Silk Road to Perdition

Trump pardoned the notorious Dark Web crypto-criminal Ross Ulbricht. Why?

Ensconced in a cubby in the Science Fiction section of a public library in the Glen Park neighborhood of San Francisco, surrounded by the works of Philip K. Dick and Robert Heinlein and Ursula K. Le Guin, a 29-year-old Millennial sat working on his Samsung laptop. He was thin, pale, and, with his smiling eyes and Texas grin, handsome in a boyish sort of way. He looked like a graduate student—which, not that long ago, he was.

No one in the Glen Park Branch Library that brisk autumn day would have guessed at his true profession, or what this harmless-looking dork was actually doing on that laptop. His name was Ross Ulbricht. Online, he went by the handle “Dread Pirate Roberts”—a nod to the Cary Elwes character in The Princess Bride. He was the beneficial owner and mastermind of the Silk Road marketplace, the “eBay of drugs,” a sprawling criminal enterprise that operated on the Dark Web. And he was worth over a hundred million dollars (which would come as a surprise to his roommates).

On that first day of October, 2013, six FBI agents materialized in the Science Fiction section of the Glen Park Branch Library. As an undercover agent communicated with Ulbricht online, two of the agents pretended to argue, to distract him. As soon as the Dread Pirate Roberts turned his head, a third snatched his laptop—on which was all the evidence the DOJ needed to put him away for a long, long time.

“The Silk Road is an online black market that as late as last month was hosting nearly 13,000 sales listings for controlled substances, including marijuana, LSD, heroin, cocaine, methamphetamine and ecstasy,” Brian Krebs, the security reporter, explained at the time. “Much like eBay sellers, merchants on the Silk Road are evaluated by previous buyers, who are encouraged to leave feedback about the quality of the seller’s goods and services.”

How was such a thing possible? “The Silk Road is not available via the regular Internet,” Krebs explains. “Rather, it is only reachable via the Tor network, an anonymity network that bounces its users communications across a distributed network of relays run by volunteers all around the world.”

Tor is both an abbreviation of The Onion Router and, perhaps, a nod to the hallowed science fiction publishing imprint. I logged into it a few times myself, out of curiosity, after Ulbricht’s arrest. It was clunky and slow and reminiscent of the primitive World Wide Web of the dial-up mid-nineties—which is when it was first developed, by computer scientists from the U.S. Naval Research Lab. Whatever its shortcomings, Tor offered users a way to bypass electronic surveillance and browse the internet anonymously—useful technology during the Arab Spring of 2010, and perhaps even more useful to us now, in Trump Redux.

But in the case of Silk Road, Ulbricht hid behind Tor’s anonymity in order to flaunt the law and reap the benefits. Here is how federal prosecutors described his operation:

ULBRICHT created Silk Road in approximately January 2011, and owned and operated the underground website until it was shut down by law enforcement authorities in October 2013. Silk Road emerged as the most sophisticated and extensive criminal marketplace on the Internet, serving as a sprawling black-market bazaar where unlawful goods and services, including illegal drugs of virtually all varieties, were bought and sold regularly by the site’s users. While in operation, Silk Road was used by several thousand drug dealers and other unlawful vendors to distribute hundreds of kilograms of illegal drugs and other unlawful goods and services to well over a hundred thousand buyers, and to launder hundreds of millions of dollars deriving from these unlawful transactions.

ULBRICHT deliberately operated Silk Road as an online criminal marketplace intended to enable its users to buy and sell drugs and other illegal goods and services anonymously and outside the reach of law enforcement. ULBRICHT sought to anonymize transactions on Silk Road in two principal ways. First, ULBRICHT operated Silk Road on what is known as “The Onion Router,” or “Tor” network, a special network of computers on the Internet, distributed around the world, designed to conceal the true IP addresses of the computers on the network and thereby the identities of the networks’ users. Second, ULBRICHT designed Silk Road to include a Bitcoin-based payment system that served to facilitate the illegal commerce conducted on the site, including by concealing the identities and locations of the users transmitting and receiving funds through the site.

The vast majority of items for sale on Silk Road were illegal drugs, which were openly advertised as such on the site. As of September 23, 2013, Silk Road had nearly 13,000 listings for controlled substances, listed under such categories as “Cannabis,” “Dissociatives,” “Ecstasy,” “Intoxicants,” “Opioids,” “Precursors,” “Prescription,” “Psychedelics,” and “Stimulants.” From November 2011 to September 2013, law enforcement agents made more than 100 individual undercover purchases of controlled substances from Silk Road vendors. These purchases included heroin, cocaine, ecstasy, and LSD, among other illegal drugs, and were filled by vendors believed to be located in more than ten different countries, including the United States, Germany, the Netherlands, Canada, the United Kingdom, Spain, Ireland, Italy, Austria and France.

