Web Culture

The Rise and Fall of Ross Ulbricht, AKA the Dread Pirate Roberts

Dann Albright 24-02-2015

Silk Road, before it was shut down, was one of the most notorious dark web Journey Into The Hidden Web: A Guide For New Researchers This manual will take you on a tour through the many levels of the deep web: databases and information available in academic journals. Finally, we’ll arrive at the gates of Tor. Read More sites on the Internet – a BitCoin powered Amazon for the black market. Its pseudonymous leader, Dread Pirate Roberts (DPR), often espoused an anti-establishment, libertarian philosophy — but what else do we know about him?


Since Ross Ulbricht’s arrest, we’ve come to learn that he’s just as interesting a character as the site that he ran.

Who Is Ross Ulbricht?

If you haven’t been following the news, Ross William Ulbricht, of Austin, Texas, was unmasked as the Dread Pirate Roberts – a title that he claims was passed between leaders of Silk Road. Ulbricht had been a student of physics and materials engineering, but near the end of his studies at Penn State, it started to become clear that his interests lied more in, as the Wall Street Journal put it, “perfecting economics in a virtual setting.”

Ulbricht definitely had a strong libertarian bent. Here is a post from his LinkedIn page:

Now, my goals have shifted. I want to use economic theory as a means to abolish the use of coercion and aggression amongst mankind… The most widespread and systemic use of force is amongst institutions and governments, so this is my current point of effort. The best way to change a government is to change the minds of the governed, however. To that end, I am creating an economic simulation to give people a first-hand experience of what it would be like to live in a world without the systemic use of force.

That “economic simulation,” most people believe, was Silk Road – a place where mostly unregulated free trade would reign. One phrase that often comes up in discussions of Ulbricht’s economic ideas is “Austrian school of economics.” This school of thought is based around the writings of, among others, Ludwig von Mises. Mises championed complete economic freedom, which Ulbricht sought to create through Silk Road.

Of course, one of the crucial factors of a successful online black market system is anonymity — ensured by Tor and Bitcoin. By creating Silk Road as an onion site How to Find Active .Onion Dark Web Sites (And Why You Might Want To) The Dark Web, in part, consists of .onion sites, hosted on the Tor network. How do you find them and where to go? Follow me... Read More , Ulbricht kept users in the dark about who they were dealing with, and by using Bitcoin, he thought that the transactions couldn’t be traced back to buyers, sellers, or him (turns out he was wrong about that one).



Ulbricht was an avid Bitcoin user, and a few outlets have characterized him as a “Bitcoin entrepreneur.” One of his defenses in court was that, although he had earned millions of dollars in Bitcoins, he had done this through Bitcoin trading — not through taking a cut of black-market transactions.

Silk Road was the culmination of Ulbricht’s ascription to the Austrian school of economics, and his interest in showing the world what such a free market could provide. Silk Road, if all went to his plan, would “grow into a force to be reckoned with that can challenge the powers that be and at last give people the option to choose freedom over tyranny.”

A quote from the Forbes‘ profile of Dread Pirate Roberts sums up his views very well:


We can’t stay silent forever. We have an important message, and the time is ripe for the world to hear it. What we’re doing isn’t about scoring drugs or ‘sticking it to the man.’ It’s about standing up for our rights as human beings and refusing to submit when we’ve done no wrong. Silk Road is a vehicle for that message. All else is secondary.

A noble ideal? Maybe. The best way to go about it? Probably not.

Dread Pirate Roberts

The origin of the Dread Pirate Roberts pseudonym is much less clear than Ulbricht’s history. Some people say that the original owner of the site called himself Dread Pirate Roberts, then passed the mantle on to Ulbricht when he got out of the business. Ulbricht reportedly got himself noticed after pointing out a security flaw in the site.

Another origin story says that another user of Silk Road, known as Variety Jones or Cimon, was responsible for the name. According to Wired, Ulbricht had been running the site as “Admin,” and Jones recommended the name change so that he could maintain further privacy and use the legend of The Princess Bride (the novel in which the Roberts character was created) to claim that he had only been one of the administrators, and had passed it onto someone else.

(If you want to read more about Variety Jones, Wired has a great article about him—he’s another interesting character.)


This ended up being one Ulbricht’s defenses in court—he stated that he had been DPR, but that the current holder of the title was Mark Karpelés, founder of Mt. Gox – the Bitcoin exchange made infamous by losing $450 million in Bitcoins in 2014 (an event that had some peopled worried about the future of the Bitcoin economy Does The Fall Of Mt. Gox Mark The Beginning Of The End For Bitcoin? [MUO Debates] Does 2014 mark the beginning of the end for Bitcoin?Or, is this only a bump in the road along the evolution of this new form of currency? MakeUseOf.com debates. Read More ).

Of course, the idea of Ulbricht receiving the title from someone else doesn’t jibe well with what he said about creating an economic simulator — it very much seems as though it was his idea from the start, and that he saw it through. And the FBI did show that he had been collecting Bitcoins from Silk Road until the marketplace was shut down.

Regardless of where the title originated, Ulbricht took his privacy seriously. When he was approached (as DPR) by a reporter from Forbes, he refused to make contact in any way other than via Silk Road. It took the reporter eight months to actually get to a conversation with DPR, who said that he doesn’t even meet with his closest advisors in person. When the reporter asked for his name and nationality, DPR disappeared for a month.



