The Saga of Silk Road

Summary

Stuff You Should Know - "Processing..." Episode Summary

Release Date: November 19, 2024
Hosts: Josh Clark and Chuck Bryant
Production: iHeartRadio

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Introduction

In the November 19, 2024 episode of Stuff You Should Know, hosts Josh Clark and Chuck Bryant delve deep into the intricate world of the Dark Web, focusing prominently on the notorious online marketplace, Silk Road. This comprehensive exploration unpacks the origins, operations, downfall, and lasting impact of Silk Road, providing listeners with a nuanced understanding of one of the internet's most infamous ventures.

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The Genesis of Silk Road

Silk Road is often heralded as the first major illicit marketplace on the internet. Launched in 2011 by Ross Ulbricht, operating under the alias Dread Pirate Roberts, Silk Road revolutionized the way illegal goods, particularly drugs, were bought and sold online.

"[Ross Ulbricht] built it originally. He ran the thing by hand almost single-handedly for a very long time." [04:14]

Ulbricht's vision was to create a platform that mirrored legitimate e-commerce sites, fostering trust through user reviews and stringent seller guidelines. This approach not only differentiated Silk Road from traditional street-based drug dealing but also laid the groundwork for future darknet marketplaces.

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The Pillars Supporting Silk Road

Three critical technologies converged to make Silk Road feasible:

1. Tor Network: Provided anonymity by routing users through multiple servers, concealing their IP addresses.
2. Bitcoin: Facilitated untraceable transactions without the need for traditional banking systems.
3. Libertarian Ideology: Ulbricht's belief in economic freedom and self-ownership fueled the platform's ethos.

"One was Ross Ulbricht... The second is Tor... And then the third thing is Bitcoin." [05:00]

The integration of these technologies not only ensured operational security but also attracted a user base committed to privacy and economic autonomy.

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Ross Ulbricht: The Mind Behind Silk Road

Ross Ulbricht, armed with a Bachelor of Science in Physics and a Master's in Material Science and Engineering, transitioned from legitimate business ventures to founding Silk Road out of frustration with conventional economic systems.

"He became interested in libertarian economic theory... that you can either get rich and remove yourself from that game or ... make it much more fair and equitable." [20:43]

Ulbricht's self-taught coding skills and entrepreneurial spirit were instrumental in developing and maintaining Silk Road. His commitment to the platform's foundational rules—prohibiting activities like child pornography, weapons sales, and hitman services—demonstrated his intent to create a regulated yet illicit marketplace.

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Operational Mechanics and Growth

Silk Road's success can be attributed to its user-centric design, fostering trust through features like:

• Seller Ratings: Encouraged honesty and quality by allowing buyers to rate sellers.
• Escrow System: Ulbricht personally managed transactions to ensure fairness.
• Detailed Listings: Provided comprehensive descriptions of products, akin to legitimate online retailers.

"There were a ton of people selling pot and acid and ecstasy and heroin and cocaine... the dealers were competing with one another." [11:49]

This competitive environment promoted reliability and safety, attracting a large and diverse user base.

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The Downfall: Law Enforcement's Pursuit

Despite Silk Road's sophisticated operations, law enforcement agencies were determined to dismantle the platform. The turning point came with Operation Onion Peeler, led by FBI agent Chris Tarbell.

"Tarbell was sitting there analyzing the traffic... and eventually he struck gold and stumbled onto the real IP address of Silk Road." [29:14]

By infiltrating Silk Road's infrastructure, Tarbell and his team were able to trace the actual server location to Iceland, obtaining critical evidence that led to Ulbricht's arrest.

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Legal Proceedings and Controversial Sentencing

Ross Ulbricht was apprehended in 2013, leading to a high-profile federal case. Despite Ulbricht's attempts to portray himself as a libertarian idealist striving for economic freedom, the prosecution painted him as the mastermind behind a global drug cartel.

"The judge said it was your opus, you wanted it to be your legacy." [41:35]

Ulbricht was sentenced to a cumulative 20-year prison term for charges including conspiracy to commit money laundering, conspiracy to commit computer hacking, and conspiracy to traffic narcotics. Additionally, he received life sentences for alleged involvement in murder-for-hire schemes, although no murders were ever executed.

