The ‘Dark Web’ Isn’t Going Anywhere

In a courtroom drawing, defendant Ross Ulbricht listens to proceedings from the defense table in January.

In a courtroom drawing, defendant Ross Ulbricht listens to proceedings from the defense table in January. Elizabeth Wlliams/AP

The government may have won its case against Silk Road's Ross Ulbricht, but the hidden sites are getting bigger—and smarter.

The Wednesday conviction of Silk Road creator Ross Ulbricht on seven felony charges demonstrated at least one thing pretty clearly: U.S. law enforcement can not only find, but successfully prosecute online operators of the drug market who cloak their criminal dealings behind hidden web addresses—especially when those operators slip up by, say, talking about their drug deals in messages linked to a personal Gmail account.

Yet beyond sending a 30-year-old to prison, what does Ulbricht's conviction mean for the so-called "dark web," which continues to grow even after the government shut down both the original Silk Road and its immediate successor? That's far murkier, say experts on cybercrime and privacy issues.

In many ways, the largest shift came when federal agents arrested Ulbricht in October 2013 and accused him of being the mastermind of Silk Road, the $1.2 billion criminal enterprise that operated on the hidden Tor network and used Bitcoin as its currency. With Ulbricht in the headlines, the price of Bitcoin plummeted, and the closures of Silk Road and Silk Road 2.0 forced other major hubs of the dark web to add new levels of security to evade law enforcement.

Ulbricht's arrest and conviction was a victory for the feds, which had caught him "literally with his fingers on the keyboard" at a San Francisco library after a Department of Homeland Security agent had infiltrated Silk Road and posed as one of Ulbricht's employees.

Using his laptop, journal, chat logs, and the network's servers in Iceland and Pennsylvania, prosecutors unloaded a mountain of evidence against Ulbricht and identified him as the man behind the pseudonym, Dread Pirate Roberts. Ulbricht, they said, had even asked applicants to his "bitcoin startup" to use his eponymous Gmail address. A college friend testified that Ulbricht had confided to him that he created Silk Road, and the FBI traced $13.4 million in bitcoins back to Ulbricht's e-wallet, according to Wired. The jury took less than four hours to convict him.

At the same time, however, the high-profile trial gave a lot of publicity to the dark web, and both the number of sites and the volume of people using them have increased since Silk Road was shuttered, notes The Dark Net author Jamie Bartlett, director of the Centre for the Analysis of Social Media at Demos. "I think it's a mixed bag for law enforcement," Bartlett said by phone on Thursday. "The long-term impact was the sites got smarter. They got more careful."

The cat-and-mouse game may shift as well. Newer dark sites (two major ones are Agora and Evolution) are likely to protect their servers by basing them in countries "hostile to U.S. law enforcement," said Nicholas Weaver of the International Computer Science Institute in Berkeley, California. "The markets will keep moving overseas, but law enforcement will keep going after the dealers," he said, referring to the people who actually ship and deliver the drugs sold online.

On another front—the Fourth Amendment concerns raised by the FBI's discovery of the Silk Road server—Ulbricht's case may set less of a precedent than Internet-freedom advocates originally feared. To the surprise of Weaver and other close observers of the trial, Ulbricht's defense team never fully challenged the government's seizure of the Silk Road server on constitutional grounds, because to have legal standing under the Fourth Amendment, he would first have had to state definitively that the server belonged to him—in other words, he would have had to admit to being the mastermind of Silk Road.

Yet as Weaver writes, such an admission would not have been as devastating as it sounds, because it would not have come in open court, with the jury present.

Such a declaration is not an admission of guilt: It can only be used by the prosecution if the defendant testifies. So as long as Ulbricht doesn’t testify, the jury never learns that Ulbricht admits to controlling the server.

The judge tossed Ulbricht's motion to suppress the government's evidence from the server, and he did not end up testifying in his own defense. While not denying his involvement with Silk Road, his lawyer, Joshua Dratel, had argued he was framed and that he was not the site's creator. Dratel said he'll appeal the conviction over judge's decision not to allow the presentation of certain evidence and witnesses, The Wall Street Journal reported.

In an interview Thursday, Weaver said the judgment against Ulbricht was sound even if the investigation was not. "It is fortunate for us that it looks like this case will have no legal precedent," he said.

For now, Ulbricht sits in jail, awaiting both his sentence and his appeal (and a second, related trial on murder-for-hire charges). The dark web that he helped to build and popularize goes on, with the FBI attempting to track increasingly sophisticated hidden drug, munitions, and hacking markets.

"How will law enforcement try to strategically undermine these sites?" Bartlett asked. The answer, he said, might lie in the same undercover methods of monitoring and infiltration the government has used to take down vast child pornography networks, as well as Silk Road. "It becomes a little more like good, old-fashioned policing," Bartlett said, "but in a new space."

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