The end of the Silk Road: The problem with a life online

About nine months ago, the entrepreneur behind a wildly successful internet start-up allegedly decided that he needed to have one of his staff killed. According to an indictment filed in a US District Court in Maryland last week, Dread Pirate Roberts, as he is said to have called himself, had come to believe that one of his employees had stolen money from users of The Silk Road, the anonymous drugs marketplace that he had set up about two years previously. This employee had also been arrested, making him something of a liability. At first, the entrepreneur apparently just wanted the guy beaten up, and forced to return the money, stored in bitcoins, an online currency that allows its users to maintain a healthy distance from their transactions. Accordingly, it is said, he contacted a dealer with whom he had previously done a little business to see if he might be able to help.

After this first contact, though, it seems that Dread Pirate Roberts (DPR) started to see things differently. His employee had been in prison before, and he was worried that he would reveal the secrets of the business if the police put him under pressure. He apparently emailed his contact again. "Can you change the order to execute rather than torture?" the indictment says that he asked. He had, he added, "never killed a man or had one killed before, but it is the right move in this case".

His contact said he could do it, and agreed a price of $80,000. In further discussions, DPR refined his instructions. The hitmen, he is reported to have requested, "should probably just … let him use his computer to send the coins back, and then kill him". He wanted proof of death, he added, a video if possible, but if not, then pictures would do.

A few weeks later, he received a message notifying him that the job had been done. His employee had died of "asphyxiation/heart rupture" while being tortured. DPR was sent a photograph of his victim's corpse. "I'm pissed I had to kill him … but what's done is done," he said, according to the indictment. "I just can't believe he was so stupid … I just wish more people had some integrity." When justifying his actions to his hired killers before the job was undertaken, he apparently explained that the target could not be trusted. "Considering his arrest," DPR supposedly wrote, "I have to assume he will sing."

"Singing", or squealing, or ratting somebody out, are unforgivable sins in the world of organised crime. At least, that's what I understand from the movies. Among a number of other self-conscious bits of phrasing quoted in the indictment, Dread Pirate Roberts's use of that verb rather makes me think that he, too, had formed his sense of the underworld in the cinema. Of course, he is far from the first alleged criminal to imitate his own cultural representation: the feedback loop between the Mafia and movies such as Goodfellas and The Godfather is well documented, and there are several reports of drug-dealers adopting "burner" disposable mobile phones after watching The Wire. The tricky question with him is exactly what that language represents.

DPR posted often on The Silk Road's message boards. The character he projects there, it is safe to say, is not that of a violent criminal but of a self-styled modern mystic, a libertarian true believer who invites the users of his website to become part of a movement. "Don't be tempted by this short-term easy fix of 'let the government handle it'," he writes in one post. "Their time is coming to an end. The future is OUR time... The future can be a time where the human spirit flourishes, unbridled, wild and free! Don't be so quick to put on that harness and pull for the parasites."

There is something of Assange about this. But the delusions of grandeur on display are quite at odds with the coldly business-like approach exhibited in those private messages. And, as it turns out, both are hard to square with the real-world person who is allegedly behind the Pirate. After a lengthy investigation, the FBI last week arrested one Ross William Ulbricht, sending at least six officers to take him as he sat using his computer in the science-fiction section of the San Francisco public library. The killers he allegedly thought he was hiring in his private chats, and the murder he supposedly thought had been committed on his orders, were in fact a figment: a story concocted by undercover agents to see how far he would go.

The comparison of Ulbricht's on- and off-line existences has a lot to tell us about the seductive, dangerous deceptions that are so often perpetrated on the internet. For this man, it is safe to say, does not seem like your stereotypical drug kingpin or, indeed, like a prophet of a new world order. On his LinkedIn profile, he explains how he has spent the past few years creating an "economic simulation", a radically different interpretation of the Silk Road experiment, if that is what he is talking about, than that which he allegedly propagated in his piratical guise. On YouTube, there's a 2012 video of him talking to a friend for the American oral history project Storycorps about his hopes for the future. The friend asks him to summarise his plans for the next five years in one sentence. "Um… ehhh… I'm into a few things, so one sentence isn't enough, damn it," Ulbricht says, presumably mindful that it would be foolish to discuss his hopes for The Silk Road. "But I'm pretty sure I want to start a family and just make more friends and close people I love. I want to focus on being more connected to people."

