Pod Insights Killer Stories with Harvey Guillén The Dread Pirate Roberts and the Silk Road: Anatomy of a Darknet Killer About this episode A libertarian idealist known only as “The Dread Pirate Roberts” builds the Silk Road—an anonymous online black market that explodes into a billion-dollar empire—until the digital kingpin is unmasked, revealing how one man’s dream of radical freedom spiraled into crime, paranoia, and downfall.
Sources for this episode include:
American Kingpin by Nick BiltonJoshuah Bearman’s reporting for Wired magazine
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Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:06 Harvey Guillén? I've always loved a good mask, not the scary kind, the theater kind, the kind that lets you try on someone else's face for a while, just to see how it fits. When the internet shows up, it hands everyone a mask. Usernames instead of real names, avatars instead of faces, encrypted accounts instead of a paper trail. A space where anyone, idealists, criminals, even government agents, can slip into a role no one could see. And in that world, one mask stands out. It belongs to a young guy named Ross Ulbricht, or as the internet comes to know him, the Dread Pirate Roberts.
0:48 Harvey Guillén? Under that name, he becomes the faceless king of Silk Road, this hidden online marketplace built for people who never want their names on anything. Some people see Ross as a kind of a digital freedom fighter. Others see him as a criminal mastermind. And here's the thing, he's not the only one in costume. I'm Harvey Guillén, and this is Killer Stories.
1:36 Harvey Guillén? It's early 2011. The internet isn't quite what we know it as today. Instagram has only been around for a few months. Snapchat doesn't even exist. And Bitcoin is trading for just a few dollars. The average person has heard of the dark web, the hidden corners of the internet that seem mythical. But for most people, it feels like a curtain they don't want to peek behind. But others find the open web suffocating. They don't want the government, corporations, or social media tracking them. Enter Tor, an encrypted network browser that, at the time, was mostly used by hackers and dedicated activists. It routes traffic through multiple servers masking who and where you are.
2:22 Harvey Guillén? Somewhere inside Tor is a new website, an anonymous marketplace for people who want to stay in the shadows. It's called Silk Road. It works kinda like Amazon if Amazon sold drugs, forged documents, and just about anything else you don't want associated with your real identity. So you do your online shopping and, you know, add cocaine and a fake ID to your cart, then message the seller through an encrypted inbox. But unlike Amazon, you don't pay with a credit card. You pay through Bitcoin, which at the time is widely believed to be untraceable. Once you get your secret package in the mail,
3:06 Harvey Guillén? you can even leave a review for the seller. Five stars, very discreet, would commit a felony again. At the center of it all is Ross Ulbricht, the creator of Silk Road. But just like everyone else on Tor, he doesn't use his real name. Instead, he goes by an alias, lifted straight from The Princess Bride, the Dread Pirate Roberts. To the people using Silk Road, Dread Pirate Roberts isn't just a site admin. He's kind of a prophet. He writes long posts about freedom and why he thinks the government should stay out of people's choices. He says every transaction on Silk Road is a way to push back against the man.
3:51 Harvey Guillén? And even though what he's doing is illegal, Ross doesn't present himself as a criminal. He thinks he's building a better world, and in a way, he's not totally wrong. The Silk Road is known for having surprisingly low levels of violence and fraud compared to real-world street drug markets. This is because Ross establishes and enforces a clear set of rules: no weapons, no child exploitation, and no stolen goods.
4:23 Harvey Guillén? People buy into Ross's philosophy and make the Silk Road a huge success. By the spring of 2012, Silk Road has tens of thousands of active buyers and sellers for more than a dozen countries. At its peak, analysts estimate Silk Road moved over $1 billion in total sales. Every transaction kicks a percentage back to Ross. At a moment when most 27-year-olds are staring down student loans and unpaid internships in the shadow of the 2008 recession, Ross is taking home around $80 million in commission. He's earning more money than most CEOs from a laptop.
