Engrossing account of the rise and fall of Ross Ulbricht, founder of the now-shuttered online drug bazaar the Silk Road.
Vanity Fair special correspondent Bilton (Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal, 2013, etc.) ties his interest in technology to a gritty pursuit tale of the drug underground as it migrated to cyberspace. As the author writes, the Silk Road “could be living proof, Ross fantasized, that legalizing drugs was the best way to stop violence and oppression in the world.” Seemingly another bright, restless millennial, Ulbricht enacted his libertarian beliefs by founding a drug marketplace intended to make purchasing safer and undermine the drug war. Utilizing the “Dark Web” technologies of TOR and bitcoin, Ulbricht’s site opened in 2011 and immediately thrived: “Hundreds of people were now selling drugs on the site, and thousands were buying.” An outlaw subculture quickly developed, drawing in dealers, acolytes, hackers, and scammers; Ulbricht encouraged the notoriety, developing a menacing alter ego, the “Dread Pirate Roberts.” However, he overestimated his ability to avoid law enforcement scrutiny, beginning with low-level mail inspectors suddenly finding numerous identical envelopes of Ecstasy: “Ross had picked a fight with the biggest bully on earth, and the bully was about to punch back.” Chapters generally alternate between Ulbricht’s efforts to stabilize the website while covering his tracks with a self-consciously romantic fugitive lifestyle and the increasingly frantic investigation, which involved competing teams from different agencies (a few of whose members were later convicted of siphoning Ulbricht’s bitcoins and other malfeasance). Ultimately, the Silk Road spun out of Ulbricht’s control, to the point that he was soliciting murders for hire and allowing disguised federal agents to infiltrate the site’s administration. Dramatically arrested by the FBI in a San Francisco library in 2013, he received a life sentence. Bilton writes in a breezy, colloquial style, punctuated by occasional pulpy asides, and he aptly manages the technological arcana of this sprawling story.
A fast-paced, readable true-crime tale that frames the likely future of the underground economy.