41: Diving Into The Dark Web: Dark History of Silk Road
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This episode is brought to you by Progressive Insurance. Most of you listening right now are probably multitasking. Yep, while you're listening to me talk, you're probably also driving, cleaning, exercising, or maybe even grocery shopping. But if you're not in some kind of moving vehicle, there's something else you could be doing right now. Getting an auto quote from Progressive Insurance.

It's easy and you can save money by doing it from your phone. Drivers who save by switching to Progressive save nearly $750 on average. And auto customers qualify for an average of seven discounts. Discounts for having multiple vehicles on your policy, being a homeowner and more.

So just like your favorite podcast, Progressive will be with you 24, 7, 365 days a year. So you're protected no matter what. Multitask right now. Quote your car insurance at Progressive.com to join the over 28 million drivers who trust Progressive.

This is an ad by BetterHelp. What?

What are your self-care non-negotiables? The things you know make you feel better, even when it's impossible to make time for them. Like that workout you try to squeeze in between kids' activities, work, and everything else you have going on, and before you know it, it gets pushed to tomorrow.

Sound familiar? But it's the moments when you feel like you have no time for yourself when those non-negotiables are more important than ever. Those are the things that keep you strong, healthy, motivated, and prepared to take on everything life demands of you. So why not make therapy one of them?

BetterHelp Online Therapy makes it easy to get started with affordable phone, video, or live chat sessions you can do from anywhere, and the option to message your therapist between sessions if anything comes up. Never skip therapy day with BetterHelp. Visit betterhelp.com slash darkhistory today to get 10% off your first month. That's betterhelp, H-E-L-P dot com slash darkhistory.

Hi friends! I hope you're having a wonderful day today. My name is Bailey Sarian and I'd like to welcome you to the Library of Dark History.

Welcome, welcome. This is a safe space for all the curious cats out there who think, hey, is history really as boring as it seemed in school? Oh, nay, nay. This is where we can learn together about all the dark, mysterious, dramatic stories our teachers never taught us in school. Or maybe just like glossed over, you know? Anyway, so I had this idea. I wanted to do the dark history of the internet. But when I went down that rabbit hole, I was like...

okay, what's like step one, you know? Should I do a dark history of MySpace? If I did that, I'd have to talk about my MySpace page, which was honestly amazing, but that's not the point.

So it's like, okay, well, what about Twitter? Wealthy white dude, start a company and gets even wealthier. Where's the story in that? And I can't do a dark history of Google because let's face it, Google's fucked up and they'll probably cancel me and kill me and like, whatever. They're up there with Nestle. Doesn't Google own YouTube? Yeah, I can't. That's my daddy. He pays me. Anyways, but then I remembered an article I discovered that told the story of a place on the internet where drugs were sold. Mm-hmm. Mm-hmm.

It was a lot like Amazon, except instead of shower curtains, you could buy cocaine. I mean, it was wild. And it sounds too good to be true, right? Well, because it was. It only lasted a few years, but in those few years, wow, baby girl, this story, it has everything. We're talking murder for hire, a cat and mouse chase with the FBI, and a whole lot of ecstasy pills. So today, we're going to be covering the dark history of...

Silk Road. Okay, so let me open up my dark history book. Let me go to the Silk Road chapter here in my book of dark secrets.

Found it. And let's hop skiddily-doo right into this story, shall we? So this is probably the most recent story we've covered on Dark History, but if you know anything about Silk Road, you know why I want to tell this story. But it's impossible to tell you the story of Silk Road without learning the story of a man named Ross Ulbricht.

Ross was born to Kirk and Lynn Ulbricht on March 27th, 1984 in Austin, Texas. His friends called him the Ross Man and described him as carefree but also caring, as well as being bright but not whiz kid bright. So far, so good, right? When he was little, Ross's parents signed him up for the Boy Scouts and Ross loved being in the Boy Scouts. I mean, he was awesome.

always curious about how trees grew, how to find food in the woods, I mean everything. So the scouts were just a natural fit. And while in Boy Scouts, he learned the value of following the rules to get ahead. But it turns out Ross had a bit of a dark side. When he was in high school, rule-abiding Ross started wondering what would happen, you know, if he broke the rules every once in a while.

So he started small, you know, like most teenagers do, by smoking a little bit of the devil's lettuce with his friends and hanging out with them at all hours of the night. But then Ross wanted to push it to the next level. So he started experimenting with much harder drugs. I mean, everything from mushrooms to DMT, which is like a hallucinogenic chemical. I mean, really whatever he could get his hands on. Ross loved drugs. He

He once said his drug intake was like, quote, a guy who jumped into the deep end of a pool and stayed underwater for as long as he could hold his breath, end quote. Is that a bad thing? Is that bad? So you might think this is the point where everything starts to go wrong for Ross, right? No, no, of course not. Because while Ross was experimenting with every drug he could find, he collected enough merit badges as a Boy Scout to become an Eagle Scout.

He also received a $1,460 on his SATs and got a scholarship to the University of Texas at Dallas. So, I mean, he's doing just fine, okay? He decided to major in physics, and once Ross got to college, Ross partied hard. But he studied even harder and got a grad school scholarship to Penn State.

I mean, at this point, Ross was living two lives. By day, he was like this cheery, rule-following, physics-studying, Eagle Scout, you know? But by night, Ross was seeing just how far down the rabbit hole he could go and experimenting with more and more drugs. And no matter how far down the rabbit hole he went, I mean, Ross was like still a very successful student. The end. No, I'm just kidding. I'm so funny. I know. But he wasn't happy. Look.

