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So you think you know Silk Road? Day 3 of Trivia Quiz and answers

The third question of my Silk Road trivia quiz turned out to be a tough one.

The question posed to Reddit and Twitter users was:

In May 2013 which former Silk Road moderator had their account taken over by law enforcement, eventually leading to HSI officer Jared der Yergihan being able to infiltrate Silk Road, working undercover as a trusted staff member?

(a) Nomad Bloodbath

(b) Scout

(c) Cirrus

(d) Inigo

(e) Chronicpain



(Only 4 options allowed on Twitter polls)


(a) Nomad Bloodbath

Nomad Bloodbath was one of the first forum moderators on Silk Road, taking up the role in August 2011. Although popular he had a few issues and was considered a bit flaky. His role and access were minimal and he was eventually stripped of his mod privileges by Dread Pirate Roberts (Ulbricht). He had a store on Silk Road that sold popular handmade chalkboard skulls.

(No, that’s not a euphemism for some fancy drug. They were literally decorative skulls made from a chalkboard substance that he shipped with pieces of white and colored chalk so that recipients could color them in)

Although not immediately clear how law enforcement compromised him, Bloodbath would have been pretty low-hanging fruit. However, having been stripped of his mod privileges he had no more access than any other vendor. In May, “Nomad Bloodbath” (actually law enforcement, probably Jared der Yergiayan – see LaMoustache’s analysis of why) returned to the forums after months of inactivity. He announced in the private forum for vendors that he was holding a sale on his custom-made chalkboard skulls, offering a 50% discount.

A couple of key people ordered those skulls to be shipped to their homes: Silk Road moderators SSBD and Scout.

With Bloodbath’s account under the control of law enforcement, they now had the addresses of two Silk Road staff members. SBBD was all the way on the other side of the world, in Australia. But they hit the jackpot with Scout. Silk Road’s first and only female staff member lived in Texas. She had been appointed in January 2013 and was a popular and trusted member of the team.

Homeland Security agent Jared der Yeghiayan paid Scout a visit and made her an offer she couldn’t refuse. In July 2013, Scout handed over the keys to her moderator account and der Yeghiayan assumed her identity, eventually renaming the account ‘Cirrus’.

This was the beginning of the end. Cirrus was an active moderator and trusted member of staff. He was instrumental in bringing Silk Road down, ensuring that Ross Ulbricht was logged into the administrator panel when he was arrested.


29-year-old Texan Ross William Ulbricht was cap- tured in a dramatic arrest in a San Francisco public library. Ulbricht, who had an advanced degree in chemical engineering, and who had developed a cult-like following among the Silk Road users as Dread Pirate Roberts, criminal mastermind, was caught in the sci-fi section logged in to the master control panel of Silk Road, as well as various other incriminating sites and applications.

The arrest was carried out by FBI agents who had been keeping the young Texan under surveillance and suspected that he sometimes logged on to administer Silk Road from a local café or the library. When he entered the library, they had to make sure he was logged in to the backend of Silk Road. What DPR didn’t know was that one of his staff members, Cirrus, had been compromised. She had been ar- rested in July and her account taken over by an undercover agent, Jared Der-Yeghiayan.

The FBI had to make sure Ulbricht was logged in as DPR when they seized his computer, or there was little doubt that the laptop would be encrypted and of no more use to them than a brick. To do so, they had ‘Cirrus’ strike up a chat with him. If DPR was actively chatting to a staff member, they could grab the laptop while he was logged in and have access to the inside of the Silk Road website.

The plan was executed perfectly. Two officers staged a domestic dispute, and while that distracted Ulbricht, another officer grabbed his open laptop. On that laptop was a goldmine. He not only kept a journal on the hard drive documenting the establishment and growth of the site, he meticulously kept records of the real-time chats he had with everyone involved in Silk Road, something that was drummed into his staff they were forbidden to do.

Thousands of pages of logs recorded every conversation DPR had had with his various staff members. They also revealed the existence of the hitherto unknown Variety Jones. Unfortunately for some, the open laptop also held the unencrypted ID documents of Silk Road staff.

Five days after Ulbricht’s arrest, high-ranking members of Silk Road met to discuss a replacement. A month later, on 6 November 2013, Silk Road 2.0 was launched.

Of course, at the time, the community was completely clueless that all this was going on.

(Both Chronicpain and Inigo were also compromised by law enforcement in different ways, later on – their stories are also featured in The Darkest Web)

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