Interestingly, despite Roberts’ apparent penchant for security, a few sloppy mistakes led to his unmasking and subsequent arrest (including using an email address that contained his real name). His mistakes actually formed part of his defense at one point — the claim was that the real, current DPR was very secretive and technologically knowledgeable, while Ulbricht didn’t seem to be. Especially compared to Variety Jones / Cimon, who reportedly moved around the world regularly and flew his family to a secret location to see him twice a year.

No matter how the Dread Pirate Roberts entered the business or exactly what his goals were, the members of Silk Road thought very highly of him. Forbes wrote that:

Commenters on the site describe Roberts as a “hero,” a “job creator,” “our own Che Guevara” and a “name [that] will live [on] among the greatest men and women in history as a soldier of justice and freedom.”

Silk Road, illegal as it was, clearly stemmed from demand. People wanted a free market where they could buy the things they believed they had a right to partake in, and they appreciated DPR’s efforts to create that market.

Was Ulbricht Such a Bad Guy?

Up until this point, Ulbricht seems, at worst, misguided. He’s a strong libertarian, wants to establish ultra-free markets, and let people go about their business away from the watchful eye of government. He even set rules on what could be sold on the site, keeping the worst things—child pornography, stolen credit cards, assassinations, weapons of mass destruction — off of the listings (though high-powered weapons were sometimes available on the site). Is he such a villain?

There’s a darker side to Ulbricht’s story that suggests he might be. According to an indictment issued in Maryland, Ulbricht had a falling out with one of his employees, who he accused of stealing tens of thousands of dollars worth of drugs from customers. The employee was subsequently arrested. Dread Pirate Roberts sent the following message to a drug smuggler:

I’d like him beaten up, then forced to send the bitcoins he stole back. like sit him down at his computer and make him do it

It was shortly followed up by a much more disturbing message:

can you change the order to execute rather than torture?

He sent the drug smuggler $40,000 to get started, and promised another $40,000 after he had received video or pictures proving that the employee had been killed. He received the pictures, and sent the second payment. He said he was “a little disturbed, but I’m ok,” and “I’m sure I will call on you again at some point, though I hope I won’t have to.”

Unfortunately for Ulbricht, the drug smuggler was an undercover federal agent, and the photos that he received were staged. Ulbricht was out $80,000 and in deep trouble.

But it doesn’t end there. A few weeks later Dread Pirate Roberts put out another hit order, on a user who was trying to extort him with a threat of releasing Silk Road user information – this time for $150,000. There’s no indication that this order went through a federal agent . . . but there’s also no evidence that the murder was actually committed. It appears that Ulbricht got ripped off. Again.

Obviously, setting up a highly illegal international drugs marketplace that did tens of millions of dollars in business requires someone who’s not hesitant to take risks and potentially protect their investment. It’s not exactly a surprise that Ulbricht ordered these hits.

Dead End for Silk Road

Eventually, and with assistance from his own mistakes, the law caught up with Ulbricht. His minimum sentence is 20 years, and he faces the potential for life in prison. And that’s aside from another trial for attempting to secure murder-for-hire services. He’s going away for a long time.

Ross Ulbricht, Dread Pirate Roberts, DPR — no matter what you call him, he was a fascinating guy. Certainly someone you wouldn’t want to be involved with, but fascinating nonetheless. His arrest and subsequent conviction mean we won’t be seeing much of him for a long time, though with the rise and fall of Silk Road 2.0 Twitter IPO, Android Profit, Silk Road Returns, PS4 Exposed [Tech News Digest] 37signals helps you work remotely, Silk Road 2.0 is launched, the Internet Archive is damaged in a fire, the innards of the PlayStation 4 are exposed to the world, and an iPad Air gets badly... Read More , and the fact that Variety Jones / Cimon is probably still out there – along with millions of other people with similar views – you never know when another stranger-than-fiction character like Roberts will appear.

Image credits: Burners.me.

Related topics: Bitcoin, Tor Network.

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  1. charles tullous
    March 1, 2015 at 5:50 am

    Ross Ulbricht said in his manifesto, that he wanted to spread Libertarian values (whatever that is.) So what did he do? Did he join organizations and activists to elect Libertarian political candidates? Nope. Did he promote libertarian legislation? Nope. He instead decided to be an Illegal Narcotics dealer, in order to monopolize the ermerging dark web drug market. And also try and kill a bunch of people. .....There's your principled Libertarian. Hopefully he will stay in jail for a very long time.

    • Dann Albright
      March 2, 2015 at 4:42 pm

      Yeah, he didn't really seem to go about doing things in a very effective way, did he? Establishing a free marketplace might have been a good idea, but for it to become the world's go-to place for drugs was sure to have it brought down in short order.

      And I agree—I hope he gets put away for the rest of his life. Not a guy we want out on the streets again.

  2. dragonmouth
    February 24, 2015 at 9:14 pm

    The Politically Correct thing to do is to excoriate Ulbright and to call for his head. However, knowing how the government likes to opverreact and deal in hyperbole (see Edward Snowden), IMO, the indictment does fit the crime. The Feds would like us to believe that Ulbright was a combination of Pablo Escobar and Nicky Barnes with liberal sprinkling of Michael Corleone. As far DOJ is concerned, Ulbright committed the ultimate and unpardonable sin of evading governmet controls.

    • Dann Albright
      February 25, 2015 at 10:18 am

      He may have been evading government controls, but he also enabled the sale of millions of dollars worth of illegal substances and materials and was involved in two murder-for-hire contracts. Seems like pretty good justification for indictment to me. :-)