Nobody is Ross, get in line. And at age 22, Ross started to realize he had no idea what he was even doing. He found himself depressed because of how monotonous lab research was. And he was worried that like all the years of work might not even lead to anything meaningful or any kind of money, you know?

The future started to look grim. Ross was at a dead end and he felt trapped. But one day, Ross was scrolling around online when he discovered the writings of an Austrian economist named Ludwig von Mises.

I think that's how you said it, you say it. Ludwig wrote about how people are trapped in life if they don't have economic freedom. Government enforces taxation and taxation funds the government to enforce violence upon its citizens, trapping them into a lifelong cycle of poverty.

If a citizen is not free economically, they'll just never be free. Well, Ludwig's writings freaking rocked Ross's world. All Ross wanted was to be free. And now he discovered a philosophy that promoted the kind of freedom like he was craving. He was like, "Sign me the F up, please and thank you." So after Ross graduated from Penn State in 2009, he decided to give up physics and focus on making money to get that freedom.

So he moved back home, okay, and he started working for a company called Good Wagon Books, which was a business that collected used books and sold them online. Great, love that, dream job.

While there, Ross built Goodwagon's website. Yeah, he learned how to like manage a business inventory and he made a custom internet script that would determine a book's price based on how it was ranked on Amazon. Ross did so well at the company that when the owner left, he passed the company off to Ross. And under Ross, Goodwagon Books thrived. Mm-hmm.

December 2010 was the best month ever for the company pulling in $10,000. Ross loved the power that came from running his own company, but the particular company wasn't pulling in enough money. So on the side, Ross started trading stocks on the internet to make a little extra cash. And one day he saw something that would really help him get to the next level. Because one of the ways people were buying stocks was with something called Bitcoin. Bitcoin.

Now fully explaining what Bitcoin is would take a long ass time. Plus it's complicated. So I'm just gonna give you the quickest definition I possibly can. Bitcoin is a crypto currency, which sounds like a scary robot skeleton or something, right? Very Terminator, but it's not. Cryptocurrency is actually just digital money, profit.

Point blank period. You can buy cryptocurrency with normal money, usually with like a credit or debit card. And then the cryptocurrency becomes digital money. So like that's stored in something called a blockchain. Yeah, I lost you probably.

Come back, pay attention. A blockchain is a digital ledger book that manages all your cryptocurrency transactions, but it's encrypted and technically like no one can trace it. It's untraceable. On top of all of that, the value of Bitcoin isn't based out of central baking like most of currency is. Instead, it's based on how much of a demand there is for it. That's it, really, I guess. People are gonna be like, that's not it, blah, blah, blah.

Shut up. There's a lot more to Bitcoin than that, but the easiest way to look at why people use Bitcoin is to think of it as money that isn't tied to the government in any way. It's untraceable too. And most importantly, people assume the transactions were anonymous. Ross was blown away by Bitcoin and it gave him an idea. Light bulb. What if he could create a website where people could buy anything they wanted

but it was completely anonymous. And what if it wasn't just normal stuff that you'd buy online? What if you could buy, I don't know, whatever you wanted? Like let's say drugs.

You see, Ross believed that all drug use was a personal choice and the government should stay the hell out of people's personal choices. Plus, Ross believed the war on drugs was a total failure, which we talked about here on Dark History, remember? It was.

Thank you. So by making a website that ignored the government and their quote unquote war on drugs, Ross saw an opportunity to create the kind of freedom of choice he wanted to see in the world. Trailblazer. Now the biggest problem Ross faced was that, well, drugs are illegal and selling drugs online also illegal. I mean, you can't just like set up a normal website with drugs for sale and call it a day.

And this is where something called the dark web comes into play. The dark web, if you don't know, is a super secret hidden part of the internet that you can't access on a normal web browser. The dark web is hidden behind a lot of encryption. So you need a special web browser to access it. And unlike cryptocurrency, it's actually, it is anonymous. So why exactly is it called a dark web?

Well, the dark web is so anonymous and unregulated, it's an easy place for journalists or whistleblowers from across the world to avoid censorship.

But because of the lack of regulation, it also leaves people on the dark web vulnerable to illegal activity. The dark web is home to everything from illegal guns for sale to stolen credit cards and social security numbers. This makes the dark web one of the world's biggest black markets in illegal activity. The kind of activity that usually happens in the shadows, hence...

Dark web. You get it. So to Ross, the dark web was the perfect home for his brand new website. And cryptocurrency? Oh, perfect for anonymous transactions.

On December 31st, 2010, Ross wrote a New Year's resolution into his personal diary that said, quote, in 2011, I am creating a year of prosperity and power beyond what I have ever experienced before. This website is going to become a phenomenon.

And at least one person will tell me about it, not knowing that I created it, end quote. And at the beginning of 2011, Ross closed down Goodwagon Books for good and officially launched his brand new website, which he called Silk Road. But first, let's pause for an ad break.

This episode is brought to you by Progressive Insurance. Most of you listening right now are probably multitasking. Yep, while you're listening to me talk, you're probably also driving, cleaning, exercising, or maybe even grocery shopping. But if you're not in some kind of moving vehicle, there's something else you could be doing right now. Getting an auto quote from Progressive Insurance.

It's easy and you can save money by doing it from your phone. Drivers who save by switching to Progressive save nearly $750 on average. And auto customers qualify for an average of seven discounts. Discounts for having multiple vehicles on your policy, being a homeowner and more.

So just like your favorite podcast, Progressive will be with you 24-7, 365 days a year, so you're protected no matter what. Multitask right now. Quote your car insurance at Progressive.com to join the over 28 million drivers who trust Progressive.