"He was convicted for creating and operating Silk Road and got five sentences, got a 20-year sentence, a 15-year sentence, a five-year sentence, two life sentences with no chance of parole." [41:35]

This harsh sentencing sparked debates about the proportionality of punishments for non-violent offenses and the influence of media portrayal on judicial outcomes.

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The Aftermath and Legacy

Silk Road's shutdown did not mark the end of darknet marketplaces. Silk Road 2.0 and numerous other platforms emerged, perpetuating the cycle of illicit online trade.

"Silk Road definitely opened that whole door. And I don't know if they can shut them down as fast as they can be born at this point." [46:08]

Moreover, Ulbricht's case has become a touchstone in discussions about digital rights, privacy, and the extent of governmental power in prosecuting online crimes. Supporters argue that Ulbricht's sentencing was disproportionate and unjust, advocating for clemency and policy reforms.

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Notable Quotes

• Ross Ulbricht in Court

  "Do you not know the Dread Pirate Roberts reference?" [17:56]
  Ulbricht defended his alias by referencing the classic film "The Princess Bride," explaining the concept of multiple individuals adopting the same persona over generations.

• Chuck Bryant on Libertarian Ideals

  "This is very important because you're taking the drugs for yourself and that's your choice. It's personal choice." [21:29]
  Highlighting the philosophical underpinnings that justified the creation and operation of Silk Road.

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Conclusion

The "Processing..." episode of Stuff You Should Know offers an in-depth analysis of Silk Road, weaving together technological, ideological, and legal narratives to present a holistic view of its rise and fall. Through thoughtful discussion and insightful commentary, Josh Clark and Chuck Bryant illuminate the complexities surrounding darknet marketplaces, the individuals behind them, and the broader implications for society and law enforcement.

For listeners seeking to understand the delicate balance between privacy, freedom, and legality in the digital age, this episode serves as an essential guide through one of the internet's most controversial chapters.

Transcript

[Chuck Bryant]

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[Josh Clark]

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[Chuck Bryant]

Welcome to Stuff youf Should Know, a production of iHeartRadio.

[Josh Clark]

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 drugs and hitmen you can buy on.

[Chuck Bryant]

Sorry, I was still doing my vocal warmups.

[Josh Clark]

I didn't know that that helps. What does that help?

[Chuck Bryant]

20 dwarves took turns doing push ups on the lawn. I'm ready.

[Josh Clark]

Okay, good. Well, so welcome to the podcast, everybody.

[Chuck Bryant]

I figured it should start warming up, you know, 17 years into this. 18? How long?

[Josh Clark]

Yeah, 16ish. A little over 16. Coming up on 17.

[Chuck Bryant]

Chuck, just wait till you hear the way my lips move in this episode.

[Josh Clark]

They're so loose. So did you loosen your lips up just specifically because the content of this episode is so thrilling?

[Chuck Bryant]

I thought you say something about sinking ships. No, I didn't. But this is a good one. If everyone heard our episode on the dark web from 2020, some of this will be familiar, but this is just more in depth about the notorious Silk Road itself.

[Josh Clark]

Yeah, for sure. Yeah. And we were talking about Silk Road. For those of you history buffs, Middle Eastern history buffs who are disappointed, sorry. But you should stick around because this is going to be a pretty interesting episode.

[Chuck Bryant]

I didn't think about that. When are they going to talk about Cinnamon?

[Josh Clark]

We did a whole episode on Cinnamon, so relax there, guy. Yeah, 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 2011, shut down in 2013. It had a very, very brief run. It was like the Beatles of illicit drug trading websites. And its 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 just the way everything that law enforcement threw at this case and the court case as well was just so nuts that it's just a heck of a story. How about that brownie?

[Chuck Bryant]

That's great. Boy. There were 15 filthy jokes. I was going to say when you said the most outrageous thing anyone had done on the Internet up until that point, I was like, I had a rolling terminator like scroll about all the early Internet nasty memes that would go around.

[Josh Clark]

You couldn't pick any of them. No.

[Chuck Bryant]

I just didn't want to say any of them out loud because then kids would look them up.

[Josh Clark]

I gotcha. Yeah. I was wondering, and we probably should have talked about this before we recorded, Are we going to call out any active sites or anything like that?

[Chuck Bryant]

Nah.

[Josh Clark]

Okay. Because I know some. I looked them up.

