The Most Important Trial in America

The federal government’s case against the proprietor of a ‘darknet’ website could forever alter how we all use the Internet.

01.14.15 10:55 AM ET

One of the potentially most important and far-reaching trials in recent memory has just begun without much fanfare. And if you care about due process, Fourth Amendment protections against illegal searches, the limits of government surveillance, and Internet freedom, you should pay attention.

Ross Ulbricht, 29, stands accused by the federal government of being “Dread Pirate Roberts,” the pseudonymous proprietor of the notorious website Silk Road. Launched in 2011 and shuttered in 2013, Silk Road was known as the Amazon or eBay of the “darknet,” an anonymous, Bitcoin-enabled marketplace where “buying drugs online became safe, easy, and boring.” The site boasted an estimated 900,000 users and generated more than $1 billion in annual sales. And since being closed down, multiple new sites selling narcotics have appeared, a testament to the futility of war on drugs.

In his opening statement, defense attorney Joshua Dratel admitted publicly for the first time that Ulbricht did in fact found Silk Road. But as Wired’s Andy Greenberg reported from the courtroom:

Dratel went on to explain that the site was meant merely to be a kind of “economic experiment” that Ulbricht only controlled for a brief time. The eventual adoptive owners of the Silk Road, Dratel claimed, would later trick Ulbricht into serving as the “fall guy” when they sensed an impending law-enforcement crackdown.

“After a few months, he found it too stressful for him, and he handed it over to others,” Dratel told the jury, describing the Silk Road’s early days. “At the end, he was lured back by those operators to… take the fall for the people running the website.”

“Ross was not a drug dealer,” Dratel added. “He was not a kingpin.”

Ulbricht was nabbed by federal agents in a San Francisco public library. Soon after, stories began to circulate about how a mild-mannered math whiz had transmogrified into a vengeful drug lord who ordered executions of a half-dozen real and imagined rivals. That story arc is compelling, for sure: Ulbricht was literally an Eagle Scout who was constantly doing charity work before allegedly becoming a violence-prone Professor Moriarity of Internet crime.

A year ago, The New York Times Magazine published “Eagle Scout. Idealist. Drug Trafficker,” a cover story heavy on that characterization. The feds created a fake drug dealer and hitman named “nob,” who they say Ulbricht/Dread Pirate Roberts (D.P.R.) asked first to torture and then kill a dealer who had ripped him off. As the Times cinematically recounted it:

“I’d like him beat up, then forced to send the Bitcoins he stole back,” D.P.R. wrote. “Like sit him down at his computer and make him do it.” Soon, D.P.R. had a change of heart. “Can you change the order to execute rather than torture?” he asked nob, explaining, “I’m afraid he’ll give up info.”

In the trial taking place in New York, though, Ulbricht isn’t charged with any murders (in a separate case pending in Maryland, he does a face a count of hiring an undercover DEA agent to kill a former Silk Road partner). Instead, he’s facing the equivalent of life in prison for drug trafficking, computer hacking, conspiracy to traffic in fake IDs, running a criminal enterprise, and money laundering.

Yet prosecutors will still be allowed to enter evidence that he sought to bump off six of his enemies. And they don’t have to prove anything on that score. Incredibly, Judge Kartherine Forrest ruled, that “evidence that defendant sought to protect this sprawling enterprise by soliciting murders for hire is... not unduly prejudicial.” Additionally, the judge refused to let the defense know what witnesses would be testifying against Ulbricht until a week before the trial actually began.

Her reasoning? The defendant might order hits on them from his jail cell. Even though Ulbricht doesn’t have email access and his communications are monitored.

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These sorts of maneuvers don’t engender confidence in the judicial system. Neither does the fact that the FBI has refused to explain exactly how it tracked down Ulbricht. If nothing else, that leaves the defense in the position of being unable to contest whether evidence was legally obtained or whether it’s even authentic. As Wired’s Greenberg has noted, the feds plan to show screen captures of Ulbricht’s computer, images that can easily be faked and thus have been disallowed in similar types of cases. In pre-trial hearings, reports Greenberg, the prosecution “all but admitted” that the federal agents had hacked into Silk Road’s site without a warrant, thus conceivably poisoning most if not all of the feds’ case.

There remain serious questions, too, about whether the feds illegally availed themselves of NSA information about the server’s location and then faked a “parallel construction” trail of evidence that they present in court. The NSA is not supposed to be tracking the information of citizens within the United States, of course, and it’s not supposed to be lending its capabilities to domestic law enforcement, either. But as Bruce Schneier writes, it’s well-known that the NSA funnels information to the FBI and DEA “under the condition that they lie about it in court.”

It’s things like this that moved me to give $100 to Ulbricht’s defense fund a month before the trial started. Beyond starting the site, I have no idea if he is guilty of all or some of the other charges against him, but the manner in which his prosecution is playing out should disturb anyone who cares about justice.

For me, the most potentially troubling aspect of the case ranges beyond conventional questions of due process (as disturbing as those are). It’s the larger chilling effect this sort of prosecution may end up having. Silk Road users employed Tor, a free software bundle that allows users to maintain anonymity online. Ironically, the creation of Tor was partly funded by the U.S. State Department as a way of giving political dissidents a way of communicating. Yet as Ulbricht’s defense fund notes, “the government equates the desire for privacy... with criminal intent.”

That’s an increasingly and appallingly widespread sentiment even in post-Snowden America, where we still have cops and pundits who insist that only people with something to hide worry about the end of privacy. As Harvey Silverglate, the author of Three Felonies a Day: How the Feds Target the Innocent, could tell you, in today’s America, we’re all guilty of multiple crimes even before we get up in the morning.

Hovering all around the Silk Road prosecution is the incredibly liberating legal immunity that ISPs and websites have enjoyed at least since the passage of the Communications Decency Act (CDA) in the mid-1990s.

Although mostly an odious attempt to regulate Internet content in the name of protecting “the children,” the CDA established that, as long as a site’s owners and operators were generally ignorant of activities taking place on its pages, they weren’t liable for them.

“The fact that tech companies are not liable for malicious content posted to their sites is what’s given rise to Wikipedia, Craigslist, Facebook, and Twitter,” wrote Caleb Garling in a 2013 San Francisco Chronicle article cheekily titled, ”Contract Killing Aside, Silk Road May Have Been Legal.”

That’s not to say that defamation and libel laws don’t exist online, but that users and commenters, rather than site operators, are generally responsible for their own words and actions. If you try to sell heroin on Craigslist, you’re in trouble, not Craigslist.

As the Electronic Frontier Foundation’s Matt Zimmeran explained, simply pointing to illegal activity taking place in an online marketplace isn’t enough to lower the boom on the site’s owners and operators. “A prosecutor would have to show that the tech company knew about some specific illegal activity,” he writes. “Generalized knowledge that illegal things happen on a service isn’t enough.”

That part of the CDA—Section 230—only applies to state laws and it doesn’t offer exceptions for the posting of copyrighted materials. Depending on how Ross Ulbricht’s trial plays out—and what charges the prosecution is able to make stick against him—it may well mark the beginning of a federal clampdown on the broad, governing spirit of the Internet that has made the online world an unrivaled experiment in innovation, freedom, and experiments in living.

Which means it may end up affecting even those of us who never buy anything online that’s more potent than cough syrup.