The outcome of the case against the man who allegedly ran online black market could redraw the limits of personal freedom and state power in the digital age

It was an afternoon like any other. Then, Lyn Ulbricht’s life changed shape, speed and direction, in a single moment.

In November 2013, a journalist called Ulbricht’s home in Austin, Texas. Her son Ross had just been arrested, and was accused of running the Silk Road website, known as an Ebay for illegal drugs. Ross was, said the FBI, a drugs kingpin. Lyn Ulbricht says she went into shock, and panicked: “This can’t be true, there must be some mistake.”

“Ever since then, I’ve had the feeling of being carried along by a tidal wave,” she says.

That day, the phone was “ringing off the hook. There were TV camera crews coming into our neighbourhood and filming the house.”

Small wonder. Not only was her 29-year-old, physics graduate son accused of being the criminal mastermind of a revolutionary, online multimillion dollar worldwide drug-smuggling network, he was also, at that point, allegedly the cold-blooded author of two gangland hits. Later, that number would increase to six.

At his bail hearing, the prosecution added four more murder-for-hire charges, and said he paid for the torture and murders of blackmailers and informers. It was alleged he paid undercover officers $500,000 in Bitcoin, the anonymous currency used at the Silk Road, to kill his enemies.

“Ross was a wonderful child – the easiest baby I have ever met, and sweet with it,” says his mother. “I know every mother thinks that. But he was a sweet, compassionate and caring adult, too.

She can’t comprehend the possibility that we would casually order a hitman.

“He’s a totally peaceful person who never hurt a soul. Anyone who knows him will tell you that it’s inconceivable that he would ever have anything to do with murder. He is a man of staunch principle. I cannot imagine him betraying those principles by harming others with violence or in any other way – especially for selfish reasons. It is too out of character.”

Ulbricht’s charges

Five of those murder-for hire charges have now been dropped. “For very good reason,” says Lyn Ulbricht. “I suspect that is because they do not have the evidence.”

He is still facing one hire-for-murder charge in Maryland, though a trial date has not been set.

Even though Ulbricht is not now formally charged with all of the original murder charges, they are included in submissions to the jury who will decide his fate. The case is due to start in January and many legal experts say could it define the limits of law in the digital age.



Now, Ulbricht faces charges for which he could be jailed for life: narcotics trafficking; computer hacking; money-laundering; engaging in a criminal enterprise, and conspiracy to traffic in fraudulent identities.

The court must decide if he is guilty of these, or if the FBI has over-reached itself in the pursuit and capture of one man who, with breathtaking audacity, and acting mainly alone, is alleged to have outgunned the war on drugs on multiple fronts: legal, technical, economic, and philosophical.

Facebook Twitter Pinterest Ross Ulbricht is shown with his lawyer, Brandon LeBlanc, in a courtroom sketch. Photograph: STRINGER/Reuters

Ulbricht’s lawyers say the case represents a turning point in legal history, and without admitting liability or any wrongdoing, have questioned whether an owner of a website can be found guilty for the crimes of its users. They say the case has the potential to reconfigure the boundaries of state power in the pursuit of justice.

Ulbricht’s lawyer is Joshua Dratel, the first civilian attorney to defend a Guantanamo case. He took the case on at cut-price rates, describing it as containing “naked allegations”. He says the Ulbricht trial matters for every American who cares about freedom and privacy in the digital age.

“The case does represent an effort by the government to expand the concepts of vicarious liability over the internet – ie what is the responsibility of a website operator for the uses to which people put products sold on that site? – and to demonise certain very legitimate means of personal privacy protection, such as [the anonymsing software] Tor and Bitcoin.

“There are also legal issues with respect to the government’s ability to monitor, collect, and, or intercept electronic communications, and the means by which the government can collect information on the internet. Can the government hack, geolocate, or use illegal means to pursue an investigation?”

A legal and ethical precedent

The answers to these questions could set a legal and ethical precedent for an entire generation of web users, redrawing the limits of personal freedom and state power in the digital space.

The FBI claims that Ulbricht is “Dread Pirate Roberts”, the pseudonymous, swashbuckling, owner-operator of a website that enabled anyone with an internet connection to buy illegal drugs with little chance of capture. DPR, as he was known, was prone to rabble-rousing, Libertarian-themed speeches on the site rejecting state power over individuals: “I won’t rest until children are born into a world where oppression, institutional violence and control, world war, and all the other hallmarks of the state are as ancient history as pharaohs commanding armies of slaves. The drug war merely brings to light their nature and shows us who they really are,” wrote DPR on the site’s forums.



His mother, unsurprisingly perhaps, insists her son is innocent of all charges.

At its peak, the Silk Road had almost 1 million user accounts registered and a turnover of over $20m a year, and has inspired dozens of imitators.



Whatever the allegations, his mother says she is now obsessed with getting her son a fair trial. “It dominates every moment I’m awake – I’m thinking: ‘What can I do for Ross?’ As the trial approaches it becomes more intense. I have come to realise that this case is about more than Ross. The outcome will set a precedent that will have implications for internet freedom,” she says.