[Chuck Bryant]

Hey, just text us to me. It's fine.

[Josh Clark]

Okay, so let's start from the start. Right. We're going to start with a guy named Ross Ulbricht. And the reason we're introducing him early on is because he is the mastermind behind Silk Road. It was his idea. He built it originally. He ran the thing by hand almost single handedly for a very long time. And you just really can't talk about Silk Row 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.

[Chuck Bryant]

Yeah. And big thanks to Kyle, first of all, our friend and contributing writer from across the pond for his work on this. But Kyle is keen to point out just a little bit about the Dark Web. We have a whole episode from 2020 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 that's just 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 believe in the freedom and anonymity that you should have on the Internet.

[Josh Clark]

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. Right, yeah.

[Chuck Bryant]

Just to sell me stuff.

[Josh Clark]

Exactly. 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 ProPublica and other journalists that have dark websites to where you can submit information. And even ProPublica doesn't know who you are. And with Silk Road specifically, there were three things that came together that made Silk Road exist. And without any of them, I don't think it would have ever existed. One was who I already introduced, Ross Ulbrich. The second is Tor, the Tor network, which basically, when you go onto the dark web using Tor, the first 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 websites 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 involve, like, a central bank or some other third party like that.

[Chuck Bryant]

Yeah, for sure. And, you know, Bitcoin was huge because it was. They were good for each other. Like, Ross Ulbricht 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 in illegal drug trading, they use Bitcoin exclusively. So the rise of Bitcoin and the rise of things on the dark web kind of go hand in hand.

[Josh Clark]

Yes, for sure. And this is also a time where, like, the early 2010s, this was in, like, disruptive technology, was just coming out left and right from Silicon Valley, where it's like, well, say goodbye to newspapers, say goodbye to printed books, say goodbye to music. And, I mean, it 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 Ulbricht to basically a darker version, if there is such a thing, of some of those Silicon Valley bros who started up a lot of those disruptive tech companies.

[Chuck Bryant]

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 2011, when the silk Road went live, wrote for Gawker and wrote this big expose on the Silk Road just a few months later, including how to get there, what 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 been, I think.

[Josh Clark]

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 peddle drugs online that we have ever seen.

[Chuck Bryant]

And they all went, yeah, exactly. You nailed it.

[Josh Clark]

Yeah. Right. And so because of that Tor 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, 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 Ulbricht.

[Chuck Bryant]

Yeah. And they also were pretty smart early on, or I guess Ulbricht was by making it a familiar shopping, online shopping experience. 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 have your little shopping basket and you would have your items that you could, you know, are all categorized and listed that you could sip through and you could look at customer reviews and, 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 you should really sell the thing that you're trying to sell and you'll stay in business.

[Josh Clark]

Right. Just like if you're, like, you have terrible customer service and you're selling, like, widgets. Sure. I was thinking, like some sort of sewn strawberry potholder or something in the shape of a strawberry.

[Chuck Bryant]

So much better than a widget.

[Josh Clark]

But you tell all of your customers who say, like, the stitching's coming loose that they can go to hell and die.

[Chuck Bryant]

Yeah.

[Josh Clark]

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. 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, 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 happen to come together and support this site until the Fed shut it down.

[Chuck Bryant]

Yeah. They had a seller's guide where if you were 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 pretty safely. Vacuum sealing and 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 your. I thought you were singing that Queens of the Stone Age song there for a second.

[Josh Clark]

Which one?

[Chuck Bryant]

I don't know. 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.

[Josh Clark]

That doesn't sound very great.

[Chuck Bryant]

No, it wasn't one of their best songs. I was into them for a minute.

[Josh Clark]

I like that one hit song of theirs. It's really good.

[Chuck Bryant]

No one knows. Maybe.

[Josh Clark]

Yes, that's the one I didn't know.

[Chuck Bryant]

It's a good song. 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, tar heroin that you could find if you've 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 get very detailed descriptions of stuff and 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 probably much safer than going to some drug dealer's house, maybe. I don't know.

[Josh Clark]

That's a big deal. So one of the things that was touted by supporters of Ross Ulbricht and Silk Road was that it was a site for harm reduction.

[Chuck Bryant]

Yeah.

[Josh Clark]

That it was so vastly safer than buying drugs on the street, often from some rando you don't even know or at a club or something like that.

