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Due to the graphic nature of this episode, listener discretion is advised. This episode features discussions of substance use and violence that some listeners may find offensive. Consider this when deciding how and when you'll listen.
Curtis Green was drowning. His lungs burned, deprived of oxygen, filling his chest with fire. He thrashed and flailed in the tub, trying to break free, but he was helpless. His screams trapped in bubbles, unable to reach the surface. His torturer's elbows dug deep into his spine, keeping him submerged, fanning the flames in his lungs.
Then, the Torturer grabbed a fistful of Curtis' hair and yanked him out of the water. Curtis gulped in air, trying to extinguish the fire in his lungs. Another man shoved a camcorder into his sopping, sputtering face. The Torturer was secondary to getting the shot, because in truth, the drowning was all for show.
The videographer, DEA agent Carl Force, clucked an annoyance and stopped the recording, rewinding the tape. He shook his head. "I think we should do it again." Before Curtis could protest, the torturer dumped him back underwater. Force pressed the red record button and explained, "We have to make it look real." Months of undercover work on the Silk Road had finally paid off for Agent Force.
This staged waterboarding would bring him closer to bringing down the man he knew only as the Dread Pirate Roberts. He was about to catch the untraceable kingpin of the Silk Road.
Welcome to Conspiracy Theories, a Spotify podcast. I'm Carter Roy. You can find us here every Wednesday and be sure to check us out on Instagram at The Conspiracy Pod. And we would love to hear from you. So if you're listening on the Spotify app, swipe up and give us your thoughts. This is our final episode on Ross Ulbricht, also known as Dread Pirate Roberts and his online black market, The Silk Road.
Last week, Ulbricht built an anonymous marketplace where consumers could escape the watchful eyes of the government and companies looking to mine their data. This week, it all comes crashing down. Stay with us.
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Hello there, I'm Mike Flanagan, and welcome to Spectre Vision Radio's production of Director's Commentary. Director's Commentary is a deep dive into a film through the eyes of the filmmaker or filmmakers who made it. It combines an in-depth interview format with a classic Director's Commentary track, the likes of which used to be common on physical media releases, but sadly are becoming more and more rare these days. Filmmakers talking about film with filmmakers. For people who love film.
and filmmakers. Before we get into this story, amongst the many sources we used, we found Joshua Behrman's reporting for Wired Magazine and Nick Bilton's book American Kingpin extremely helpful to our research. If you're a Spotify Premium subscriber, you can listen to Bilton's audiobook for free. Check the link in our show notes.
By January 2013, nearly two years after its launch, the Silk Road was making money hand over fist. It was a virtual black market where anyone could sell anything anonymously. 28-year-old Ross Ulbricht, the site's creator, had banked millions of dollars in untraceable Bitcoin from his share and commissions.
But just because Ulbricht's Bitcoin fortune was untraceable didn't mean it was safe. Neither was his business. The site was under constant assault by hackers,
Every other day, the Silk Road sprang another security leak, letting in malicious web bandits. Even with extra support staff, Ulbricht was deluged with threats. He was currently being blackmailed by a few especially aggressive hackers who repeatedly knocked the Silk Road offline. Eventually, Ulbricht agreed to pay the hackers $50,000 a week to stop. The situation made him furious.
But his friend and sometimes mentor, username Variety Jones, reassured him. This was the cost of doing business. Think of it as protection money, but even worse than the outside threats. Ulbricht was dealing with treason from one of his lieutenants, username Chronic Pain, who'd recently been arrested by the DEA.
Ulbricht worried that Chronic Pain would strike a deal for leniency in exchange for information on the Silk Road's inner workings. Shortly after the arrest, Ulbricht discovered that Chronic Pain had walked off with a cool $350,000 from various users' accounts. It wasn't the money that Ulbricht chafed at — he was a millionaire now — it was the disrespect.
Ulbricht reached out to another friend from the Silk Road, username Nob, asking for help organizing retaliation. Ulbricht believed that Nob was a drug lord moving millions of dollars worth of heroin and cocaine every year. In reality, Nob was undercover DEA agent Carl Force. So when Ulbricht asked him if he knew anyone who could beat up Chronic Pain and make him return the money he stole, Force was delighted.