5:07 Harvey Guillén? He's basically the Jeff Bezos of contraband. And yet, none of it looks like money. Ross lives in a small apartment in Austin, Texas. He's living out of two garbage bags, one for clean clothes, one for dirty. His wardrobe is minimalist: hand-me-down shirts, hand-me-down socks, hand-me-down... let's just stop there. You'd never guess he's running the most successful illegal marketplace on the internet. His alter ego Dread Pirate Roberts allows him to compartmentalize his life. In The Princess Bride, the title gets passed down from person to person. The mask stays alive even when the man underneath it disappears. Ross likes that idea.
5:52 Harvey Guillén? If something ever goes wrong, maybe the blame could go elsewhere. Maybe no one could pin it on him. After all, only two people in the world know he's behind Silk Road. For a while, the separation works. Ross is Ross in the real world, quiet and unassuming, and on Silk Road, he's a hero creating a new society. But while Silk Road keeps growing, the cracks are already forming. The first serious problem doesn't come from some angry cartel leader or a rival darknet site. It comes from a man who doesn't fit into any of those worlds at all. His name is Curtis Green.
6:38 Harvey Guillén? Curtis lives in Utah. He's a 47-year-old Mormon, husband, and father. Not exactly who you picture when you imagine a dark web lieutenant. Curtis finds Silk Road the same way a lot of users do: through online drug forums and word of mouth. He's living with chronic pain ever since his back injury ended his career as an EMT. He's on disability, stuck at home more than he wants to be, so he does what a lot of people would do in that situation. He spends a lot of time on the internet. Because of his injury, Curtis reads obsessively about medications, especially opiates. He wants to understand how they work,
7:22 Harvey Guillén? how tolerance builds, and how things go wrong when people don't know what they are doing. It's less party culture and more consumer safety manual. He's also interested in psychedelics and spends time on online forums with wild names like The Shroomery. It's in one of these forums that he finds out about Silk Road. He chooses the username Chronic Pain and starts browsing. Curtis isn't really interested in buying or selling. He's there for the community. And because he fancies himself an expert on harm reduction, he starts answering questions and giving advice. He's warning people about fentanyl and teaching safe drug habits.
8:07 Harvey Guillén? At one point, he has to clarify to someone that injecting peanut butter or shooting heroin into your eyeballs is, in fact, a terrible plan. This was the exact thing Ross liked to see. Silk Road isn't supposed to be chaotic. It's orderly and controlled, almost responsible. Before long, Ross notices Curtis educating users, so he offers him a job as an admin. Curtis becomes kind of a customer support guy for the site. Suddenly, he's working 80-hour weeks from his couch, mediating disputes between buyers and sellers and resetting passwords. But there's a catch.
8:51 Harvey Guillén? Ross asks Curtis for a scan of his driver's license. It's presented as a loyalty test, a way to ensure everyone on the inside is accountable. Curtis hesitates. He understands the risk of being exposed while Ross gets to keep his identity secret. But he also believes they've built a trusting relationship, so he sends the scan. And then, a few months later, chronic pain, aka Curtis, goes offline.
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11:55 Harvey Guillén? Curtis Green is at home when the package arrives. It's around 11:00 AM in January 2013. Curtis is half awake, but he slumbers to his front door and collects the mail. The box is heavy. There's no return address, but it's postmarked from Maryland. Well, Curtis hasn't ordered anything from Maryland, but he brings it inside. He opens a box with scissors and
12:21 Harvey Guillén? white powder explodes into the air. It coats Curtis's face, his shirt, his hands, his tongue goes numb. And before his brain can catch up to what's just happened, someone bursts through the front door. Men in tactical gear flood the house. They've got their guns out and they're shouting. Someone yells for Curtis to get on the floor! And then, he's handcuffed. He's blinking through white dust, trying to process what on earth is happening.
12:54 Harvey Guillén? Curtis is taken to the police station. It turns out, the package contained high-grade cocaine. More than a kilogram of it. Enough to justify a serious charge. Enough for authorities to get some leverage. The officers start interrogating him. "Where did you get the cocaine? Who do you work for? Who is Dread Pirate Roberts?" Curtis keeps saying the same thing. "He didn't order this massive box of cocaine. He doesn't know where it came from. He doesn't buy or sell drugs. He's just a guy who answers questions online." He insists, "It's a mistake. They've got the wrong guy." But, it's not a mistake at all. It's a setup.
