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

Why did the FBI arrest Ross Ulbricht for an attempted murder by Dread Pirate Roberts?

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 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.

Have you tried new the Independent Digital Edition apps?
ebooksAn evocation of the conflict through the eyes of those who lived through it
Flocking round: Beyoncé, Madame Tussauds' latest waxwork, looking fierce in the park
travelIn a digital age when we have more access than ever to the stars, why are waxworks still pulling in crowds?
Arts and Entertainment
Arts and Entertainment
Judi Dench appeared at the Hay Festival to perform excerpts from Shakespearean plays
tvJudi Dench and Hugh Bonneville join Benedict Cumberbatch in BBC Shakespeare adaptations
Is this how Mario Balotelli will cruise into Liverpool?
Ronahi Serhat, a PKK fighter, in the Qandil Mountains in Iraqi Kurdistan
Arts and Entertainment
Poet’s corner: Philip Larkin at the venetian window of his home in 1958
booksOr caring, playful man who lived for others? A new book has the answer
Arts and Entertainment
Exhibition at the Centre Pompidou in Metz - 23 May 2012
Matthew McConaughey and his son Levi at the game between the Boston Red Sox and the Houston Astros at Fenway Park on August 17, 2014 in Boston, Massachusetts.
advertisingOscar-winner’s Lincoln deal is latest in a lucrative ad production line
Life and Style
Pick of the bunch: Sudi Pigott puts together roasted tomatoes with peppers, aubergines and Labneh cheese for a tomato-inspired vegetarian main dish
food + drink
Arts and Entertainment
Alfred Molina, left, and John Lithgow in a scene from 'Love Is Strange'
Travel Shop
the manor
Up to 70% off luxury travel
on city breaks Find out more
Up to 70% off luxury travel
on chic beach resorts Find out more
sardina foodie
Up to 70% off luxury travel
on country retreats Find out more
Have you tried new the Independent Digital Edition apps?
Independent Dating

By clicking 'Search' you
are agreeing to our
Terms of Use.

iJobs Job Widget
iJobs General

Junior Quant Analyst - C++, Boost, Data Mining

£25000 - £35000 per annum: Harrington Starr: Junior Quant Analyst - C++, Boost...

Service Desk Analyst- (Desktop Support, Help desk)

£25000 - £35000 per annum: Harrington Starr: Service Desk Analyst- (Desktop Su...

Junior Quant Analyst (Machine Learning, SQL, Brokerage)

£30000 - £50000 per annum: Harrington Starr: Junior Quant Analyst (Machine Lea...

UNIX Application Support Analyst- Support, UNIX, London

£45000 - £55000 per annum: Harrington Starr: UNIX Application Support Analyst-...

Day In a Page

Air strikes? Talk of God? Obama is following the jihadists’ script

Air strikes? Talk of God? Obama is following the jihadists’ script

The President came the nearest he has come yet to rivalling George W Bush’s gormless reaction to 9/11 , says Robert Fisk
Ebola outbreak: Billy Graham’s son declares righteous war on the virus

Billy Graham’s son declares righteous war on Ebola

A Christian charity’s efforts to save missionaries trapped in Africa by the crisis have been justifiably praised. But doubts remain about its evangelical motives
Jeremy Clarkson 'does not see a problem' with his racist language on Top Gear, says BBC

Not even Jeremy Clarkson is bigger than the BBC, says TV boss

Corporation’s head of television confirms ‘Top Gear’ host was warned about racist language
Nick Clegg the movie: Channel 4 to air Coalition drama showing Lib Dem leader's rise

Nick Clegg the movie

Channel 4 to air Coalition drama showing Lib Dem leader's rise
Philip Larkin: Misogynist, racist, miserable? Or caring, playful man who lived for others?

Philip Larkin: What will survive of him?

Larkin's reputation has taken a knocking. But a new book by James Booth argues that the poet was affectionate, witty, entertaining and kind, as hitherto unseen letters, sketches and 'selfies' reveal
Madame Tussauds has shown off its Beyoncé waxwork in Regent's Park - but why is the tourist attraction still pulling in the crowds?

Waxing lyrical

Madame Tussauds has shown off its Beyoncé waxwork in Regent's Park - but why is the tourist attraction still pulling in the crowds?
Texas forensic astronomer finally pinpoints the exact birth of impressionism

Revealed (to the minute)

The precise time when impressionism was born
From slow-roasted to sugar-cured: how to make the most of the British tomato season

Make the most of British tomatoes

The British crop is at its tastiest and most abundant. Sudi Pigott shares her favourite recipes
10 best men's skincare products

Face it: 10 best men's skincare products

Oscar Quine cleanses, tones and moisturises to find skin-savers blokes will be proud to display on the bathroom shelf
Malky Mackay allegations: Malky Mackay, Iain Moody and another grim day for English football

Mackay, Moody and another grim day for English football

The latest shocking claims do nothing to dispel the image that some in the game on these shores exist in a time warp, laments Sam Wallace
La Liga analysis: Will Barcelona's hopes go out of the window?

Will Barcelona's hopes go out of the window?

Pete Jenson starts his preview of the Spanish season, which begins on Saturday, by explaining how Fifa’s transfer ban will affect the Catalans
Middle East crisis: We know all too much about the cruelty of Isis – but all too little about who they are

We know all too much about the cruelty of Isis – but all too little about who they are

Now Obama has seen the next US reporter to be threatened with beheading, will he blink, asks Robert Fisk
Neanderthals lived alongside humans for centuries, latest study shows

Final resting place of our Neanderthal neighbours revealed

Bones dated to 40,000 years ago show species may have died out in Belgium species co-existed
Scottish independence: The new Scots who hold fate of the UK in their hands

The new Scots who hold fate of the UK in their hands

Scotland’s immigrants are as passionate about the future of their adopted nation as anyone else
Britain's ugliest buildings: Which monstrosities should be nominated for the Dead Prize?

Blight club: Britain's ugliest buildings

Following the architect Cameron Sinclair's introduction of the Dead Prize, an award for ugly buildings, John Rentoul reflects on some of the biggest blots on the UK landscape