It only added to the mounting pile of evidence of Ulbricht's drug trafficking and kingpin crimes. Force and another agent staged a video where they waterboarded chronic pain, real name Curtis Green. But even though the circumstances were fake, the torture was, as Green said, a little too realistic. We'll leave you to your own judgments of Agent Force's strategy. Before Force sent the torture tape,
Ulbricht changed his mind. He didn't just want Chronic Pain roughed up. He wanted him dead. Forrest agreed to arrange the hit for $80,000. And now he had Ulbricht on record plotting a murder. Forrest sent Chronic Pain a list of instructions to fake his death. As laid out in Nick Bilton's book, American Kingpin, Forrest told him...
"Dunk your head in water as if you've been 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. Finally, so we have something to show, have your wife snap a picture of your lifeless body with your cell phone." Green followed the instructions to a T. When Force sent the stage photo to Ulbricht,
The kingpin didn't reply for a few moments, seemingly shaken by the disturbing image. Filling the silence, Force typed that the torturers brought Chronic Pain back with CPR a few times to draw out the pain, but eventually his heart gave out. When Ulbricht didn't say anything, Force asked if he was alright. Ulbricht typed, "A little disturbed, but I'm okay. I'm new to this kind of thing is all."
But Ulbricht was only rattled by death for so long. Once he got used to the idea, he was emboldened by his first murder-for-hire. Ulbricht started blaming Chronic Pain for his own death. If he had had more integrity, Ulbricht wouldn't have been forced to kill him. When Ulbricht echoed this sentiment to Variety Jones, he agreed. Jones wouldn't lose any sleep over Chronic Pain's death.
Business was business. And the next time Ulbricht felt his empire was threatened, he easily dealt out another death sentence. According to Joshua Barrowman's reporting in Wired Magazine, the next threat was existential. A dark web bandit, username FriendlyChemist, threatened to release the real names and addresses of hundreds of Silk Road users hacked from the site.
This would compromise the entire purpose of the Silk Road, unless Ulbricht forked over $500,000. Ulbricht reached out to username RedAndWhite, who claimed to be a member of the Hell's Angels biker gang. Ulbricht had already recruited members of the gang to help him when situations like this came up. Ulbricht gave RedAndWhite friendly chemists real name, age, and vicinity.
He railed to Red and White about how Friendly Chemist had dared to go after users' anonymity, a sacrosanct tenant of the Silk Road. For that, he had to die. For 1,655 bitcoins, at the time worth about $150,000, the Hell's Angels dispatched with Friendly Chemist. But when Red and White sent the photo evidence of the assassination, he had bad news for Ulbricht.
Shortly before Friendly Chemist died, he tried to make a bargain. He confessed that he had four other associates who also had access to the lists of users' names and addresses. What did Ulbricht want to do about the others? When Ulbricht had learned of Chronic Pain's betrayal a few months before, it took him a full day to decide murder was the only option. Now, he replied to Red and White almost immediately.
Take care of them. He wired an additional $500,000 for four more hit jobs. In his log of work activity for the day, Ulbricht noted that he sent a payment to the Hell's Angels for the killings. It was followed by, very high load took sight offline and refactored main and category pages to be more efficient. Just another day at the office on the dark web.
Ulbricht was finding it harder to maintain his double life. He had no permanent address. He lived in a friend's spare bedroom in San Francisco. He was constantly terrified that they'd spot the holes in his cover story and discover his real job.
So in June of 2013, Ulbricht decided it was time to divide his two worlds. He moved out of his friend's apartment and into a Craigslist room share. He paid the $1,200 rent in cash and told the house's landlord his name was Joshua Terry. He kept Joshua's backstory simple. He was a currency trader from Texas.
He vowed to never bring anyone who knew him as Ross Ulbricht to the new apartment. He needed a fortress of anonymity. Once he assumed the role of Joshua Terry, Ulbricht realized how useful it might be to have more backup aliases in case he needed to run for his life. He ordered nine fake IDs with nine different names issued in nine different states and countries from a vendor on the Silk Road.
