A new judicial order in the Silk Road drug trafficking case has dealt a harsh blow to suspect Ross Ulbricht's defense—less than a week before his criminal trial is scheduled to begin.

Ulbricht's lawyer sought to remove the government's evidence about the alleged six murders-for-hire from the case, but late Wednesday, US District Judge Katherine Forrest wrote that she will allow that evidence to be put in front of a jury, even though Ulbricht does not currently face charges of attempted murder.

The 45-page order sides with the government on almost every key point. This is likely the last major pre-trial order, and it tips the balance decisively in the government's favor. The question now is whether it will push Ulbricht toward making a plea deal. If no deal is reached, Ulbricht will face a jury trial in a Manhattan courtroom next Tuesday morning.

Ulbricht was arrested in a San Francisco public library last year, and the government has said he's "Dread Pirate Roberts," (DPR) the man who ran a large-scale drug marketplace through the Tor-enabled Silk Road, part of the so-called "darknet." Ulbricht has previously pleaded not guilty.

Buyers and sellers used bitcoins to buy drugs and other illicit goods, and they established trust by rating each other after each transaction, eBay-style. Silk Road, and by extension its creator DPR, allegedly acted as a trusted broker, taking a cut of every deal. Federal prosecutors allege that Ulbricht, as DPR, took in tens of millions of dollars in bitcoins.

Violence and drugs

In addition to accusing him of being an online drug kingpin, the government says Ulbricht tried to pay for no less than six murders of people connected to the site. None of those killings appear to have been carried out.

One of the "hitmen" was actually a Drug Enforcement Agency agent who staged the death of a target and then sent a fake bloody photo to "prove" the deed had been done. The other five murders, all offered by a Silk Road supplier named "redandwhite," weren't carried out either—although redandwhite apparently did get paid, a total of about $650,000 in bitcoins at the time.

But Ulbricht isn't actually charged with attempted murder. He faces seven other charges, all of which which relate to drug trafficking, computer hacking, money laundering, and selling stolen IDs.

Despite the fact that the government is only pressing forward with the nonviolent charges, prosecutors have worked to get evidence about the murder-for-hire allegations into the case, saying the communications help prove Ulbricht's supervisory role in running Silk Road.

Ulbricht's lawyer, Joshua Dratel, countered that the supposed murder-for-hire solicitations are "irrelevant to the charged offenses" and shouldn't be admitted "even as background information." His argument is that it wouldn't be fair to present a jury with talk about murders in a case where all the actual charged crimes were nonviolent.

The government argued that Ulbricht initiated the killings "in order to protect his criminal enterprise from theft, extortion, and threats of exposure to law enforcement," as Judge Forrest summarized. According to prosecutors, Ulbricht's threats of violence were like those of a "traditional drug dealer on the street who uses violence to protect his corner or turf from rival dealers, or to prevent informants from cooperating with law enforcement."

The judge agreed with prosecutors that the attempted murder evidence is relevant to the offenses Ulbricht is charged with. The evidence about the attempts at violence are not only connected to the drug business, but it goes toward establishing that Ulbricht is, in fact, DPR, which he has denied since his arrest in October 2013. For instance, dates in conversations that DPR had with his desired hitman appear to correspond to log entries that were recovered from Ulbricht's laptop.

"To be sure, the evidence is prejudicial to Ulbricht, and it does inject an element of violence into the case," acknowledged Forrest. "However, the prejudicial effect is reduced by the Government’s stipulation that no actual murders were carried out."

But the fact that the evidence doesn't look good for Ulbricht doesn't mean it stays out of the case.

"[A]ll incriminating evidence is prejudicial to a criminal defendant," she wrote.

In addition to allowing the government's critical murder-for-hire evidence, Forrest sided with prosecutors on several smaller, but still significant, pretrial evidentiary disputes. For instance, the government wanted to use pictures of Silk Road product listings and show evidence related to narcotics seizures at Chicago's O'Hare Airport and elsewhere that they say are connected to Silk Road—all of which the judge allowed in.

Dratel, Ulbricht's lawyer, tried to exclude screenshots, Silk Road forum posts, and many other exhibits that aren't described in the order. Forrest excluded almost none of the evidence Dratel objected to, although she left some decisions about what to allow for the trial itself, "after the Government lays a foundation."

Ulbricht won only a few minor points. The government won't be able to point to certain books sold on Silk Road, such as Silent but Deadly and Homemade C-4: A Recipe for Survival. Those exhibits "unnecessarily inject elements of violence and explosive devices that are not otherwise part of this case." Nor would Forrest allow the government to bring up the fact that weapons and pirated copies of books were apparently available for sale on Silk Road. The government won't be able to point to contraband that doesn't relate to the charged offenses, which all revolve around "narcotics, computer hacking materials, and fraudulent identification documents," she wrote.

First hit

The judge's order offers a new level of detail to the murder-for-hire allegations. According to the government, Ulbricht's first solicitation of a murder-for-hire was against a former Silk Road employee who he believed stole about $350,000 of Bitcoins from Silk Road vendor accounts.

The government's evidence consists of logs of online conversations between Ulbricht and two co-conspirators, identified in the order as CC-1 and CC-2, as well as testimony from an unnamed cooperating witness. (The order uses Ulbricht's name throughout, but a footnote points out that Ulbricht's involvement in any online conversations, and alleged identity as DPR, "is subject to proof at trial.")

