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Author Andy Greenberg on how a group of investigators untangled the Dark Web

Greenberg’s new book “Tracers in the Dark” tells the true stories of crypto crime—and the investigators trying to bring them to justice.

Author Andy Greenberg on how a group of investigators untangled the Dark Web

[Source photo: David McBee
/Unsplash]

BY Sarah Lynch4 minute read

Crypto crime hit an all-time high in 2021, with scammers taking home some $14 billion. That same year, the IRS’s Criminal Investigation announced that cryptocurrency made up 93% of its seizures—a statistic made even more eye-popping when one considers that Bitcoin only burst onto the scene in 2009. 

Andy Greenberg, senior writer at Wired and author of the new book Tracers in the Dark, tells true stories of the dogged investigators chasing crime lords through the crypto underworld. Through interviews with prosecutors, agents, analysts, and even the criminals themselves, Greenberg covers the most momentous crypto cases from the past decade, from the Silk Road to web’s biggest child abuse site

He recounts how clues in the blockchain and increasingly sophisticated tools allowed investigators to follow the money––and in doing so, shines a light on privacy and anonymity on the web. “There was both a really juicy, true crime, detective narrative that spanned a decade, but then also an ideological sea change in how people think of the privacy properties of cryptocurrency that had occurred over that time,” Greenberg says.  

Fast Company talked with Greenberg about the intricacies of covering the dark web and the big ticket busts that caught some of its most notorious reprobates. This interview has been edited for length and clarity.

What was it about the dark web and cryptocurrency, specifically, that intrigued you? 

The dark web, and online anonymity in general, has always had this fascination for me because it creates this interesting drama of seeing people pretend to be someone else or show you who they really are in secret. That creates some incredible stories and circumstances. When Bitcoin first appeared in 2011, the thing that interested me about it was that it seemed to be this cypherpunk holy grail of actual untraceable digital money. I was interested in the ways that Bitcoin could facilitate and monetize this new, completely anonymous economy for good or for ill.   

Just to be clear, though, I initially misunderstood the privacy promises of Bitcoin. I slowly underwent this evolution in my thinking about it, noticing over the decade that followed that, actually, this is quite traceable. In 2020 or so, I just noticed the sheer number of cases where Bitcoin tracing was a key part of an investigation. So I kind of had this slow-motion epiphany that Bitcoin was in fact the opposite of untraceable, and that it had in fact served as almost a trap for people who had believed the privacy promises it once seemed to offer.   

Was there a story or stories that you’re excited for readers to learn about, in particular?   

The first is AlphaBay. I’ve always wanted to tell that story because it’s simply the biggest dark web bust of all time. In fact, it was not only a takedown of AlphaBay across five countries, but a kind of one-two punch sting operation that’s never really been accomplished before or since. To finally be able to report out that whole story in detail was just really gratifying. For some parts of it, I’m not sure I’ve ever assembled a scene from so many points of view at the same time before. That was really fun and I hope produces a truly cinematic experience for the reader.  

But then a later case in the book, the Welcome to Video child sexual abuse materials dark web case, turned out to be equally compelling and meaningful. I’ve always sort of averted my eyes––as I think many reporters, even cybersecurity reporters, do––from the problem of child sexual abuse materials. To look that square in the face was an emotional roller coaster that I’ve never gone on as a reporter before. To know that this world exists does change my idea of the internet forever. 

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Interviewing people for this book was, to put it lightly, not simple. You spoke with government agents, researchers, and even these dark web actors themselves. How did this experience compare to other pieces you’ve written? 

One thing that was really different for me was that I’ve rarely told stories from law enforcement’s perspective. Whenever possible, I’ve told defendants’ stories, from their perspectives, but the real backbone of this story came from the investigators—from the detectives’ perspective. The trick turned out to be getting that story from agents, prosecutors, analysts—who don’t always want to tell you the full story.   

But just because law enforcement agents are some of the main characters, I don’t want to give the impression here that all cryptocurrency is used for crime or that all cryptocurrency tracing is good––it’s much more complicated than that. It’s a kind of financial surveillance, and as powerful as that is for solving crimes, it also raises all the issues that surveillance always raises, all the trade-offs of what privacy is left to us. There are people who need financial privacy, and whether they’ll ever be able to get it remains an open question. It’s fun to tell stories about cops and robbers, but it’s not that simple. 

You quote a Reddit user (and others echoed this sentiment) who said “the Great Game of whack-a-mole never ends.” Will it ever end or will these dark web marketplaces keep popping up in the crypto underworld? 

It’s true that the game of whack-a-mole never ends in terms of the dark web drug markets, specifically, but it’s also true that there’s a new arms race mentality there. These very well-resourced cryptocurrency tracing firms are developing new techniques all the time, but then people seeking privacy, and criminals, are developing new techniques to skirt their tracing or to create truly anonymous money.   

The whack-a-mole continues, the cat-and-mouse game goes on, but when there is a blockchain involved––this permanent, immutable record––it’s worth noting that the cat-and-mouse game favors the cats. Because you can’t go back and erase evidence from a blockchain, whenever the cat catches up, they truly catch up on years’ worth of mistakes.

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