American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road

"American Kingpin" was a perfect book to read early on in my "Year of Crime and Punishment". The "Silk Road" online drug market roared to life during my last year of college and the founder, Ross Ulbricht (a.k.a. "The Dread Pirate Roberts"), was taken down shortly after I graduated. Having followed the news on these events in real-time, I appreciated Bilton's neat synthesis of the entire saga and his detailed portraits of the people involved on each side. Bilton writes in a brisk, compelling style as befits a Vanity Fair journalist and I read the entire book in just two or three sittings.

Ross Ulbricht's story interested me because his motivation was not only financial, but also idealogical. Bilton goes into detail about Ulbricht's libertarian philosophy and his belief that the government should not regulate what people are able to buy. In many ways, Ulbricht's thoughts about minimalism, techno-utopianism, and libertarianism mirror those of many computer programmers I went to school with. And his coding skills seem to have been quite amateurish. What's fascinating is that the DPR doesn't appear to have been exceptional in any way except for his willingness to break the law. And some aspects of his personality struck dangerously close to home...

"DPR was constantly recommending books to his followers"

Some of the most serious charges against DPR related to his ordering of a hit against one of his subordinates who was stealing money from him. I expect this will be one of the major focuses of the book club conversation - was DPR justified in ordering a hit? Our immediate reaction is, "No, of course not!" But DPR was essentially running a shadow government for the black market and a defining feature of governments is their monopoly on (and use of) violence to enforce social norms. Our own government has killed thousands of militants and over a hundred civilians by drone strike since 9/11. Was DPR's real crime that he challenged the sovereignty of the United States?

Bilton leads us from cliffhanger to cliffhanger as he follows the various law enforcement teams that tracked down DPR. In a vindication of my 2018 focus on financially-motivated crimes, it was the idea "to follow the money rather than the drugs" that ultimately led to DPR's unmasking and capture. We catch glimpses of the investigative process and the many dead-ends and frustrations along the way. "American Kingpin" spurred my interest in learning more about the mechanics of cybercrime and I plan to read several more books in this vein over the rest of the year.

"American Kingpin" was my February 2018 book club selection.

My highlights below.

No man, for any considerable period, can wear one face to himself and another to the multitude, without finally getting bewildered as to which may be the true. —Nathaniel Hawthorne, The Scarlet Letter

PART I

The address on the front had been typed, not written by hand. That was generally a telltale sign for customs agents that something was amiss. As Mike knew, addresses are usually typed only for business mail, not personal.

There was, as every government employee in Chicago knew, an unspoken rule that drug agents didn’t take on cases that involved fewer than a thousand pills.

He would need it to show his “babysitter.” Every newbie agent in HSI was assigned one — a training officer — during their first year. A more seasoned officer who knew the drill, made sure you didn’t get into too much trouble, and often made you feel like a total piece of shit.

You paid for the drugs with this online digital currency called Bitcoin, and you shopped using an anonymous Web browser called Tor.

His lifestyle was also part of an internal experiment to see how far he could push himself to extremes without any wants or needs.

To make matters worse, Jared’s success made other agents look ineffective by comparison.

He explained how wonderful it would be to build a seasteading experiment.

Julia had started a new business, which she called Vivian’s Muse, where she photographed half-naked women for their husbands. Her pitch was simple: What do you get the man who has everything? Sensual pictures of his wife, almost nude. And so, several days a week Julia would set up candles throughout the main room of the apartment, play sensual techno music, and snap thousands of boudoir pictures.

The latest show they had become obsessed with was Breaking Bad.

For inspiration, Arto suggested that Ross should read a relatively unknown novel titled A Lodging of Wayfaring Men. The novel tells a tale of a group of libertarian freedom seekers who create an alternate online society on the Internet that operates using its own digital currency, free from government control. In the book this online world grows so quickly that the U.S. government becomes petrified by its power. FBI agents are sent out to try to stop the Web site before it destroys the very fabric of society.

He spent innumerable hours writing front-end code, back-end code, and code that helped sew those digital dialects together. Ross was teaching himself all of these programming languages on the fly. He was technically doing the equivalent of building eBay and Amazon on his own, without any help and without any knowledge.

