The Ingenious and Accidental Take-down of the Biggest Cyber Drug Lord of all Time

How Ross Ulbricht and the Silk Road Fell


The dark web is defined by Wikipedia as “the World Wide Web content that exists on darknets: overlay networks that use the Internet but require specific software, configurations, or authorization to access.” For whomever reading, you most likely know the dark web as the part of the Internet where people sell drugs, pay for hit-men, and engage in all sorts of illegal activity unmonitored by investigative authority. One website on the dark web known as Silk Road, in reference to the infamous trade route in Asia over 2000 years ago, was one of the most, if not the most, unregulated e-commerce sites anyone had ever seen. The premise? Buy or sell ANYTHING anonymously. Kind of like Amazon, but for drugs. Ross Ulbricht was the creator of the site and ran it under the name “Dread Pirate Roberts,” and anyone reading who has seen The Princess Bride would understand how clever that name is, insinuating that more than one person ran the account. DPR, as we will be calling him from now on, was the head honcho of the site and over the course of some years quickly became a multimillionaire from the revenue and traction the site got on a daily basis. So, what happened to the Silk Road? What about DPR, or Ross Ulbricht? Let’s get into it.

To start out, let me introduce you to the cast of characters we will be looking at.

  • DreadPirateRoberts: Ross Ulbricht, owner of Silk Road
  • Lucydrop: one of top vendors on Silk Road (seller)
  • FriendlyChemist: claimed to be middleman between Hell’s Angels and Lucydrop, supplier for Lucydrop
  • RedAndWhite: claimed to be from Hell’s Angels, who FriendlyChemist is in debt 700,000 dollars to

The beginning of the end starts on March 13th, 2013 with FriendlyChemist messaging DPR about a “life and death” situation. FriendlyChemist is very frantic in his messaging and claims that he is in debt 700,000 dollars to the Hell’s Angels because he sold Lucydrop 900,000 dollars worth of product and only got 200,000 dollars before Lucydrop disappeared. He also claims that he has the identities of over two dozen top vendors and thousands of Silk Road customers and that he will leak them if DPR doesn’t get him back his money. DPR, realizing he is getting blackmailed, then contacts Lucydrop asking for FriendlyChemist’s name, home address, and description since both Lucy and Chemist worked together in person. Turns out, Lucydrop’s account on Silk Road was taken over by another one of his/hers partners; Xin. So RealLucydrop contacts DPR and exchanges Chemist’s info for 1000 dollars in bitcoin, as a treat.

In their private messages, which are viewable via government transcripts online, DPR tells Lucy that he wants to have Chemist ‘taken care of’ so he doesn’t have to deal with him and his blackmail shenanigans any longer. Lucy is wary of this idea as Chemist also has incriminating info on himself/herself and does not want to go to prison. DPR then asks Chemist to refer him to whomever he/she owes money to to solve the whole debacle. That is when RedAndWhite enters the scene as a member of the notorious Hell’s Angels criminal organization in Canada, professionally dealing drugs across the country. 

DPR, in a cunning manner, contacts RedAndWhite offering his services on the Silk Road as a potential business venture for Hell’s Angels, as well as providing any info they need on FriendlyChemist. RedAndWhite takes the bait and seems interested in the possibility of selling on Silk Road. R&W also informs DPR that Xin is ‘taken care of’ and they are no longer interested in Chemist, as their vendetta against the thieves has been taken care of. While this is already incredibly incriminating on Ulbricht’s part, as he has already allowed a man to be killed on his watch, things only get far far darker. In a horrifying flex of financial power, DPR sends this message to RedAndWhite: 

“I hate to come to you with a problem when we are just starting to get to know one another, but Blake (FriendlyChemist) is causing me problems. Are you still looking for him or now that you’ve found Xin have you given up? I would like to put a bounty on his head if it’s not too much trouble for you. What would be an adequate amount to motivate you to find him? Necessities like this do happen from time to time for a person in my position. I have others I can turn to, but it is always good to have options and you are close to the case right now. Hopefully this is something you are open to and can be another aspect of our business relationship. Regards, DreadPirateRoberts.”

In other words, DPR is asking how much money in bitcoin would it take to kill FriendlyChemist. If Ulbricht hadn’t done anything highly incriminating before this, maybe he would have had a chance in court, but alas. Making almost thirty million dollars in only two years of operation of Silk Road, he had turned sour and bloodthirsty. R&W is open to this idea and agrees to have Blake executed for 150K in bitcoin. Through a picture sent by R&W of Blake’s lifeless corpse, the deed is done.

Through a period of some months, DPR uses his affiliation with R&W to execute five more people, resulting in about a million dollars of bitcoin used on hits. That would be about sixty-one million dollars today.

If this is where the story ended, it truly would be a sad, sad tale. But thankfully for the conscious of us all, there is a little bit more we need to discuss.

Through an advertisement posted by user Altoid on a drug forum in 2011 for Silk Road, the FBI tracked Altoid’s account and eventually traced it back to Ross Ulbricht, who was swiftly put on the FBI’s watch list. Feds knew that his computer would encrypt itself if it were closed, so they needed to get it while it was open. In the fall of 2013 at the Glen Park Branch Library in San Francisco, detectives created an altercation that made Ross get up from his seat with his laptop open. Feds snatched it and saw him on Silk Road, found hundreds of incriminating messages, and even a full diary about the creation of Silk Road as written by Ross. They booked him in and a trial ensued.

Now, I bet you’re wondering, “That’s great and all, but why talk about the whole blackmail assassination scenario?” Well, as it turns out, all of the characters in our little play for the damned besides Ross himself were all the same person. They successfully and intuitively persuaded Ross out of a million dollars at the time, and like I said, about sixty-one million dollars today. So, that means that nobody was injured, kidnapped, or killed in the process, but Ross didn’t know this. He genuinely believed that he had paid for the murderings of six people through this one scammer, and this fact resonated through the jurors in court. If Ross wasn’t going to get life in prison for running Silk Road in the first place, the deals that this unknown scammer made with Ross surely solidified his fate in prison.

Ross Ulbricht now faces a life sentence with the following charges of which we was convicted of all: distributing narcotics, distributing narcotics by means of the Internet, conspiring to distribute narcotics, engaging in a continuing criminal enterprise, conspiring to commit computer hacking, conspiring to traffic in false identity documents, and conspiring to commit money laundering.