Me that silver spoons? Red lobster?

Speaker 2 (43:49):
Yeah, No, that's fine. Red Lobster was a very I
imagine is a very duble, fancy dinner. We just didn't
go out to you much. Don't feel bad.

Speaker 1 (43:58):
Yeah. I think the fancy part also is really largely marketing, Chuck.
I think when you see the actual product in front
of you, it's not not super fancy. Yeah. Although, did
you hear I think they filed bankruptcy because of endless Shrimp.

Speaker 2 (44:13):
Yeah, it was a disaster. Yeah.

Speaker 1 (44:15):
Can you imagine? That's like it's like an onion headline.

Speaker 2 (44:19):
Yeah. I read quite a bit about that for some
reason because it was just so interesting to me. It's sad,
you know, it's it's an American icon. Yep, who knew?

Speaker 1 (44:28):
Well, since we talked about Red Lobster, of course, that
triggered listener mail everybody.

Speaker 2 (44:35):
I'm gonna call this the Stuff you Should Know, Bump. Hey, guys,
longtime listener, first time caller, love the show. I'm curious
if you've ever tracked the Stuff you Should Know, Bump?
Does it even exist? I know that every time you
mentioned a documentary with more info or something like that,
my wife and I end up coming through our streaming
services to find it and learn more. Most recently, we
watched tread after the Killdozer episode. Now I'm teeing up

(44:58):
American Anarchist. After swatches, he said, oh wait, I may
have mixed that up with the Anarchist cookbook episode. Anyway.
And by the way, everyone, we forgot to mention the swatchguards.
I feel so bad about that. We heard from a
lot of people on that.

Speaker 1 (45:13):
Oh yeah, I forgot all about that.

Speaker 2 (45:16):
I totally forgot about swatchguards.

Speaker 1 (45:18):
Yeah.

Speaker 2 (45:18):
Anyway, swatchguards are little rubber things that went over the glass,
not the bezel. I was wrong about that. The bezel
is the ring that holds the glass.

Speaker 1 (45:27):
So, man, I understood it before, but not now.

Speaker 2 (45:31):
You know, you look at a watchface and I said,
I think I said the glass was the bezel. I
just misspoke. The bezel is the ring that holds that
glass in place.

Speaker 1 (45:38):
Okay, I think I got it that second time around.

Speaker 2 (45:40):
Yeah, all right, back to the email anyway, guys, it
made me think that other viewers like me, If there
were other viewers like me, there could be a noticeable
bump in views or listens every time a documentary or
song or something gets mentioned creating your own version of
the cold Bear bump. We need statistics or get meta
and do a SYSK episode about the st SK bump.

(46:02):
I think you just gooped up on that last part.
That's Andy from Baltimore. Andy. We don't have data on this,
but we definitely had people send in. I can't remember
what song it was that you referenced, but it ended
up like ranking in Spotify or something, and we like
to think that was because of us.

Speaker 1 (46:22):
Well we know it was because remember we conducted in
an experiment and talked about Barry Manilow now in Black
Sabbath's War Pigs. Yeah, yeah, they showed up in the
top form of Spotify's are just that's right.

Speaker 2 (46:36):
So hey, I guess we should plug Silverspoons. Then that
Josh Clark Life Story, and we'll see if that gets
a bump on wherever that's streaming.

Speaker 1 (46:43):
Speaking of bumps and plugs, there is one other podcast
I'd like to plug. Chuck. You know, our friend and
colleague Daniel Whitson from Daniel and Jorge explained the Universe podcast.
Oh yeah, so the their podcast just came to an end.
But ever the productive person, Daniel came up with another
one that just launched, called Daniel and Kelly's Extraordinary Universe.

(47:06):
He said, new podcasts, same universe. So if you're into
all the stuff that is very interesting, like space and
time and aliens and black holes and philosophy and just
the whole coolness of the universe we live in. Then
go check out Daniel and Kelly's Extraordinary Universe podcast for
a recommendation.

Speaker 2 (47:25):
Sounds great, good people.

Speaker 1 (47:27):
Well, if you want to be like who is that,
that's send us the stsk.

Speaker 2 (47:30):
Ama Andy from Baltimore.

Speaker 1 (47:32):
All right, If you want to be like Andy from
Baltimore and get in touch with us, then we would
love to hear from you. You can wrap it up,
spank it on the bottom, and send it off to
Stuff Podcast at iHeartRadio dot com.

Speaker 2 (47:46):
Stuff you Should Know is a production of iHeartRadio. For
more podcasts my heart Radio, visit the iHeartRadio app, Apple Podcasts,
or wherever you listen to your favorite shows.

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