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

American Kingpin (2017) is a work of narrative nonfiction by journalist Nick Bilton. A former columnist for The New York Times and special correspondent for Vanity Fair, Bilton is also the author of the book Hatching Twitter (2013), which explores the origins of the major tech platform. American Kingpin, a New York Times bestseller, chronicles the rise and fall of Ross Ulbricht, the libertarian idealist who created the billion-dollar anonymous drug marketplace known as the Silk Road. The book follows multiple narratives surrounding Ulbricht’s creation and details the sprawling, multi-agency federal manhunt destined to unmask and capture him. The narrative explores The Disconnect Between Ideology and Real-World Impact, The Corrupting Influence of Anonymity and Power, and how Technology Shapes Crime and Policing.

This guide refers to the 2018 Portfolio/Penguin trade paperback edition.

Content Warning: The source material and this guide feature descriptions of substance use, addiction, graphic violence, death, physical abuse, and cursing.

Summary

In October 2011, Department of Homeland Security (DHS) agent Jared Der-Yeghiayan intercepted a single pink ecstasy pill at Chicago’s O’Hare airport. A subsequent interview with the recipient’s roommate revealed the drug was purchased from a dark-web marketplace called the Silk Road, an anonymous “Amazon for drugs” (51) that used the Tor hidden services browser and Bitcoin. Finding no other government agencies actively investigating the site, Jared launched his own inquiry.

The narrative flashes back five years to Ross Ulbricht, an idealistic physics student from Austin, Texas. Adrift after a painful breakup and a series of failed ventures, Ross moved to Pennsylvania State University for graduate school, where he met Julia Vie and became deeply immersed in libertarian philosophy, passionately arguing for the legalization of all drugs. After failing his PhD qualifying exam, Ross returned to Austin with Julia, where his feelings of failure intensified as his new business ideas failed to materialize.

In 2010, inspired by his libertarian ideals and the emergence of Bitcoin, Ross began coding his anonymous marketplace. He secretly cultivated nearly 100 pounds of magic mushrooms in a remote rental property to serve as the site’s initial product. In January 2011, Ross launched the Silk Road, using the pseudonym “Altoid” on drug forums to attract its first users. The site’s profile exploded in June 2011 after a Gawker article detailed its operations, prompting Senator Chuck Schumer to call for an immediate federal shutdown. The resulting publicity brought a flood of new users, causing technical problems and intense stress for Ross, which strained his relationship with Julia.

Fearing the consequences of his creation, Julia confided in her friend, Erica, about Ross’s role. After a falling out between the two women, Erica posted a public message on Ross’s Facebook wall exposing his connection to the website. Panicked, Ross broke up with Julia. Fearing exposure, he decided to leave the country for Australia, telling his friend, Richard Bates, the only other person besides Julia who knew his identity, a cover story that he had given away the Silk Road.

Ross met a mentor on the site known as Variety Jones (VJ), a seasoned drug dealer and security expert. VJ advised Ross to adopt the persona of the “Dread Pirate Roberts” (DPR), a character from The Princess Bride who passed down his title. This solidified Ross’s cover story and allowed him to grow more confident, embracing his role as the “captain” of the enterprise. Meanwhile, multiple law enforcement agencies began their own investigations. Carl Force, a jaded Drug Enforcement Administration (DEA) agent in Baltimore, joined the “Marco Polo” task force and went undercover online as “Nob,” a high-level Dominican drug smuggler. Jared Der-Yeghiayan in Chicago began making controlled drug purchases to trace vendors, while Chris Tarbell, a top FBI cybercrime agent in New York, also decided to target the Silk Road, sparking intense inter-agency rivalries.

Under DPR’s leadership, the Silk Road expanded to include weapons and other contraband. The Marco Polo task force orchestrated a sting, arranging for DPR to facilitate a one-kilo cocaine deal through Nob to a Silk Road administrator named Curtis Green in Utah. In January 2013, the task force arrested Green. During the arrest, Secret Service agent Shaun Bridges, a member of the task force, secretly gained access to Green’s administrator account and began stealing Bitcoins, ultimately siphoning $350,000.

DPR discovered the missing Bitcoins and believed Green was the thief. To get information, he asked Nob to have Green physically beaten. Carl Force and other agents staged a fake torture session, videotaping it for DPR as “proof.” Convinced Green was a thief and a liability who might cooperate with law enforcement, DPR, after consulting with VJ, ordered Nob to murder Green for $80,000. Carl faked the murder, sending DPR a staged photo of Green’s “dead” body as confirmation.

While the Baltimore task force was mired in corruption, the disparate investigations began to converge. Gary Alford, a meticulous IRS agent in New York, discovered the early “Altoid” posts and traced them to an email address registered to Ross Ulbricht. Chris Tarbell’s FBI team found a leaked IP address on the Silk Road’s login page, tracing the main server to Iceland and gaining full access to its back end. Ross ordered nine fake IDs to his San Francisco address, which were intercepted by customs, leading a DHS agent to question him directly.

At a tense multi-agency deconfliction meeting, the FBI revealed they had seized the Silk Road server. Impressed by his deep knowledge of the site, the FBI invited Jared to New York, where he took over the account of a low-level moderator, “Cirrus,” becoming an undercover employee for DPR. Fearing exposure, Ross moved to a new apartment under the alias “Josh.” Meanwhile, Carl Force created new fake personas to act as a corrupt government mole, selling sensitive information about the investigation to DPR for over $750,000.

The net tightened as Gary Alford rediscovered the DHS report on Ulbricht’s fake IDs and connected Ulbricht’s previous San Francisco address to Momi Toby’s, the café identified from the server’s IP address. On a conference call, Gary revealed an old post on the programming site Stack Overflow by a user named “Altoid,” an account name associated with both Ross Ulbrict’s name and the fake email address “frosty@frosty.com.” Tarbell confirmed the Silk Road server was also named “Frosty,” and they now had their man.

On October 1, 2013, the FBI tracked Ross to the Glen Park Public Library in San Francisco. Jared, as Cirrus, lured DPR into the site’s administrative “Mastermind” panel. Two undercover agents staged a loud argument to distract Ross, allowing another agent to seize his open laptop. Ross was arrested, and the computer was found to be unencrypted on the DPR side, containing his diary, chat logs, financial spreadsheets, and proof he was logged in as the site’s administrator.

In January 2015, the trial of United States of America v. Ross William Ulbricht began. The prosecution presented the overwhelming digital evidence from the laptop. The defense argued that Ross created the site as an economic experiment but handed it off to the “real” Dread Pirate Roberts, who then framed him. After just three and a half hours of deliberation, the jury found Ross guilty on all seven counts. Judge Katherine Forrest sentenced him to two life sentences plus 40 years without the possibility of parole.

In the aftermath, corrupt agents Carl Force and Shaun Bridges were caught after investigators traced the stolen Bitcoins back to them, and both were sentenced to federal prison. Variety Jones (Roger Thomas Clark) was arrested in Thailand, and other high-level Silk Road administrators were apprehended around the world with Jared’s undercover assistance. The principal investigators moved on to new roles. Gary Alford received an award for his work, Chris Tarbell left the FBI for the private sector after his family was threatened, and Jared Der-Yeghiayan continued his work at DHS.