He had taken the proper precautions to stay covert during his shroom-growing phase and even read the book The Construction and Operation of Clandestine Drug Laboratories, which was essentially a Dummies guide for setting up a felonious drug lab.

PART II

From a financial standpoint the site was so successful and was processing so many orders that he had now become a millionaire. Though being frugal Ross, he didn’t buy anything showy with the money, beyond a few nice meals. All of his possessions still fit snugly in a small bag.

The ability to accept anyone was in many ways Ross’s superpower.

PART III

All the cops and government employees in New York had local watering holes they burrowed into after work. The FDNY went to Social Bar on Eighth Avenue, the NYPD had Plug Uglies on Third, and the Cyber Division of the FBI’s New York office lived at the Whiskey Tavern. Special Agent Chris Tarbell of the FBI and his team of agents frequented the shit-hole dive bar at least five nights a week.

As they settled in for a night of revelry, it was Tarbell who was the star of the show. After all, he was the one responsible for recently taking down an infamous hacker group, called LulzSec, that the media and security experts had asserted could never be stopped.

It was no accident that Tarbell had ended up where he was, rising through the ranks of the FBI. He had planned it this way, just as he planned everything. Tarbell had worked hard to earn his master’s degree in computer science, then became a cop. After more than a decade of eighteen-hour days, he had made his way up through the FBI to become a special agent. And he didn’t stop there. When he wasn’t with his wife and kids, he continued to study computer forensics for any technology platform imaginable.

The safest place he had found to work was a small café on Laguna Street called Momi Toby’s, which was conveniently located a block from René’s apartment on Hickory Street.

The CEOs of these other start-ups were no different from Ross, either. They had all read the same Ayn Rand books.

But it was the second detail, which was equally important, where they had failed dismally: It was crucial to capture each suspect on his or her laptop with the computer open. If the hackers closed their computers and those computers were encrypted, the data inside would be locked away forever. Even with the fastest and most advanced FBI computers, it could take more than a thousand years to figure out the password of a properly encrypted machine.

DPR was constantly recommending books to his followers — a litany of literature from the Mises Institute. Jared wanted to understand Dread’s thinking and read along too.

After months of research and seeking the advice of Variety Jones, it turned out the Commonwealth of Dominica, where citizenship can be picked up for an “investment” of around $75,000, would serve as the perfect place for Ross to hide the Dread Pirate Roberts from the Feebs. It was also the ideal spot for Ross to stash his millions of tax-free dollars without Uncle Sam asking where all that money came from.

Inspired by the clubs he had joined back at Penn State, and as a remedy for his loneliness, Ross had started Movie Night on the Silk Road, as well as the Dread Pirate Roberts’s Book Club.

While most start-ups are in the red for the first few years of their existence, the Silk Road had mushroomed to be worth more than the value of the entire country Ross was visiting right now, Dominica.

“Tell me about your diet,” Carl asked. “Minimize carbs,” DPR replied, “no bread, no pasta, no cereal, no soda. I eat lots of hard boiled eggs.” One reason Carl was able to chat with DPR for so long was because it was apparent to him that Dread was lonely.

Carl also taught him how international drug-smuggling routes worked through “dead drops,” where dealers leave drugs or guns in a location like a storage locker at a train terminal and then give the buyer the locker combination so they can grab their stuff and leave the money behind without the two ever meeting in person. The perfect way for the Silk Road to avoid the mail system.

But in the coming days, without the knowledge of anyone else inside that little house on East 600 North Street in Spanish Fork, Utah, or within the U.S. government, Shaun Bridges of the Secret Service was about to do the unthinkable. He started tinkering with the computer that belonged to Green and furtively siphoning $350,000 out of other people’s accounts on the Silk Road, all using Curtis Green’s log-in credentials. Rather than turning this money in to the U.S. government as evidence, Shaun would instead secretly transfer that $350,000 into his own personal accounts online.

they had discussed Rothbard’s War, Peace, and the State, which explained why you could use violence against any “individual criminal” trying to harm you or steal your personal property.

