Ray William Johnson: True Story Podcast
The Downfall of the Silk Road - The Ross Ulbricht story
Wed, 02 Apr 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.
How did Ross Ulbricht start the Silk Road?
So this guy is about to go to prison for starting a website? Now the guy, let's call him Pirate. And Pirate is 27 and he hates the US government. He hates how they regulate and intervene and everything. And one day in 2011, he comes up with an idea. An idea to get around all that government regulation. He's going to 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-pews, 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, 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, Pirate's 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 US government.
And so the feds start 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 feds 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, f*** 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.
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