13:39 Harvey Guillén? Back in April 2012, a new message landed in Ross's inbox. Not his real inbox, the one on Silk Road, where he goes by Dread Pirate Roberts. The message came from someone with the username Nob. It read, "Mr. Silk Road, I am a great admirer of your work. Brilliant, utterly brilliant. I will keep this short and to the point. I want to buy the site. I've been in the business for over 20 years. Silk Road is the future of trafficking." Ross is flattered and curious. The next day, he wrote back to Nob, "I'm open to the idea. Uh, what did you have in mind?" But Nob isn't really a Dread Pirate Roberts fanboy.
14:24 Harvey Guillén? He's actually a DEA agent named Carl Force. He's messaging Ross from Baltimore, where he's been investigating the Silk Road for months. Agent Force, which, come on. Is that not a perfect name for law enforcement? Agent Force! Anyways, Agent Force has done undercover work before. He knows how to make himself sound credible. As Nob, Force messages Ross back. He tells him he made a fortune through a decades-long drug smuggling career. He's well-funded and well-connected. And he's serious about the offer.
15:05 Harvey Guillén? The next day, Ross tells the agent that the Silk Road is bigger than money. It's a movement, so it's not really for sale. Unless Nob happens to have a casual one billion. So Force changes his strategy. He stops asking to buy the site and instead positions himself as a partner. Someone useful who can bring even more growth to the Silk Road. Over the next few weeks, Ross and Agent Force trade messages back and forth, never knowing exactly who is on the other end. But they don't just talk business. They kind of become friends. They start talking about life.
15:46 Harvey Guillén? Not anything with details like locations or names, nothing that would blow their cover. But Ross tells Agent Force about his paleo diet, and Force tells Ross to skip the latest Batman movie because The Dark Knight Rises, he did not like. By the end of 2012, Force is one of Ross's most trusted contacts. So Force says it's time to act. He submits a proposal to his superiors. He thinks he knows exactly how to catch the Dread Pirate Roberts. To move the plan forward, Agent Force reaches out to Ross with a problem. He tells him he's looking to move a kilo of cocaine quickly and quietly, and he wants to know if the Silk Road can help.
16:31 Harvey Guillén? Ross doesn't hesitate. Of course it can. This is literally the business. He's running the Amazon of drugs. You need something discreet, well-reviewed, and delivered on time. Ross is your guy. Within a few days, the deal is arranged. Because the quantity is large and because Force claims he doesn't know the buyer personally, he asks Ross for a favor. He wants a trusted middleman, someone inside the operation. Ross suggests one of his own people. An admin who's proven himself over and over again.
17:08 Harvey Guillén? Chronic Pain, AKA Curtis Green. The plan is simple. Agent Force ships the kilo to Curtis. Curtis holds the package. Once the buyer sends payment, the drugs get forwarded to their final destination. Clean, controlled, and professional. Exactly the kind of system Ross prides himself on. Except, none of this is really about selling cocaine. Force is using the deal as bait. The moment the package lands, the DEA plans to raid the house and arrest Curtis. They're hoping they can get him to talk. Curtis is one of Ross's direct reports. He has access.
17:50 Harvey Guillén? He understands how Silk Road actually runs. Even if he can't name the man behind the mask, he can still bring investigators closer than they've ever been. The plan goes off without a hitch. And that's how Curtis landed in a police interrogation room, covered in cocaine. Meanwhile, Ross has realized something is very, very wrong. He's expecting an update on the deal with Knob, but he hasn't heard from Curtis in hours. Ross sends message after message. Silence. Two days later, the situation gets worse.
18:34 Harvey Guillén? A huge chunk of Bitcoin vanishes. And he traces the theft straight to Chronic Pain's admin credentials. From Ross's point of view, his trusted employee has gone rogue. In reality, Curtis hasn't touched a thing. Someone is using his credentials to access the funds. Well, we'll get to that later. But Ross doesn't know that. Mm-mm. All he sees is betrayal layered on top of disappearance. Then comes the final gut punch.
