Right now, a 30-year-old engineer is on trial for founding and operating an enormous online black market—the Amazon of drugs. The outcome of his trial could change the way we use the internet.

In 2011, it was possible to buy pretty much any illegal drug you desired on a single website—The Silk Road. Today (right now!), the United States is trying to put away Ross Ulbricht, the man they say ran the operation. This is more than just the trial of an alleged drug dealer: The outcome of this case will shape how the public looks at emerging technologies like bitcoin, online privacy, and the role of the federal government in policing the web. Motherboard put it well:

The case will address many issues that have never before been argued in a US court, and many believe it will set precedents for privacy and the extent to which the government holds people responsible for content on their sites and servers.

As the internet uneasily settles into its new role as as a global commerce hub and powerful driver of immense economies, governments have become increasingly aggressive in ensuring their interests are represented—even, and maybe especially, when it means betraying ideals of anonymity and freedom held dearly by the web's early adopters.

If Ulbricht—a name to a face—goes down for the Silk Road—a drug market for the faceless—it'll discourage a lot of would-be imitators who want a narcotics free-for-all, and represent the most high-profile way the internet's promise of true anonymity has been undermined by the state. But if "Dread Pirate Roberts" eludes the FBI once again, it'll make the darker corners of the internet a whole lot more confident to do what they please in the shadows.

Silk Road

Before Gawker's Adrian Chen revealed it to the world, hardly anyone had ever heard of the Silk Road, and it flourished. You could browse the site pretty much like you'd browse any other e-commerce destination—so long as you were accessing it via an anonymous connection—buying as much or as little of your preferred narcotic from a wide variety of pseudonymous vendors. It wasn't the prettiest website (screenshot below), but it was functional and straightforward.

What allowed the Silk Road to work was anonymity. It could be accessed only through Tor, a piece of software that allows encrypted, anonymous access to hidden websites around the world—perfect for both a foreign dissident and a drug dealer.

Silk Road was also quite possibly what popularized bitcoin, so perfectly suited for illicit transactions.

"Dread Pirate Roberts": Silk Road's Mastermind

Because of the collective anonymity of the site's participants, it was impossible to tell who was in charge. The site's administrator went by "Dread Pirate Roberts." Feds say the man behind "Dread Pirate Roberts" is Ross Ulbricht.

Details gleaned after his arrest show a surprisingly ordinary man; certainly not someone who screams INTERNATIONAL DRUG MASTERMIND:

Browsing Ulbricht's social media accounts show a pretty normal, nerdy guy. Ulbricht graduated from the University of Texas in 2006 with a degree in Physics and went to the Pennsylvania State University for grad school, where he studied engineering and wrote a master's thesis on "Growth of EuO Thin Films by Molecular Beam Epitaxy." According to property records, he owned a home in State College, PA, which he sold in 2010 for $187,0000. Curiously, the indictment misidentifies his grad school as the University of Pennsylvania.

He's got a Facebook page full of beer pong pics and, of course, was a vocal supporter of Ron Paul, donating $200 to his campaign in 2007. "He doesn't compromise his integrity as a politician and he fights quite diligently to restore the principles that our country was founded on," Ulbricht told the Penn State student newspaper in 2008.

Nonetheless, police accuse him of making an enormous amount of money on the Silk Road:

According to the indictment, Silk Road was bigger than anyone had suspected: It boasted over $1.6 billion in sales from 2011-2013, which resulted in $80 million in commissions. (Researchers had previously estimated that Silk Road was doing about $22 million in total sales per year.) According to the indictment, which claims that FBI agents obtained a mirror of the server that housed Silk Road's business from law enforcement in an unidentified foreign country, Ulbricht "alone has controlled the massive profits generated from the operation of the business." He used some of the profits to pay a team of administrators as much as $2,000 a week each. And yet, he only paid $1,000 a month in rent for his San Francisco apartment, according to the indictment.

The Investigation

According to a detailed Wired account of the investigation, a DHS informant in Baltimore told the feds about Silk Road. Cops managed to identify site moderators and administrators, and started making arrests to get closer to Dread Pirate Roberts.

How did they pull that off? As Wired puts it, the "FBI's Story of Finding Silk Road's Server Sounds a Lot Like Hacking":

As bureau agent Christopher Tarbell describes it, he and another agent discovered the Silk Road's IP address in June of 2013. According to Tarbell's somewhat cryptic account, the two agents entered "miscellaneous" data into its login page and found that its CAPTCHA—the garbled collection of letters and numbers used to filter out spam bots—was loading from an address not connected to any Tor "node," the computers that bounce data through the anonymity software's network to hide its source. Instead, they say that a software misconfiguration meant the CAPTCHA data was coming directly from a data center in Iceland, the true location of the server hosting the Silk Road.

Is Ross Ulbricht "Dread Pirate Roberts"?