Progressive Casualty Insurance Company and affiliates. National average 12-month savings of $744 by new customer surveyed who saved with Progressive between June 2022 and May 2023. Potential savings will vary. Discounts not available in all states and situations. This is an ad by BetterHelp. What are your self-care non-negotiables? The things you know make you feel better even when it's impossible to make time for them.

Like that workout you try to squeeze in between kids' activities, work, and everything else you have going on, and before you know it, it gets pushed to tomorrow. Sound familiar? But it's the moments when you feel like you have no time for yourself when those non-negotiables are more important than ever. Those are the things that keep you strong, healthy, motivated, and prepared to take on everything life demands of you. So why not make therapy one of them?

BetterHelp Online Therapy makes it easy to get started with affordable phone, video, or live chat sessions you can do from anywhere, and the option to message your therapist between sessions if anything comes up. Never skip therapy day with BetterHelp. Visit betterhelp.com slash darkhistory today to get 10% off your first month. That's betterhelp, H-E-L-P dot com slash darkhistory. When you hear the name Silk Road, close your eyes, what do you picture?

'Cause I picture, what's that? Isn't it like that vegan milk? It's not vegan. Isn't it called silk something? That's what I think of, that. I think of milk. Well, that's not why Ross called it Silk Road. Ross actually got the name Silk Road from a real thing in history.

Hence the name Dark History. Full circle. Full circle. I can't talk today. More than 2,000 years ago, there was a trade route that carried everything. Porcelain, cannabis, spices, gold, gunpowder, and silk.

But it wasn't just goods that were traded on the original Silk Road through China. It was religion, philosophy, and information. All of these things would lead to innovations in technology that changed the world forever. And that's why Ross chose the name Silk Road. I mean, he was hoping his website would do for the internet what the original Silk Road did for the real world. But there's one other thing we need to know about the original Silk Road for this story.

There was a third thing that spread across the Silk Road. Can you guess? It was the bubonic plague. Remember bubonic plague?

Bubonic plague. So even though the original Silk Road spread ideas and goods, it also spread disease and death. LOL. Anyway, Ross launched his site Silk Road in February of 2011. But he had one problem. He freaking didn't have access to the things he wanted to sell on Silk Road, aka he didn't have the

the drugs to sell, you know? Not to mention that because of how the dark web worked, nobody was going to find his website by accident like they would like on the normal internet. So Ross needed product and he needed a way to get people to his site. So one day Ross went online and found out that it's actually really freaking easy to make homemade hallucinogenic mushrooms. Good for him. He's just DIY king over here.

So Ross started his website off by selling shrooms. And to promote his magic mushrooms, Ross posted on forums all over the normal internet under the screen name Silk Road. He advertised this amazing new website on the dark web, which is also called Silk Road. And you can buy magic mushrooms there. So head on over and get started now. Ross grew 10 pounds of mushrooms and sold all 10 in under a week.

I'm sorry, in just under a week. I feel like that just makes a big difference. Almost immediately, other people started to notice Silk Road's potential and they wanted in on the action. So other people started selling drugs on Silk Road. Silk Road was already becoming a success, but in June 2011, things really started to take off when the website Gawker wrote a glowing review of Silk Road on the normal internet.

The article went viral and within weeks, Ross pulled in his first million dollars. Yeah, within weeks. Good for him. But the busier the website got, the less time Ross had to enjoy his newfound wealth. Ross was the only person working on Silk Road at this time and he was starting to get a little overwhelmed, okay? He knew that in order to sustain the website's success, he would need some freaking help.

And that's when Ross received an email from somebody named Variety Jones.

Now, Variety Jones wasn't this guy's real name. His actual name was Roger Clark, but Ross, he didn't know that. Like everybody else Ross met on the dark web, Variety always just went by his screen name. We don't know too much about Variety Jones, except that he was an internet hacker who noticed a hole in Silk Road's code that could allow other hackers to steal thousands of Bitcoin from Silk Road's customers. Now, even though Variety Jones could have taken down Silk Road, he didn't want to.

In fact, Variety Jones wanted in. So he emailed Ross about this hole in Silk Road's code and Ross fixed it like right away. And then the two kept talking, quickly becoming good friends. And eventually Variety Jones even became Ross's mentor in how to run a criminal enterprise. Now Variety had a lot of experience committing crimes on the internet, or at least that's what he told Ross. And Variety gave Ross an important piece of advice.

What Silk Road was doing was illegal, so Ross needed to protect himself from the government. And in order to do that, Ross needed a new name. And Variety even had that figured out too, obviously. The name he said Ross should use was the Dread Pirate Roberts. So Dread Pirate Roberts. Look, I'm not going to say that a hundred times, okay? Okay.

This name comes from the movie The Princess Bride. You remember that movie? The character of the dread pirate Roberts is the most fearsome pirate in the world. But the twist is he isn't a real person.

Oh, that makes sense. Yeah. It's a name adopted by somebody who proves themselves to be the best pirate around. So whoever the Dread Pirate Roberts is, whenever they get tired of being the Dread, I'm going to call him DPR, okay? Whenever they get tired of being the DPR, they can just hand the name off to somebody else. Okay.

Variety told Ross this would be like the perfect cover, you know? If the law ever came down on Ross, he could pass the name off to someone else and pretend he was just filling the role, right? So in early 2012, Ross officially retired his old Silk Road username and deleted all his old forum posts about mushrooms on the internet so he could cover his ass and then officially became known as the Dread Boss.