[Chuck Bryant]

Oh, yeah, that's dangerous.

[Josh Clark]

It just. Yeah, that it was actually providing a service that actually made the world safer. It didn't fly very well, as we'll see. But that was a big talking point for them.

[Chuck Bryant]

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 between all the participating parties.

[Josh Clark]

Precisely. Yeah. For sure. Yeah. It's just crazy to me that it ever worked.

[Chuck Bryant]

Should we take a break?

[Josh Clark]

Yeah, let's take a break and we'll come back and talk about some of the nuts and bolts of the whole thing.

[Chuck Bryant]

All right. We'll be right back.

[Josh Clark]

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[Chuck Bryant]

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[Chuck Bryant]

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[Chuck Bryant]

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[Josh Clark]

Yeah, his quote in court was, do you not know the Dread Pirate Roberts reference?

[Chuck Bryant]

Right. Yeah. They were like, who? Why would you name yourself that?

[Josh Clark]

Right.

[Chuck Bryant]

And he said, have you never seen the Princess Bride?

[Josh Clark]

Yes. And for the people who haven't seen the Princess Bride, number one, go see the Princess Bride. And number two, Dread Pirate Roberts was the name of a, well, a pirate who was essentially like a character that different people over the years and generations inhabited. So say Dread Pirate Roberts was 200 years old because he was made up of successive pirates who wore that mask and use that name.

[Chuck Bryant]

Yeah, for sure. So Ulbricht 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 2009 when he tried a few different initial companies. Basically, he had a video game company tried. He found the most success with a secondhand 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 low six figures in a year.

[Josh Clark]

Yeah, yeah. And he had like five employees sorting like 50,000 books. And not bad. They were selling them on Amazon like you do. Like you can buy used books on Amazon. That's just what they did. But his heart wasn't in it. And after the shelves that he had built in this warehouse to hold the books all collapsed, he was like, I'm not going to pick those up. I'm just going to set this warehouse on fire and walk away.

[Chuck Bryant]

That's really funny. That sounds like something I would do.

[Josh Clark]

I would do the same thing.

[Chuck Bryant]

I wouldn't set it on fire and walk away, but I'd just walk away.

[Josh Clark]

So 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. 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 a slave to the grind. They've got you, essentially, and that you can either get rich and remove yourself from that game or that rat race, or you can try to change the rules 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.

[Chuck Bryant]

Yeah, he. I don't know. Explain it.

[Josh Clark]

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. Is illegitimate. Okay, so. So drug laws specifically are illegitimate and terrible. To libertarians, 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.

[Chuck Bryant]

All right, I'm glad I asked.

[Josh Clark]

Yeah, I'm glad you asked too, because I really wanted to get that off my chest.

[Chuck Bryant]

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 Inigo. Oh, also from Princess Bride. Yeah, didn't notice that. Libertas Smed. And then another one. Chronic pain. One word, the first C is 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 sort of put a pin in that guy.

[Josh Clark]

Yes, for sure. So the, the he gets the website launched in 2011, around the beginning of 2011. 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, 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 by some people as like an early proving ground that showed like, yep, bitcoin works. It does exactly what 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 its stuff. And it really did because it worked. And one of the other reasons it worked too is because Ross Ulbricht was honest. He hand, He, I guess hand 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, he would release the money to the. To the seller. At any point in that string, he could have been like, thanks for the money chumps. Thanks for the money chumps. Thanks for the money chumps. And just taken 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.

[Chuck Bryant]

Yeah, for sure. So as the site is 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 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 it when they don't like the word manifesto. So I think all this other political stuff definitely drew even more attention and ire maybe than it would have.

[Josh Clark]

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?

[Chuck Bryant]

Yeah, 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.

[Josh Clark]

Right. So it's interesting to see, too, the evolution of him going from a libertarian idealist to what the feds eventually described as like the kingpin of a global drug cartel, which is really overblown, as we'll see.

[Chuck Bryant]

Yeah.

[Josh Clark]

But in the beginning, he, even, as a libertarian, said, nope, 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 going to boot you off the site and we're going to hunt you down and sic 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 Bride and doesn't love it. Prove me wrong. I will prove you wrong. So all of that kind of combined almost 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.