In addition to HSI in Chicago, a task force in Baltimore, and another group of local and federal officials in New York City, there was now a new agency hunting for the Dread Pirate Roberts: the Cyber Division of the FBI, and the Eliot Ness of cyberspace would be leading the charge.

PART IV

Midway through his briefing Gary was informed that since nothing else had worked, the task force wanted to try a new strategy. They instructed Gary to follow the money rather than the drugs.

Gary had heard stories about that New York City serial killer known as the Son of Sam so many times as a kid that it was impossible to forget. But what had always stuck out to him, he explained to the agent, was the way authorities caught the murderer. It had all taken place between 1976 and 1977 in the same neighborhood where Gary was raised. At the time, the Son of Sam had gone on a killing spree in New York, terrorizing the city and making fools of the NYPD. No matter how many police officers and detectives City Hall threw at the investigation, it was unsolvable. A task force that was set up to find the murderer went nowhere. Yet shortly after the blackout of 1977, one police officer decided to try a new and creative angle to find the killer. Rather than search the crime scene looking for weapons or clues, the officer decided to look for cars in the areas of the murders that had received parking tickets around the same times as the crimes.

Thankfully for DPR, the site was bustling with business. By the end of July, the Silk Road was on track to register its one millionth user. All in the span of a little over two years.

Over the coming days Gary contacted these forums and, using his government credentials, requested the names and e-mail addresses that were associated with the “Altoid” accounts. It appeared that they had been registered to someone with the e-mail address “frosty@frosty.com,” which wasn’t a real e-mail account and went nowhere. But as Gary dug further, he discovered that the Altoid username had another e-mail address associated with it that had since been deleted but still existed in the forum’s database. The account, he discovered, belonged to a “RossUlbricht@gmail.com.”

“I think a man is his own God and can decide for himself what’s right and wrong,” Ross said. “As a man, I decide for myself.”

PART V

His street clothes were taken away, exchanged for a red prison jumpsuit with ALAMEDA COUNTY JAIL written across the back.

had trafficked $1.2 billion in drugs, weapons, and poisons, in just a couple of years.

Ross had chosen Dratel because he saw him as a lawyer who subscribed to the philosophy that someone’s beliefs shouldn’t be a crime and that the system should offer everyone—even alleged terrorists—a fair trial.

The FBI had tried to find the bodies of the people murdered on the site, the ones DPR had paid to have killed, but no database matched the crimes. It appeared that either the Hells Angels had disposed of the bodies perfectly or, more than likely, no one had actually been killed at all. Rather, the Dread Pirate Roberts had been scammed for hundreds of thousands of dollars.

What Ross didn’t know at the time was that the laptop the FBI had managed to slip out of his hands had not been as secure as he hoped. Ross’s booby traps had failed, and his password (“purpleorangebeach”) had too, as the FBI team managed to find the password hidden in the computer’s RAM.

While he waited for the trial to commence, life inside MCC became as monotonous as in its Brooklyn counterpart. Ross made friends. He taught yoga classes to some inmates, offered others help with their GEDs, and gave impromptu explanations of physics, philosophy, and libertarian theory to the guards.

Dratel then argued that Ross had been framed by the real DPR.

“Mr. Ulbricht, it is my judgment delivered here, now, on behalf of our country, that on counts two and four you are sentenced to a period of life imprisonment,”

“In the federal system,” the judge continued, “there is no parole and you shall serve your life in prison.”

With that data the researchers noted that the year after the Silk Road opened for business, as many as 20 percent of respondents started to purchase drugs online. When the researchers asked these people why they chose to buy drugs on the Internet and not on the street, the users explained that they were nearly six times more likely to be physically harmed on the street. Clearly Ross had fulfilled the goal that had led him to start the Silk Road, and tens of thousands of people feel safer being able to buy drugs online.

Tarbell now works for a major cyberconsultancy in New York City, where he assists companies and the government in computer-related crimes.

While so many people spoke to me for the book, through his family and lawyers, Ross Ulbricht declined to be interviewed.