Throughout that interview, Ulbricht seems like a stereotypical Silicon Valley nerd: a mild, raggedly good-looking intellectual with a tendency to egocentricity. It is hard to square him with the murder he apparently tried to commission the next year. Hard, too, to imagine him ordering another murder about a month later, in the same chillingly distant language, the same ham-fisted impersonation of a gangster. "I would like to put a bounty on his head if it's not too much trouble for you," another indictment says that he wrote, this time allegedly hoping to have a user who was blackmailing him, "FriendlyChemist", assassinated. "What would be an adequate amount to motivate you to find him?"

Again, according to the indictment, Ulbricht was told that the killing had been carried out and given photographic evidence; this time, the FBI were not fooling him, but police could find no proof that it had ever really happened. Still, the blackmail never appears to have been carried out. Perhaps this was the appropriate resolution for Dread Pirate Roberts, who always seems, on one level, to be play acting, like most people in positions of power, doing an impression of authority in the hope that the real thing will follow. Given a gun and told to bring his plans to fruition himself, would the meek Ross Ulbricht ever pull the trigger? It is hard to imagine.

As technology and globalisation advance, there are bound to be more and more examples of this disconnection when the consequences of our actions are pushed a few degrees of separation away: few of us would demand that a child work in abysmal conditions so that we might have a cheap T-shirt if we had to do it face to face, but many of us are willing to do so when a supply chain mediates the process. One wonders, likewise, if the drone operators who drop bombs remotely have as difficult a time in dealing with it as pilots who must make the journey with their deadly weapons.

Above all, it's a phenomenon found online, where bullies and paedophiles and sexists are liberated to express their darkest selves in ways that they might never unbutton in person. But it's important to express this point the other way round, too: a digital age does not invent new impulses, but rather creates different ways of expressing the ones that are already there. These transgressions are not the fault of technology. They are the faults of people. We'll learn more about Ross Ulbricht in the weeks and months ahead.

Dread Pirate Roberts, at least to judge by his remarks on The Silk Road's message boards, was convinced he had hit upon a revolutionary means of defying the state. Confident, even cocky, he was also always looking over his shoulder. The Silk Road, he posted, "could literally change the world as we know it. It is bigger than any one of us". But, he added, "as a community, if we are going to survive, we need to adopt a LONG-TERM vision. Getting the most out of this thing before it gets taken down is NOT going to bring us success. In that world, The Silk Road will be a shooting star that burns out quickly and dies as little more than a dream."

He was, as it turns out, right. He was right that he had found a means of staying hidden from the authorities online and right that there was a risk that this revolutionary site could be taken down before it had really taken off. His only omission was the source of that risk, if the charge sheets are to be believed: himself.

Ross Ulbricht, according to one of those documents, was connected to DPR by nothing more complicated than an internet search. The indictment says that an FBI agent found an early reference to The Silk Road on an online forum under the username "Altoid", in a message supposedly posted by a prospective customer but transparently in fact an attempt to drum up business. Two days later, the same username cropped up using a different forum, again recommending The Silk Road. And then, eight months later, "Altoid" posted another message advertising a job – and asking interested parties to write to rossulbricht@gmail.com. For all his technical prowess, he could still be undone by a simple lapse of concentration.

If Ross Ulbricht really is Dread Pirate Roberts, it seems safe to say that he did not have as secure a grip on the future of the internet as he claimed; in fact, even he was having trouble dealing with its present, with the strange way that it makes us anonymous and indelible at the same time. As he contemplates a charge of attempted murder, he may reflect: this is not who I really am. But to the rest of the world, that will mean nothing. You can try to keep your selves apart as hard as you like. They will always come together in the end.