Ray William Johnson: True Story Podcast - The Downfall of the Silk Road - The Ross Ulbricht story

Episode Date: April 2, 2025

The Ross Ulbricht case centers on the creator of the Silk Road, an infamous dark web marketplace used for buying and selling illegal goods. Operating under the alias “Dread Pirate Roberts,” Ulbricht was arrested in 2013 and later convicted on charges including money laundering, computer hacking.

So this guy is about to go to prison for starting a website? Now the guy, let's call him Pirate. And Pirates 27 and he hates the US government. He hates how they regulate and intervene in everything. And one day in 2011, he comes up with an idea, an idea to get around all that government regulation. He's gonna build a website. And on that site, you would be able to buy or sell anything you want,

anonymously like fake passports, drugs, illegal pew-pues, things like that. And it would be like an Amazon for buying illegal stuff. And so he gets to work and he hires someone to help him build this. And eventually he launches it on the dark web. Now the site, it's called the Silk Road. And it's pretty successful right away, like people flock to it and they buy all kinds of crazy stuff. And they pay for it all in Bitcoin, making things harder to trace.

And just like Amazon, the site even allows you to rate and review sellers. Like, oh, this Zaza was pretty dank. Five stars. Anyway, about a year goes by, and it's now 2012, and business is booming. And at this point, Pirates got like 10 employees working for him. The site is making half a million dollars in sales a week.

It has a bunch of active users, people are buying and selling all kinds of illegal stuff from one another, but, you know, mostly drugs. And Pirate himself makes commission off of each sale, so he is raking, in the money. He's now apparently worth tens of millions of dollars. Dude is rich, and he barely spends it. He's like too busy running the site, I guess. And this success is great and all. However, here's the problem with Silk Road being so successful so quickly. Because so many people know about it

and so many people are talking about it, guess who now has their eyes on it? The one thing pirate hates. The U.S. government. And so the Fed starts. investigating and that is when this DEA agent gets involved. Carl Force and Carl Force he goes undercover and he becomes an active user on Silk Road and he gets involved in the community and he eventually becomes online friends with Pirate. And at some point Carl Force and other agents discover the identity of one of the people working for Pirate. The worker's name is Chronic Pain because they all go by their usernames. So Carl Force and the Fed set up a

sting operation to bust Chronic Pain and bam, they go in and they arrest him. Here's his mugshot. Now, once Pirate finds out that Chronic Pain has been arrested, he gets worried, as he should be because it's only a matter of time before the feds figure out who he really is. And if Chronic Pain snitches on him, this could bring down Silk Road and his entire operation. Plus, Pirate has gotten word that Chronic Pain was stealing Bitcoin from the site or the company. So he's thinking, fuck that guy. So in 2013, Pirate does the only thing he can think of.

He allegedly decides to hire a hitman to find Chronic Pain and get rid of him for good so that he won't snitch and so that he'll stop stealing money from the site. And by the way, Chronic Pain was never stealing money from the site, just so you know. But anyway, so Pirate gets to work and he contacts a buddy who he believes might be able to hire a hitman and unalive his former employee. That buddy ends up being Carl Force, the undercover DEA agent. And so Pirate hits up Carl and he's like, Hey, I'll pay you $80,000 if you unalive someone for me.

And Carl Force is like, what the hell? I mean, I. Now, we know Carl Force is a DEA agent, so he's not just going to go and assassinate someone. So he collaborates with chronic pain and they stage some photos together and they make it look like some hitmen captured chronic pain and that they are waterboarding him in a bathtub. Then they make him lay down on the floor and they pour soup on him and they make him look unalived. And they take a bunch of pictures and Carl Forst sends those pictures to Pirate and now Pirate believes Chronic Pain has been unalived.

Oh and by the way, Pirate also allegedly orders five more hits on other people at different times. Like, bro is just crashing out. Allegedly. Now, at this point, in 2013, various factions of the U.S. government are investigating Silk Road, because it's getting pretty popular. And they're still trying to figure out who is running the operation. Because the whole Silk Road site is run anonymously. Like, even the guys who work for pirate don't know who he is or his real identity,

because they all go by their usernames. And so the feds want to know who is. Pirate. Now eventually they finally discover the IP address of the Silk Road site and they trace it to a couple of different places One of those places being a little internet cafe in San Francisco and Pirate the real guy happens to live near there and so the feds start putting clues together and ultimately they conclude that Pirate is the guy running this Silk Road and that this is where he lives So cool, now they can go get him, right? No, there's a problem. The feds can't just rush in and bust him because pirate is a smart guy. His electronic devices are very likely locked and password protected.

And if they can't get into his laptop, they won't have enough evidence to convict him. And so what do they do? They set up a little sting operation to get his laptop away from him while it's still open while he's logged in so that they can break into it. And so first they find Pirate and they surveil him for a while. Then once they know his routine, they follow him to the San Francisco Public Library, where he chills sometimes and works off their Wi-Fi. After that, some undercover agents go to this library. Then two of the agents pretend to be a romantic couple arguing,

and one of the people in this fake couple starts cussing the other one out. Now this causes Pirate to stop what he's doing and turn around and look at this fake couple. couple. Then one undercover agent posing as the wife in this couple punches the other undercover agent, which creates a huge distraction. And now that Pirate has all his attention focused on this fight and he's nice and distracted, boom, another agent swoops in and grabs his laptop while it's still open while he's still logged in. And pow, another undercover agent grabs Pirate before Pirate can react and bam, they arrest him. Here's his mugshot. And listen to this. Allegedly Silk Road, had made $1.2 billion worth of sales in just these few years that the site was live.

While Pirate himself made from what I saw about $184 million. Oh my god. But here's the crazy thing though. Silk Road sold a lot of drugs as it was designed to do. And at least six people that we know of at some point died from overdosing on drugs that they had bought off that site. So when this whole case goes to trial, family members of people who had overdosed show up and they like cry in court and they give personal statements against Pirate and the Silk Road. And this has a huge impact on the case. Plus, the prosecution brings up the fact that Pirate allegedly tried to hire Hitman to unalive some people, although they never formally charge him with that. I guess they have enough against him with illegally running the Silk Road.

Or maybe he never tried to unalive those people. I don't know, but they never charge him with it. And because of all that, at the end of it all, pirate is found guilty. And he gets life in prison without the possibility of parole. Which a lot of people feel is really harsh. Life without parole for running a website? Oh, but that's not even the craziest part.

The craziest part is that Carl Force, the DEA agent who was working on the case, he was secretly extorting Pirate the whole time into giving him some of that money that the site was making. Pirate ended up giving him like $750,000 in Bitcoin. And so Carl Force, the DEA agent, also gets convicted in this scheme and he gets six years in prison. Here's a picture of the guy.

Not only that, but also another agent gets busted for stealing Bitcoin from the site while they were working on this very case. And he gets like five years in prison total. Here's his picture. But then it all changes one last time. Because in 2025, in a crazy twist after Pirate had been in prison for around 10 years or so, the government officially steps in and pardons him. So he's actually out now.