In addition to illegal narcotics, other illicit goods and services were openly bought and sold on Silk Road as well. For example, as of September 23, 2013, there were: 159 listings under the category “Services,” most of which offered computer-hacking services, such as a listing by a vendor offering to hack into social networking accounts of the customer’s choosing; 801 listings under the category “Digital goods,” including malicious software, hacked accounts at various online services, and pirated media content; and 169 listings under the category “Forgeries,” including offers to produce fake driver’s licenses, passports, Social Security cards, utility bills, credit card statements, car insurance records, and other forms of false identification documents.

Using the online moniker “Dread Pirate Roberts,” or “DPR,” ULBRICHT controlled and oversaw every aspect of Silk Road, and managed a small staff of paid, online administrators who assisted with the day-to-day operation of the site. Through his ownership and operation of Silk Road, ULBRICHT reaped commissions worth tens of millions of dollars generated from the illicit sales conducted through the site. ULBRICHT also demonstrated a willingness to use violence to protect his criminal enterprise and the anonymity of its users. ULBRICHT even solicited six murders-for-hire in connection with operating the site, although there is no evidence that these murders were actually carried out.

Ulbricht was charged with one count of narcotics conspiracy, one count of engaging in a continuing criminal enterprise, one of count of conspiracy to commit computer hacking, and one count of money laundering conspiracy; found guilty on all charges; and sentenced to life in prison. In addition, he owed the federal government a massive debt, to the tune of $156 million—which was how much money in commissions prosecutors calculated he raked in during the two years the Silk Road marketplace was up and running.

Let me stress again: Ulbricht was a huge dork. This wasn’t Gus Fring or Avon Barksdale or Tony Soprano. “Book smart,” his ex-girlfriend described him to CBS News, “not street smart. He was not at all a drug kingpin....He never even used the money he made....I mean, most kingpins buy furs and jewels and they’re living the life. He didn’t even have a car!”

Ulbricht was heavily influenced by an even bigger dork, the late Canadian economist Samuel Edward Konkin III (1947-2004). SEK3, as he is dorkily known, developed a “new libertarian” political philosophy grounded in nonviolence and counter-economics, which he called agorism, for the agora, or open marketplace. “The society of the open marketplace as near to untainted by theft, assault, and fraud as can be humanly attained is as close to a free society as can be achieved,” Konkin wrote. “And a free society is the only one in which each and every one of us can satisfy his or her subjective values without crushing others’ values by violence and coercion.”

This is similar to what Ulbricht shared on his LinkedIn profile about Silk Road: “The most widespread and systemic use of force is amongst institutions and governments, so this is my current point of effort. I am creating an economic simulation to give people a first-hand experience of what it would be like to live in a world without the systemic use of force.” (That argument was more convincing before he started using the Dark Web agora of his invention to solicit contract killers.)

Almost immediately after his conviction, Ross Ulbricht became a cause célèbre for the libertarian/crypto enthusiast/douchebro set. Brian Doherty, senior editor of the libertarian magazine Reason, saw Ulbricht’s life sentence as “insanely harsh,” given that he’d committed “crimes that amounted to operating a web site that other people used to sell drugs”—a view widely held by Big Tech. This advocacy was self-serving. After all, if the Dread Pirate Roberts could be sent up the river for maintaining a platform for users he’d never met IRL to sell heroin, offer hacking services, or sex-traffic women, the equally-dorky CEOs of Facebook and Twitter might be held responsible for nasty content posted on those sites—and we can’t have that. Free speech!

The crypto community wanted to #FreeRoss. The libertarians wanted to #FreeRoss. Elon Musk wanted to #FreeRoss. JD Vance wanted to #FreeRoss. In his failed presidential campaign, Robert F. Kennedy, Jr. promised to #FreeRoss. So did Donald Trump. And free him he did—on the second full day of Trump Redux. “I just called the mother of Ross William Ulbright to let her know,” POTUS wrote on his propaganda network, Truth Social. “The scum that worked to convict him were some of the same lunatics who were involved in the modern day weaponization of government against me.”

One of those “scum” “lunatics” was Preet Bharara, a frequent Trump foil back in the day. As the United States Attorney for the Southern District of New York in 2013, it was Bharara who’d announced the indictment of Ulbricht in Manhattan federal court.

Everything old is new again.