Kirk and Lyn Ulbricht: ‘It dominates every moment I’m awake’ Photograph: The Guardian

She and her friends pledged $1m after her son’s arrest – with many placing their homes as security. Despite Ulbricht having no previous criminal record, the judge refused his bail, ruling the now-dropped murder-for-hire charges indicated he was a dangerous criminal that posed a flight risk.

“Twenty-seven friends and family (none wealthy) stepped up and pledged their homes, life savings and property towards bail,” says Lyn. “Over and over again they told me they weren’t worried. They knew Ross was a man of his word and he’d never do that to them.”

Ulbricht has been in jail in Brooklyn for over a year, forbidden even from exercising in the open air. He was initially jailed in solitary confinement for six weeks. “It was horrendous seeing him brought in wearing an orange suit, in handcuffs. We were in adjoining locked rooms and talked through plexiglass,” says his mother.



Ross was, she says, a physics graduate fond of hiking and respected as a generous, peaceful man. “Ross would never deliberately hurt or cheat anyone. He is one of the most compassionate, non-violent, life-loving people I know. He is known for his integrity and honesty. He is an outdoorsy, nature-loving person,” says Lyn. “He has not been outside to feel the breeze for 15 months, to see the sky. He can see the sky a little bit from one window.”

Friends recall how he would often wander into class shirtless; others reveal how he once lost a bet and wore a skintight dress to an exam as forfeit. All speak of a fiercely intelligent student who could master any discipline he focused on.



How did investigators identify the server?

After months teaching yoga and physics to fellow inmates, Ulbricht has only recently gained access to the evidence the government will use to prosecute him. On a PC – without internet access – Ulbricht must examine over 6TB of data.

Curiously, the mass of data does not contain technical details of what security experts say is a critical piece of evidence: how investigators identified the server where the illegal marketplace was hosted.

Ulbricht’s lawyers had claimed that the FBI’s search and seizure of the Silk Road server, which they carried out without a warrant, violated Ulbricht’s Fourth Amendment constitutional rights, which protect US citizens against unreasonable search and seizure.

In October, district dudge Katherine Forest of the Southern District of New York, ruled that the Fourth Amendment did not apply in Ulbricht’s case, as his lawyers did not, despite repeated opportunities, claim ownership of the server – meaning he had no right to claim Fourth Amendment protection.

But Ulbricht was in an impossible catch-22: admit ownership of the server, and he would have admitted ownership of the site. By refusing to stake a claim in the illegally searched server, though, he waived the protection that the US constitution would have offered him.

Facebook Twitter Pinterest A screengrab of Silk Road takedown notice. Photograph: David Colbran/David Colbran/Demotix/Corbis

Police say Ulbricht was captured as he was logged on to the Silk Road server’s admin panels in a public library in San Francisco. The FBI says it found a Bitcoin wallet containing approximately 144,000 bitcoins, equivalent to more than $20m at the time. It also claims to have found an asset sheet and journal in which he detailed the set-up, history and day-to-day operation of the site.

The FBI’s submission of how it found the server is, by their own account and according to several experts, not only technically impossible but also demonstrably untrue.

“The logs provided to the defence by the FBI don’t match the FBI’s own story,” says Nicholas Weaver, of the International Computer Science Institute, a non-profit research centre in Berkeley. “To put it simply: the FBI agent says: ‘I did this’, but the FBI’s own evidence to the defence says: ‘He probably didn’t.’

“The investigation itself was just sloppy. A good online investigator should have a continuous log of all activity, including full packet captures of any non-encrypted traffic. There appears to be none of this.”

Robert Graham, another cybersecurity expert, calls the FBI’s claim gibberish. “I cannot read his declaration and figure out what, exactly, he did to find the servers. It’s clear that [the FBI officer who lead the search for Ulbricht] doesn’t understand what he’s talking about.”

Nicholas Weaver says defence arguments about the constitutionality of the server capture are now immaterial.

“The defense refused to declare a fourth amendment interest in the server even after the judge provided multiple chances. Such a declaration would constrain Ulbricht’s testimony, but is not an admission of guilt. Because he did not claim the server as his, Ulbricht has no formal privacy interest which would impact his fourth amendment rights. As such, the FBI’s tactics don’t matter: since Ulbricht never claimed that the server was his, the judge couldn’t consider the constitutionality of the search.”

In a Facebook posting on Independence Day four years ago, Ulbricht reflected on freedom – personal, political, and individual – in an essay that four years later, resonates with dark irony as he faces the rest of his life in a jail cell.

“We live in a most unique time, and are freer, as a generation, than any that has come before us. Let us be thankful for our freedom, and build a world where we, and the generations that follow us, will be freer than any that have come before!” he wrote.

In a New York City winter as and her son’s trial approaches, Lyn Ulbricht recalls Ross’s brightest memory this year.

“In the summer, Ross was so happy. The sun began to slant in one of the windows. He and a prisoner from the Domincan Republic would lie in the ray. He told me that it gives him energy. He said: ‘You don’t realise how you miss it until you’re deprived of it.’

• The headline on this piece was amended on 26 December 2014 to more accurately reflect the article’s contents