Pirate Roberts. Under his new name, Ross hired some employees to help him run Silk Road by using an encrypted chat program on the dark web and paid them in Bitcoin. They must be super rich now. They all had weird screen names. Cirrus,

Digital Alchemy, Smedley, like all of them are anonymous, but all of them way more experienced in drug crimes than Ross. Within months, Silk Road was completely overhauled by Ross and his new employees. One historian described the new and improved Silk Road as user-friendly and, quote, almost hilariously similar to Amazon, complete with a cart in the upper right-hand corner, end quote.

But, you know, instead of TVs, makeup, or pet products, there were helpful icons for cannabis, ecstasy, opioids, opioids.

Sorry, I'm struggling with opioids. There we go. And then there was even a seller's guide section that had like helpful instructions on how to vacuum seal or hide drugs when shipping them. So just very helpful. Criminals helping criminals, love to see it. So to Ross, this was the freedom he had been searching for his entire life, okay? He had gone from a book dealer to a successful drug kingpin overnight. I would call him a drug entrepreneur.

How about that? I like that better. He was pulling in millions of dollars from all over, boom, boom, boom, the globe. But you can't make that kind of money in the USA without attracting attention from the government. So just a few months after Silk Road launched, Ross became one of the freaking most wanted men on the planet. Let's pause for an ad break.

This episode is brought to you by Progressive Insurance. Most of you listening right now are probably multitasking. Yep, while you're listening to me talk, you're probably also driving, cleaning, exercising, or maybe even grocery shopping. But if you're not in some kind of moving vehicle, there's something else you could be doing right now. Getting an auto quote from Progressive Insurance.

It's easy and you can save money by doing it from your phone. Drivers who save by switching to Progressive save nearly $750 on average. And auto customers qualify for an average of seven discounts. Discounts for having multiple vehicles on your policy, being a homeowner and more.

So just like your favorite podcast, Progressive will be with you 24-7, 365 days a year, so you're protected no matter what. Multitask right now. Quote your car insurance at Progressive.com to join the over 28 million drivers who trust Progressive.

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Your cash back really adds up. So let's recap for a second. Ross Ulbricht really likes drugs, but he also wanted to make a name for himself. He stumbled upon Bitcoin and the dark web and got the idea to combine all of his interests into a website that sold drugs for Bitcoin anonymously.

and became a millionaire basically overnight. But there's one important part of the story I haven't told you yet, because it turns out from the very beginning of this Silk Road story,

There's been another character lurking in the background. And that character? Homeland Security. Yeah. Boo. Homeland Security is the branch of the government responsible for public security and are focused primarily on border security, cyber security, and catching terrorists. So it's kind of a big deal that Silk Road was on their radar. Okay? Okay.

But it didn't start as public enemy number one. I mean, at first, the Homeland Security team just wanted to get a little drugs and party, you know? And then they were like, oh, whoops, can't do that. I'm just kidding. At first, it was just one Homeland Security agent who noticed something wasn't right about Silk Road. This guy's name was Jared. Oh, God, Jared. Remember the subway guy, Jared? Yeah, he turned out to be a shithead, huh?

Fuck that guy. Anyways, one day in June of 2011, Jared was sitting in his office when he got a call from a guy named Mike. Mike worked as a border protection officer at Minnesota Airport, and he told Jared, like, hey, we intercepted this piece of mail. It's an envelope, but on the inside, it's just a single pink pill. The weird thing is, it has a squirrel engraved on the side.

End quote. Now, normally when Homeland Security gets a call like this, it's not treated like as a big deal. Most agents have gone on record saying that crimes this small get logged and forgotten. We appreciate the honesty. And since there are bigger cases like to work on involving like felony level amounts of drugs, this would have just normally would have been nothing, right? But Jared had only been working for Homeland Security for two months. So to him,

He's got something to prove and this was an interesting lead to follow. He's trying to reclaim the name Jared and make it a good name because that subway Jared really ruined it for everyone. He told Mike he couldn't just fly out to Minnesota to check out like a single pill, but gave him his personal number and told him to report back if anything similar happened again, which I'm sure he was like, sure, call me back if something happens.

thinking like nothing's gonna happen, you know? So for a few months, Mike went about his daily business of checking the mail, coming through the Minnesota airport for anything suspicious to report back to Jared. But he didn't really find anything until October 5th, 2011, when he found another plain white envelope with a single bump in the middle. And sure enough, the bump was another tiny pink pill with a squirrel.

That sounds cute. Just like the one he found before. So Mike picked up the phone and dialed Agent Jared. Now apparently Agent Jared had become a bit obsessed with small drug seizures ever since that first phone call. And the pink pill was like, I guess it was an ecstasy tablet because he took it and he was like, what? No, I'm just kidding. Wouldn't you though? I would. Wouldn't you? I'd be like, what's this?

I don't wanna find out. But he finds out it's an ecstasy tablet somehow. Wink, wink. And Jared had started hearing about like a number of similar discoveries of single ecstasy tablets down at Chicago's O'Hare Airport, the one where they filmed "Home Alone." When Jared first heard about these pills, there were only three to five packages every other day that contained small amounts of ecstasy.

But by the time Mike called Jared in October, I mean, there were now like 30 to 50 packages like these every single day at the O'Hare airport. Each package was addressed to an individual person at their homes, which is just kind of messy when you think about it. But the easiest ones to find were drugs taped like on the inside of CD and DVD cases or single pills in envelopes.

But some of the other drugs were more cleverly hidden. For example, there was this one package that had nothing in it but a small piece of cardboard.

