In defence of Dread Pirate Roberts

The man behind the infamous darknet market Silk Road, Ross Ulbricht, has been convicted on multiple charges. To many, however, he is a hero.

Read time 8min 20sec
ITWeb Security Summit 2015

For more on this topic, do not miss the summit, at which Roger Dingledine, president, director and co-founder of The Tor Project, will discuss attacks on Tor.
26 to 28 May, Vodacom World, Midrand
Book today!

The case of Ross William Ulbricht was never going to be just another drugs bust. Ulbricht allegedly operated the infamous darknet market Silk Road, on which millions of dollars worth of narcotics, prescription medication, weapons, false documents, and other illicit goods and services were traded.

He has been convicted on multiple charges, related to computer hacking, being a "kingpin" in narcotics trafficking and conspiracy to launder money. The conviction is comparable to that of an organised crime leader.

Notably, the charges did not include murder. There is reason to suspect Ulbricht of having conspired with a member of the Hell's Angels (which controls much of western Canada's drug trade) to kill five people who tried to blackmail him and his customers. However, no bodies have ever been found, and authorities cannot establish the targets even existed. He will be tried on this matter in a separate case, but an acquittal seems likely.

Still, on the Silk Road conviction alone, Ulbricht faces 20 years to life in prison. He intends to appeal the conviction.

A month before his arrest by US law enforcement on 3 October 2013, he gave an anonymous interview to Forbes magazine. He picked his publication well: Forbes is known to be strongly pro-market, and sympathetic to black markets that emerge when governments prohibit or tax the sale of goods and services.

According to Forbes, Ulbricht, then known only by the clever, inheritable pseudonym "Dread Pirate Roberts", had a political agenda.

"He sees himself not just as an enabler of street-corner pushers," it wrote, "but also as a radical libertarian revolutionary carving out an anarchic digital space beyond the reach of the taxation and regulatory powers of the state - Julian Assange with a hypodermic needle."

"We can't stay silent forever," the publication quotes him as saying. "We have an important message, and the time is ripe for the world to hear it. What we're doing isn't about scoring drugs or 'sticking it to the man'. It's about standing up for our rights as human beings and refusing to submit when we've done no wrong. Silk Road is a vehicle for that message. All else is secondary."

On his LinkedIn profile, he states an equally grand libertarian vision: "I want to use economic theory as a means to abolish the use of coercion and agression (sic) amongst mankind. Just as slavery has been abolished most everywhere, I believe violence, coercion and all forms of force by one person over another can come to an end. The most widespread and systemic use of force is amongst institutions and governments, so this is my current point of effort. The best way to change a government is to change the minds of the governed, however. To that end, I am creating an economic simulation to give people a first-hand experience of what it would be like to live in a world without the systemic use of force."

The Silk Road market was that experiment. It was named after the legendary land and sea routes that brought the grand civilisations of China, India, Persia, Arabia, Syria, Turkey, Greece and Rome together in peaceful trade between the second century BC and the 15th century.

Because Ulbricht's modern-day Silk Road was based on strong encryption, the anonymising network Tor, and the crypto-currency bitcoin, it existed - for a while - outside the reach of government, the wielder of the monopoly on force in most of the modern world. As a consequence, goods and services that were dangerous to trade through traditional channels, like drugs and weapons, became the stock in trade of Silk Road.

Its effect on these markets was profound. Because drug and weapons sales are illegal in many countries, or subject to strict government controls in others, their sale is often linked to violent criminal enterprises. The drug cartels of Mexico are a particularly gruesome modern example, but the rule is general.

During the alcohol prohibition in the US from 1920 to 1933, moonshiners tore around in hotrods wielding tommyguns, to outmuscle both rivals and the police. It made for great films, but very bad public order.

The infamous "Drug War" has not improved on this record. It has incarcerated or killed many thousands of people, even for relatively minor offences, yet it has met only with failure in curbing the use or availability of drugs.

