The Capture of The Dread Pirate Roberts: A victory for the rule of law

February 10, 2015

The American war on drugs has a well-documented track record of disproportionately impacting racial minorities and the poor. That’s why the arrest, trial, and conviction of a man who called himself “The Dread Pirate Roberts,” a reference to the 1987 movie The Princess Bride, is noteworthy. Ross Ulbricht now stands convicted of federal money laundering, narcotics trafficking, and hacking charges—he has also been accused of soliciting the torture and murder of his underlings in an attempt to conceal his true identity.
Ulbricht is no Mexican cartel kingpin, nor is he a crip or a blood; he’s a Boy Scout, literally, actually an Eagle Scout. The Dread Pirate Roberts was an attractive twenty-nine year old libertarian, with an advanced degree in physics. Federal agents unmasked Ulbricht and he now stands convicted of running the Silk Road, a “Deep Web” like service where drugs and violence were bought and sold. In addition to drugs, buyers on Silk Road could purchase services from soldiers of fortune; everything from hacking to murder-for-hire was for sale to anyone with a Bitcoin wallet.
The federal government’s takedown of Silk Road and the conviction of its operator is a huge achievement for law enforcement. Substantial, because Silk Road did over a billion dollars in sales in the two years it operated. Facilitating the sale of drugs and fee for service crime was lucrative—and now its chief executive will be teaching yoga classes in federal prison for the rest of his life. Symbolic, because it demonstrates that law enforcement can intellectually and technologically out maneuver a sophisticated thug like Ulbricht.
The “Deep Web” is the platform nine and three quarters of the Internet. It’s not accessible via traditional web browsing and it’s more voluminous than the “surface web” that most of us see via search engines and http addresses. Accessing the Deep Web requires obtaining special software and a Tor browser. This secrecy, along with some ultimately inaccurate notions about the anonymity of Bitcoin allowed Silk Road to thrive.
Ulbricht is now a POW in the war on drugs, a war that has generally been effective at catching the violators who are most accessible to law enforcement. Arresting the low hanging fruit may be the simplest use of limited resources—but the collateral consequences of mass incarceration on minority and poor communities are becoming more than an exceptional country should abide. The arrest, trial, and conviction of Ulbricht are a welcome change and a victory for the rule of law.
Convictions like Ulbricht’s are an ounce of flesh for a pound of deterrence. There is specific deterrence because Ulbricht can’t do this again and that matters because his skill set was rare. Ulbricht isn’t expendable like most drug dealers, running a black market on the Deep Web doesn’t lend itself to the next man up style of gang or cartel leadership.

Most people with Ulbricht’s intellect and ability would rather be an Investment Banker. Perhaps that makes Ulbricht more culpable. Unlike the typical drug war casualty Ulbricht had good economic options.

Much like the convictions of Leopold and Loeb, the law scores the biggest victory when it punishes those who think they can’t be caught. Whether it’s a corrupt politician who thinks their position of power places them above the law, or someone like Ulbricht who believes their intellect seperates them from the rules we live by in a civil society—no one is above the law.
According to Ulbricht’s now defunct Linkedin profile, beyond the rule of law is exactly where he aspired to be. He wrote:
The most widespread and systemic use of force is amongst institutions and governments, so this is my current point of effort . . . . I am creating an economic simulation to give people a first-hand experience of what it would be like to live in a world without the systemic use of force.
Many believe that quote was about Silk Road. Either way Ulbricht’s new reality is the quintessential use of systematic force, prison. He may get his wish after all: his new home has an illicit black market, devoid of formal regulation, with a proxy currency— prices are measured in honeybuns and cigarettes.
In the end Ulbricht’s anti public institution refrain was hollow. He had no problem enjoying government benefits—while deriding the force necessary to protect them. Both of his college degrees were from public schools. The faux libertarian that he was, it’s not surprising that the feds arrested him while he was conducting his Silk Road business, as he often did, on the free Wi-Fi at the San Francisco public library.