19:11 Harvey Guillén? Less than a week later, a Google Alert lands in Ross's inbox. It's tied to Curtis's real name, which Ross had demanded as a condition of employment. The alert links to a news article announcing Curtis's arrest. And there it is, buried in the copy. Silk Road: Mentioned by Name. Now Ross isn't just dealing with a missing employee. He's staring down the possibility that his entire operation could unravel because one person got caught and decided to save himself. At this point, Ross turns to his newest confidant, his late-night sounding board, Knob.
19:55 Harvey Guillén? Ross has no idea that Knob is actually Carl Force, the same DEA agent who orchestrated Curtis's arrest. So the two of them talk it through, like partners. What matters more right now? Getting the money back or sending a message? Knob tells him he knows people who can handle either problem. Ross types back that he wants Curtis beaten up. Don't kill him, just scare him. Because, here's the thing. The money itself isn't really the issue. $350,000 might sound enormous, but for Ross at this point, it's not catastrophic. What really stings is the backstabbing.
20:36 Harvey Guillén? He'd shown Curtis kindness, trust, and opportunity. And in Ross's mind, that generosity had been repaid with betrayal. As Ross waits for Knob to make arrangements, he vents to another longtime confidant, Variety Jones. He admits this is the first time he's had to call in muscle, and he hates it. This isn't who he thought he was. I mean, Silk Road was supposed to be different. Variety Jones doesn't agree. He reframes it for Ross. This isn't philosophy class. This is the criminal underworld. And Ross isn't just a guy with ideas anymore. He's running an empire.
21:20 Harvey Guillén? Curtis didn't just steal from him, he disrespected him. And at some point, Jones asks, "Don't you have to decide when enough is enough?"
21:32 Harvey Guillén? Ross reaches back out to Nob. He changes the order. Can you change it to execute rather than torture? On the other end of the keyboard, Agent Force doesn't hesitate. He tells Ross it won't be a problem. He knows someone who can handle it for about $80,000. As they discuss logistics, Ross reassures himself in writing. He says he's never killed a man or had one killed before. But this is different. Curtis was on the inside. He knows way too much.
22:14 Harvey Guillén? And when Ross logs off, believing he's just crossed a necessary line, Carl Force does something else entirely. He opens a new document and starts drafting a plan to fake an assassination.
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23:33 Speaker 03 Witness the beginning of the revolution.
23:37 Speaker 04 Hey Mitch, you've been trying to take down these games from the start.
23:39 Speaker 03 Film for IMAX.
23:41 Speaker 04 Make them remember you.
23:44 Speaker 03 The Hunger Games: Sunrise on the Reaping, November 20th, rated PG-13.
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24:20 Harvey Guillén? Curtis Green is dead. Or at least, that's what Ross Ulbricht thinks. He's staring at a series of photographs on his screen. They show Curtis lying motionless on a tile floor. His hair soaked, face pale. There's water everywhere. It looks like a body fresh out of a drowning. The man Ross thinks he's hired to solve a problem, a drug smuggler named Nob, is actually a DEA agent named Carl Force. The same Carl Force who helped set Curtis up in the first place is now helping stage his assassination. And in case you're wondering, "Who approved this?", the answer is, nobody.
25:05 Harvey Guillén? Agent Force didn't ask his supervisors for permission. He's gone totally rogue.
25:13 Harvey Guillén? Just a few days before Ross received those photos, Curtis was at a hotel room in Provo, Utah. At this point, Ross had only ordered Nob to torture Curtis. He didn't want him dead. Well, not yet. Force convinced Curtis to go along with a fake torture plan. He framed it as part of a undercover operation, something that will push Dread Pirate Roberts into revealing himself and how the Silk Road actually works. Something that, in the long run, could help Curtis. It's not like Curtis is thrilled about the idea of faking his own torture, but he has no leverage. Saying no doesn't feel like an option. So, he agreed.
