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Pirates of the Web

Authorities crack down on modern day buccaneers using the Web to facilitate their secret activities.

Read time 4min 20sec

In William Goldman's 1973 novel The Princess Bride, the mean sword fighting skills and unforgiving nature of infamous villain the Dread Pirate Roberts (DPR) have earned him rather a frightful reputation. During the course of the fantasy novel it emerges that Roberts is actually a series of different bad guys who over the years have passed on the name, and the standing attached to that name, to a chosen successor.

Today, the man who has taken on the DPR pseudonym is not a rum-drinking, peg-leg-wielding kind of pirate. This modern day swashbuckler is alleged to captain a ship that sails the seedy hidden underbelly of the World Wide Web. If the FBI is to be believed, his real name is Ross William Ulbricht. He is a US software engineer and allegedly the creator and custodian of an elaborate online marketplace, hidden in a dark corner of the Web, trading in illegal substances, dubbed Silk Road.

But on a Tuesday afternoon in October 2013, Ulbricht's supposed illicit Internet activities caught up with him when he was arrested in a San Francisco public library. And a month later Silk Road was shut down. According to the authorities, Ulbricht was logged into a Silk Road administrator panel when he was arrested and they uncovered a journal and ledger on his laptop detailing his activities running the platform. Ulbricht now faces charges of computer hacking, money laundering and conspiracy to traffic illegal narcotics. The trail began last week.

The entire Silk Road case pivots on unveiling the true identity of the Dread Pirate Roberts. But doing so is easier said than done - particularly when dealing with an online community that champions privacy, utilises Tor anonymity software, and deals in Bitcoin to safeguard the identities of users and administrators.

And in a case of life imitating art, the plot of the Ross Ulbricht saga ? much like Goldman's classic adventure tale - most certainly does thicken; with talk of elaborate cryptocurrency-funded murder plots and suggestions that someone is attempting to frame Ulbricht. Federal prosecutors have spent a little over a year building their case against the man they believe to be the "real" DPR, with their smoking gun being a statement from an old college friend confirming Ulbricht had once confessed to running the Silk Road.

Meanwhile, the defence team is poised to paint him as a patsy. They concede Ulbricht created Silk Road, but contest he established the billion-dollar contraband bazaar as an "economic experiment" and soon handed over control of the site to another party because it had become too stressful. As such, they are adamant he is the perfect fall guy and is being framed by influential online drug lords.

In an attempt to raise reasonable doubt about the true identity of DPR, Ulbricht's legal team have suggested the mastermind behind this secret online drug kingdom is in fact Mark Karpeles, the CEO of what was once the largest Bitcoin exchange in the world, Mt. Gox. Allegations that Karpeles has vehemently denied.

Will the real DPR please stand up?

As the processes of the mighty US judicial system unfold in a Manhattan federal courtroom, outside, a small group of protestors have gathered in support of Ulbricht. The entire case raises questions about whether the administrators of a Web site should be held responsible for the activities of their users.

This modern day swashbuckler is alleged to captain a ship that sails the seedy hidden underbelly of the World Wide Web.

Should providers of online services have to safeguard their environment in order to prevent behaviour that could become risky for users? Can one take eBay, Instagram or Facebook to task because certain people are using these platforms to buy and sell guns or drugs? One protestor described the man behind Silk Road - whoever he or she may be - as a hero for taking the danger out of black market dealings by bringing typically sinister transactions online.

Hero or not, the trial is a landmark case for law enforcement who have the tough job of unveiling the truth hidden beneath the elaborate technological infrastructure that has been put in place to keep the intricacies of the Dark Web so secret. This responsibility lies in the hands of the prosecution, who will have to conclusively link online evidence with real world individuals. An important detail that Ulbricht's defence team will use to raise uncertainty around the charges no doubt.

What is certain is that the demand for this kind of marketplace is booming - with various attempts to resurrect Silk Road, or versions thereof, being observed soon after Ulbricht's arrest. As such, regardless of the verdict, The Dread Pirate Roberts will indeed live on.

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