Silk Road Trial: The Evidence & Admission that Shook The Court Room

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Posted by: Allen Hoffmann, JD

January 14, 2015

More articles about the Silk road trial at this tag: #SilkRoadTrial

It has begun. Ross William Ulbricht, charged with seven felonies, is on trial in a federal court room at 500 Pearl Street, New York, New York

There are certain aspects of this trial which I personally have expected to see since day one – for instance, I had always assumed Ross William Ulbricht would go to trial if the case couldn’t be killed on technicalities. When your options are take 30 plus years on a plea, or roll the dice and go to trial, the trial option makes sense. And so, the show get underway.

Prosecution matters

The evidence on offer from the Government is substantial in quantity, but the defense is fighting it at every turn.

The Government’s evidence list is a not insubstantial 14 pages long and canvasses a solid array of material from various different sources. It contains:

  • In the 100 series, details of drug seizures made flowing from Silk Road purchases, presumably made by LE using covert accounts, as well as Vast tracts of material acquired from the Silk Road market’s front and back ends in terms of product listings, private message correspondence between users including DPR, and material from the Silk Road forums in terms of postings. Also includes are a number demonstrations for the benefit of jurors. The 100 series concludes with the lead up to, and the eventual arrest of, Ulbricht – and makes special mention of certain chats with Silk Road member, and, later, SR 2 admin, Cirrus.
  • In the 200 series, various material captured on Ulbricht’s laptop, including Torchat, Pigeon, and lists and chats with various parties using those programs, copies of Ulbricht’s personal journals, Silk Road management specific documents, such as to do lists and interview questions for prospective employees, transaction tables and listings, PGP key tied to DPR, and communications between various SR users and DPR.
  • In the 300 series, a trip is taken down memory lane to where the government alleges it all began; membership of Ross Ulbricht at the Shroomery message boards under the name altoid, correspondence regarding renting a house in Texas, the ordering of apparently interesting equipment such as petri dishes, humidifiers, filters and pressure cookers, correspondence regarding TOR hosting provided by Vekja and other miscellaneous, circumstantial tidbits.
  • The 400 series is made up the fake id package intercepted by ICE coming in from Canada
  • The 500 series deals with ‘mastermind’, the SR admin GUI. Interestingly, also included with this is a chat with Cirrus.
  • Series 600 refers to blockchain information in relation to the ‘murder for hire that never was’ with suspected UC ‘redandwhite’.
  • The 700 series is a transaction spreadsheet maintained by SR user deezletime.
  • Series 800 deals with what appear to be UC buys completed by Homeland Security Investigations officer based in Chicago

A large proportion of the items in the evidence list are being objected to on multiple grounds by defense counsel, as one would expect.

The prosecution’s theatrics and hyperbole are going just as expected.

The prosecution strategy in its opening yesterday was not what one would call inspired – the words hackneyed and clichéd come to mind.

Unsurprisingly, the prosecution has sought to beguile the jury with histrionic, theatrical proclamations, at this stage coming from prosecutor Timothy Howard, of the evils posed by the “dark and secret part of the Internet”. Pointing at Ulbricht with a no doubt carefully choreographed flourish, he referred to him by name and alleged that he was the “kingpin of this criminal empire.” The portrait being painted by Howard’s words is not what you’d call a pleasant one, even if it is a well crafted one – “The defendant controlled everything about Silk Road, from top to bottom. A global network of drug dealers paid for the privilege of being on the site. He gave them a way to prevent themselves from being caught. He gave dealers a whole new way to find, and keep, customers. We are here to pull back the curtain on this dark and secret world. Behind the curtain was one man – Ross Ulbricht – and his laptop.”.

Later, Howard’s prose waxes lyrical in attempting to paint as vivid a picture of the dramatic take down as possible. It drifts into something akin to a bad thriller, when he described the moments before Ulbricht’s arrest “As the defendant typed away, he had no idea agents in the public library were watching his every move,”. Such is the nature of courtroom performances of lawyers who’d be better off getting their jollies performing at a local theater. But whilst there was plenty of style to Howard’s performance, there was also substance backing it up, in the form of the government’s evidence.

The prosecution is putting a very strong emphasis on the fictitious murders for hire

As stated when I analyzed the criminal complaint documents in relation to Ulbricht – the Government is seeking to push the purported preparedness of Ulbricht towards the use of violence to protect Silk Road as the lynchpin in its argument that Ulbricht is not merely the architect of the eBay of drugs, but rather, is some kind of new wave drug king pin. The fact we are aware of two of a purported six staged ‘murders for hire’ gives this some push.

The prosecution will be calling multiple witnesses, including a former SR vendor.

There is a laundry list of witnesses – several from various arms of the US Government including Homeland Security Investigations, the FBI, and even the IRS. Then, we have several whose roles/backgrounds are unknown, mixed with a Silk Road admin known as Inigo, and others involved in Silk Road activities from within, at least one of whom, one Michael Duch, appears to have been a Silk Road vendor, who apparently used the moniker “deezletime” as per some excellent forensic analysis of available documents over at Reddit which happens to have been something which was speculated upon at Reddit over a year ago. We’ve been promised a look inside the inner sanctum of how Silk Road ran on a day to day basis, and its likely we’ll be hearing about it from Mr. Duch.

The prosecution has carefully considered the need to educate the jury.