And you know how on the sides of cardboard there's like those tiny ripples and holes? Yeah, you know. Well, there were tiny pink ecstasy tablets stuffed inside of each of those holes. I love a puzzle. I mean, that's fun. So there was a lot of effort being made to send small amounts of drugs to people. And Jared wanted to know who was behind it. So Jared, Jared.

Jared now decided he had enough evidence to perform what's called a knock and talk, which is exactly what it sounds like. What does it sound like? Knock, knock. Who's there? Talk, talk. I don't know. Jared went to one of the addresses that had ordered some of these drugs and knocked on the door. But the guy who answered the door, it wasn't the person whose name was on the envelope. It was like the roommate. So,

So Jared asked the roommate if he ever noticed anything a little unusual about his roommate's mail. And the roommate immediately said, like, yeah, he's ordering a lot of drugs online from this website called Silk Road. Now, initially, Jared was like, okay, like, what is Silk Road? But the roommate had a severe case of verbal diarrhea. So he just keeps talking and talking and talking. And the roommate tells Jared, think Amazon, but for drugs. Yeah.

And.

And he goes into great detail about how you can find anything on Silk Road, how it's on the dark web, and how every order is bought exclusively with Bitcoin. Now, Jared heads back to his office. And the first thing he thinks is like, there's no way I'm the first one to stumble across this website. But he goes on his computer and finds out there are no open cases involving the words Silk Road in the Homeland Security database.

He tries typing similar keywords, but nothing comes up. You know, nothing's coming up. So with no other options, Jared Googles it. And after digging through a few hits related to the historical Silk Road, Jared comes across that Gawker article I mentioned earlier. You know, remember? This is an article on the normal internet talking about how to buy drugs on the dark web. So Jared was shooketh.

So as he reads the article, he finds out that the owner of the website is named the Dread Pirate Roberts. DPR for short. Yeah, DPR. But who is DPR? Nobody seemed to know. So Jared reports back to Homeland Security saying like, hey, there's something huge going on here. And Homeland Security, I mean, they agree. So later that fall, an investigation was officially opened into Silk Road.

At first, investigators found that most of the people who went on Silk Road were looking for a safer alternative to buying drugs. No more risk of police chases, no more shady back alley deals. I mean, this was a way to get drugs sent directly to your home. There were even anonymous community groups on the website where people would talk about keeping drug use recreational, where they would hold each other accountable to avoid becoming addicted. I mean, that sounds super great, right? Well,

Because of how accessible drugs became due to Silk Road, there was a huge increase in the United States in drug use and drug deaths. One study said that by the time Silk Road ended, nearly 20% of all US drug users had purchased narcotics from Silk Road. Or they're just saying that to like, you know, prove that they did something good, you

You decide. Across the world, drugs purchased from Silk Road were confirmed to have led to at least six overdose deaths, including two 16-year-olds who had purchased something called an NBOM. Yeah. An NBOM is supposed to be a cheaper synthetic version of LSD, but unlike LSD, you can overdose on it. Federal agencies all around the United States wanted to put a stop to this, and they wanted to put a stop to it fast.

No one's going to be making millions of dollars without me coming in, Jared, and fucking shit up, you know? So investigators decided to reach out to the FBI. Yeah. Now, drug crimes weren't the jurisdiction of the FBI, but the investigators had uncovered other stuff on Silk Road that did fall under their jurisdiction.

It turns out that Silk Road's whole like anything goes approach to retail had expanded into other illegal activities. I mean, things like guns, for-profit internet hacking, fake IDs, fake social security numbers.

Girl, you name it. Whatever. If it was shady, they were doing it. And according to the FBI, even murder-for-hire postings. Oh, yeah. You want to kill your husband, babe? Just a little beep-bop-boop. Two clicks. Check out. You're good.

So easy. What if you could murder your husband with Prime? So in September of 2012, the FBI's cyber branch began an investigation with the goal of finding the Silk Road server who was running it and ending the whole damn criminal enterprise. Burn it down. Let's pause for an ad break really quick. BRB!

This episode is brought to you by Progressive Insurance. Most of you listening right now are probably multitasking. Yep, while you're listening to me talk, you're probably also driving, cleaning, exercising, or maybe even grocery shopping. But if you're not in some kind of moving vehicle, there's something else you could be doing right now. Getting an auto quote from Progressive Insurance.

It's easy and you can save money by doing it from your phone. Drivers who save by switching to Progressive save nearly $750 on average. And auto customers qualify for an average of seven discounts. Discounts for having multiple vehicles on your policy, being a homeowner and more.

So just like your favorite podcast, Progressive will be with you 24-7, 365 days a year, so you're protected no matter what. Multitask right now. Quote your car insurance at Progressive.com to join the over 28 million drivers who trust Progressive.

Progressive Casualty Insurance Company and affiliates. National average 12-month savings of $744 by new customer surveyed who saved with Progressive between June 2022 and May 2023. Potential savings will vary. Discounts not available in all states and situations. This is an ad by BetterHelp. What are your self-care non-negotiables? The things you know make you feel better even when it's impossible to make time for them.

Like that workout you try to squeeze in between kids' activities, work, and everything else you have going on, and before you know it, it gets pushed to tomorrow. Sound familiar? But it's the moments when you feel like you have no time for yourself when those non-negotiables are more important than ever. Those are the things that keep you strong, healthy, motivated, and prepared to take on everything life demands of you. So why not make therapy one of them?

BetterHelp Online Therapy makes it easy to get started with affordable phone, video, or live chat sessions you can do from anywhere, and the option to message your therapist between sessions if anything comes up. Never skip therapy day with BetterHelp. Visit betterhelp.com slash darkhistory today to get 10% off your first month. That's betterhelp, H-E-L-P dot com slash darkhistory.

