Ross Ulbricht built an empire in the shadows—a sprawling digital bazaar called The Silk Road, hidden on the dark web. There, drugs, weapons, and stolen secrets flowed freely, all paid for in untraceable cryptocurrency. To his global clientele, he was a legend: the Dread Pirate Roberts. But after a dramatic arrest and a staggering double life sentence, Ulbricht’s fate took another twist. Just days into his second term, President Trump pardoned him, sparking outrage and debate.
So, did he deserve his punishment? Did justice prevail—or was power at play? And how did a digital outlaw become the ultimate wild card in America’s justice system?
In this episode:
- Nicholas Cristin, Online Crime Professor at Carnegie Mellon University
- David Yaffe-Bellany, Technology Reporter for the New York Times
# news #breaking #24x7
So, did he deserve his punishment? Did justice prevail—or was power at play? And how did a digital outlaw become the ultimate wild card in America’s justice system?
In this episode:
- Nicholas Cristin, Online Crime Professor at Carnegie Mellon University
- David Yaffe-Bellany, Technology Reporter for the New York Times
# news #breaking #24x7
Category
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NewsTranscript
00:00It's October 2013 and we're in an area of San Francisco, California in the United States
00:17called Glen Park. It's a classy neighborhood, full of luscious green spaces and winding tree-lined
00:26streets, a far cry from the grit of urban downtown. Glen Park Library is a cornerstone
00:34of the community. It's a square, light grey building and this is where, on a Wednesday
00:41afternoon, a young man has come to do some work. He's a good-looking 29-year-old, tall
00:49with floppy brown hair, a broad nose, strong eyebrows and an easy grin. He's sitting at
00:57a desk in front of the science fiction section, typing away on a laptop. The air is still.
01:05The library is pretty empty. All you can hear is the light tap of the man's keyboard and
01:11the occasional rustle of book pages. Suddenly, there's a commotion. A nearby couple has started
01:19arguing. First in hushed whispers and then louder. The man stops typing and looks up. The library
01:29air that just seconds before had been so still is suddenly taut and tense. The man twists his
01:38head towards the bickering duel. That's what they're waiting for. Before the man knows it,
01:46officers appear out of nowhere and slam his hands behind his back and click a pair of handcuffs
01:53around his wrists. The FBI has been trying to find him for over two years. He may not look it,
02:02but he's the mastermind behind what the FBI will later call the internet's most sophisticated and
02:10extensive criminal marketplace. A site he's been running off this very laptop, where hundreds of
02:18thousands of people anonymously trade stolen information, guns and drugs. Up until now,
02:27he's remained hidden behind his online identity, known only as Dread Pirate Roberts. But his real name
02:36is Ross Ulbricht. And his arrest will fuel North America's culture wars. A fire that's still burning today.
02:46This is a story about how one man used the internet to facilitate a digital drug empire in a country where
02:55tech bros increasingly wield incredible power. We're asking what happens when the law comes for them
03:04and who's really pulling the strings? This is True Crime Reports, a global crime show from Al Jazeera.
03:14Today's episode, Drug Trafficking on the Dark Web. Ross Ulbricht's life begins in Texas in 1984.
03:25He grows up in Austin in a close-knit family with his mum, Lynn, his dad, Kirk, and his sister, Kala.
03:33He was a literal Boy Scout, an Eagle Scout, in fact. You know, he was known as a kind of friendly and
03:40carefree guy. He smoked pot as a teenager, the way a lot of teenagers do. But there was nothing
03:46particularly strange or remarkable about his background. This is David Yaffe Bellany,
03:52a technology reporter for The New York Times. I've been covering crypto for the last three years,
03:58and it's impossible to even dip your toe into the crypto world without coming across people who hail
04:04Ross Ulbricht as a hero. You know, people who point to him as an important figure in the history
04:10and development of cryptocurrencies. David has followed Ross's life and career
04:15very closely. His parents would take the family to Costa Rica over the summer where they'd built
04:22these sort of bamboo houses near an isolated area where Ross learned to surf. And so, you know,
04:28it was a pretty kind of idyllic upbringing in a lot of ways. Ross moves away when he's 18 to study,
04:35first physics, then a material sciences and engineering masters. By the time he graduates,
04:43age 25, he's developed two passions in particular, which will be important in how his story plays out.