Governments have much incentive to keep these enterprises illegal and to keep cracking down on them. Even ignoring the opportunities for corruption, they profit handsomely from asset seizures whenever they manage to take someone down.

The Silk Road servers contained 29 655 bitcoins, and Ulbricht's own laptop contained another 144 336 of them. At the time the US Marshalls auctioned off most of them in November and December 2013, they were worth around $140 million. At today's much lower price, the haul would be worth just short of $40 million. These are not insignificant profits for law enforcement agencies.

Darknet markets like Silk Road brought a measure of civility and safety to the business. Because buyers and sellers were anonymous and transactions were concluded via escrow rather than in person, trades that before would have been very risky became safer and less likely to end in violence. Academics described it as "a paradigm-shifting criminal innovation".

As a result, Silk Road rapidly grew to billion-dollar status. Not only could merchandise be bought more safely and reliably online, but there was often a price advantage too. According to a price study, Silk Road's marijuana was more expensive, but cocaine could be had for almost half of the worldwide average street price.

Despite his public reputation, Ulbricht's case proved to be laughably simple to crack. It required no super-secret and illegal NSA technique to crack the encryption of the Tor network. In the early days of the venture, Ulbricht had posted promotional messages for Silk Road under an alias, and then used the same alias to advertise for an IT professional with knowledge of crypto-currencies. He gave as the contact e-mail. He had also bragged to a friend about Silk Road, and left crumpled-up notes related to its code in his apartment.

Other markets operators might be that sloppy about operational security, but don't bet on it. None of them have given interviews to Forbes, for example.

Despite his public reputation, [Ross] Ulbricht's case proved to be laughably simple to crack.

Soon after the closure of the first Silk Road, Silk Road 2.0 was opened. Its operator was arrested exactly a year later, on 6 November 2014, in a broad operation against darknet sites based on the Tor anonymising network. Just a day later, Silk Road 3.0 was launched.

Shutting them down is like a game of whack-a-mole. There are, at present, 28 active darknet markets listed on a popular Tor network directory. The biggest of them - having benefited greatly from Silk Road's troubles - are Agora Market and Evolution, and they have more listings than Silk Road ever did.

If the Tor network becomes unsafe, site operators can turn to the Invisible Internet Project (I2P). Silk Road Reloaded, another successor of the original site, already uses this peer-to-peer anonymity network. And if it fails too, there's Freenet, and a dozen other potential alternative technologies, waiting in the wings.

There are also decentralised clearnet markets, such as OpenBazaar, which do not intend to host illicit goods and services, but do facilitate anonymous peer-to-peer trades using bitcoin. After all, streamlining trade is a legitimate goal in any business. OpenBazaar may well become the bittorrent for online trading.

As long as there is demand, and as long as the value of illicit goods is artificially inflated by taxes or bans, there will be markets for them.

At the same time, revelations of wholesale surveillance of innocent citizens by governments, and detailed consumer tracking by companies, have caused widespread distrust among people. Many are becoming more conscious of their online privacy and security. What they learn in the process is lowering the barriers to the use of encrypted communication, crypto-currencies and hidden Web sites.

None of these markets are ideal, of course. As long as they sell illegal stuff, buyers, sellers and operators will have to protect themselves if necessary, because they can hardly turn to the police for protection. And whether or not what they sell ought to remain illegal is a separate (and complex) question.

However, anonymous online markets are far preferable to street trade for their reliability and relative safety. In the Dread Pirate Robert character, Ulbricht has made such markets famous, and overtly appealed to sound libertarian economic principles.

For all these reasons and more, darknet markets are not going away.

In a 2012 post on the Silk Road forums, Ulbricht phrased it in romantic terms: "To grow into a force to be reckoned with that can challenge the powers that be and at last give people the option to choose freedom over tyranny."

Ulbricht may be going to prison, but that call will prove impossible to silence. Society will need to learn to deal with all its implications, both positive and negative.

Login with