The allegation that the Silk Road's Dread Pirate Roberts attempted to pay for six murders has loomed over the story of that massive online drug market. How could the pseudonymous figure preaching non-violent, libertarian ideals stoop to commissioning the paid killings of half a dozen people?

Now a newly revealed chat log from the case sheds light on how the first of those paid murder attempts appears to have arisen. The logs show it was not the creator of the Silk Road who first suggested enlisting the services of a hit man, but rather his top advisor and mentor.

Earlier this week, a trove of new records from the Silk Road pre-trial hearings was unsealed, including logs of January 2013 instant-message conversations that prosecutors say were pulled from the laptop of Ross Ulbricht at the time of his arrest. In February, Ulbricht was convicted of being the Dread Pirate Roberts, Silk Road's creator and owner. But the recorded conversations, along with the other sealed documents, had been kept secret throughout Ulbricht's trial earlier this year to avoid compromising an investigation that led to the arrest Monday of two federal agents on corruption charges.

In the 21-page IM chat log, which occurred over the anonymous IM service Torchat, the Silk Road's Dread Pirate Roberts carries out conversations with his staffer Inigo, a supposed drug-dealing associate named Nob (who we now know was actually undercover DEA agent Carl Force), and a figure named Cimon, also known as Variety Jones, whom Ulbricht had described in his journal as his "mentor" and advisor. The conversations revolve around $350,000 worth of bitcoin that had been stolen from the Silk Road, which Dread Pirate Roberts and Inigo believed had been taken by Silk Road staffer Curtis Clark Green. (In fact, it seems the bitcoins had been allegedly stolen by rogue Secret Service agent Shaun Bridges, using Green's account—one of the criminal charges for which Bridges was arrested Monday.)

As they're presented by the prosecution, the chat logs seem to show for the first time how the Dread Pirate Roberts is persuaded to commission Green's murder. And he's convinced not by a federal agent seeking to entrap him in the act, but by Cimon, his own trusted mentor and advisor. That initial step into the use of violence to protect his interests and the Silk Road would eventually lead Roberts to pay for five more murders.

“Cimon: I know a guy, and he knows a guy who knows a guy, that gets things done.”

(A quick side note: In the chat logs below, I've identified the Silk Road's boss as the Dread Pirate Roberts. Though Ulbricht was convicted in February of being the Silk Road's creator and leader, he was never charged with murder, and these logs were never presented at trial. Ulbricht's defense attorney Joshua Dratel has said he's still seeking a new trial for his client, in part due to the new corruption charges brought against the two federal agents investigating the Silk Road. "Our position, as it has always been, is that Ross is not DPR who is participating in those chats," Dratel tells WIRED.)

The chain of conversations that leads to the attempted murder of Green begins when Inigo alerts the Dread Pirate Roberts to the Silk Road's massive bitcoin theft. Roberts responds that he's "sick to his stomach."

"This will be the first time I have had to call on my muscle," he adds. "fucking sucks."

Later the same day, Roberts chats with Nob, who he believes to be a high-volume drug dealer who can help provide that "muscle" to find Green and recover the bitcoins. Roberts, after all, kept a copy of all his employees' actual IDs to prevent the sort of betrayal he believed Green had committed, so he knows Green's Utah address.

But in that conversation with Nob, it's clear Roberts has no intention of killing Green, or even beating him up if it can be avoided.

Nob: do you want him beat up. shot, just paid a visit?

Roberts: I'd like him beat up, then forced to send the bitcoins he stole back. like sit him down at his computer and make him do it

Roberts: beat up only if he doesn't comply I guess

Roberts: not sure how these things usually go

Only later, when Roberts checks in with his advisor Cimon, does the question of murder arise. As Roberts explains how Green might have stolen the funds, Cimon interrupts. "Enough about the theft," he says. "Tell me about the organ donor."

A few minutes later, he brings up the idea of killing more explicitly. "As a side note, at what point in time do we decide we've had enough of someones shit, and terminate them?" Cimon writes. "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 mistrust, does that come close in yer opinion?"

"Terminate?" Roberts asks tentatively. "Execute?"

As the conversation continues, Roberts seems to become more convinced that murder is a real option. Cimon seems to imply that simply beating up Green might lead him to talk to the police.

Roberts: if this was the wild west, and it kinda is, you'd get hung just for stealing a horse

Cimon: Yeah, pretty much. At what point in time is that the response. We're playing with big money with serious people, and that's the world they live in.

Cimon: I sure as fuck don't want nob to try it, fuck up, and then have our laundry aired.

Roberts: unfortunately, there isn't much inbetween

Cimon: I know a guy, and he knows a guy who knows a guy, that gets things done.

Roberts: in a perfect world, we'd get the money back, plus our expenses and maybe beat him up or something

Roberts: but that's not realistic

Cimon: Nope. And it ain't the money, fuck, it's your fault, no one elses. Someday I'll tell you a long story from a guy who explained to me why situations like this are always yer own fault.

Roberts: so yea, it's a good quesiton I've been thinking about the last 24 hours

...

Cimon: But he came at us from inside, put many folks at risk, and facing a serious felony he's def the kind of guy that would seel what little he knows for a break with the Feebs

About three minutes later, Cimon messages Roberts again:

Cimon: So, you've had your time to think. You're sitting in the big chair, and you need to make a decision. Now, really, things could move fast in the future.

Roberts: I would have no problem wasting this guy

Cimon: Well ok then, I'll take care of it.

Less than half an hour later, Cimon messages Roberts one more time, as if to make sure he isn't about to change his mind. "You would have surprised me if you had balked at taking the step, of bluntly, killing Curtis for fucking up just a wee bit too badly. Also, if you had balked, I would have seriously re-considered our relationship," Cimon writes. "We're playing for keeps, this just drives it home. I'm perfectly comfortable with the decision, and I'll sleep like a lamb tonight, and every night hereafter."

“You're sitting in the big chair, and you need to make a decision.”

In the end, Cimon doesn't "take care of it." Instead, Roberts himself approaches Nob, who is actually an undercover DEA agent, to kill Green for an $80,000 payment. "It is, [what I want] after i had a chance to think on it," Roberts writes to Nob. "Never killed a man or had one killed before, but it is the right move in this case."

As a result of that decision, the Baltimore task force investigating Silk Road faked Green's death, sending Roberts a spoofed photo of the body. Eventually Roberts would pay to have five more people murdered, including a potential blackmailer, a scammer and his three housemates. None of those murders, it's important to note, seem to have ever taken place. Instead, the five attempted murders-for-hire following the DEA's sting all appear to have been undertaken by a con artist who merely bilked Roberts out of hundreds of thousands of dollars worth of bitcoin.

Since his conviction last month, Ross Ulbricht awaits sentencing in May for seven felonies related to his creation and control of the Silk Road. Meanwhile, the mysterious figure known as Cimon or Variety Jones remains at large. The full extent of his participation or partnership in the Silk Road isn't clear, although it's known that he helped Ulbricht deal with the Silk Road's finances, coding, security, administration, and even invented the "Dread Pirate Roberts" nickname. These latest chat logs add another, darker role for Roberts' consigliere: the initial inspiration for the Silk Road's acceptance of violence.

Read the full chat logs in the unsealed filings from Ulbricht's case below. They begin on page 31.

Ulbricht post-trial unsealed filings