The first thing the FBI tried to figure out was who the heck was DPR, okay? All around the internet, people theorized that he was an international drug kingpin or that maybe the DPR was some bored billionaire and drug trafficking was like...

this rich person hobby. One post on an old forum even theorized that DPR wasn't a person at all. He was a series of computers running advanced artificial intelligence. For a while, the internet was obsessed with finding out who this fricking pirate was.

And so was every federal agency in the United States. Get in line. There was an operation that sprang up in 2012 called Marco Polo. Oh, fun. It was made up of FBI, Homeland Security, and DEA members. They were focused primarily on unmasking the DPR. I mean, one of their agents was a man named Carl. God, all of them have such basic skills.

Carl, Jared, Mike. Anyways, Carl Force is this guy's name.

he went undercover on Silk Road using the screen name Knob. So simple. Knob. And started selling cocaine on the website. After a few sales, Knob, aka Carl, wrote DPR in December of 2012, complaining that Silk Road sales were too small to be worth his time. So DPR forwarded this email to one of his top lieutenants who went under the screen name Chronic Pain.

DPR told Chronic Pain that he needed to collaborate with Knob to set up like a bigger sale to keep Knob on as a dealer. At least he's looking out for his dealers. That's nice.

Now this part absolutely sounds 100% insane, but it's honestly how it went down, okay? Chronic pain thought it would be a good idea to have the cocaine shipped directly to his home address. Yeah, I know. He didn't even get like a P.O. box. So to nobody's surprise, chronic pain was soon arrested. So chronic pain turned out to be a man named Curtis Green.

A grandpa and a former semi-pro poker player who lived in Spanish Fork, Utah. Good for him. You go, grandpa. Curtis turned on DPR fast and became an informant for the FBI in exchange for his freedom. Wah, wah, wah.

The FBI released him almost immediately in hopes that DPR wouldn't find out like that they had a spy on the inside. Well, DPR found out anyway, and you'd think like he would have realized something fishy was going on with this Knob guy. I mean, he's a new guy. And the second he came along, Curtis got arrested. You know, like you think he'd put the pieces together. Nay, nay.

That's not what happened. In fact, DPR started complaining to Knob that Curtis was the mole. And not only that, but he thought Curtis was stealing some of the website's Bitcoin on the side. DPR wanted revenge, so after a few messages back and forth, he asked Knob if he knew anybody that could murder Curtis Green so he could get his money back.

No, DPR. Remember, Knob is literally an undercover federal agent. So Knob is loving this. He's like, yeah, I could help you out. Knob lied to DPR and said that he knew some quote-unquote pros who could get the job done for $80,000 in Bitcoin. That's expensive. You guys watch my murder mystery makeup? There was a story I did the other day where this girl offered a

this other guy, $1,000 to kill her husband. So you could get a deal in like, what was that, Alabama? Yeah. $80,000? That's a lot.

DPR agreed, anyways, on the condition that Knob sent proof of death photos of Curtis's body. Uh-oh. So Knob had a lot of evidence on this DPR guy, but there's just one big problem. Knob still had no idea who DPR even was, right? I mean, how can you arrest this guy if he doesn't know who he is? So he had to prolong the investigation by taking pictures of Curtis Green pretending to be dead.

So they put like makeup on Curtis Green and made him look dead. And they take pictures like glamour shots. And they're like, oh my God, look. And they sent them to DPR. They're like, yeah, look, dead. Now what's extra crazy about all of this is that DPR, he freaked the fuck out. He told Knob that the images were disturbing and implied that he didn't actually want the guy to be killed. Right?

He's like, you're a psycho, Knob. How could you do that? So now on top of the whole running an illegal empire charge, the FBI had solid evidence that DPR hired a hitman. And it wasn't the only time they caught him in the act because over the next few months, the FBI discovered five other instances of DPR paying someone to murder one of his enemies.

But despite all of the evidence piling up, the FBI still wasn't any closer to knowing who DPR was, okay? But then, in the summer of 2013...

They discovered a coding error on Silk Road that leaked the IP address of the website's server. Now, this might not sound like a huge deal because an IP address shows you where an internet server is located. And the FBI soon discovered that the Silk Road server was located in Iceland.

Iceland, okay. Now the FBI was fairly certain that the owner of Silk Road wasn't actually in Iceland and that the server had been like set up by someone paying a handler to run the server in another country.

So even though they knew where the server was, they decided not to take it down. They didn't want to let DPR know that they were onto him. So instead they created a mirror of it so they could see all the digital traffic coming and going. So once the FBI made a mirror, they were able to see just how big Silk Road, the Silk Road empire like had really become.

And girl, what they discovered was freaking huge. In just two and a half years, Silk Road had made over a million illicit transactions. Each of these purchases was made with Bitcoin and they equaled over $100 million in revenue. Uh-huh, that's a lot of money. But the most important lead that came from mirroring the server was access to DPR's activities.

They saw when he logged in, when he logged out, who was online currently at Silk Road, and most importantly, where Silk Road was being run. That's the most important thing. I mean, the FBI discovered that almost all of the activity was coming from a laptop in an internet cafe in San Francisco, which leads us back to Jared of Homeland Security.

By the time Jared got word that a lead was found on who DPR was in 2013, he had already made 3,600 drug seizures. Plus, he had arrested another one of DPR's top deputies, Siris. After negotiating a deal with Siris, Jared took over his screen name and started communicating with DPR for months.