Unfortunately for Ulbricht, the Canadian vendor was very popular on the site. On the same day that Ulbricht's purchase passed through customs at the San Francisco airport, several other envelopes of fake IDs were on their way to different buyers. There were so many identical-looking envelopes, it caught the attention of the customs inspector checking the mail crate.
First, the envelopes were an odd shape, square instead of rectangle. Second, it was clear that all the envelopes were addressed by the same person based on the handwriting, but the return addresses were for three different people: Cole Harris, Arnold Harris, and Burt Harris, all at different addresses in Vancouver. Ulbricht's envelope stood out from the group because of the large number of fakes inside.
The customs inspector flagged him for follow-up. On July 26, 2013, 29-year-old Ulbricht was home alone in his San Francisco room share. He stepped outside of his bedroom for a minute, wearing only shorts, but he froze in horror at what he saw on the other side of the glass door. Men with badges. Federal agents. They made eye contact with Ulbricht and rapped on the glass. They wanted to talk to him.
One of the agents said, "We're from the Department of Homeland Security. We're here to talk about these counterfeit documents that were set to be delivered here. Normal people, even normal criminals, don't order nine fake driver's licenses. It all just seems very odd to us." Ulbricht's heart caught in his throat. His entire body started to shake. This was it. This is the way the world ends. Not with a bang, but a whimper.
But the agents quickly reassured him they weren't here to arrest him. They just needed to see some real identification and verify he wasn't a fugitive or a terrorist. In truth, they didn't have enough evidence to prove he'd actually ordered the IDs and were here on a fact-finding mission. Ulbricht complied and showed them his official Texas license. Satisfied, the agents asked him one final question.
Hypothetically, how does someone go about purchasing nine fake IDs? With a hint of smugness in his voice, Ulbricht told them, "So anyone, hypothetically, could use the Tor network and go onto a site called the Silk Road and buy anything they want, including guns, drugs, or fake IDs."
Unlike the FBI and Senator Chuck Schumer, these low-level Homeland Security agents were unfamiliar with the website. They simply made a note of the information, thanked Ulbricht for his time, and went back to their car. Ulbricht was glad they didn't arrest him, but frustrated that his real name was now associated with his formerly secure address. He'd have to move again. Unknown to him,
he would soon have bigger problems than a stack of fake IDs. Around the same time he was finding a new place to live, task forces from the DEA, FBI, IRS, the DOJ, and the US Attorney's Office convened in Washington, DC. They'd all investigated the Silk Road individually, but hadn't gotten far. Now, they planned to pool their resources
to shut down the site once and for all.
In the summer of 2013, Homeland Security agent Jared Derjegian stood before a panel of agents from the DOJ, FBI, DEA, and IRS to present everything he'd discovered about the Silk Road website and its anonymous leader, the Dread Pirate Roberts. Jared, who was based in Chicago, entered the Silk Road case two years earlier when he was summoned to O'Hare Airport to investigate a suspicious package.
It was a square envelope with the address typed instead of handwritten, the first red flag. On the inside flap were two words in German: "Hier öffnen" - "open here." Inside was a single pink tablet of ecstasy stamped with the outline of a squirrel. Jared was immediately intrigued. Who would go to the trouble of shipping a single dose of ecstasy halfway around the world?
He paid a visit to the intended recipient of the envelope for a knock and talk. Unfortunately, the buyer wasn't home, but his roommate answered the door. Still looking for answers, Jared told the roommate why he was here. Did he know anything about where the envelope of ecstasy came from? He answered, "From the Silk Road. It's like Amazon.com, but for drugs." Once he heard about the website, it was all Agent Jared Der-Yeg-Yen thought about.
He was terrified by the possibilities of anyone buying anything they wanted. Kids could buy heroin, terrorists could buy guns, and it was all happily delivered to their doorstep by the USPS. Now, in the summer of 2013, after years of work and over 3,500 seized shipments, Jared presented his findings on the Silk Road to a room of about 35 agents.