---

I’m reasonably confident that Trump wouldn’t know Ross Ulbricht if he was watching Moscow hookers piss on him. The reason I say that is because, in the aforementioned Truth Social post, he gave Ross’s name as “Ross Ulbright,” not Ross Ulbricht—closer than Ross Geller, sure, but still not correct.

The question then becomes: Why did Trump feel the need to issue Ulbricht a full presidential pardon on the second full day of his second term?

There are plenty of political reasons, for sure. Freeing Ross was chum for the deep-pocketed Silicon Valley whales who went MAGA; after all, the crypto sector spent a fuck-ton of money to elect Orange Hitler, and this was a low-cost reward. The pardon was a victory for Musk and his ilk. It probably made Barron Trump happy. And let’s be fair: next to the other criminals who’ve received pardons from Donald, the Dread Pirate Roberts is Jack Sparrow Shit. Like, he didn’t even buy furs or jewels or pull up in a Lambo! He had roommates!

But there is another angle to this. At the time of his arrest, Ulbricht was sitting on a dragon’s hoard of Bitcoins. As the DOJ revealed in the indictment announcement:

To date, approximately 173,991 Bitcoins (worth over $150 million at present exchange rates) have been seized in the course of the investigation, including approximately 29,655 Bitcoins recovered from servers used to run the Silk Road website, and approximately 144,336 Bitcoins recovered from computer hardware belonging to ULBRICHT seized upon his arrest. On January 15, 2014, the Bitcoins recovered from the Silk Road servers were ordered forfeited in connection with a civil action previously filed in Manhattan federal court on September 30, 2013, seeking the forfeiture of all assets of Silk Road, including its website and all of its Bitcoins, because those assets allegedly were used to facilitate money laundering and constitute property involved in money laundering. ULBRICHT has filed a claim in the civil action, asserting that he is the owner of the Bitcoins found on his computer hardware, and contesting the forfeiture of those Bitcoins.

As of this writing, Bitcoin is at $102,897.60. The 173,991 Bitcoins that were worth $150 million in 2013 are now worth [holds iPhone sideways] $17,903,256,321.60. That’s real money! But it’s all lost and gone forever. In 2014, the federal government auctioned off the seized Silk Road Bitcoin for—yikes—$334 each. (Where’s DOGE when you need it?)

Ah, but there is a twist! Two federal agents working the case—whose names, swear to God, are Force and Bridges, which sounds like a terrible network TV cop show—wound up breaking bad. After retrieving Bitcoin stolen from Ulbricht by yet another Silk Road scumbag, the agents made off with the virtual loot:

For example, Force and Bridges took over an administrator account belonging to Curtis Green, who worked for Silk Road under the name Flush. According to the criminal complaint against Force and Bridges, in January 2013, Bridges used the Flush username to change other users' passwords, empty their Bitcoin wallets, and keep $350,000 in Bitcoins in offshore bank accounts, all while attempting to hide his activity through a series of transactions. Specifically, the complaint against Force and Bridges alleges that Bridges “act [ed] as an administrator to reset pins and passwords on various Silk Road vendors' accounts,” then exchanged the Bitcoins for U.S. dollars using the Mt. Gox exchanger. Shortly after he committed the January 2013 thefts, Bridges asked Force to chat with DPR as Nob, Force’s authorized undercover username, to get advice about how to liquidate Bitcoins. He also sought Force’s help in convincing Curtis Green (formerly Flush) to help him transfer Bitcoins to other accounts, and he ultimately tried to blame Green for the theft.

This sudden crypto-windfall led to an extremely unorthodox deal struck in February 2021, as Andy Greenberg explains in Wired:

Ulbricht finally got a break of a different kind: The nine-figure debt he owed to the US government as part of his sentence will be erased—all thanks to the fortuitous hoarding of a hacker who’d stolen a massive trove of bitcoins from his market.

Last year, prosecutors quietly signed an agreement with Ulbricht stipulating that a portion of a newfound trove of Silk Road bitcoins, seized from an unnamed hacker, will be used to cancel out the more than $183 million in restitution Ulbricht was ordered to pay as part of his 2015 sentence, a number calculated from the total illegal sales of the Silk Road based on exchange rates at the time of each transaction. Despite the fact that the more recently unearthed stash of bitcoins—now worth billions of dollars—was itself criminal proceeds, the Justice Department appears to have made a deal with Ulbricht to avoid any claim he might have made to the money: In exchange for Ulbricht’s agreement to waive any ownership he might have of the bitcoins, a portion of them will be used to pay off his restitution in its entirety.

