American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road

In summer 2012, Ross moved to San Francisco and stayed with his friend René Pinnell and his girlfriend, Selena. He adopted a routine of managing the Silk Road from Momi Toby’s café, choosing a seat with his back to the wall and using free Wi‑Fi to work unobserved.

Online, Ross clashed with his adviser Variety Jones over ideology. VJ argued they were criminals and urged Ross to hire a top lawyer, but Ross refused. VJ then asked for a 50/50 partnership, which Ross rejected; he intended to retain total control and briefly stopped communicating with VJ. Meanwhile, Ross rewarded key staff, including Smedley and Inigo, with bonuses.

Months after the LulzSec arrests, Tarbell conferred in the FBI’s Pit with agents Ilhwan Yum and Thom Kiernan about pursuing the Silk Road. He fixated on avoiding a mistake from an earlier case involving the hacker, Jeremy Hammond.

In a flashback, a SWAT team had stormed Hammond’s location; Hammond closed his laptop before capture, threatening to lock away evidence with encryption. It took six months for forensics to crack his weak password, “chewy12345,” a fortunate outcome Tarbell refused to rely on again. He established a core strategy for the Silk Road: Seize the suspect with his hands on the keyboard and the computer open.

After reconciling with Variety Jones, Ross initiated a comprehensive security overhaul. He assigned VJ to monitor the site for law enforcement activity, encrypted his Samsung 700Z laptop, added a kill switch and auto shutdown, and opted to keep files locally under strong encryption.

Ross partitioned the hard drive into separate DPR and Ross environments and enforced a strict rule never to mix identities. He added traps that locked the machine if someone probed the browser history, and he began vetting employees by requiring photo IDs, which led to his onboarding a new helper named ChronicPain. He also created an emergency file outlining a doomsday plan—encrypt, back up, destroy devices, find a cash rental, and assume a new identity—while researching second citizenship as an escape route.

HSI agent Jared Der‑Yeghiayan, accompanied by his son, Tyrus, searched a Barnes & Noble for Mises Institute books (specifically, books about libertarianism) to understand DPR’s libertarian references. Despite seizing nearly 2,000 drug shipments and arresting sellers, his inquiry stalled.

At his desk, Jared profiled DPR’s writing, noting a youthful tone, frequent use of “yea,” and nose‑less smiley faces. He learned DEA agent Carl Force in Baltimore, undercover as Nob, had been chatting with DPR. After reviewing the logs, Jared grew concerned that Carl was disclosing sensitive tradecraft. Frustrated, he felt trapped in investigative dead ends.

As part of his escape plan, Ross traveled to Dominica to apply for citizenship. En route, he and Smedley battled a major hacking attack. A hacker stalled the site and demanded payment; on Variety Jones’s advice, Ross paid a ransom that escalated to $25,000 in Bitcoin to restore operations.

Ross spent two weeks on the island, befriending locals and advancing his citizenship application. As DPR, he hosted a synchronized screening of V for Vendetta for the Silk Road community. He also researched alternate havens for potential flight. Upon returning to San Francisco, his passport scan logged his travel into a Department of Homeland Security database.

The multi‑agency Marco Polo task force in Baltimore struggled with turf wars. Carl, undercover as Nob, built a close rapport with DPR from a spare room in his home and began sympathizing with him, offering advice on evasion and legal counsel.

Carl and Secret Service agent Shaun Bridges tried to enlist the National Security Agency (NSA). Rebuffed, they briefly considered buying explosives online before dropping the idea. Carl then proposed a controlled bulk drug sale to be facilitated by DPR. DPR agreed to help Nob with a kilo transaction, treating him as a trusted associate.

In early December 2012, Ross and René visited the Contemporary Jewish Museum in San Francisco and recorded a StoryCorps conversation. (StoryCorps recordings are collected in the US Library of Congress and in their online archive.)  Ross spoke about wanting a meaningful, positive impact, maintaining the separation between his public self and his secret work as DPR.

Recently, as DPR, he had approved listings for human organs and poisons like cyanide on the Silk Road, viewing the site as a neutral platform. His separate weapons site, the Armory, had to be shut down due to shipping complications, so he reinstated weapon listings on the main marketplace.

In mid‑January 2013, the Marco Polo task force ran a controlled delivery to the Utah home of Curtis Green, a Silk Road lieutenant. A fake postal worker dropped a kilo of cocaine; after Green retrieved the package, a SWAT team raided the house. They arrested him and seized $23,000 and his Bitcoin‑mining setup.

Carl and Shaun learned Green had administrative privileges. Using Green’s credentials, Shaun secretly siphoned $350,000 in Bitcoin from users into his own accounts. Separately, Carl began to view DPR as a source of personal gain and later sold information back to DPR for Bitcoin.

A week after the raid, the task force questioned Green in Salt Lake City. DPR had discovered both Green’s arrest and a $350,000 theft and, believing Green responsible, asked Nob to beat him and recover the funds. During lunch, Carl contacted DPR and confirmed DPR held Green’s ID from the vetting process.

To produce proof for DPR and to satisfy his demand for retribution, Carl filmed a fake torture session in which a postal worker repeatedly submerged Green in a hotel bathtub as Green pleaded innocence. Meanwhile, Shaun left with Green’s laptop, saying he would submit it as evidence; instead, he used it to steal more Bitcoin. The staged violence was designed to satisfy DPR’s demand for retribution.

Convinced Green was a threat who could cooperate with law enforcement, Ross weighed his options in encrypted chats: intimidation, beating, or killing. He initially instructed Nob to beat Green and compel the return of $350,000, justifying force as defense of property.

Advisers, including Variety Jones, argued that underworld rules required a decisive response. They warned of the risk of Green cooperating with federal agents and of copycat theft if there was no harsh penalty. Ross agreed and escalated the order from a beating to a murder‑for‑hire, contracting Nob for the assassination.

In winter 2013, Tarbell’s cyber unit wanted to pursue Silk Road but faced a mandate problem since drugs fell outside its scope. A DEA agent and assistant US attorney, Serrin Turner, visited the Pit to ask for technical assistance after their task force stalled.

Tarbell’s team decided not to be a junior partner and instead framed a separate FBI investigation around the sale of hacking tools on the site—keyloggers, malware, and spyware—which fell within their cybercrime mission. Leadership approved the plan, and the team formally began the Bureau’s independent hunt for DPR.

As DPR, Ross put out an official hit on Green, promising $40,000 upfront and another $40,000 after. In February 2013, stressed after ordering the hit, Ross went camping north of San Francisco with René, Selena, and Selena’s sister, Kristal, whom he met and liked. The trip restored his mood; he swam, hiked, and began planning a visit to see Kristal in Portland.

Around the same time in Perth, Australia, 16‑year‑old Preston Bridges attended his senior school ball. At an after‑party, a teen brought N‑bomb, a potent synthetic hallucinogen purchased from a Silk Road vendor. Preston took two blotters, had a severe adverse reaction, and jumped from a second‑floor balcony. On Monday afternoon, he died in the hospital. The narrative shifts back to Ross, who returned from camping and heard from staff that nothing eventful happened while he was away, other than the fact that the Silk Road was making him a fortune.