Jared told the assembly that he'd been able to arrest a few low-level dealers. Then he commandeered each vendor's account to gain a better understanding of the inner workings of the website. With this knowledge, he tried to befriend higher-level users and moderators closer to Dread Pirate Roberts. Jared tricked one of these mods, user named Sirrus, into giving him her real name and home address. He told her he was sending a gift,
Instead, he sent federal agents. After the arrest, Jarrod offered Cirrus a deal: turn over her mod account and they'd go easier on her. She took it, and Jarrod started impersonating her on the site. Over the course of a few days, Cirrus taught Jarrod how to use Tor and access the Silk Road backend. He took notes on her mannerisms, her workflow, her speech patterns, and her emoji preferences.
Saris didn't know the true identity of the Dread Pirate Roberts, but as a moderator, she had direct access to him, and now Jared did too. He observed DPR staff meetings like a fly on the wall, biding his time for a crack in the case waiting to strike. It hadn't come yet, but he knew he was close. And that's where he was when he presented his findings to the collection of federal agents.
After 40 minutes, Jared concluded his presentation. Murmurs of approval from the assembled agents circled the table. They were impressed with his work. But the mood in the room soured when the DEA gave their presentation. While Jared had laid all of his cards on the table, the DEA was petulantly tight-lipped.
The DEA refused to talk about Agent Carl Force's undercover work as Knob, claiming that it would jeopardize his standing. Force had what he needed to take down DPR, and he didn't feel like sharing the bust. The whole presentation lasted less than five minutes, and Force hung up the conference call line. If he'd stayed, he would have known the FBI was about to beat him to the punch.
Once the room quieted, the Assistant US Attorney stated simply, "We have the server." A highly trafficked website like the Silk Road needed to be housed on its own dedicated server located in a hidden server farm. Because of the anonymity protections of Tor, Ulbricht assumed that the IP address for the server was completely untraceable.
But FBI agent Chris Tarbell had dedicated the last six months to proving that assumption wrong. Tarbell was part of the FBI cybercrime unit. He and his team trolled technical forums, looking for threads discussing the coding mechanics of the Silk Road, hoping one of them might reveal a weak spot. In early June of 2013, someone posted about a recent server update on the site.
They complained that it caused the Silk Road's IP address to leak, making it visible to the rest of the internet. Tarbell seized the opportunity and threw all his resources at the weakness before anyone on DPR's staff noticed and patched the bug. As described by Joshua Behrman for Wired Magazine,
Tarbell threw data at Silk Road. He entered usernames with bad passwords and pasted data into input fields, all the while using regular old freeware to analyze network traffic and collect the IPs communicating with his machine. Then he tested those. Eventually, he struck gold.
IP address: 193.107.86.49. When he pasted it into a browser, the Silk Road captcha field appeared. Tarbell then traced the address to a server farm in Iceland. After a few weeks and a little red tape, the Icelandic government handed over a drive with a duplicate of the server housing the Silk Road. However,
When Parbell fired it up, he realized the server was encrypted, completely useless without the password. He sulked for a full day over the blow. He thought he'd cracked the case wide open, but it was just another dead end. He lamented to Sarah and Turner at the US Attorney's Office, "Where do they go from here?" But Turner was confused. The password didn't work?
Tarbell nearly jumped through the phone to strangle the state attorney. He never said they had the password. Turner shuffled some papers on the other end of the line, looking for his notes, then said, "It's 'try to crack this NSA' with no spaces." It worked. Tarbell was in. He had access to the entire Silk Road back end.
private messages, the forums, and all Bitcoin transactions. He compiled 1,400 pages of DPR's chat logs and read every word. But even with this windfall of information, Tarbell and the FBI still couldn't figure out who DPR was. Based on the server activity, they believe he lived in San Francisco and that he worked off a machine nicknamed Frosty.
But what could they do with that knowledge? Stake out every Coder-filled coffee shop in the city? It was yet another dead end. Luckily, there was an agent in the task force with another idea: IRS agent Gary Alford. Gary Alford knew that he wielded as much power with his calculator as other agents did with their 9mm. After all, who brought down Al Capone?