25:57 Harvey Guillén? Force and another DEA agent fill the hotel bathtub with water and walk Curtis through the plan. Hold your breath, go under, don't fight. We'll pull you up before it gets too bad. The other agent, posing as one of Nob's thugs, pushes Curtis underwater. Curtis realized far too late that fake drowning doesn't feel fake when your lungs start filling with water. He started panicking. The agents lifted him back up, but it's not because Curtis was drowning, it's because Carl wanted another take. And look, I know this sounds like a deleted scene from some VHS mob movie, but unfortunately, it's real.
26:38 Harvey Guillén? This is what law enforcement came up with: a staged bathtub waterboarding with a hotel towel rack in the background. They dunk Curtis again. This time, the cameras kept rolling. Curtis choked out the lines they gave him. I didn't take the money! Eventually, Force was satisfied with the take, and the torture scene is over. Cut! That's lunch, everyone! But shortly after, Agent Force got the message from Ross. He changed his mind. He didn't just want Curtis tortured, he wanted him dead. By this time, Agent Force was already back in his office in Baltimore, so instead of
27:20 Harvey Guillén? flying back to Utah, he sent Curtis detailed instructions. There's no way to even paraphrase the message, so here's what Agent Force told Curtis. Dunk your head in water as if you were being drowned, then pop open a can of Campbell's Soup, a tomato flavor, and then pour that soup out of your mouth like you died from being held underwater. And there was a mucus-like eruption from your mouth. So, we have something to show, and then have your wife snap a picture of your lifeless body with your cellphone.
27:55 Harvey Guillén? Curtis and his wife followed the instructions to a T. The scene was set, tomato soup and all. Curtis played his part, oh, as a corpse, Academy Award winning, and his wife snapped the photos. Those images are what's now in Ross's inbox. Ross receives the images from the same account he's been communicating with for weeks, Knob. He writes back that the photos disturb him, as if he's not the one who ordered the murder to begin with. Ross sends Knob $80,000 via Bitcoin to pay for the hit. And that's the entire exchange. Like he ordered a new pair of shoes rather than a murder.
28:40 Harvey Guillén? Here's the turning point. It's a moment where Ross could have backed away, shut the laptop, deleted the files. Instead, it does something else. It flips a switch. Within hours of receiving the photos, Ross is already justifying the murder to his partner, Variety Jones. He says Curtis brought it on himself. Betrayal has consequences. This is the cost of leadership. Sometimes you have to make hard decisions like drowning a guy who steals your money. You know, CEO stuff. But remember that after Curtis got arrested, a big chunk of Bitcoin was stolen from the Silk Road. Well, Ross assumed it was Curtis, but it wasn't.
29:24 Harvey Guillén? It turns out Carl Force isn't the only rogue law enforcement agent involved in the Silk Road case. His name is Sean Bridges. He's a special agent with the United States Secret Service. He's part of the same team as Agent Force, the one assigned to take down the Silk Road. But instead of taking down the Silk Road, Bridges decides to take from the Silk Road. After Curtis is arrested, Agent Bridges gets his internal admin credentials and, like a kid in a candy store, he does ...to help himself.
30:06 Harvey Guillén? Bridges logs in, asks Curtis, and starts stealing Bitcoin from the site. Hundreds of thousands of dollars' worth, $820,000 to be exact, all deposited into his personal accounts. And if you're asking, "Wait, isn't that illegal?" The answer is yes. Very much so. But we'll return to Sean Bridges and the stolen money later. Let's return to Ross. He's emboldened by the supposed murder of Curtis Green, who he thinks betrayed him. So now he has murder in his back pocket, something he can use when he feels someone has wronged him, like a Silk Road user with the name Friendly Chemist.
30:50 Harvey Guillén? He's a hacker, and he's threatening to reveal personal data about users on the Silk Road. Friendly Chemist demands half a million to keep quiet. He says he's got real names and shipping addresses. If this information gets out, it would destroy Silk Road's most important promise: privacy. Ross panics, and then he reaches out to a user who goes by Red and White. This guy claims to be affiliated with the Hells Angels, claims he can make problems disappear. Ross gives him Friendly Chemist's name and location in Canada. For $150,000 in Bitcoin, Red and White says the job is done.