04:52The first is philosophy. He spends a lot of time thinking about things like
04:58the pursuit of truth and the meaning of freedom.
05:01It was during his studies at university that he became enmeshed in libertarian thought,
05:07this notion that the government is too intrusive. He started becoming interested in Bitcoin around
05:14the 2010, which was a couple of years after Bitcoin has started, but it's still very, very early.
05:20You know, there are online message boards where people discuss in a lot of detail the kind of
05:24philosophical and technological underpinnings of Bitcoin. And that was the world that Ross started
05:29to get involved in. The second thing Ross loves, really loves, is drugs, specifically psychedelics.
05:39Now, in the late 2000s, drugs are a hot topic in the US. Deaths by overdose have been rising for a decade
05:47already. Drug users are spending 100 billion dollars every year on things like cocaine, heroin, marijuana
05:57and methamphetamines. This is despite the government's so-called war on drugs,
06:03which began in 1971 and really ramped up during the crack epidemic in the 80s and 90s.
06:11With the aim of creating a drug-free world, the war on drugs is big business. By the time Ross leaves
06:20university in 2009, the crackdown is costing the US government billions of dollars each year. More and
06:29more people are being locked up for drug offences. Black people disproportionately so. In the 35 years,
06:37between 1980 and 2015, the number of drug offenders increases more than tenfold. But the public is
06:46starting to question whether it's actually working. I think that one of the main reasons for people's
06:53scepticism of the success of the so-called war on drugs is twofold. First, there was no significant
07:02decline in drug use or abuse, at least in the United States. It didn't seem like it was
07:10markedly changing the picture. This is Nicholas Christen. He's a professor at
07:15Carnegie Mellon University in the US who's been studying online crime for nearly 20 years.
07:22Did it really reduce the drug issues that we faced in the US? I would say unclear at best. It's not
07:32clear there was any effect, but there was definitely an effect on prison population.
07:37By the late 2000s, policymakers and researchers are starting to seriously question the war on drugs.
07:45And back home in Austin, so too is a bright-eyed recent graduate called Ross Ulbricht.
07:52Ross has a strongly held belief that drug use is a personal choice and no business of the government.
08:00Within a couple of years of leaving university, he spawns his big idea. In his own words,
08:07to create a website where people could buy anything anonymously with no trail whatsoever that could lead
08:16back to them. It's the ultimate libertarian dreamland. The only rules he initially has are
08:24no child porn, no stolen goods and no fake degrees. In January 2011, Ross launches his dream website
08:35and calls it Silk Road. He is its owner and its administrator, and he's known only by his online
08:44persona, Dread Pirate Roberts, after the pirates in the film The Princess Bride. It's an online marketplace,
08:53a bit like eBay, where anyone can buy and sell anything. You've got all the normal stuff,
09:01like furniture and clothes, as well as other, less normal stuff, like hard drugs. It's hosted on the
09:10dark web, a hidden part of the internet, which you can only access using specialist browsers,
09:18and users pay in untraceable cryptocurrency, Bitcoin. Ross thinks this is the answer to America's
09:27drug problem. Put control back in the hands of the people, and it regulates itself. No more seedy
09:35meetings in back alleys. No more gang warfare. Just simple, sweet, vendor-to-buyer transactions.
09:45Here's Nicholas. And so the idea of Silk Road was to move all of those potentially violent
09:51interactions online, anonymously. And that's why Ulbricht was saying that we won the war on drugs.
10:00I mean, we basically managed to do what you guys couldn't, which is to remove violence from the
10:06equation, which is to remove the possibility of getting scammed on, the possibility of getting
10:12inferior products from the equation. To begin with, Ross, or Dread Pirate Roberts,
10:19is the only vendor. Within a few days, he gets his first order for some homegrown magic mushrooms.