After the Joint Task Force meeting, Alford saw clearly how each agency was attacking the Silk Road problem. Carl Force and the DEA was going after DPR, trying to reach him directly through his undercover work. Homeland Security agent Jared Derjegian was going after the drug shipments, trying to make headway through the buyers and sellers, while FBI agent Chris Tarbell took aim at the site itself. Alford was brought in as a money guy,
Now that they had the records of all the Bitcoin transactions, the IRS should be able to whip out their calculators and go to work. But the Bitcoins didn't leave a real paper trail. They just provided lists and lists of anonymous usernames. With all of these different traditional angles so far proving useless, Alfred started thinking outside the box. He was inspired by the case of David Berkowitz, also known as the son of Sam,
Throughout 1976 and 1977, Berkowitz went on shooting sprees in New York City, injuring seven people and killing six. For months, he eluded capture, even though he was the subject of the largest NYPD manhunt to date. In the end, Berkowitz was identified as the son of Sam because of one $35 parking ticket.
Police tracked down every car that was sighted in the surrounding area of one of the murders. Berkowitz's car had been ticketed even though his home address was listed in Yonkers. When they searched his sedan, police found a rifle, rounds of ammunition, and reportedly even maps of the crime scenes. Alford wanted to apply this same strategy to the dread pirate Roberts.
he started looking for his own version of a parking ticket. Some kind of digital footprint that revealed DPR's true identity. So, he hit Google. The Silk Road initially hit the mainstream through journalist Adrian Chen's Gawker article published in June of 2011. That was when the site really took off beyond regular users of the dark web. But what about before then? Had anyone else written about the site?
Alfred searched for the website's complicated Tor address and set the parameters so Google only returned posts uploaded before the Gawker article was published. On January 27, 2011, a user named Altoid posted on a forum about psilocybin mushrooms called The Shroomery. Altoid suggested that the forum readers check out a new site called The Silk Road.
Encouraged, Alford ran another Google search, this time including the name Altoid along with the Silk Road URL. He found more posts by Altoid on other drug-related forums, also posted in late January 2011. On one thread about paying for heroin anonymously with Bitcoin, Altoid commented,
You guys have a ton of great ideas. Has anyone seen Silk Road yet? It's kind of like an anonymous Amazon.com. Alford was convinced. Altoid and Dread Pirate Roberts were one in the same. He subpoenaed the forum sites for Altoid's registered name and user credentials. But the email used to register the account, frosty at frosty.com, was fake. All he got was a bounce back. However...
Alfred found the Altoid username and Frosty email account on more than just drug forums. The name was also used on Stack Overflow, a forum for coding questions. In March 2013, Altoid asked, "How do I connect to a Tor hidden service using Perl in PHP?"
This Altoid was originally registered with a different email address, then changed to the Frosty account a minute later. The initial address? Ross Ulbricht at gmail.com. When Alfred ran a search on Ross Ulbricht in the federal database, he got a hit. Ulbricht had never been arrested, but he'd been interviewed by the Department of Homeland Security about a stack of fake IDs.
In the report, the DHS agent noted, "Ulbricht volunteered that hypothetically anyone could go onto a website named 'Silk Road' on Tor and purchase any drugs or IDs. It couldn't just be a coincidence." By late September of 2013, Ross Ulbricht felt like the master of his fate.
Not only was business on the Silk Road doing well, they now had over a million registered users, but Ulbricht had fully stepped into his role as boss. He didn't want to just lead his employees, he wanted to inspire them. They were on a mission to change the world after all. When one of his worker bees was burned out after a long day of dealing with user gripes, Ulbricht told them a story over chat to offer some perspective.
Once, a man came across a group of workers cutting stone blocks. When he asked what they were doing, one of the exhausted laborers said, "What does it look like? We're making blocks for the building." But the man noticed another worker smiling as he toiled away. He cut his blocks at twice the speed of the rest of the group. When the man asked what he was doing, he said, "I'm building a cathedral to the glory of God."
Ulbricht summarized for his employee, "If someone asked you what you're doing, would you say dealing with people's problems or working to free humanity?" Not only did he fully believe in his mission, Ulbricht had complete faith in his security protocols. Even when a user warned him that the Silk Road servers were vulnerable, he just brushed them off.
Tor was anonymous. Bitcoin was untraceable. He was untouchable. He told a potential new hire, "Realistically, the only way for them to prove anything would be for them to watch you log in and do your work." Unfortunately for him, that was exactly the path the government task force took.
