American Kingpin by Nick Bilton

The Epic Hunt for the Criminal Mastermind Behind the Silk Road

In 2011, a twenty-six-year-old libertarian programmer named Ross Ulbricht launched the ultimate free market: the Silk Road, a clandestine website hosted on the Dark Web where anyone could trade anything—drugs, hacking software, forged passports, counterfeit cash, poisons—free of the government’s watchful eye.

Soon the media caught wind of it, and spurred by a public outcry, the federal government launched an epic two-year manhunt for the site's elusive proprietor. All they knew was that they called himself the Dread Pirate Roberts.

The Silk Road quickly grew into a $1.2 billion enterprise, and Ross embraced his new role as kingpin, enlisting a loyal crew of allies, all addicted to the dangers and thrills of running an illegal marketplace. He then took drastic steps to protect himself, including ordering a hit on a former employee. 
As Ross made plans to disappear forever, the Feds raced against the clock to catch a man they weren’t sure even existed.

Drawing on exclusive access to key players and two billion digital words and images Ross left behind, Vanity Fair correspondent Nick Bilton offers a tale filled with twists and turns, lucky breaks and unbelievable close calls. It’s a story of the boy next door’s ambition gone criminal, spurred on by the clash between the new world of libertarian-leaning, anonymous, decentralized web advocates and the old world of government control, order, and the rule of law. 

What I thought

It's my second time returning to this and reading it in under twenty-four hours, so that speaks for itself as I rarely feel I have the time to return to older books these days. 

Since reading the first time, I've been following Nick Bilton's reporting for Vanity Fair, and have really admired his work. 

American Kingpin reads like a thriller novel. It's a story that's so entirely engrossing from the beginning that once I started reading I wasn't able to put it down. If you haven't ever read anything about Ross Ulbricht or the Silk Road—you might think to yourself, this can't be real life. 

The book begins with an introduction to the cast of characters, who each played a part in either building the Silk Road, or taking it down. 

As the story unfolds, it's told through the lens of the various people involved, and the timelines shift around, which was very clever of Bilton.

First there's Ross, a young man from in Austin, Texas. He's perceived to be very intelligent with two degrees, but nonetheless feeling like a failure in his endeavours. This leads Ross to start the Silk Road, which is well in line with his libertarian views. 

The various law enforcement agents are introduced, coming from all over the United States, and all pining the golden opportunity to take down this kingpin who could change their careers. It's fascinating to see how the various agencies work, both together and separately. 

There's also a gut-wrenching moment in the book that shows Ross winding down with a group of friends while, unknown to him, at the very same moment, the Silk Road has played a part in the death of a young teenager.

Bilton captures every scene, down to the clothes people were wearing, and the weather on that day, and the conversations that were had. He makes you feel as though you could have been in the very same room as events were happening. What's more is that Bilton's reporting made me feel real impact of the Silk Road.

When you've finished the book, you might be drawn to read Adrian Chen's Gawker article and Andy Greenberg's Forbes Q&A.

Nick Bilton has also done some excellent follow-up reporting, which you can find on Vanity Fair. This book is a roller-coaster ride. It's tremendous.

Nick Bilton, Courtesy of Twitter

Nick Bilton is a special correspondent for Vanity Fair, covering technology, business, politics, and culture. Previously a columnist for The New York Times, his articles have led to government investigations and congressional hearings and his writing was the basis for overturning the longtime ban of cell phones, Kindles, and iPads on airplanes. He is also the NYT best-selling author of the books, Hatching Twitter and American Kingpin, and the writer and director of Fake Famous, a documentary on HBO. You can follow him on Twitter.

American Kingpin is available for purchase in hardcover, paperback, or audiobook edition. Check IndieBound for an independent bookstore near you.