10:27Soon, he sold all of his £10. The sales trickle in, the trickle becomes a pile, which becomes a mountain,
10:38and within just a few months, there are dozens of customers and vendors feverishly trading things like
10:45OxyContin, heroin, and cocaine. They post photos and reviews, just like you would on Amazon.
10:55And quickly, a community develops. Nicholas says he was surprised to see who its users were.
11:03They all seemed to be pretty well-educated people, which was surprising to me when I went to the site,
11:10because I thought, okay, a bunch of people selling drugs. They must be, you know, hardened criminals.
11:15And what I found was that the writings and the level of discourse on those forums was pretty similar
11:25to what I would expect college students or graduate students to engage in. They were talking about
11:31philosophy. They were arguing politics, libertarianism and, you know, Austrian economics. So it was a fairly,
11:40I would say, elite crowd, so to speak. Silk Road's users are loving it. And some of them begin to make
11:49a lot of money. And Ross, with a cut of up to 15%, is loving it too. But you didn't see people shipping
11:59a ton of cocaine, for instance. That just didn't happen. And part of the reason is that the physical
12:06delivery mechanism that was used is basically the post office. And you're not going to ship, you know,
12:13hundreds of kilograms of drugs in the post. Part of the deal is that you learn how to avoid detection.
12:21Silk Roaders are given a checklist for how to deter law enforcement. For instance, vendors should only
12:29package drugs in parcels that are vacuum sealed. Customers should use post office boxes, not their
12:38personal ones. For the first few months, Silk Road stays a pretty well-kept secret, only for those in the
12:48know. But in June 2011, an article appears on Gawker, a New York-based online blog about celebrities and the
12:57media industry, titled The Underground Website Where You Can Buy Any Drug Imaginable. Nicholas says that from this
13:08moment, everything changed for Ross. And immediately, some people that read Gawker at the time, mostly,
13:16you can imagine, tech, young crowd, got interested in it and started to flock to that site. And so,
13:23through word of mouth, after this article, things started to pick up. At some point, Ross upgrades the
13:31site's offer. Soon, it's not just drugs that's being sold, but also software for budding computer
13:39hackers, including password stealers and remote access tools. For a time, he also set up a section
13:47for gun sales. It wasn't very successful, and he eventually closed it down. It's the drugs people want.
13:56Six months in, news of what's going on online reaches the US Senate. Senator Chuck Schumer calls it a scandal,
14:06and calls for the federal authorities to shut the site down. Ironically, according to Nicholas,
14:13this just increased sales. So, all of a sudden, that website was mentioned in not, you know,
14:21the tech, edgy type of venues that you would expect it to be mentioned in, but in the popular press,
14:29which led to massive advertising. And at that point, people started to flock to the site.
14:34It's now 2012. In its first year, Silk Road has collected tens of thousands of users, mainly in the US,
14:46but also in Canada and across Europe. Up until last summer, Ross had been running the site from a small
14:53apartment in Austin. He then moved briefly to Australia, before landing in the tech center of the
15:01World San Francisco in 2012. By now, he's got at least two secret identities. To girls he meets on
15:11dates, he introduces himself, not as Ross, owner of the by now quite infamous website Silk Road, but
15:19Josh, a currency trader. His housemates will later describe him as a quiet man, who was always buried in
15:27his laptop. To his devoted Silk Roaders, and to the small number of people he's hired to help him run
15:35the site, he's just three words. Dread Pirate Roberts. Nobody knows who he is. By now, Ross has banked more
15:47than $100,000. And his commissions have crept up to 25 grand a month. Nicholas, tracking the site from
15:57his office at Carnegie Mellon University in those first months of 2012, thought the site would earn
16:04about $16 million that year. That's, you know, a mid-sized business, I would say. It's not small,
16:14but it's not Amazon, obviously. But as the months go on, it becomes clear
16:20it's worth a lot more than that. Nicholas says that by the summer of 2013, using the same computations
16:29he'd been making, the annual worth is actually closer to $250 million. Drugs account for 70% of sales.
16:43So in a very, very rapid
16:47fashion, the site literally multiplied its revenue by 5x, 10x over just a matter of months. This is how
16:57fast it grew. But with money and power comes unwanted attention. And what Ross doesn't yet know
17:06is that the FBI is watching him closely. Two and a half years in, Silk Road is doing booming business.