When IRS agent Gary Alford, DHS agent Jared Dreyegan, and FBI agent Chris Tarbell finally put all their separate pieces together, the signs clearly indicated that Ross Ulbricht was the Dread Pirate Roberts.
They'd found the name Frosty on the Silk Road servers. They'd connected Frosty to Ross's name on Stack Overflow, asking a question about a piece of code they also found in the Silk Road's backend. And they knew that Frosty frequently logged in at a coffee shop around the corner from the address where Homeland Security had interviewed Ross Ulbricht about his shipment of fake IDs. But nothing was a smoking gun.
The Justice Department wouldn't approve an arrest or a wiretap on Ulbricht's computer. They had to find more. So they watched him from a distance, trying to prove the connection. Jared was still posing as one of Ulbricht's moderators, username Siris. Through this access, Jared could see whenever DPR logged onto the Silk Road. And at the same time, in the real world, the surveillance team watched Ross Ulbricht sit down at his laptop and work.
Their activity was identical. Every time DPR was online, Ulbricht was at his computer. When Ulbricht signed off, so did DPR. By the end of September of 2013, the DOJ was satisfied that Ulbricht was a person of interest in the Silk Road case. The FBI started planning their apprehension strategy. Agent Carl Forrest was not included.
Locked on the outside, looking in after the DEA's behavior in the Joint Task Force meeting, perhaps out of jealousy, he tried to warn Ulbricht that it was time to pay attention to the signs around him and run. As Nob, he typed, "You are like one of my family, but I have to tell you that I have had several people killed who were sent to jail. It is very easy and cheap." But Ulbricht ignored the guidance. He had nothing to worry about.
Knob may understand the heroin trade, but he didn't understand cybersecurity. On October 1st, 2013, the FBI prepared to arrest Ross Ulbricht in his apartment. It was a controlled environment perfect for an ambush. They planned to monitor Ulbricht's Wi-Fi traffic to make sure that he was logged into the Silk Road at the time of the bust.
Without that concrete connection, all they had was circumstantial evidence and the dread pirate Roberts would go free. Once they confirmed he was working on the site, the FBI would storm the house and collect the laptop for evidence. But agent Chris Tarbell saw a huge flaw in this plan.
A few years earlier, he'd apprehended a well-known hacker, Jeremy Hammond, who was part of a larger group of hacktivists called LulzSec. They'd taken the same approach in that arrest, sending in a SWAT team. And the moment Hammond heard the battering ram crash through the door, he calmly shut the lid to his laptop, instantly locking it, encrypting the contents, and effectively destroying all evidence.
As Nick Bilton described in his book on Ross Ulbricht, it was the equivalent of doing a massive drug bust and the suspect flushing the drugs down the toilet before the cops made it into the bathroom. Tarbell knew from the chat logs on the Silk Road server that Variety Jones taught Ulbricht how to install a kill switch on his laptop, a secret keystroke that would instantly wipe the computer's hard drive. It would be lolsec all over again.
But even though Tarbell and the DC Cybersecurity Task Force had done the majority of the legwork on the case so far, they were in San Francisco now. That meant it was the local field office's jurisdiction, and they wanted a raid. Around 2:30 p.m. on October 1st, Agents Tarbell and Der Yegian sat in an unmarked van outside Ross Ulbrich's apartment, keeping an eye on their target.
But at about 2:45 p.m., Jared saw DPR log off on the Silk Road back end. The entire mission was compromised. Then, a few moments later, Ulbricht exited his apartment building. His laptop bag slung over his shoulder. He stepped into the coffee shop next door, but stepped out just as quickly. It was too crowded and there was nowhere to sit and charge his computer.
Jared and Tarbell watched him continue down the block and into a public library. The agents debated what to do for a few moments, but ultimately decided to follow him. They let the SWAT team know. Change of plans. Tarbell told the few agents in the area to take positions in the library. Ulbrich sat down at a large table in a back corner of the library. He opened his laptop and fired it up.
