The Other Side Of The Infamous Silk Road Case


The government and tech world are increasingly at odds as Congress, the courts, and law enforcement jerry rig existing law to fit new technologies and their uses.

But the controversial case of Ross Ulbricht, creator of the online black marketplace Silk Road, which involved massive drug sales and murder-for-hire allegations, most closely embodies the tensions created by colliding worlds of law and order and the civil liberties prized by the anonymous and unpredictable nature of the Dark Net.

Alex Winter’s documentary Deep Web, which debuts on the Epix cable network Sunday, takes a look at the political ramifications of Ulbricht’s case, the growing body of anonymous communities, and the government’s attempt to hold users accountable for their behavior online — beyond the reach of search engines.

Most internet users only access a fraction of the internet, or Surface Web, which encompasses anything that can be found through Google. The Deep Web, however, consists of all the uncategorized but secure data websites host, such as banking information.


But there’s an area of the Deep Web called the Dark Web or Dark Net that can be accessed through Tor, which lets users anonymously surf the internet on a volunteer-run, encrypted network. The Dark Net is used by journalists, government officials and whistleblowers, and privacy enthusiasts, but it was also home to the Silk Road.

“There are a lot of issues the Silk Road case bumps up against directly or indirectly, such as search and seizure laws, surveillance and privacy, the battle against encryption, the drug war and drug policy,” Winter told ThinkProgress. “It’s a very compelling story about the unpredictability of anonymized communities and networks, and the government’s attempt, however clumsy, to try cases in that space and enforce the law.”

Ulbricht, 31, was convicted in February for several drug trafficking charges and faces up to 20 years in prison. He is set to be sentenced May 29. Deep Web takes place in the months leading up to the conviction, and primarily focuses on the circumstances that make the case so uniquely important for casual users and tech libertarians alike, who value privacy and an internet free from government surveillance.

“In the [1980’s], you had all the things you have on the Dark Net today — these privacy and anonymity oriented communities, clubs and markets around various interests, like music, art. You had drug markets, you had encrypted email. But it was on a much smaller scale and required some amount of technological know-how because there was no ‘Web’ yet and even when there was, it was in its infancy,” Winter said.

Deep Web displays a mash-up of flawed policy, such as the war on drugs, conflicting opinions within the government on how much online activity should be policed, and “all of the extremely, maddeningly contradictory facts of who [Ross Ulbricht] supposedly is,” Winter said.


But just like the casual internet user doesn’t see beyond what can be searched through Google, the viewer never sees or hears from Ulbricht. Beyond glimpses provided through court sketches, old photos and videos, Ulbricht’s story — and the political issues surrounding his case — is told by those who know him best: his parents and Wired journalist Andy Greenberg, who had the only media interview with him as his Silk Road persona Dread Pirate Roberts.

Winter said he didn’t have “as much as a phone conversation” with Ulbricht, not because he was unattainable but because telling the story from the viewpoint of “two people who didn’t know how to use their cell phones” who become digital rights activists to defend their “son who was arrested and may be guilty of horrible crimes.”

Ulbricht’s arrest put a human face on the complexities behind a long-brewing standoff between the online world and government intervention that had been swelling for decades.

“I think the government is really trying to wrap their brains around anonymous communities that they don’t have control over — and that they may be the biggest threat of all. That scares the shit out of people. Digital currency and the block chain and its disruption potential. And then you add into those two things large scale drug transactions, it’s a powder keg. Of course they’re going to come at it hard,” Winter said.

“There’s a point in the movie where you go ‘Jesus, he might be both of those things!’” — a ruthless drug lord who would kill to protect the freedom Silk Road enables, or a sweet kid who just wanted to create a private solace online.

“And we don’t know,” which it is, Winter said. “There’s this man in a prison cell who may not have all of the answers himself, frankly.”