17:16It's got nearly one million users worldwide, almost a third of which are Americans. It has 13,000
17:25listings for drugs under categories including psychedelics, ecstasy and opioids. There are 800
17:33listings for so-called digital goods, like hacked Netflix accounts, and close to 200 listings for
17:41for forgeries, including driving licenses and car insurance records. The FBI will later discover that
17:49Ross himself buys at least nine fake IDs from Silk Road. In one, he's a Brit called Nathaniel. In another,
17:58he's an Australian called Sean. But Ross doesn't know yet that he's being tracked. Just a few months
18:07after he founded the site, the FBI began their investigation, called Operation Marco Polo. David,
18:15the technology reporter with the New York Times, says that despite Ross's efforts to cover his tracks,
18:22like using private browsers, he also made some basic mistakes, which eventually became his downfall.
18:31He was setting up the Silk Road. He was active on various web forums asking for advice about how to set it
18:38up. And it was actually not through any kind of creative law enforcement strategy that agents were
18:46able to track him down. It was through simple Google searches and sort of following a kind of trail of
18:51online breadcrumbs that he had left behind that they were able to link the Dread Pirate Roberts persona
18:57to Ross Ulbricht at gmail.com.
19:00And on the first of October 2013, the net finally closes in. The FBI has tracked Ross's location down
19:10to an area near San Francisco's plush neighbourhood of Glen Park, and agents have spent the last few
19:17weeks following him, waiting for the right moment. It's around three o'clock in the afternoon, and we're on
19:25Diamond Street in San Francisco, just outside a small light grey building, marked with the lettering
19:33Glen Park Library. A small number of undercover agents are spread out along the road. A tall,
19:41young man walks along the street. He doesn't notice them. He crosses the street and walks through the
19:49library's front doors. The officers shift on their feet, waiting. Then, movement. The group splits. Some of
20:00the agents stay where they are, and some cross the street and follow the man into the building.
20:08This is their task. They must arrest him and swipe his laptop while the laptop is still open.
20:17If the man manages to quickly close it, high-level protections kick in, and it would be impossible
20:26to break into. David says that everything hung on the laptop.
20:32One of the foundational law enforcement challenges of this case was how do you link a person in the
20:37real world to an online identity? And to do that, it was crucial to basically catch him red-handed,
20:45to say, look, this person in the physical world had his laptop open and was, you know, engaging via his
20:52online avatar. And so, it was critical that they catch him when the laptop was open, that he not have
20:57an opportunity to quickly slap it shut. Outside the library, one of the agents is sitting on a bench
21:04with a laptop of his own. For the past few weeks, he's been impersonating a Silk Road employee,
21:11and has managed to get Ross, or Dread Pirate Roberts' trust. So, he types out a message to Dread Pirate
21:19Roberts, asking him to log in to the site to check something, and hit send.
21:25Meanwhile, the agents inside the library have followed the man to the science fiction section.
21:34They watch him choose a desk, sit down, and open his laptop. He reads something on his screen,
21:43types out a message, and hits enter. Outside, the agent sitting on the bench gets his reply.
21:52Sure, says Dread Pirate Roberts. Let me log in. This is what happens next.
22:01Two agents have taken a seat, just behind the man. They begin to argue. They start quietly,
22:09then get louder, puncturing the still air. People are looking. The arguing gets louder and louder,
22:18and then they start shouting. The man, Ross, can't ignore it anymore. He looks up from his screen,
22:26turns his head. His laptop is open in front of him. It's what they've been waiting for.
22:33A couple of FBI agents kind of staged an argument right behind him that distracted him for long
22:38enough that another agent, sitting across the table from him, pretending to be somebody just
22:44hanging out at the library, was able to reach across and grab the laptop, which was open,
22:48and which showed that, yes, he was logged in as the administrator of Silverado.
22:52More agents appear out of nowhere, and quick as a flash, Ross is in handcuffs. The laptop is taken
23:00to a computer forensics van parked outside, where they get started on gathering the evidence,
23:07and they uncover a gold mine. They get access to almost the entire conversation history between
23:15Dread Pirate Roberts and his Silk Road employees. Thousands of messages about drugs and gun sales.