31:33 Harvey Guillén? A few days later, Red and White messages Ross again. There's a problem. Apparently Friendly Chemist wasn't acting alone. He had four other associates, each of whom also had access to the stolen data. Red and White asks what Ross wants to do. Ross doesn't hesitate. He authorized four more hits. He wires over half a mil in Bitcoin. And in his personal log, Ross even notes the expense, right next to a to-do list about debugging Silk Road's front page. You know, just business as usual. Friendly Chemist's identity remains a mystery to this day. And rest assured, no one was actually killed. But Ross believes they were.
32:16 Harvey Guillén? And the fact that he thinks he's ordering murders, five of them, is more than enough for prosecutors. At this point, Ross is making six figures a week in Bitcoin commissions, but running a billion-dollar operation from behind a laptop is exhausting and dangerous, especially when you're living like a couch-surfing minimalist. Ross has no permanent address. He's left Austin. He's crashing in a friend's spare bedroom in San Francisco, and he's constantly on edge, worried someone will connect the dots. In June 2013, he decides it's time to separate his two lives.
32:59 Harvey Guillén? He finds a room to rent on Craigslist and pays $1,200 in cash. He introduces himself to the landlord as Joshua Terry, a currency trader from Texas. Ross vows not to let anyone from his old life know where he lives. No real names, no loose ends. He wants a clean break, a private hideaway where Dread Pirate Roberts can run his empire without blowing Ross's cover. Once he settles into the new apartment, he starts preparing for the worst. He orders nine fake IDs from a Silk Road vendor. Nine different names, nine different states and countries, all just in case he needs to bolt.
33:44 Harvey Guillén? But the vendor is popular, a little too popular. On the day Ross's envelopes arrive at the San Francisco airport, several identical packages also come through customs. They're oddly shaped, and they all have similar handwriting, but different return addresses: Colt Harris, Arnold Harris, Bert Harris, all from Vancouver. That's enough to raise a red flag. Customs open the envelopes and find stacks of fake IDs. Ross's package stands out because of the sheer number of fakes inside. His name is flagged for follow-up. On July 26, 2013, Ross is home alone.
34:28 Harvey Guillén? He's typing away at his laptop, making updates to the site when there's a knock at the door.
34:35 Harvey Guillén? It's a federal agent posing as a mail carrier. He's here to talk about the fake IDs. Ross talks his way out of it, barely. But the incident confirms what he's been feeling for months. He's being watched. From here, the walls start to close in. Investigators track Ross's movements. They build a digital map of his logins, messages, and transactions. They piece together how the Silk Road works and who's really behind the mask. In October 2013, Ross walks into a public library in San Francisco. He sits down with his laptop, just another day at the office.
35:20 Harvey Guillén? Moments later, a team of agents surrounds him. One grabs a laptop before he can shut it. It's still open to the Silk Road admin page. When agents sort through the files, they find everything. The murder-for-hire messages, the chat logs with Knob, even a list of countries without extradition treaties, bookmarked no less. There are even diary entries that complain about how hard it is to be a digital drug lord. For someone so obsessed with living a quiet, secret life, Ross left a shocking amount of receipts. Ross is arrested and charged with conspiracy to commit money laundering, computer hacking, and drug trafficking.
36:04 Harvey Guillén? He isn't charged for the murder-for-hire scheme since no one actually died, but federal prosecutors use the information to argue he's dangerous during his trial, which starts in January 2015. Ross pleads not guilty. His defense rests on the same idea he's been seeding for years. He may have built the Silk Road, but he didn't run it. He created the system and then handed over the keys. Someone else became the Dread Pirate Roberts. Someone else should go to prison, but he never says who. The jury doesn't buy it. On February 4th, 2015, Ross is found guilty of seven federal felonies.
36:49 Harvey Guillén? At sentencing, Ross is 30 years old. He tells the court he regrets what he did. He asked for leniency. But Judge Catherine Forrest doesn't see a man swept up in something bigger than himself. She sees a man who built something enormous and kept going, even when it turned dark. "You are no better a person than any drug dealer," she tells him. "You were captain of the ship as the Dread Pirate Roberts, and you made your own laws." Then she sentences him to life in prison without the possibility of parole. As for the other players in the story, well, they don't get away clean either.