[Chuck Bryant]

Yeah. Like, he created a kinder, gentler drug trade in a lot of ways.

[Josh Clark]

Yeah.

[Chuck Bryant]

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 for this kind of thing, maybe up to $50,000 a week. Wired 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 50 grand per week in protection. But considering they ended up making about $1 billion over what, two years or so, that's, you know, pennies in the fountain.

[Josh Clark]

Yeah, for sure. But protection is in quotes like that was from the very hackers who are like, we're going to shut your site down if you don't give us like.

[Chuck Bryant]

Any other mob protection.

[Josh Clark]

Exactly. We're not going to wreck your store for sure.

[Chuck Bryant]

Yeah.

[Josh Clark]

So yeah, he would get blackmailed all the time. People were trying to shut down the site like it was a there. Like criminals were attracted to Silk Road and there's plenty of criminals who, they're like speculators. So blackmailers are, you know, they're not actually doing anything productive. They're just making money off somebody else's work. Right? Yeah. So yeah, it 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 Ulbricht too. He was a self taught coder, so he was teaching himself how to keep this massive 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 while.

[Chuck Bryant]

Totally. And besides the drugs, he also had a team of crocheters making those strawberry oven mitts.

[Josh Clark]

A lot to keep up with for sure.

[Chuck Bryant]

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 said impossible, but clearly not, but really, really hard to find out any real information about who these people were, where they were, where their computers were. So the FBI got involved initially in trying to take down Tor. It was called Operation Onion Peeler and I'm pretty sure we talked about that in the dark web app. But in 2013 there was an agent named Chris Tarbell that identified a secret server at a data center, a Tor data center in Iceland. And this is really what got the ball rolling.

[Josh Clark]

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 passwords and stuff like that, and then tracking what IP addresses came back. And then he copied the IP addresses and he'd put them 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. 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.

[Chuck Bryant]

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 Bill or Ted? Bill.

[Josh Clark]

Bill.

[Chuck Bryant]

Alex Winner from Bill and Ted's Excellent Adventure in Bubbles.

[Josh Clark]

And don't forget, he was a vampire in Lost Boys too.

[Chuck Bryant]

Yeah, good point. He made a film called Deep Web that. Jeez, was that out this year?

[Josh Clark]

I think so. Or last year? Very recent.

[Chuck Bryant]

Yeah, pretty recent film, I think 24. Where he, you know, 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 Ulbricht's Fourth Amendment rights, and that you hacked Silk Road, you didn't have a warrant to do so, and you had some sort of, you know, mass scanning going on on the Internet for passwords, and you lied about all this.

[Josh Clark]

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 you were like, okay, whatever. They're trying to take down the site. It's the FBI. Well, the gist of that is that they did that first, 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 illegal search and seizure were violated.

[Chuck Bryant]

Yeah. And if it's all just sounds, like, weird and screwy because it's online, it would be no different than if they, like, 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.

[Josh Clark]

Right?

[Chuck Bryant]

Yeah.

[Josh Clark]

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, all working. Like each one had a task force trying to take down this website, competing with one 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 IP address and then the server for Silk Road and all of the evidence that that yielded, but he was there on the day and helped orchestrate. This guy was a cybercrime 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 Ulbricht, which in and of itself was just fantastically amazing.

[Chuck Bryant]

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 login, 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 through the irs, chipping in this time, like you said, so many agencies involved, and they matched the San Francisco lead. So they were like, this is all lining up, you guys. There was an IRS agent named Gary Alford who saw a post about Silk Road on forums, and I think a couple of years, 2011 and 2013, from a username Altoid. And the email in the post history said Ross ulbrichtmail.com They found out that he lived near that cafe, and all roads all of a sudden were pointing to Ross Ulbricht.

[Josh Clark]

And then supposedly, the really damning piece of evidence was that that user, Altoid, quickly changed their username 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 too good to believe.

[Chuck Bryant]

Yeah. And then it went down like a movie. And you know what? Maybe that's a great time for a little cliffhanger, huh?

[Josh Clark]

Oh, boy.

[Chuck Bryant]

All right, we're going to see what movie we're talking about, right after.