What makes this fishy is that the U.S. Attorney who struck the deal with Ulbricht didn’t bother to consult with Bharara’s former mates in the Southern District of New York:

In a bizarre twist, the agreement to erase Ulbricht’s restitution payments appears to have been made without the involvement—or even the knowledge—of prosecutors in the Southern District of New York, the Justice Department attorneys who handled Ulbricht’s case. “This resolution was not coordinated with SDNY,” one former Justice Department staffer told WIRED. “To not coordinate with the prosecuting authority that obtained the judgement is extremely unorthodox.”

While there were perfectly legitimate reasons for doing this—to avoid litigation from Ulbricht’s attorneys, and thus delay the seizure, as Greenberg explains in the article—it still raises eyebrows, not least because the deal was struck in February of 2021, before Merrick Garland was confirmed as AG, and was thus likely negotiated in the waning days of the first Trump Administration.

---

Fast forward four years, to January 2025. Trump has decided to free one of the most famous champions of crypto a few days after he and Melania rolled out their own cryptocurrency. Donald’s was given the oh-so-clever name of TrumpCoin, and now trades at almost $30. As for the First Lady, she put out an enigmatic tweet advertising a “Melania Meme,” with a link that led to a Telegram channel that tried to exact your personal data. There was also a string of numbers and letters that I believe has something to do with a crypto wallet:

FUAfBo2jgkM3lan1a1sar3tir3ds3xw0rk3rRxM1P

(It’s fine print, so I may have made some errors typing it out; my apologies.)

Ross Ulbricht will presumably be extra motivated to help POTUS in whatever way he can. How long before he joins the board at Trump Media?

There’s also the pesky detail revealed in Noelle Dunphy’s lawsuit against Rudy Giuliani: the allegation that Trump’s former personal attorney was peddling pardons for $2 million a pop. Here are the two relevant paragraphs:

132. [Giuliani] also asked Ms. Dunphy if she knew anyone in need of a pardon, telling her that he was selling pardons for $2 million, which he and President Trump would split. He told Ms. Dunphy that she could refer individuals seeking pardons to him, so long as they did not go through “the normal channels” of the Office of the Pardon Attorney, because correspondence going to that office would be subject to disclosure under the Freedom of Information Act.

and

119. To bolster his claims about the need to keep Ms. Dunphy’s employment “secret,” Giuliani told Ms. Dunphy about other schemes he undertook to reduce the amounts he owed to his ex-wife. For example, Giuliani told Ms. Dunphy that someone owed him $1 million, but Giuliani hinted that instead of having the money paid to him, he had his friend, Robert Stryk, hold it for him. He said, “Robert Stryk just got me a million-dollar payment.” This statement was recorded.

Ross Ulbricht made a number of “rookie mistakes” that led to his arrest, so he wasn’t the savviest crook in all the land. However, I find it hard to believe that the tech genius who ran the Silk Road marketplace, and who accumulated 173,991 Bitcoin, wouldn’t have a secret crypto wallet the feds never found out about—the Dread Pirate Roberts’s buried treasure, if you will. To be clear: I’m not suggesting that Ulbricht bought his freedom. There’s no evidence to suggest that he did. I’m merely suggesting that he could have. And if he were to do so, what better way to transfer the funds than to buy up the Trump token? Donald made a fortune on that crypto deal; the money had to come from somewhere.

For all the lofty, idealistic talk of agora marketplaces and counter-economics and individual liberty and the right to privacy, crypto would not exist if the criminal underworld did not require an alternative means to anonymously transfer funds from one scumbag to another. Cash, as anyone who watched Ozark well knows, has so many drawbacks. It needs to be physically transported and physically stored. It can be “marked.” It can burn up in a fire. It can be chewed up by mice. With crypto, criminals can send millions of dollars hither and yon with a few clicks of a different kind of mouse.

Simply put: no money laundering, no bitcoin.

It’s no accident that there’s such a big overlap between the crypto sector and organized crime. (Is Sam Bankman-Fried still sharing a prison cell with Diddy?) It’s no coincidence that some of the biggest seizures the federal government have ever made involve crypto. It’s no random occurrence that the convicted felon POTUS launched TrumpCoin days before his second inauguration. And it’s not for nothing that the character from The Princess Bride Ross Ulbricht chose to name himself after was the Dread Pirate Roberts.

The idea that Trump would pardon Ulbricht and get nothing in return is—as Vizzini would say—inconceivable.

---

Photo credit: FBI. Ross Ulbricht’s infamous laptop.

NOTE: I am away the rest of this week. PREVAIL will resume on Tuesday.