According to the government, Ulbricht told CC-1 about the $350,000 theft in January 2013:

Later that day, Ulbricht told CC-1 that he knew the identity of the Employee, that the Employee had been arrested on narcotics charges, and that he (Ulbricht) had arranged for “muscle” to “get to [the Employee] quickly.” (Id.) CC-1 assured Ulbricht that "you always have me at your disposal if you locate him and need someone to go handle it." (Id.) Ulbricht responded, "thanks. I want to kick his ass myself, but let’s leave it to the pros."

The next day, Ulbricht spoke with CC-2 about the possibility that the employee-thief was cooperating with law enforcement. CC-2 remarked to him:

[A]s a side note, at what point in time do we decide that we’ve had enough of someone[’]s shit, and terminate them? Like, does impersonating a vendor to rip off a mid-level drug lord, using our rep and system; follows up by stealing from our vendors and clients and breeding fear and mis-trust, does that come close in your opinion.

Ulbricht wrote back, “terminate? execute?” He then stated, “I would have no problem wasting this guy." On February 5, Ulbricht told CC-2 the employee was "captured and interrogated" about the theft. "A few hours later, Ulbricht told CC-2 that the Employee had been executed," wrote Judge Forrest, summing up the government's accusations. "On February 23, 2013, Ulbricht reported to CC-1 that he had successfully arrange the Employee's capture and execution."

The man who pretended to carry out the murder-for-hire orders, however, was an undercover agent. That evidence became the basis of a second indictment filed in Maryland in October 2013, although those charges weren't ultimately pursued. The employee turned out to be Curtis Clark Green, who went by the handle "chronicpain."

Second hit

After Ulbricht dealt harshly with a thief—or so he believed—he was ready to use the same strategy against an extortionist, says the government.

According to government evidence, on March 13, 2013, a Silk Road user named FriendlyChemist messaged DPR to tell him that he would reveal a list of real names and addresses of Silk Road users unless he was paid $500,000. FriendlyChemist wrote:

what do u . . . think will happen if thousands of usernames, ordr amounts, addresses get leaked? all those people will leave sr and be scared to use it again. those vendors will all be busted and all there customers will be exposed too and never go back to sr.

FriendlyChemist allegedly needed the cash to pay off his narcotics supplier, who was also a Silk Road user, going by the handle "redandwhite," which are also the colors and a known moniker of the Hells Angels motorcycle club. On March 25, redandwhite reached out to DPR, who wrote back:

In my eyes, FriendlyChemist is a liability and I wouldn't mind if he was executed... I'm not sure how much you already know about the guy, but I have the following info and am waiting on getting his address.

FriendlyChemist ramped up the pressure a few days later, writing:

u leave me no choice I want 500k usd withn 72hrs or i am going to post all the info i have. . . . i hate to do this but i need the money or im going to release it all. over 5000 user details and about 2 dozen vender identities. wats it going to be?

Hours later, DPR sent a message to redandwhite saying he wanted FriendlyChemist dead and asking how much he would charge. "This kind of behavior is unforgiveable to me," DPR explained. "Especially here on Silk Road, anonymity is sacrosanct."

redandwhite offered two price points: a "clean" murder for $150,000 or a "non-clean" one for $300,000. DPR complained about the price. "Not long ago, I had a clean hit done for $80k. Are the prices you quoted the best you can do?"

Apparently, redandwhite wasn't up for bargaining, and DPR ended up paying the agreed-upon price of 1,670 bitcoins, then about $150,000. Twenty-four hours later, redandwhite sent DPR a note saying "Your problem has been taken care of... Rest easy though, because he won't be blackmailing anyone again. Ever."

DPR asked for a picture of the victim, next to a paper with random numbers he had supplied. The picture was sent—an apparent forgery, since the government admits no murders took place. On April 5, DPR wrote: "I've received the picture and deleted it. Thank you again for your swift action."

Third, fourth, fifth and sixth hits

When redandwhite told DPR that FriendlyChemist had been killed, he also said FriendlyChemist "spilled everything he knew" when he was questioned by his "workers." redandwhite said that Silk Road user tony76 was on board with the extortion scheme and had been running scams on Silk Road "for a couple of years."

DPR was eager for another hit. “I would like to go after [tony76]. . . . If he is our man, then he likely has substantial assets to be recovered. Perhaps we can hold him and question him?"

redandwhite said tony76 "works/lives with 3 other people and they all sell product together." He said he would prefer to do all four hits at once and asked for $500,000 to do the deed. DPR suspected that the targets had stolen money on them; redandwhite assured him that any recovered "product/money he may have" would be split 50-50.

On April 8, DPR wrote, "hmm . . . ok, I’ll defer to your better judgment and hope we can recover some assets from them." He sent payment of 3,000 bitcoins, then about $500,000, to redandwhite's address.

The government says information on Ulbricht's laptop corresponds to the Silk Road messages describing the hits. Ulbricht's log file allegedly contains an April 6 entry that says "gave angels go ahead to find tony76," referring to the Hells Angels, which Ulbricht thought his hitman was connected with. An April 8 entry allegedly reads "sent payment to angels for hit on tony76 and his 3 associates."

The narrative about the killings in Forrest's order ends there; it paints a picture of a criminal mastermind whose obvious intelligence is mixed with deep naiveté. The government has no evidence that any murders ever happened. Whoever DPR is, he was smart enough to build a profitable online drug market—but he couldn't avoid getting scammed, repeatedly, to the tune of hundreds of thousands of dollars.

As to whether DPR is Ross Ulbricht, that will soon be up to a jury to decide. Ars will be on the scene, reporting from the courtroom.