23:24They discover Ross' personal stash of around 600,000 Bitcoin. At this time, this is worth around $80 million.
23:36That same day, Silk Road goes dark. Here's Nicholas.
23:42Nicholas We can rewrite history. We can wonder what would have happened if he had a laptop that was
23:49fully encrypted and that he had time to unplug it or turn it off when the police arrested him.
23:56I think the case would have gone probably quite differently.
24:00The trial begins in New York, just over a year later, in January 2015. Ross faces seven charges,
24:10including conspiracy to traffic narcotics, conspiracy to hack computers, and engaging in a criminal enterprise.
24:19It's a huge trial. Ross' family is there, and crowds of Ross supporters line the streets outside,
24:27waving banners which say things like,
24:30free Ross and web hosting is not a crime. It stretches over four weeks.
24:39The trial was a huge spectacle. It took place in Manhattan at the federal courthouse there,
24:45which is the site of some of the highest profile trials in the country. And it was packed every
24:50day with Ross' family, with Ross' supporters, with members of the press. And you can see why. I mean,
24:56this was like the largest drug marketplace in history. It had been taken down and also kind of
25:00interacted with all of these ideas about libertarianism and freedom of expression on the internet.
25:07The prosecution's case is that, online or not, there's no difference between Ross and a traditional
25:15drug lord. They say he was responsible for an empire which oversaw the sale of 200 million dollars
25:24worth of drugs, sometimes to minors, they allege. They also rely on the stories of six individuals,
25:33who tragically died after overdosing on drugs which they bought from Silk Road.
25:40These overdose deaths were a powerful thing for the prosecution to bring up. And actually,
25:44when Ross was eventually sentenced, the father of one of the people who died addressed the court
25:51and said, all Ross Ulbricht cared about was his growing pile of bitcoins. It wasn't about anything
25:57else. It was about that. It was about greed, and greed that had resulted in the death of this man's
26:02child. And the idea here was to show this isn't just some sort of abstract thing on the internet
26:09that represents some theoretical ideals. It's a market force in the real world that had real
26:14consequences for actual people. Ross pleads not guilty. His lawyers say he was trying to minimize
26:22drug crime. And anyway, they go on. He just set up the site. Other people did the selling.
26:30They say he deserves leniency. He's not a bad guy, they argue. And look, we've got testimonies to prove
26:38it. They produce nearly 100 letters from Ross's family and friends about his good character. An old
26:46school friend describes him as one of the most guileless and non-aggressive people I've ever met.
26:53But the prosecution wins. The jury unanimously agrees that he's guilty on all seven counts.
27:03In his pre-sentencing statement, Ross says Silk Road was supposed to be about giving people the
27:11freedom to make their own choices, to pursue their own happiness, however they individually saw fit.
27:19It turned out to be a naive and costly idea that I deeply regret. But not even the prosecution is
27:29prepared for the sentence the judge hands down. Normally, running a criminal enterprise holds a mandatory
27:37minimum of 20 years. But Ross receives a double life sentence, plus 40 years with no parole.
27:49He's also ordered to pay 183 million dollars in restitution. In the world of internet crimes,
27:57and in the world of non-violent drug crimes, it's unprecedented. The judge dismisses
28:04Ross's defense that he was trying to minimize violence in the drug trade. She says no drug dealer
28:12from Harlem or the Bronx would have made these arguments. It's an argument of privilege. Here's
28:19David. There was a sense right away that this was kind of an extreme punishment. He was condemned to
28:26die in prison as a result of that sentence. And that was because he had committed incredibly serious
28:31crimes that resulted in deaths. But this, you know, community sort of united in opposition to that.