[Josh Clark]

Banking with Capital One helps you keep more money in your wallet with no fees or minimums on checking accounts and no overdraft fees. Just ask the Capital One Bank Guy. It's pretty much all he talks about. In a good way. He'd also tell you that this podcast is his favorite podcast, too. Thanks. Capital One bank guy. What's in your wallet? Terms apply. See capital1.com bank capital1, NA member FDIC.

[Chuck Bryant]

You know, friends, we know you like to support companies with a strong sense of purpose. So we're going to talk to you about AT&T, which really makes customers feel good about their choices. And we're talking specifically about their Back to school initiative. Because AT&T provided 20,000 backpacks filled with laptops, school supplies, and personalized notes to students all across America.

[Josh Clark]

Yeah, a lot of us don't really think twice about having our tech, our phones, our laptops, our wifi. But not everyone has access to those things, which is why what AT and T is doing is just amazing.

[Chuck Bryant]

Yeah. And let's talk about Seattle. We love Seattle. AT&T and CompuDocT delivered 250 refurbished laptops and fully stocked backpacks to students all over Seattle, ensuring that they're going to have those tools that they need to succeed.

[Josh Clark]

And everybody loves stories like this where you can see real change happening for real people. And it's not just happening in Seattle. ATT is doing this all across the country in places like Indiana, Philadelphia. They're helping connect the next generation to brighter futures.

[Chuck Bryant]

Yeah. And you know what, buddy? That's pretty exciting.

[Josh Clark]

Connecting changes everything.

[Chuck Bryant]

AT&T. Hey, everybody. The holidays have always been a time of joy in coming together, but let's face it, shipping out all those gifts can be a bit of a hassle, right?

[Josh Clark]

Yeah. And to help ease the load, turn to the United States Postal Service for all your holiday shipping needs. With over 600,000 employees working in sync all over the country, USPS serves over 167 million addresses six and seven days a week.

[Chuck Bryant]

Yeah. And the best part? Their enhanced network is built to deliver your packages reliably and on time. And if you're looking for an affordable shipping option, USPS Ground Advantage has you covered. It's a complete ground shipping solution for all your holiday needs.

[Josh Clark]

Yeah, it's reliable with upfront pricing, no hidden costs, and it's fast helping you stay on top of your holiday plans. So why not take your packages on a true holiday ride this season? Visit USPS.com HolidayRide to get started. United States Postal Service. Chuck, I'm going to guess the movie is Old Yeller. Is it? Am I right?

[Chuck Bryant]

You nailed it.

[Josh Clark]

Okay. Poor Old Yeller. I hate how this goes.

[Chuck Bryant]

I was gonna spoil Old Yeller, but I decided not to watch it. That dog may live. You never know.

[Josh Clark]

Good for you for not spoiling a 60 year old film.

[Chuck Bryant]

Yeah, and a book, I think, too, right?

[Josh Clark]

Yes. Although there was a sequel, it wasn't very well received.

[Chuck Bryant]

Old Yeller do. Really?

[Josh Clark]

It turns out the little kid missed the first time. He didn't in the second film, though.

[Chuck Bryant]

And now he'll hold Yellers back for revenge. Yeah, write that down.

[Josh Clark]

That's a good one. Okay, so, okay, what movie are we talking about then? How about, what type of movie are we talking about?

[Chuck Bryant]

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 chatting with him and obviously surreptitiously undercover. And while this was happening, they drew his attention away by starting a little quarrel among some other people, also FBI actors or whatever. And there was a woman, another FBI agent sitting across from Ulbricht at the time when this happened. And Ulbricht turns around and is like, what's going on over there? She grabs that laptop, and because he could probably, in a single swipe of a keystroke 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.

[Josh Clark]

And boy, oh, boy, did they find some just damning evidence. It turns out Ross Ulbricht 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. Exactly. Chronic pain really hurt my feelings today. 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. He had spreadsheets like tracking Silk Road. I mean, just, if a prosecutor could be like, I want this, this, this, and this for evidence, it couldn't get any better than what they found on Ross Ulbricht's laptop.

[Chuck Bryant]

Yeah, so they also traced about $80 million 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?

[Josh Clark]

Yes.

[Chuck Bryant]

Okay, that's what I figured. I just didn't know for sure.

[Josh Clark]

And I think it was a reasonable cut. I don't think it was some massive take or anything like that. And he would just transfer it once a week, like his accumulated cuts from that week. He was very honest in that sense.