A young woman sat down across from him and opened her book. Jared sat on a bench in front of the library, his own laptop in front of him, waiting to see if DPR would appear on the Silk Road. Tarbell paced on the sidewalk, swearing under his breath and constantly checking his Blackberry for updates on the SWAT team. Then Jared saw it. DPR was back online. Jared knew that to make an airtight case against Ulbricht,
They needed evidence that he was more than just a user on the Silk Road. He had admin privileges. Jared needed to make him log into the back end of the site before the bus could go off. As Sirrus, he asked over chat if DPR would check a flagged complaint. Seconds stretched to minutes before Ulbricht typed back. Sure, let me log in. It was go time.
Tarbell furiously typed instructions on his Blackberry to the rest of the team. Get the open laptop first, then worry about Ulbricht. He stressed, let the guy run if you have to, but don't let that computer close. Ulbricht sat working at the table in the library, hunched over his screen. He didn't notice a scruffy-looking couple sidle up behind him. Then the woman suddenly screamed at her mate, F*** you!
The shrill yell cut through the silence of the library, drawing a few glances, but Ulbricht remained oblivious, still typing away. Then the man she was with cocked back his right arm, readying to punch the howling woman in the face.
The other patrons in the library gasped and called out, trying to stop him. Even Ulbricht was now caught up in the scene. He turned around in his chair, away from his computer. While he was distracted, the young woman seated across from him casually grabbed Ulbricht's laptop and slid it away. He tried to scramble across the table after her, but the fighting couple grabbed his arms and twisted them behind his back. FBI! FBI!
They swiftly got a hold of him and snapped handcuffs on his wrists. One agent walked Ulbricht downstairs while another walked his laptop. The latter held his prize like it was made of glass, dutifully touching the trackpad every few seconds, making sure the machine wouldn't idle and lock. Jared and the laptop agent climbed into an FBI van.
They connected the computer to a power source and immediately started copying the contents. It was a goldmine. The laptop was nicknamed Frosty. It was logged into the main Silk Road website, the admin backend of the website, and a third dashboard called Mastermind. They had everything they needed.
To fully complete the bust, federal agents in Iceland raided the server farm that housed the Silk Road website and seized control. Now, when users logged on, they found a huge warning message: "This hidden site has been seized by the Federal Bureau of Investigation." Tarbell took custody of Ulbricht and walked him to another waiting FBI van. Ulbricht demanded to know what he was being charged with.
Tarbell showed him a federal warrant authorizing the arrest of Ross Ulbricht, aka Dread Pirate Roberts, aka DPR, aka Silk Road. At first, all Ulbricht said was, "I want a lawyer." Then, a few blocks later, he half-jokingly offered Tarbell a bribe. If he gave him $20 million, would he let him go? Tarbell countered, "Even if I could, what about this guy?"
As he pointed to the driver, "Have to take care of him too, right? How much money do you have?" Ulbricht didn't answer, perhaps realizing that revealing his wealth only implicated himself further. But the FBI discovered his trove of 144,000 bitcoins soon enough, worth between 18 and 30 million dollars, depending on the day. And that wasn't all they found.
As many protocols and encryption measures as he'd taken, in the end, the FBI was able to easily retrieve Ulbricht's password, purple-orange-beech, from the computer's RAM. It was the same problem that had plagued Ulbricht from the inception of the Silk Road. As smart as he was, as much as he taught himself, he wasn't an expert in cybersecurity. Agents found a folder on his hard drive called "Scripts"
Inside were the coding protocols for all the encryption protections he'd used. Ulbricht had gone to the trouble of putting 15 locks and chains on the door, then been careless enough to leave the keys sitting under the mat. Two weeks after his arrest, Ulbricht was transported to New York to stand before a federal judge. He faced seven charges, including narcotics trafficking and criminal conspiracy.
The most severe charge was running a continual criminal enterprise, aka the Kingpin Statute. If convicted, Ulbricht could be sentenced to a minimum of 20 years in jail and a maximum of life imprisonment. However, there was one charge the government hadn't been able to bring against Ulbricht yet, murder charges.
If the U.S. Attorney could prove that Ulbricht murdered someone as part of his business, he could receive the death penalty. In the recovered chat logs, there was evidence of six hired hits: Chronic Pain, Friendly Chemist, and the four other associates murdered by Red and White in the Hells Angels. However, while Ulbricht believed he'd ordered Chronic Pain's death, the state knew that the assassination was just for show.
