The second Dread Pirate Roberts (DPR)—the enigmatic owner of Silk Road, the online drug bazaar designed for anonymous transactions—has entered retirement. And now that he’s gone, other Silk Road staffers can reflect more candidly on what life is like being employed by a darknet kingpin.

"Privacy is a right we deserve"

In our earlier interview with him, DPR 2.0 said, “All I now seek to ensure is that if I do go down, I don't take Silk Road down with me.” On this count, he succeeded. In the wake of DPR 2.0’s departure, Silk Road appointed an interim leader who goes by the pseudonym Defcon, and the site remains up. The same cannot be said of Silk Road’s predecessor site, which went down in October 2013 after the arrest of its alleged owner and original Dread Pirate Roberts, Ross Ulbricht.

DPR 2.0’s retirement concludes a tense period for the site. In December, two alleged Silk Road moderators were arrested and indicted on drug, hacking, and money laundering charges. Following these events, a spooked DPR 2.0 even imagined he saw FBI cybercrime agent Chris Tarbell. (Tarbell led the investigation and arrest of Ulbricht.)

In the throes of paranoia, DPR 2.0 destroyed his computer, went on the lam, and left his staff with these words:

“I don't know how long I will be walking free but we live and we die, and this is my legacy. Keep the road going... ...this project is what I will always be associated with and the fact it didn't burn down with me is testament to the idea I have lived and will die for.”

Once the fog of paranoia cleared and it became evident that the arrests were limited to the two moderators, DPR 2.0 returned. As Senior Silk Road staff member DoctorClu told Ars, “He resurfaced a short time after [disappearing], sending messages with a unique cryptographic signature to prove his identity and restore his access to the site.”

Paranoia is hardly unusual on the darknet (the informal name for the host of websites not accessible to ordinary Web browsers). The space always seems to be swirling with intrigue and suspicion. This very suspicion may have been what drove DPR 2.0 to make the most controversial decision of his tenure.

Though DPR 2.0 ran a site for which anonymity was paramount—many dealers and customers wouldn’t trust it otherwise—he was not keen on extending that same anonymity to his staff. In a private forum accessible only to Silk Road employees, DPR 2.0 demanded they send him their encryption key along with its associated password, which would enable him to decode their communications. DPR 2.0 wrote:

“Failure to do so will mean automatic expulsion from the staff team. There is absolutely nothing you should have which is beyond our privilege to view so if such an occasion arrives it is likely because we are making an investigation into somebody you have previously talked to (even if it was months ago so let us know when your last key change was if we ask).”

The spectrum of staff responses to this assault on their privacy echoed the broader public debate on privacy and the NSA. They ranged from servile loyalty (“Hugs to ya DPR”) and terse obedience (“Message received”), to measured opposition (“BOTTOM LINE is—Got it. But I will say this...”) and firm denunciation (“I find this request to be disturbing”). DPR 2.0 countered that “nothing personal should ever be disclosed anyway and personal contacts be kept separate from official duties.” He explained that his “main area of focus is keeping law enforcement off our backs” and alluded to “some disturbing intelligence I am not comfortable disclosing.” The Silk Road leader continued:

“I would not be asking you this as an off-hand comment or to investigate a minor issue, and this is certainly not a judgment I have made without weighing in the factors you have already raised. Our enemies are cunning and operate in closed-rank secrecy, and so to counter the threat all available intelligence must be accessible.”

Senior staff member Stealth stood up to DPR. “I never agreed as part of my employment to hand over a private key or password either, and frankly I find this request to be disturbing.” The irony of an anonymous marketplace infringing on employees' privacy was not lost on staff member DoctorClu either. DoctorClu countered:

“The regurgitation of 'If you have nothing to hide, you have nothing to fear,' is the excuse always thrown at us following catastrophic events. My response to this has always been 'In that case, I will be placing a camera in your shower. You have nothing to hide so there shouldn't be a problem with this.' Privacy is a right we deserve. …hell, PGP [a type of encryption many on the darknet rely on] stands for 'Pretty Good Privacy'. You are essentially telling us that we should not have privacy on the forums. You control it going forward. I know this is blunt, but we hide on an anonymous network and have worked very hard to secure ourselves even further on it because we cannot maintain privacy on the clearnet. Now this privacy is once again in jeopardy on an environment that was established as safe.”

DPR ended up quietly dropping the matter. No one was punished for failing to send over their encryption keys.

A "brilliant" man

Despite this controversy, staff still have some affection for their former boss. For instance, Stealth, the same staff member who likened DPR 2.0's demand for their encryption keys to the NSA, nonetheless described DPR 2.0 as “generous” and a “sincere believer” in the radical freedom of transactions that Silk Road represents to its proponents.

DoctorClu agreed that the former leader could be quite generous, recounting the time a staff member was drafting plans for a new security network. The employee asked DPR 2.0 for his opinion, but DPR 2.0 gave more than that. According to DoctorClu: “DPR2 replied, 'Send me a wallet address, I will throw you a couple coins.' After he did, the next morning $15,000 was in his wallet.”

DoctorClu also said that whenever someone was in trouble financially—staff and vendors alike—DPR 2.0 would help them out. DoctorClu estimates the Silk Road leader spent a total of around $100,000 in such cases. “When people would prove to us that they were in danger, DPR gave whatever he could,” DoctorClu said.

Despite such moments, staff also describe DPR 2.0’s “hubris” and “arrogance.” DPR 2.0 once blithely announced to staff that a competing anonymous market called Agora “is going down” for simply posting unsolicited adverts for their site on Silk Road forums. The pretext upon which he wanted Agora's site hacked was so apparently flimsy that the hacker DPR 2.0 paid to carry it out ended up resigning in disgust.

DPR 2.0 could also be authoritarian, casually dictating to staff what they weren't allowed to do without first asking for input. For example, he once privately informed staff:

“As moderators, your role is explicitly to moderate the forum and no further duties unless requested. You should not be undertaking 'investigations,' trying to drag up any dox or information, or commenting on theories flying around the forum. All such matters and information should go straight to myself & Defcon which you can do by making a topic addressed to us and encrypt it to our PGP keys. Communicating with people outside of SR forums on such matters is still outside of what duties you have been asked to perform and is still in violation of the principle. Staff should not be sharing information with each other regarding such theories of whatever 'dox' somebody has sent them, this comes to me and Defcon without fail and isn't a topic for discussion.”

DoctorClu described DPR 2.0 as “brilliant, egomaniacal, and paranoid.” He elaborated: "As you got to know DPR2, you could tell very quickly that he was a brilliant man. When you began to learn more about him combined with how he spoke, his hubris turned him into somewhat of an egomaniac. After his disappearance, his true paranoid side came out.”

Defcon, Silk Road’s interim leader, is a hacker whom staff describe as more technically capable than his predecessor. Whether or not Defcon will don the black mask of “Dread Pirate Roberts 3.0” is uncertain, though the site’s attitude about free access to drugs remains: “As you wish."