[Chuck Bryant]

So he would get his small percentage, a bottle of Dilaudid and a strawberry.

[Josh Clark]

Oven mitt for every transaction every Saturday night.

[Chuck Bryant]

So we mentioned earlier 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 sell. It did not work. He was convicted for creating and operating Silk road and got five sentences, got a 20 year sentence, a 15 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.

[Josh Clark]

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 in 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 proportion to the charges he was facing, like conspiracy to commit, like drug trafficking and fraud. 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 he was. There was evidence found of five to six murder for hire 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 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 charges, we're not prosecuting him for that. But seriously, let us just tell you about that. And so they're like, he was tainted by the media. He had a bad reputation from that point on because that's totally different from setting up a libertarian illicit drug marketplace. Now you're ordering hits on people that 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. 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 changeo, you're no longer a felon.

[Chuck Bryant]

Yeah, he was actually would likely have been indicted for a murder conspiracy in Maryland. It was dropped because he got convicted for whatever, life and beyond. It was dropped because he was convicted on the other charges for a gazillion years or whatever with no chance of parole. But it was a pretty interesting situation with what ended up being a corrupt DEA agent and a Secret Service agent and a. In a sting operation, basically. Right.

[Josh Clark]

Yeah. One of the guys who was really pursuing him from the outset was a guy named Carl Force, a DEA agent. And, 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 sell tips and stuff about the investigation against Silk Road to Dread Pirate Roberts for like 100 grand. He stole 350 grand in Bitcoin, which was one of the reasons why Dread Pirate Roberts ordered a 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 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 not. We're not even going to try this one.

[Chuck Bryant]

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.

[Josh Clark]

Right.

[Chuck Bryant]

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 judge and the sentencing and everything. He was. I believe in Alex Winter'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 2.0 after this. Yeah, they got sentences of like six years on average. And so there's been a lot of calls for clemency that it was, you know, it was too stiff of a sentence. Yeah.

[Josh Clark]

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 try it. They just didn't follow through on that. Which makes his sentence all the more unfair.

[Chuck Bryant]

Yeah.

[Josh Clark]

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.

[Chuck Bryant]

Yeah.

[Josh Clark]

Just doing that to one person and then not following up you. That's just. That's just wholly unfair. And again, possibly a violation of the Sixth Amendment rights to a fair trial.

[Chuck Bryant]

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 going to throw 10 books at them. But it didn't stop anything. Like I just mentioned, there was a Silk Road 2.0 that was closed in 2014, along with 26 other sites doing similar things. So Silk Road definitely opened that whole door. And I don't know if they can shut them down as fast as they can be born at this point. Probably.

[Josh Clark]

It seems like the kind of thing like mushrooms just cropping up, like, you pluck one, and two more grow 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 you wonder if somebody else would have come up with this concept, had first, you know.

[Chuck Bryant]

Yeah, yeah, I'm sure someone would have come along.

[Josh Clark]

There's a freeross.org website which his supporters created, that's still around. And if you're asking, like, 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 Ulbricht did not order those hits, that he's a good guy, 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 who are like, that kid is never getting out. He just put such a thumb in the eye of the U.S. government and law enforcement that. I don't know. I don't know if he'll ever get clemency.

[Chuck Bryant]

Yeah. The night sky thing, it's definitely better than saying Olive Garden get more sympathy.

[Josh Clark]

I don't know, man. Never ending breadsticks.

[Chuck Bryant]

That's true. I think that. Oh, never mind.

[Josh Clark]

Okay. Let's go get some breadsticks after this, okay.

[Chuck Bryant]

Oh, that'd be great. Oh, boy. Remember that time we went to Red Lobster? Yeah.

[Josh Clark]

In Silver Springs.

[Chuck Bryant]

Yeah. And I had never really eaten there much. And that was one of your special things as a kid, right? Eating those cheddar biscuits or whatever?

[Josh Clark]

Yeah.

[Chuck Bryant]

Kid and adult.

[Josh Clark]

I love those things. Yes. I introduced you to them is what you're saying, right?

[Chuck Bryant]

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.

[Josh Clark]

You always make me feel so bad about my upbringing, which was not wealthy or well to do in any way, shape or form.

[Chuck Bryant]

You were silver spoons. Are you kidding me?

[Josh Clark]

Not silver spoons. Red Lobster.