Ulbricht doesn't deny creating the Silk Road—just using it to sell drugs. On the first day of Ulbricht's trial, Motherboard reports his attorney did not deny that his client founded the site:

However, while Ulbricht's attorney Joshua Dratel admitted for the first time in court Tuesday that Ulbricht did create Silk Road as an "economic experiment," he claims thedefendant passed the site to other administrators when running it became "too stressful" after just a few months in 2011.

But feds have a lot of evidence linking Ulbricht to the Dread Pirate Roberts drug baron identity.

Over at the Daily Dot, you can view a rough outline of what the FBI is trotting out against Ulbricht in court. Vast chat transcripts, screenshots from Ulbricht's laptop, and internal Silk Road communiques are at the ready. Photos like this one, which law enforcement says was on Ulbricht's laptop screen (the "mastermind" controls for Silk Road) when he was arrested in San Francisco:

Or this one (his strangely ample collection of fake IDs)—

—could go a long way in convincing a jury that he was indeed responsible for a criminal conspiracy to traffic narcotics around the globe and throughout the United States.

But it's important to note that Ulbricht's criminal defense doesn't hinge on distancing himself completely from the Silk Road—simply showing that some other person (or persons) could have been operating the Dread Pirate Roberts persona, acting as the drug market's chief administrator and leader. Proving that a single person is the sole operator of a pseudonymous internet account based on pseudonymous software channels will not be easy for the feds.

The Trial

Bitcoin is still so new, complex, and untested that it's tough to explain what it is to a layman, let alone prove that it was instrumental in Dread Pirate Roberts' global drug ring. To how many people could you stop on the sidewalk and easily explain the functionality of Tor? Even if the prosecution can provide a convincing argument that Dread Pirate Roberts and Ross Ulbricht are one in the same, can they prove beyond a reasonable doubt that this in itself was a crime, and not just an internet screen name?

But the verdict could change the way we use the internet—and the way the government regards it, too. The Silk Road trial is a simple drug trafficking case in some ways, but it's also going to make us confront the difficult reality that just because certain online activities have managed to skirt or challenge established law so far doesn't mean that the internet will forever remain a Wild West. As Woodrow Hartzog, an associate professor of law at Samford University and scholar at the Stanford's Center for Internet and Society, put it:

Online black markets are likely to continue to be created and shut down. Yet this trial has also reminded us of the limits of technology. When the Internet was in its infancy, many thought online activity was also beyond the reach of the law. We've seen time and time again this is just not true. Bitcoin is a very powerful and interesting technology, but it is important not to overestimate innovation. It's equally important not to underestimate how our offline actions can make us vulnerable online. Perhaps the most significant impact of this trial is to serve as a reminder not to be overly confident in online anonymity, particularly in the face of substantial resources.

Australian security consultant and fervent Silk Road analyst Nik Cubrilovic told me he thinks the trial has already altered the net, verdict aside:

Consequences of the Ulbricht trial are already being felt. They are good or bad depending on your viewpoint. First thing is that many vendors, users and market administrators who are less confident in their ability to shield themselves from federal law enforcement have given up. The administrators of Agora [another darknet market] are considered the most technically and security adept and they spent the 2 weeks [after November '14 darknet raids by police]…in a complete state of panic.

Even having hidden markets like Silk Road raided—let alone prosecuted—has been enough to push copycats deeper underground, says Cubrilovic:

Gone are the days where starting a market was as simple as Googling 'how to setup a tor hidden service' and then installing some off-the-shelf market software. Those guys have all been arrested, and anybody with that lower level of skill has been scared away.

The End of Anonymous Browsing?

Most importantly, the FBI will be free to use the same, possibly illegal methods it employed to take down the Silk Road on future targets:

The FBI has also done a good job of keeping their methods and techniques close to their chest. There has been a level of cooperation here from the justice system and the presiding judge—what usually happens is that to convict someone or to grant them a fair trial the methods used in the arrest would have to be scrutinized. The pre-trial in Ross' case concluded that the FBI didn't have to reveal their server uncovery method - and even if it was hacking it would still be ok. This means law enforcement are free to apply the same methods again, they didn't have to 'burn' their techniques.

This would be a huge win for any government apparatus that wants to decrypt the channels we've been assuming are safe—it wasn't so long ago that Edward Snowden relied on Tor to protect his whistleblowing activity.

Security expert and CloudFlare researcher Marc Rogers sees two courses depending on the jury's decision. If the FBI manages to convict Ulbricht, Rogers "suspect that the primary long term effect of this is that we will see further prosecutions of hidden Tor services."

This means further attempts to de-cloak services which violate US law and that may lead to collateral damage as not all hidden services are illegal drug markets. Undermining one category of hidden services potentially undermines them all.

A not guilty verdict, however, "carries the most risk."

Prosecutors and law enforcement are under immense pressure to "do something" about the underground drug markets. Failure to successful prosecute the single largest and longest running of these will almost certainly add fuel to the call for more and stronger laws to arm the justice department.

It was only a matter of weeks before Congress capitalized on the Sony hack to give the odious CISPA legislation another go. If the FBI can't pry the darknet's drug baron out of hiding, there's every reason to expect it'll just ask for scarier tools.

Illustration by Jim Cooke