The most disturbing part of the Dread Pirate Roberts (DPR) story is also the strangest: how the boss of the Silk Road drugs marketplace attempted to arrange not one but six murders-for-hire.
No murders actually took place. The first "hit" was purchased from an undercover DEA agent and was meant to take out a former Silk Road staffer; it has been charged in Maryland. But the story of the other five came out at the recent New York City trial of Ross Ulbricht, accused of being DPR and developing the Silk Road site, through a remarkable 33-page transcript of private messages that prosecutors harvested from the Silk Road server after it was captured by the government.
The transcript makes for astonishing reading as Dread Pirate Roberts dispenses cash and orders hits without bothering to verify even basic details about those he interacts with. Looking up the mentioned transactions in Bitcoin's blockchain shows that the transfers did in fact take place; whatever happened here, at least one party seems to have thought it was real—even if the dialogue often reads like a bad movie script.
Who is the Dread Pirate Roberts? Last Wednesday, a jury convicted the 30-year-old Ulbricht on seven counts related to drug trafficking and dealing in other illicit goods; evidence gathered from his laptop showed him communicating with others as DPR. (Ulbricht will be sentenced in May.)
As for the other characters in this sordid drama, they remain elusive. There's FriendlyChemist, the man who writes frantic and broken sentences to DPR saying he'll be killed if he doesn't get $500,000—and fast. FriendlyChemist poses as a narcotics middleman who got scammed by a Silk Road seller named LucyDrop.
Then there's RealLucyDrop, who claims that he was one half of the LucyDrop selling duo—but is now on his own after his partner split with the product. He says he knows FriendlyChemist, who is desperate and scared.
Finally, there's redandwhite, the genteel, well-spoken and murderous businessman who FriendlyChemist owes money to. He claims to be a major player in the drug trade, and is also a mentor, educating DPR about the cost and technique of killing one's enemies. DPR, meanwhile, tells redandwhite how to use secure chat channels and how to scrub photo metadata so that a picture of the murdered man can be sent safely once the job is done.
Most of the private messages between these parties span a single month in early 2013, but we know that communication between DPR and redandwhite did not end. Silk Road logs, found on Ulbricht's laptop, confirms their continued communication, likely via the Pidgin secure chat that DPR helped redandwhite set up.
"loaning $500k to r&w to start vending on SR," reads one log entry on Ulbricht's laptop.
Then later, under a longer entry dated with the range "06/05/2013 - 09/11/2013," it's written: "r&w flaked out and disappeared with my 1/2 mil."
Between the initial "hits" and the "loan," Dread Pirate Roberts paid redandwhite US$1.15 million in bitcoin. The payments for the fake hits came from Ulbricht's own bitcoin wallet, one more piece of damning evidence that his defense lawyers couldn't explain away to the jury.
Scamming a pirate?
We've published the "murder chats," in full, below, apart from some addresses of alleged Silk Road buyers. Since there are no bodies, the question arises: exactly what are we reading?
It all seems to have been an elaborate ruse, in which a scam artist (or artists) operating under multiple personas made off with $1 million from the world's most successful online drug dealer, securing more cash in the end than FriendlyChemist had even hoped for at the beginning.
"The bitcoins [from DPR to redandwhite] sat there until August 2013 (which alone should have tipped out the Dread Pirate about a possible scam; if someone wants that amount of money, why would they just sit on it when it was supposed to go pay some hitman?)," said Nicholas Weaver, a University of California-Berkeley computer researcher. The bitcoins were "only then moved away in bulk, split up, and perhaps sent to Bitcoin exchanges or other cashout."
During closing arguments at Ulbricht's, prosecutor Serrin Turner said that Ulbricht "may have fallen for a big con job," but said that only goes to show he wasn't a "criminal super-genius" but rather a criminal who made mistakes—and was willing, eager even, to use violence to protect what he'd built.
"For him, it was trivial," said Turner. "The click of a mouse, send $500,000, half a million dollars' worth of bitcoins, wait for the picture of a dead body. Thank goodness it does not look like any murders occurred. Thank goodness that this man's power trip was stopped before he managed to connect with a true hitman through his criminal website."
 FriendlyChemist |
To: Dread Pirate Roberts, 3/13/2013can u please get dread pirate roberts to message me RIGHT away ? |
 DreadPirateRoberts |
To: FriendlyChemist, 3/14/2013What can I do for you? |
FriendlyChemist |
To: Dread Pirate Roberts, 3/14/2013what is going on? when are u payin lucydrop? i have been waiting and waiting and he |
DreadPirateRoberts |
To: FriendlyChemist, 3/14/2013I'm really sorry for your situation. I have never had such a conversation with lucydrop. |
FriendlyChemist |
To: Dread Pirate Roberts, 3/14/2013i find it verry hard to believe. he showed the chat loggs talking to u about u making him |
DreadPirateRoberts |
To: FriendlyChemist, 3/15/2013I will get in touch with lucydrop and get back to you. |
DreadPirateRoberts |
To: LucyDrop, 3/15/2013Hi Lucydrop, |
FriendlyChemist |
To: Dread Pirate Roberts, 3/15/2013i didnt have to harvest anything - lucydrop kept a log of every single transaction he made [Ed. note: long list of addresses from around the world redacted] and the log goes like that up til today every day. nd that it just 1 of his accts.. he has 3 |
DreadPirateRoberts |
To: FriendlyChemist, 3/15/2013I'll let you know when I hear from lucydrop |
FriendlyChemist |
To: Dread Pirate Roberts, 3/15/2013when will that be? i dont think u guys understand how serious this is |
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