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In American Kingpin, the Silk Road ends in a farce

Who was Ross Ulbricht?

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Ross Ulbricht

Few startup founders over the past decade have inspired as much mythology as Ross Ulbricht. In October 2013, the FBI arrested Ulbricht as he sat working inside a San Francisco branch library. When they grabbed his open laptop, they found what they had been seeking for more than two years: evidence that Ulbricht, a 29-year-old Texas-born Eagle Scout, was the mastermind behind a fast-growing dark web black market called the Silk Road.

To friends and family, Ulbricht was a good-natured if frustrated entrepreneur who liked to spend his free time discussing libertarian politics. To the FBI, he was the Dread Pirate Roberts — the man responsible for building an anonymous marketplace for selling drugs and firearms that was processing millions of dollars in sales each month.

How had one become the other? How did Ulbricht himself make sense of his dual lives? And how did he inadvertently give himself away? These questions have fascinated observers for years, and now they get a book-length treatment in American Kingpin, a breezy account of the Silk Road’s rise and fall from Vanity Fair special correspondent Nick Bilton.

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Ross Ulbricht’s fake IDs

American Kingpin is Bilton’s first book since Hatching Twitter, an account of that social network’s lunatic rise to prominence. Bilton scored interviews with each of Twitter’s four founders to paint a rich portrait, resulting in the first definitive account of its oft-embellished origins. But Ulbricht, who is appealing his conviction while serving a life sentence, declined to speak with the author. That forced Bilton to rely on extensive chat logs between Ulbricht and his employees, as well as interviews with Ulbricht’s friends and family, to paint a portrait of the man he calls kingpin.

The broad outlines of the case — and many of its more bizarre details — have already been chronicled in “The Untold Story of the Silk Road,” a riveting 2015 series in Wired by Joshua Bearman. (Bilton contributed reporting to the series; Bearman and his colleague Joshua Davis are likewise credited as contributors in American Kingpin.)

Bilton’s book takes the facts of the case and casts it as a high-stakes game of cat and mouse. On one side sits Ulbricht, determined to make his mark on the world by “advancing the cause of freedom.” By creating an anonymous, anything-goes marketplace, he reasoned, he could help to end the drug war — and become a captain of a newly legal industry in the process. On the other is the cadre of law enforcement officials closing in on him — a crew that in Bilton’s telling is nearly as motley as the gang running the Silk Road, and in some cases just as prone to criminal activity.

The Coen brothers are said to have expressed interest in making a movie based on the series, and it’s easy to see why. Ulbricht’s tale plays out like a high-tech version of Fargo, in which a ne’er-do-well protagonist makes a series of escalating moral compromises that ultimately lead to his undoing.

Nearly every character in American Kingpin seems to have wandered in from one Coen brothers movie or another — Ulbricht’s girlfriend is a born-again Christian who runs an erotic photography business; one of his chief confidantes is an undercover DEA agent who begins stealing from him; and the man who discovers his true identity is a nerdy IRS agent who reads every sentence three times.

The action unfolds in a series of brief chapters that are smothered with promises of the kingpin’s eventual comeuppance. “One was about to put the other in jeopardy,” Bilton writes of Ulbricht’s girlfriend and the newly launched Silk Road. “He didn’t foresee that this kind of message would have vast and grim consequences,” we’re told after Ulbricht agrees to an email interview with a reporter. One chapter ends with this bit of symbolism: “A violent storm was on the horizon, ominously moving closer to land.”

Still, it’s a page-turner: Bilton’s account of Ulbricht’s efforts to evade capture is never less than suspenseful. The kingpin and his top lieutenant, who goes by the irresistible name of Variety Jones, talk constantly about the seemingly inevitable moment that FBI agents will arrive on their doorsteps. Ulbricht’s dual life is made literal when he creates separate logins on his laptop for Ross and for the Dread Pirate Roberts; he also builds a series of boobytraps into his laptop that will render them useless at the touch of a button.

It takes a team of federal agencies (barely) working together to bring Ulbricht down. Perhaps the biggest break comes when the IRS agent, Gary Alford, discovers the email address used to post an early forum comment promoting the Silk Road: RossUlbricht@gmail.com. A security flaw on the Silk Road server points the FBI to a cafe in San Francisco. The walls close in Ulbricht with each passing page.

It all leads to a spectacular set piece at the Glen Park Branch Library. For the government, it wouldn’t be enough to simply arrest Ulbricht — the FBI needs to do it while his laptop his open, while he is logged in as the Dread Pirate Roberts, and before the kingpin can hit the kill switch that will destroy all the evidence. That they pull it off — through a series of hilarious subterfuges I won’t spoil here — is a testament to the creativity of law enforcement.

American Kingpin is written as a drama, but so many events in Ulbricht’s life read as farce. His over-the-top conversion to libertarianism; a disastrous early experience as a psychedelic mushroom farmer; his paying hundreds of thousands of dollars for revenge murders that never happened; and his ultimate discovery at the hands of his email address. He was never much of a programmer, and it’s unclear that he was a great businessman, either.

What Ulbricht did have was a truly novel idea — an anonymous marketplace for drugs, powered by Bitcoin, delivered by the US Postal Service — and it all worked relatively well, until it didn’t. He had the audacity of a great Silicon Valley founder, but ultimately not the talent. And who would have had the talent to succeed in the long run, with the entire arsenal of the United States government lined up against them? That Ulbricht even tried it still beggars belief.

Ulbricht is now behind bars, where he’s likely to remain for the rest of his life. Despite Bilton’s best efforts, Ulbricht remains almost as mysterious at the end of American Kingpin as he is at the beginning. Did chat logs capture Ulbricht as he really was, or were they mostly posturing? Behind his libertarian bluster and wiseguy threats, he could sound a lot like any other startup founder: simultaneously cocky and desperate. But it’s difficult to tell where the persona ends and the person begins. It’s not clear that an interview with Bilton would have cleared that up — Ulbricht continues to deny many of the charges against him — but it could have painted a fuller picture.

At times Ulbricht seems to have fancied himself a real-life Walter White — he adored Breaking Bad — but other times he just wanted to run away with a girl and start a new life. Ultimately he got neither. We can pore over his chat logs all we want, but the real Ross Ulbricht remains frustratingly out of reach.