Five stupid things Dread Pirate Roberts did to get arrested

Everyone thought the shady figure behind the Silk Road website was a criminal mastermind. The reality tells a different story

But despite his apparent success building 'the eBay of hard drugs' through anonymous servers and a hidden identity, the man known as 'Dread Pirate Roberts' began to leave a trail of traceable activity social media.

So how did Dread Pirate Roberts get himself arrested?

• He boasted about running his international multimillion dollar drugs marketplace on his LinkedIn profile

Despite the fact that he presumably had few plans to re-enter the traditional workforce, Ross Ulbricht maintained a profile on LinkedIn even while he was allegedly running the Silk Road.

In it, he makes veiled references to his present activities. “Ulbricht states in his LinkedIn profile that, after … time in graduate school, his ‘goals’ subsequently ‘shifted’,” says FBI agent Christopher Tarbell in his criminal complaint delivered to the Southern District of New York.

“Ulbricht elaborates, obliquely, that he has since focused on ‘creating an economic simulation’ designed to ‘give people a first-hand experience of what it would be like to live in a world without the systemic use of force’ by ‘institutions and governments’… I believe that this ‘economic simulation’ referred to by Ulbricht is Silk Road.” 

• He used a real photograph of himself for a fake ID to rent servers to run his international multimillion dollar drugs marketplace 

In July 2013, a package from Canada was intercepted at the border as part of a routine mail search, and found to contain nine fake IDs, each with a different name but all with a photo of the same person.

Homeland Security was duly dispatched to the address the parcel was headed to, and found Ulbricht there, who Tarbell says “volunteered that ‘hypothetically’ anyone could go on to a website named ‘Silk Road’ on ‘Tor’ and purchase any drugs or fake identity documents the person wanted".

Why did Ulbricht need nine fake IDs? An earlier posting on the Silk Road forums may explain it. Dread Pirate Roberts explained that he “needed a fake ID [to] rent servers”. Tarbell adds that “server hosting companies often require customers to provide some form of identity documents in order to validate who they are”.

Which is fine, except that if you are posting a photocopy of a fake ID to a server hosting company, you don’t need to put your real face on it. And if you’re running an international multimillion dollar drugs marketplace, keeping your real face away from the public is probably a good idea.

• He asked for advice on coding the secret website for his international multimillion dollar drugs marketplace using his real name

As well as not using your real face, it’s probably best not to use your real name. Especially when asking for coding tips about your secret drugs marketplace.

In March 2012, a user registered on the coding Q&A site Stack Overflow with Ulbricht’s email address and the username 'Ross Ulbricht'. He then proceeded to post the question “How can I connect to a Tor hidden service using curl in php?”.

Publicly posting under your real name that you run a hidden website (using the anonymous browsing tool Tor), probably isn’t a great idea. Posting an example of the code that you actually run on that hidden website, still under your real name, is a terrible idea. And yet Tarbell says:

“The computer code on the Silk Road web server includes a customised PHP script based on ‘curl’ that is functionally very similar to the computer code described in Ulbricht's posting on Stack Overflow, and includes several lines of code that are identical to lines of code quoted in the posting.”

• He sought contacts in courier firms, presumably to work out how to best ship things from his international multimillion dollar drugs marketplace, on Google+, where his real name, real face and real YouTube profile were visible

“Anybody know someone that works for UPS, FedEX, or DHL?”, asked Ulbricht on Google+. On his YouTube profile, linked to from that page, Ulbricht saved a couple of videos for later, including one from the ultra-libertarian Mises Institute titled “How to Get Away with Stealing”.

Even that is used as evidence against him. Tarbell says “DPR’s user ‘signature’ in the [Silk Road] forum includes a link to the ‘Mises Institute’ website … moreover … DPR has cited the ‘Austrian Economic theory’ and the works of Ludwig von Mises … as providing the philosophical underpinnings for Silk Road.”

• He allegedly paid $80,000 to kill a former employee of his international multimillion dollar drugs marketplace to a man who turned out to be an undercover cop

In a second criminal complaint, from the state of Maryland, it is alleged that Ulbricht “communicated with the UC [undercover cop] via the internet, and told the UC that the employee had been arrested by law enforcement and that the employee had stolen funds from other Silk Road users”. Ulbricht apparently told the cop “I’d like him beat up”, before changing the order the next day “to execute rather than torture”.

The complaint says that Ulbricht “agreed to make two payments of $40,000 each for the murder of the employee, ‘half down now and half after the job is done.’”

After seeing staged photos of the employee being tortured, Ulbricht wrote that he was “a little disturbed” and that “I’m new to this kind of thing”.

He duly paid up.

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