As Cirrus, Jared worked with DPR on a lot of transactions, but they would even talk about more mundane things like movies they liked and what are you doing? You know, just being cute. Eventually DPR promoted Jared to assistant manager of the entire Silk Road operation and even put him on a salary. But no matter how much Jared pried, he just couldn't figure out who DPR was.

While all of this was happening, there was a massive bust on fake IDs going down in San Francisco. I mean, there were nine fake IDs that had been discovered in the mail and traced back to the same address in San Francisco.

So a team of border protection agents who weren't even like involved in the Silk Road investigation went down to the address to investigate. So they knocked on the door and when the door opened, the man pictured in the IDs was standing right there in front of them. He told the agents, quote, my name is Ross Ulbricht. It was Mr. DPR himself.

Ross denied knowing about the IDs at first, but eventually he said that he'd heard of this website called Silk Road, where you can buy anything you wanted, like fake IDs. He just wanted to help the agents however he could. Since the agents weren't part of the Silk Road investigation, this didn't raise any red flags for them, so they let Ross go and just filed a report, which made its way back to the FBI cyber branch

who was now working with Agent Jared. What a small little world, huh? When Jared heard about all this, everything started to add up, right? San Francisco, fake IDs, even the chats Jared had with DPR were timestamped with the Pacific time zone. All right.

But the final piece of the puzzle came when Jared met a special agent for the IRS named Gary Alford. The IRS was interested in collecting taxes for all that sweet drug money, so Gary's number one priority was figuring out, again, who DPR was. And like Jared...

Whenever he hit a dead end, he turned to Google and started searching for Silk Road. One day after digging almost a thousand pages back on Google, that's dedication. Because sometimes you go to page two and you're like, I'm tired, right? Yeah. I don't think I've ever gone to page three. Have you?

You're psychotic if you do. Gary, going way back, discovered postings on a Bitcoin forum that dated back to 2011. Now the person making the post was talking about magic mushrooms, asking questions about how to make them and how to sell them on the internet. And as Gary dug a little deeper, he found posts from the same users promoting a new website called, drum roll please, Silk Road.

And then Gary finally found the smoking gun everybody had been waiting for. That very same user had made a post asking for anybody familiar with web design to contact the email rossolbricht at gmail.com. Poor guy. If only he used a fake name. Darn it!

This was the first time Ross's name had ever come up in any of the Silk Road investigations. Wow. All they had to do was go back a couple pages on Google. Who would have thought? Anyways, and when Gary met Agent Jared, they started sharing their notes.

All the pieces fell into place and everybody knew the truth. The dread pirate Roberts is Ross Ulbricht. After putting out a subpoena for Ross's Gmail, they discovered that every single time Ross logged onto his computer, DPR logged onto Silk Road.

Now this was their guy. So within 10 days, the US Attorney's Office drafted a criminal complaint. The FBI got an arrest warrant and the entire investigation team headed down to San Francisco. Road trip! But first, let's pause for a little ad break.

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In order to fully nail Ross's involvement with Silk Road, the task force knew that they couldn't do like a normal knocking talk. Remember where they knock and they talk? They needed access to his laptop. Now, conventional search warrant could lead to, I don't know, Ross destroying his computer. So,

So they had to be smart about this, right? And that's where Agent Jared came in. Jared still had access to the Cirrus screen name and was still messaging DPR like almost every day. Jared was involved, let me tell you. So Jared headed down to the same internet cafe Ross hung out at in San Francisco. When he got there, Jared saw Ross leave the cafe and walk down the street to the library.

Now, undercover FBI agents followed him. Ross enters the library with his laptop and walks upstairs. He sits down and sets his laptop down next to a woman. Meanwhile, Agent Jared is down the street sitting on a park bench and he's watching his laptop to see if DPR signs online. Then, Agent Jared, he hears a ping at his computer. The Dread Pirate Roberts is online.

Yes. So Agent Jared heads inside, sits at the bottom of the stairs, and starts messaging Ross as serious. The plan was for Jared to tell Ross that there was something weird going on with one of the Bitcoin transfers, and he wanted to know if Ross could check it out for him. Now to do this, Ross had to navigate to a specific screen on the Silk Road email hub labeled flagged.

The idea was to get him to this page so when the feds swooped in and took the computer, it would be on the flagged screen and prove DPR equals Ross. So they need him to be on that screen. That's how they're going to get him. Meanwhile, there were SWAT teams on the move a few miles away heading to the library, but they were freaking all running a bit late.

All the FBI agents were getting very anxious and Ross had just finished his coffee and was like starting to get ready to leave. Mayday. Mayday. The supervisor in charge of the bus sends Jared an email saying, quote, let the guy run if you have to, but do not let that computer close. End quote. The message was clear and everybody decided, well,

Fuck the plan. Let's improvise a bit. At 3.14 p.m., Ross was in the middle of typing a message to Jared saying that the flagged section had been checked when a middle-aged man and woman started hobbling towards Ross. Now, Ross thought they were a couple of like random drunks, so he tried to ignore them. But then the woman had screamed, fuck you, right in Ross's ear. Ross turned around like just for a second.

Now remember how I said Ross sat next to a woman at the table? Yeah, well, that woman turned out to be an FBI agent. Great. Well, not great for Ross. So she snatches the computer. Ross dove across the table for his computer, but he was too late. The agent grabbed the computer.

handed it off to another agent, and the rest of the FBI on site swarmed Ross and cuffed him. While Ross was cuffed, the FBI looked at his PC and were amazed to see that the screen was still on. And the website opened on the computer? None other than Silk Road, baby. Hey. Oh, and it was logged in from the administrative side. Even better.

