Inside the Fight to Clean Up the Crypto Underworld

Andy Greenberg: “In July of 2017, I learned from a Department of Justice press conference that AlphaBay, the biggest-ever dark web market for drugs and other crime, had been torn offline in a massive bust known as Operation Bayonet. Even more remarkably, Dutch police announced they’d taken over the second-biggest dark web market and run it in secret, setting an elaborate surveillance trap for AlphaBay’s refugees. I immediately knew that this was a story that needed to be reported out and told in detail. Getting that story took me the next five years, and it turned out to be more dramatic than I could have possibly imagined.”

AG: “Before becoming a dark web kingpin, AlphaBay’s creator and boss, Alpha02, began his career as a credit card fraudster. There’s no better journalism about that world than Kevin Poulsen’s book Kingpin. Published in 2011, it captures in gritty detail the credit-card-focused era in the history of cybercrime from both the perspective of Max Vision, the legendary hacker who took over that digital underworld, and the cops trying to bring him down. Here’s an excerpt of the book published in WIRED, where Poulsen worked at the time (and where I desperately wanted to.)”

AG: “When I was first writing about Bitcoin in the spring of 2011, I stumbled across the Silk Road dark web drug market while looking for places where people might spend this weird new cryptocurrency, but mistook the site for a scam or a janky stoner’s experiment. Just two months later, Adrian Chen at Gawker proved in the first news feature about Silk Road that it worked, and that real customers were truly using it to buy narcotics of every possible description. In just over a thousand words, he made this science-fictional new dark web drug market a household name (and scooped me so badly I have yet to recover.)”

AG: “After Chen’s piece, I became obsessed with the Silk Road and in particular its strange creator, a pseudonymous figure who called himself the Dread Pirate Roberts. The Dread Pirate (often abbreviated DPR) seemed to be more than a dark web criminal: He was also an ideological figure on the Silk Road, who saw his work as part of a libertarian revolution, regularly posting political manifestos and even assigning readings in Austrian Economics to a ‘Dread Pirate Roberts Book Club.’ I eventually convinced him to give me the only real interview he ever sat for, communicating over his anonymous messaging system—he was arrested a few months later in an enormous bust led by the FBI and revealed to be a 29-year-old Texan named Ross Ulbricht.”

AG: “A year and a half after Ulbricht’s arrest, Joshuah Bearman published this definitive two-part magazine feature on the Silk Road, the story of its idealistic young founder and the law enforcement investigators who took him down. Bearman’s piece blew my mind: I couldn’t believe the details he got not only from those investigators, but from a journal and chat logs that Ross Ulbricht kept, amazingly, on his laptop, which Bearman obtained from law enforcement. (Bearman also collaborated with journalist Nick Bilton, whose resulting book on the Silk Road, American Kingpin, is a masterful telling of the story.) The result is a narrative that not only revealed incredible, untold drama within the Silk Road case, but also changed my sense of how cinematic a piece like this could be.”

AG: “Shortly after the conclusion of the Silk Road trial in which Ross Ulbricht was, shockingly, sentenced to life in prison without parole, this epic story took another bizarre twist: Two corrupt federal agents were revealed to have pocketed hundreds of thousands of dollars from the Silk Road while working on the Baltimore task force investigating the site. One, a DEA agent, had sold secret law enforcement information to the Dread Pirate Roberts while the other, a Secret Service agent, had stolen a small fortune from the site using the hijacked credentials of one of DPR’s employees. In this piece, Cyrus Farivar and Joe Mullin detail the winding and complex investigation that led to these two corrupt cops—including how cryptocurrency tracing was used for the first time in US law enforcement history to catch them.”

AG: “Aside from the Dread Pirate Roberts, the most colorful character in the Silk Road story was Ulbricht’s second-in-command—and sometimes mentor—known online as Variety Jones. Jones, who turned out to be a Canadian man in his 50s named Roger Thomas Clark, served as a kind of lothario figure in the Silk Road’s story of corrupted ideals: Ulbricht’s chat logs would reveal how Clark slowly coached him into becoming less of a revolutionary and more of a hardcore criminal, including pushing him to have one of his employees’ killed. Joe Cox at Vice’s Motherboard tech news site got in deep with Jones after Ulbricht’s arrest, and in the midst of reporting this profile Clark went so far as to invite Cox to visit him in Bangkok—a city that would turn out to be the home of AlphaBay’s notorious dark web drug lord, too.”

AG: “The dark web power vacuum left in the wake of the Silk Road takedown led to a game of whack-a-mole in which one market after another vied to take that top spot in the online underworld. But Patrick Howell-O’Neill’s piece in April of 2017 captures what made AlphaBay different: It was growing into an unprecedented hub of both narcotics sales and cybercrime—and it seemed untouchable. Published just a few months before AlphaBay’s epic takedown, it captures just how unique and dangerous AlphaBay and its enigmatic creator Alpha02 seemed at the time.”

AG: “Dark web drug lords like Ross Ulbricht and Alexandre Cazes lived double lives, Dr. Jekyll-and-Mr. Hyde-style. Paul Leroux was a very different sort of crypto kingpin. A computer programmer who created widely used encryption tools early in his career, he eventually became a more traditional crime boss, expanding from online drug sales into running a full-blown global cartel with its own hierarchy and contract killers working on his payroll. Evan Ratliff’s book The Mastermind, first published in a serialized version on the Atavist longform journalism site, definitively tells this story of one computer-savvy criminal’s descent into unfathomable evil.”

AG: “No journalist, perhaps, has gotten deeper into the dark web than Eileen Ormsby, an independent Australian investigative reporter who practically embedded within the Silk Road community. In this piece, Ormsby writes about Besa Mafia, a purported hitman-for-hire dark web site, revealing that—like so many other online contract killer services—it was a scam. Ormsby was later herself threatened with murder by the site’s creator.”

AG: “There are darker things on the dark web than drug markets. In another excerpt from my book Tracers in the Dark, published as a WIRED cover story last spring, I delved into the investigation and takedown of Welcome to Video, the biggest child sexual abuse materials website on the dark web. As harrowing as that case was, it has something of a happy ending: Cryptocurrency tracing led to no fewer than 337 of the site’s users being arrested around the world, and 23 children were rescued. As one prosecutor on the case told me, ‘The darker the darknet gets, the way that you shine the light is following the money.’”