28:37And its hand was probably strengthened politically because the sentence seemed so harsh. Ross is sent to
28:45prison in Colorado. And almost immediately, his parents take up arms. His mum, Lynn, sets up a free Ross
28:54campaign online. And hundreds of thousands of Ross fans add their signatures. Lynn
29:01says that the depiction of her son as a, quote, dangerous kingpin is a fiction that maligned a
29:09peaceful and gentle man. The campaign reaches epic proportions. By 2021, the billionaire Elon Musk
29:18is sending words of support to the family. And the philosopher Noam Chomsky is calling it a, quote,
29:25shocking miscarriage of justice. Nicholas explains that Ross's case garnered such enormous attention
29:35because of who Ross was perceived to be.
29:38Ross Ulbricht is a very interesting character. This is a 20 something year old student or freshly
29:47graduated student that started a website. Libertarian ideals. People are dealing drugs. They have a book
29:55club. They have all of that. It's this has nothing to do with your typical image of a kingpin.
30:00David points out the significance of Ross's background and what he represents for his supporters.
30:07It's impossible to disentangle the support for Ross Ulbricht from the fact that he was a successful
30:14upper middle class white man who is technically sophisticated and who was kind of engaged in this
30:21intellectual movement. He had these groups of people, the crypto community, the libertarian
30:26community who were allied with him and willing to kind of step up and try to support him. And that's
30:31not something that a drug offender from a different racial or economic background might have.
30:38On the 20th of January 2025, Donald Trump entered the White House for the second time.
30:45Throughout his campaign, he'd promised to pardon Ross if elected. And just two days into his new term,
30:53he did just that, pronouncing,
30:56the scum that worked to convict him were some of the same lunatics who were involved in the modern
31:03day weaponization of government against me. Watching their hero walk free after 11 years in prison,
31:12Ross Ulbricht fans screamed and celebrated around the world. For David, the significance of the
31:21pardoning goes way beyond what it means for Ross. For Ross, it was the key to his freedom. You know,
31:29basically the only way that he could escape from the situation was through a presidential pardon.
31:34But for the crypto industry, it really was a sign that they have a lot of influence with this
31:39president. And so the fact that this went from crypto industry talking point to campaign talking
31:45point to an agenda item that was accomplished so quickly is really testament to the power and
31:50influence that the industry now wields.
31:52So did Ross Ulbricht deserve the sentencing he got? Nicholas says there are two schools of thought.
32:01If Ross is seen as the mere creator of the site, with no responsibility for what went on on it,
32:08a bit like a landlord with criminal tenants, then the answer is no. But there's another side too.
32:17You can look at it from a tech perspective, libertarian perspective, where you have a guy who sets up a
32:25website that is not directly selling drugs, but that is facilitating the sale of drugs. Is he morally,
32:33ethically responsible for it? Or are people who are selling those drugs and buying those drugs
32:40responsible for those traits? If you consider that he is equally responsible,
32:45then the sentencing is in line with what, you know, big drug dealers, kingpins, are going to get.
32:53And yet his sentence was overturned. In the eyes of the law, justice was initially served, but then
33:03it was retracted. What does this mean for the stability of the US justice system? And is it a sign of more to
33:11come? Since he walked free, Ross has given small indications of where he plans to funnel his efforts
33:20next. In February 2025, he posted on the social media platform X in support of a man called Roger Ver,
33:29also known as Bitcoin Jesus, who faces life in prison for tax fraud of up to $50 million. And there are
33:38calls for President Trump to pardon him next. Whether that happens remains to be seen. But Ross was just
33:47one of more than 1,500 individuals pardoned by the new president in his first days in office, all of
33:55whom had been charged or convicted of federal criminal offences, including the January 6th Capitol riots.
34:04So the question that many are now asking is whether this is just the start, the dawn of a new era of impunity.
34:16The precedent that this sets, I think, really has a lot to do with how influence works over Donald Trump.
34:22And basically what it shows is that if you can get close to people in Trump's circle, if you can get the
34:28right sort of political cards laid out, then you can achieve a lot with this president. He's an explicitly
34:35transactional president.
34:37This was True Crime Reports, a global crime series from Al Jazeera. In our next episode,
34:45we're in China, where up to 100,000 children go missing every year. A startling statistic that links
34:54back to the one child policy. We're hearing the story of one of those kids and the mother who never
35:01stopped trying to find him. Thank you for joining. See you next week.
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