They couldn't charge him for murder if the victim was still alive. Even more complicated, Ulbricht had ordered Chronic Pain's death as retaliation for stealing $350,000 in Bitcoins from users' accounts. But it turned out Chronic Pain never touched that money. A Secret Service agent, Sean Bridges, who was present during Chronic Pain's arrest, was responsible for the theft.
While everyone else was bagging up evidence, Bridges quietly moved the digital currency into his own account. He'd later be sentenced to 71 months in prison. So if they charged Ulbricht for anything related to chronic pain, it opened the door for his defense attorney to lambast the agents involved in the case. As far as the other five hits that Ulbricht sent to Red and White and the Hells Angels, investigators also came up empty.
It seemed that Red and White had scammed Ulbricht out of $650,000 without actually bumping anyone off. In the end, it was a lucky break that spared Ulbricht's life. Still, Ulbricht faced a considerable amount of jail time if convicted. When his trial arrived in January 2015, Ross Ulbricht's defense attorney relied on the strategy that he'd set up years prior.
He was not the real Dread Pirate Roberts. It was just a title. Yes, he'd invented the Silk Road, but he'd given it away to someone else when it became too dangerous and unwieldy to run. The buyer framed Ulbricht when he realized the Feds were moving in. But for four weeks, the U.S. Attorney for the Southern District of New York presented the piles of evidence pulled from Ulbricht's computer.
Thousands of pages of chat logs between him and his lieutenants about site maintenance and user issues, including the conversation with Knob about murdering Chronic Pain. Millions of dollars in Bitcoin, his own diaries documenting the daily struggle of being a digital kingpin. On February 4th, 2015, 30-year-old Ross Ulbricht was convicted on seven felony counts.
The jury deliberated for less than four hours. At sentencing four months later, Ulbricht asked for leniency. He made a mistake in creating the Silk Road and he truly regretted it. But Judge Katherine Forrest didn't offer any mercy. She said, "You are no better a person than any other drug dealer.
In the gallery, Ross Ulbricht's mother wept.
In the wake of the shutdown of the Silk Road, many online activists have come to Ulbricht's defense. They attest that there are, in fact, several Dread Pirate Roberts and that Ulbricht was unfairly targeted and punished. Indeed, after the shutdown of the Silk Road, subsequent iterations of the site have appeared on the dark web. They have also been shuttered by law enforcement.
Ulbricht's co-conspirators also had their day in court. Red and White was charged with two counts of narcotics trafficking, conspiracy, and one count of money laundering in May 2023. Roger Thomas Clark, better known as Variety Jones, was sentenced to 20 years in prison in July 2023.
In addition, DEA agent Carl Force was later indicted for crimes he committed during his undercover work as Knob. Force had run into trouble earlier in his DEA career, blurring the line between his undercover and real life, tempted by the very things he was trying to corral. And history repeated itself in the Silk Road case. Force found himself tempted by the millions of digital dollars in front of him.
Posing as several different users while undercover, Force had offered to be a government informant for Albrecht. He sent him several inside tips for Bitcoin payments of $50,000 a pop. When Force was tight-lipped with the rest of the investigation, he wasn't concerned about sharing the glory. He was worried he would be exposed. He was later sentenced to more than six years for extortion and money laundering.
Many of Ulbricht's supporters point to this impropriety as proof that the investigation was corrupt. But the overwhelming amount of evidence drawn from Ulbricht's laptop is unequivocal proof that he and DPR are one and the same. As of 2023, Ross Ulbricht is serving his life sentence at a maximum security facility in Tucson, Arizona.
His supporters continue to maintain his innocence on a new website, freeross.org. Ulbricht unsuccessfully filed and lost an appeal for a reduced sentence in 2017.
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Conspiracy Theories is a Spotify podcast. This episode was written by Abigail Cannon with writing assistance from Julian Boisreau, edited by Maggie Admire, fact-checked by Laurie Siegel, and sound designed by Alex Button. Our head of programming is Julian Boisreau. Our head of production is Nick Johnson, and Spencer Howard is our post-production supervisor. I'm your host, Carter Roy. This episode is brought to you by Hills Pet Nutrition.
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