37:34 Harvey Guillén? Carl Force, the DEA agent who posed as Nob, ends up facing charges of his own. Turns out, the temptation was too much. He'd been moonlighting during the investigation, shaking Ross down for Bitcoin under other usernames and pocketing the money. Oh, and don't forget the whole fake assassination plot. He'd essentially waterboarded a key witness in the case. When it all comes out, Force is sentenced to more than six years in federal prison. Then there's Shawn Bridges, the Secret Service agent who stole over $800,000 in Bitcoin from the Silk Road while pretending to investigate it. He got caught too.
38:19 Harvey Guillén? He's sentenced to 71 months in prison. And finally, there's Variety Jones, well, real name Roger Thomas Clark, the man who helped Ross through the site's rise, the one who convinced Ross that Curtis Green needed to die. In 2023, he was sentenced to 20 years in prison.
38:42 Harvey Guillén? And speaking of Curtis Green, well, he lived. Despite being in the crosshairs of one of the weirdest murder-for-hire plots in internet history, Curtis made it out the other side. He was sentenced to time served and put on probation. He later co-wrote a memoir called Silk Road Takedown, where he talks about his arrest, his time working for the site, and the bathtub torture scene that, yes, really happened. It's all there. He also joined Twitter, and if you scroll far enough, you'll find him cracking jokes about tomato soup and waterboarding and, oh, this one time when he had to play dead for
39:22 Harvey Guillén? a fake murder photo shoot, because honestly, what else can you do but laugh? And that could have been the end of the story, but the Silk Road trials do something strange. They turn Ross into a symbol. In the months and years that follow, supporters rally around his case. They say he wasn't Dread Pirate Roberts, or if he was, he shouldn't be imprisoned for life. They argue the system went too far, that he was made into an example. His family launches a site called FreeRoss.org. They push for clemency, they raise money. The case becomes a cause. Meanwhile, the Silk Road doesn't disappear.
40:07 Harvey Guillén? New versions pop up, the next generation of darknet markets, and while most of them get shut down eventually, the idea doesn't go away. The toothpaste is out of the tube. Ross was supposed to die in prison, life without parole. But on January 21, 2025, something unexpected happened. Just one day after taking office, President Donald Trump announced that he had granted Ross a full and unconditional pardon.
40:40 Harvey Guillén? He'd been hinting at this move for months. During a speech at the Libertarian National Convention, he called Ross's life sentence ridiculous and promised to "set Ross free." Now, he kept that promise. And he wasn't alone. Libertarians and digital privacy advocates had been campaigning for years. They argued that the punishment didn't fit the crime, that the Silk Road was more of a philosophy experiment than a criminal empire. Yes, they argued that Ross had made a mistake, but he didn't deserve to die in prison for them. And now, he won't. At the time of his release, Ross had served nearly a decade of his life sentence.
41:24 Harvey Guillén? He walked out of prison, still in his 30s, with the rest of his life ahead of him. People still argue about who Ross really is. Some call him a digital pioneer who believed the internet could be a freer, fairer place. Others see him as a kingpin in coders' clothing, the architect of a billion-dollar empire built on drugs, fake IDs, and stolen data. But, like most things on the internet, his story doesn't fit neatly into either myth. Because Silk Road didn't fall apart because one mask slipped, it fell apart because everyone was wearing one.
42:07 Harvey Guillén? Ross, the agents, the users, the guy ordering a hit, and the guy faking his own death with tomato soup. Nobody was exactly who they claimed to be. And in a world where you never have to show your face, it turns out, the lies don't just fool other people. They start to fool you, too. And that's the trouble with masks. They're easy to put on, but harder to take off. And after a while, you start to forget where the performance ends, and the person begins. Thanks for tuning in to Killer Stories, a Spotify podcast. New episodes release on Mondays.
42:52 Harvey Guillén? If you liked today's story and want to learn more, we drop some of our favorite sources in the episode description. Until next time, I'm Harvey Guillén. Stay safe out there.
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