The team dug deeper and found fake identities, chat logs, and Ross's personal journal. One FBI agent said later that he'd never seen more incriminating information in one spot in 11 years with the FBI. The FBI arrested Ross and charged him with seven counts, including drug trafficking, computer hacking, money laundering, and a super rare charge called a kingpin statute.

which is usually reserved for mafia dons and like cartel leaders. Bravo, Ross, you made it. Just goes to show you that like what the feds thought of Ross and Silk Road, right? Ross was initially charged for the murder for hire plots too. So it's just like not looking good for him. Most of those charges ended up being dropped, but one is still pending. I mean, to this day, everybody who had known Ross was in complete shock.

Shock. Ross? The Dread Pirate Roberts? Inconceivable. Ross smoked a ton, a lot of weed, drove an old car, and his friends called him Rossman because of how chill he was. How could this guy be a criminal kingpin? There's just no way. It didn't make sense. Eagle Scout? Come on. Come on.

Come on. The trial came in January of 2015. The defense argued that Ross did in fact create Silk Road, but had handed it off to others, who then lured him back in to take the fall. Now this had been called the Dread Pirate Roberts defense, and well...

It didn't work. The prosecution responded with hundreds of exhibits, including testimony from frigging agent Jared about the bust and his time as Ross's right-hand man. And there were like chat logs straight from Ross's computer.

And lawyers read aloud from Ross's personal journal. I mean, the evidence was so overwhelming that after only 12 days of trial, the jury found Ross guilty on all counts, sentencing him to two life sentences plus 40 years. And since he was tried federally, he was not eligible for parole, but he got to go to a nicer prison. And they get free healthcare. The only place you get free healthcare in America, in prison.

The Silk Road fiasco made a huge impact we're still feeling today. I mean, cryptocurrency is more popular than ever and has expanded way past Bitcoin. I mean, have you been to the movies lately? There's a commercial for cryptocurrency playing in between movie trailers starring none other than Matt Damon. At the end of the commercial, he's like, "Buy crypto because fortune favors the brave." Whatever the fuck that means.

So yeah, Silk Road didn't hurt crypto at all. If nothing else, the media circus brought Bitcoin to like a way bigger audience and made drugs accessible. And even though Ross was arrested, the dark web didn't go away. In fact, some of Ross's former employees started a website called Silk Road 2.0 a month after he was arrested.

At the time, it was the most successful site on the dark web, but it shut down just a year after it began. Even as recently as 2021, websites like Dark Market popped up that follow Ross's Anything Goes retail model with like a twist.

They banned weapons and fentanyl, among other things. Unfortunately, Dark Market ended up being a bit disappointing too. With all its success at its peak, Dark Market also only managed to gain a fraction of the web traffic Ross's website did. That said, some of the Silk Road successors got much bigger. They learned from Ross's many fuck-ups.

AlphaBay sold close to half a billion dollars worth of drugs and other illicit goods before getting shut down. And even as recently as 2021, law enforcement agencies across three continents came together to bust a dark web drug ring that saw more than 150 arrests and over $3 billion in Bitcoin. So Ross and his creation continue to have an impact.

Damn, how can I find these websites? Let me know down below. Let me know. Send me the links, thank you, for research. Anyways, you guys, wasn't that a fun story? I just love talking about drugs. And honestly, like, really interesting.

- Mm-hmm, great. So here's my biggest problem with this story and stories similar to it. When you Google drug deals on the internet, almost every story is about busts on the dark web. When you change your search to say drug deals on Facebook,

You can find a 2021 report that found thousands of posts on Facebook, Instagram, and other social media websites selling heroin and other opioids. One of the Instagram posts from early 2020 was live for over a year. I'm not here to demonize anybody for using or selling drugs. Uh-uh, nay-nay. And Silk Road clearly had a flaw in the whole anything-goes approach to retail.

Murder for hire happened because of Silk Road in case you forgot. I mean, if they would've just dropped that, it would have been okay, right? ♪ Bring it back, bring it back ♪ Plus, it's not just drugs you can find on social media. A 2020 report on human trafficking showed that over 40% of defendants in active sex trafficking cases met their victims on social media. Almost 60% of victims were recruited on Facebook.

The point is a lot of really sketchy shit happens on social media on the normal internet, okay? So why don't we kind of fix that first? Just a thought. But nobody comes to me for answers.

What do I know? So just because it's called the dark web, that's not the only place dark shit happens. The problems faced on Silk Road exist on the normal internet too. And there's way more people on social media than there are on the dark web.

Plus, judging by the numbers I said earlier, it may be even worse, right? Yeah. Well, everyone, thank you for learning with me today. Let me know what you learned down below. Remember, don't be afraid to ask questions to get the whole story because you deserve that. Now, I'd love to hear your reactions to this story, so make sure to use the hashtag darkhistory so I can follow along. Join me over on my YouTube where you can watch these episodes on Thursday after the podcast airs.

And also catch Murder, Mystery, and Makeup which drops every Monday. I hope you have a great day today. You make good choices. And I'll be talking to you next week. Goodbye.

Dark History is an Audioboom original. This podcast is executive produced by Bailey Sarian, Kim Jacobs, Dunja McNeely from 3Arts, Justin Cummins, and Claire Turner from Wheelhouse DNA. Produced by Lexi Kiven. Research provided by Tisha Dunstan. Writers Jed Bookout, Joey Scavuzzo, and Kim Yeagid.

Edited by Jim Lucci. Shot by Tafazwa Nemarudwe. And a big special thank you to our historical consultant, Nicholas Christian. And I'm your host. Why am I last? God damn it. I'm your host, Bailey Sarian. Goodbye.