[Chuck Bryant]

Yeah, no, that's fine. Red Lobster was a very, or I imagine is a very doable, fancy dinner. We just didn't go out to eat much. Don't feel bad.

[Josh Clark]

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 super fancy. Although, did you hear? I think they filed bankruptcy because of Endless shrimp.

[Chuck Bryant]

Yeah, it was a disaster.

[Josh Clark]

Can you imagine? That's like. That's like an Onion headline.

[Chuck Bryant]

Yeah, I've read quite a bit about that for some reason, because it was just so interesting to me and sad. You know, it's an American icon.

[Josh Clark]

Yep.

[Chuck Bryant]

Who knew?

[Josh Clark]

Well, since we talked about Red Lobster, of course, that triggered listener mail, everybody.

[Chuck Bryant]

I'm gonna call this the Stuff youf Should Know Bump. Hey, guys. Longtime listener, first time caller, love the show. I'm curious if you've ever tracked the Stuff youf Should Know Bump. Does it even exist? I know that every time you mention a documentary with more info or something like that, my wife and I end up combing through our streaming services to find it and learn more. Most recently, we watched Tread after the Killdozer episode. Now I'm teeing up 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 swatch guards. I feel so bad about that. We heard from a lot of people on that.

[Josh Clark]

Oh, yeah, I forgot all about that.

[Chuck Bryant]

I totally forgot about swatch guards.

[Josh Clark]

Yeah.

[Chuck Bryant]

Anyway, swatch guards 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, man.

[Josh Clark]

I understood it before, but not now.

[Chuck Bryant]

You know, you look at a watch face 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.

[Josh Clark]

Okay, I think I got it that second time around.

[Chuck Bryant]

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 Colbert bump. We need statistics. We're getting meta and do a sysk episode about the ST SK bump. I think he just goofed 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.

[Josh Clark]

Well, we know it was because, remember, we conducted an experiment and talked about Barry Mano.

[Chuck Bryant]

That's right.

[Josh Clark]

I think even now in Black Sabbath's War Pigs showed up in the top 10 of Spotify searches.

[Chuck Bryant]

That's right. So, hey, I guess we should plug Silver Spoons, then the Josh Clark life story, and we'll see if that gets a bump on wherever that's streaming.

[Josh Clark]

Speaking of bumps and plugs, there is one other podcast I'd like to plug. Chuck, you know our friend and colleague Daniel Weitzen from Daniel and Jorge explained the Universe podcast.

[Chuck Bryant]

Oh, yeah.

[Josh Clark]

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. He said new podcast, 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.

[Chuck Bryant]

Sounds great. Good people.

[Josh Clark]

Well, if you want to be like, who was that that sent us the STSK email?

[Chuck Bryant]

Andy from Baltimore.

[Josh Clark]

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 stuffpodcastiheartradio.com.

[Chuck Bryant]

Stuff youf Should Know is a production of iHeartRadio. For more podcasts from iHeartRadio, visit the iHeartRadio app, Apple Podcasts, or wherever you listen to your favorite shows. Hey everyone. We're brought to you today by the Capital One Quicksilver card. Earn unlimited 1.5% cashback on every purchase everywhere. Plus, there's no limit to the amount of cash back you can earn, and rewards don't expire for the life of the account. It's that simple. The Capital One Quicksilver Card what's in your wallet? Termsupplyccapital1.com for details. Hey friends. The holidays are a time for family, friends and of course, shipping gifts. But you don't need to stress about it. Turn to the United States Postal Service to handle all of your holiday shipping needs with an enhanced network. USPS serves over 167 million addresses six and seven days a week. And if you're looking looking for an affordable option, USPS Ground Advantage has you covered reliable shipping with upfront pricing and no hidden costs. So why not take your package on a true holiday ride this season? Just visit USPS.com HolidayRide to start shipping. Welcome to the world of Bose Ultra Open Earbuds, the perfect gift for the music lover in your life. And now they're $50 off until December 29th. They even made Oprah's Favorite Things gift guide for 2024. Picture this a walk on a sunny winter day. You can hear the satisfying crunch of snow beneath your feet and your favorite holiday song playing. That's the magic we're talking about. Hear life and music at the same time. Act fast to shop Bose's holiday [e-mail] iheartradio.