Again, as predicted, the government is having to lead the jurors by the nose through the technical aspects. Series 100 in the exhibits the prosecution will be leading includes demonstrative breakdowns of how to access Tor, how prospective users would go about getting to Silk Road, and how the Silk Road payment system worked, because presumably, these jurors don’t know (and if they did know from experience, they certainly aren’t likely to be admitting it).

Defense matters!

The defense is prepared to concede Ross Ulbricht created Silk Road….

With the Government finishing its spiel, it was time for Joshua Dratel, Ulbricht’s attorney, to step up to the plate. And he dropped an unexpected bombshell about Ulbricht’s involvement in Silk Road. Per Dratel; “He created it. As a free-wheeling, free market site, that could sell anything, except for a couple items that were harmful. It was an economic experiment. After a few months, it was too much for him. He handed it off to others.”

Considering the strength of the Government’s case, I always expected to see a few concessions made. For instance, Dratel later conceded that yes, Ulbricht had used bitcoin, and had even made money from it. But Ulbricht admitting that yes, he did indeed found the original Silk Road, was not one I expected.

… but say he was lured back by unnamed other parties…

Seeking to explain how it was that Ulbricht came to be arrested logged on to the DPR account in a public library, this was apparently a set up;

“In the end, he was lured back by those operators, lured back to that library, that day. They had been alerted that they were under investigation, and time was short for them. Ross was the perfect fall guy. Silk Road was his idea.”

Dratel’s approach is to paint Ulbricht as a fall guy, lured to the library where he would be arrested, by as yet unnamed ‘others’ who were aware they had come under surveillance. Dratel is emphatic in his approach to the issue of the ‘real’ DPR still being out there, and even references the appearance of SR2 – “The real Dread Pirate Roberts is still out there… Silk Road Two was online within weeks.”

… and I mean, if this guy is the mastermind you are claiming he is, how could he be so stupid as to get caught like this…?

Oddly, there are two other lines which Dratel appears to be pushing in the defense agenda – first, that if Ulbricht really is the true DPR, he’d never have been caught with his hand in the proverbial cookie jar in the first place. “Would DPR have gone to the public library that morning and used the website on a public network, at a public library? Would DPR have sat there with his laptop open, with a BitTorrent client operating, as Ulbricht had been?”.

…and besides, people pretend to be other people on the internet all the time.

In a move probably intended to soften the impact of the murder for hire matters, Dratel takes the time to remind everyone that perhaps, if, and that’s if, Ross had at some point been DPR, maybe it wasn’t all real. “People create and fabricate profiles of themselves and others, in ways we weren’t able to imagine 20 years ago. It’s like a dating site. You get all kinds of information – then you meet someone in person, and it may not be the same.” Dratel took the time to remind the jury, in not so many words, of that Steiner cartoon from the 1990s… “On the Internet, nobody knows you’re a dog”. Why? We’ll find out soon enough.

Other factors

The Silk Road user “Cirrus” was almost certainly an undercover officer, and apparently lured Ross Ulbricht into the situation which allowed LE to arrest him.

There is one key issue in the order of the evidence presented in the evidence list which bears further consideration – exhibits 128A through 129E appear to deal chronologically with the day of Ulbricht’s arrest. The exhibits start with pictures of various locations in San Francisco, to the library where Ulbricht was arrested in the 128 series, then in the 129 series, screenshots apparently taken from the computer of ‘cirrus’ around the time of Ulbricht’s arrest – how exactly does the Government have pictures of messages on Cirrus’ computer? One media source has indicated that Ulbricht was engaged in a chat with an undercover federal agent who was a member of the Silk Road support staff at the moment he was arrested. It has been speculated previously by various parties that Cirrus, who went on to be an admin at Silk Road 2, was the Homeland Security Investigations undercover operative who brought down SR 2. Ulbricht’s laptop is the first item exhibit listed in the 200 series – 201A, the first item after the laptop itself, is photograph depicting Cirrus chatting with Ulbricht. Later in the 200 series, close up pictures indicate the use of the chat program ‘pidgin’. It seems that those suspicions held by many will likely be confirmed in the coming days.

The prosecution bears the heavy cross of having to prove Ulbricht’s guilt on every issue beyond reasonable doubt – and whilst innocence was always going to be an uphill battle for Ulbricht, the concessions made in the opening day of the trial that he was not without sin may be the basis upon which his acquittal is built.

Innocence of an allegation and being acquitted are very, very different things in the legal world. Its not what you know, its what you can prove.The line the defense is following is not one where Ross Ulbricht walks away with his name unsullied or his reputation unscathed. The fact that admissions have been made that, yes, Ross was the visionary who brought about Silk Road in the first place means that he’s probably guilty of at least something, but its not sufficient to prove the massive conspiracy allegations the Government is alleging. The defense’s objective is not to prove Ulbricht is an innocent man; the silence of defense counsel on just how much BTC Ulbricht actually does hold is a telling feature – in that if Ulbricht has told counsel of some massive, as yet undetected stash of BTC, counsel is not in a position to lie to the court about having heard of it. The approach that if Ulbricht were infact DPR, he would never have made such an OPSEC breach as that which gave rise to the library arrest, is indicative of a defense strategy built on undermining the prosecution case, rather than asserting his client’s innocence. Its intended do one thing – that is, create reasonable doubt, which will be sufficient to secure an acquittal.

Updated: 2015-01-14