Ross Ulbricht: the FBI agent who caught him and two calls for freedom

The Short Version

Chris Tarbell, the former FBI agent who tracked down and arrested Ross Ulbricht, says the Silk Road case was built on ordinary mistakes: a time zone setting, a Gmail address and chat logs and a diary that Ulbricht kept [3]. He also insists the internet overlooks that the FBI believed Ulbricht had ordered six murders, although no one was killed and those allegations were never pursued in court [3]. Michael Malice and Dave Smith, on The Joe Rogan Experience, each call for Ulbricht to be freed, Malice in a plea to President Biden's staff and Smith in an appeal to Donald Trump; Malice calls him nonviolent, and Smith notes that the murder-for-hire accusation never led to a conviction [1][2]. Tarbell does not join them, but he treated Ulbricht with compassion, believes his libertarianism was sincere, admits the takedown may have backfired, and says only a presidential pardon could free him [3].

Table of contents

What They Said

Chris Tarbell: what Silk Road was

Tarbell describes Silk Road as the first real dark market website [3]. You could buy almost anything on it, he says, with two exceptions: "You couldn't buy guns because that was a different website. And you couldn't buy fake degrees" [3]. The listings he names include heroin, hacking tools and hacking for hire [3]. He says he once saw a posting for baby body parts, and that he highlighted it inside the FBI to show the case was more than a drug case [3]. He is open about why: "I had to find the worst thing on there that I could possibly find" [3].

The trade was mostly narcotics. "It was primarily drugs. And that's where it started," he says, with Ulbricht growing mushrooms in California and selling them [3]. Behind it was a libertarian belief that people should be free to put whatever they want in their bodies [3].

What made the site new was the combination of Tor, the onion router originally developed by the US Navy, with cryptocurrency [3]. Cybercrime investigators normally follow either the IP address or the money, Tarbell explains, and Silk Road blocked both [3]. With onion routing, traffic is wrapped in layers of encryption and passed through a chain of publicly listed relays, each knowing only the relay before and after it, so even the hidden service does not know who is asking [3]. Tracing it back would mean physically rebuilding a live circuit across machines, which he calls practically impossible [3].

Tarbell: how the FBI found him

The FBI's case, Operation Onion Peeler, began when Tarbell's squad in New York noticed that cases kept closing with the explanation that "it was Tor" [3]. They identified 26 onion sites with a hacking nexus, with Silk Road as the golden ring [3]. Other agencies had taken a drug approach, following buyers up the chain, but buyers never knew their dealers, so Tarbell's team tried a cyber approach [3].

The team located the Silk Road server in Iceland [3]. Tarbell declines to say exactly how they found it and denies that NSA mass surveillance was involved, joking that he would not tell Lex Fridman if it were [3]. The copied server contained every chat log, which he compares to a Facebook of criminal activity, along with evidence of drug sales large enough for kingpin-level charges [3]. The infrastructure also showed the public site on a server in France, a Bitcoin vault only Ulbricht could access, and backups in a Philadelphia data center, which Tarbell regards as a major mistake because it put infrastructure in the United States [3].

The clues that identified a person were simple [3]. An HSI agent named Jared had started his own Silk Road investigation after a strange package came through O'Hare, and had worked his way up undercover to become a Silk Road administrator [3]. He noticed that Dread Pirate Roberts had his Jabber chat client set to Pacific time [3]. An IRS agent then found early forum posts, under the name Frosty, from someone starting an onion site and asking for cryptocurrency help, signed with Ulbricht's own Gmail address [3]. The computer logging into the Philadelphia backups was also named Frosty [3]. Surveillance then matched Tor traffic from Ulbricht's home to the times when Dread Pirate Roberts was online [3].

Tarbell's judgment of Ulbricht as an operator is unflattering. "I don't think he was a mastermind of setting up an infrastructure that would protect his online business," he says, and he lists the errors: "keeping chat logs, keeping a diary, putting infrastructure where it shouldn't be" [3]. He adds that site administrators had to send Ulbricht real ID, and that all of the IDs turned out to be genuine [3].

The takedown had three prongs: arrest Ulbricht in San Francisco, seize the Bitcoin, and seize the site so that no one else could take control [3]. Tarbell went about four days without sleep coordinating agents in Iceland and bosses in Washington and New York [3]. The case was supposed to be announced by the president and the attorney general, but a government shutdown two days earlier meant the public saw only the affidavit with Tarbell's signature, which is how he became known [3].

Tarbell: murder for hire

This is the part of the story Tarbell says the internet overlooks [3]. During the investigation, the FBI believed six murders had been ordered [3]. Ulbricht wrote in his diary about having people killed and paid large sums in Bitcoin, Tarbell says, and his attitude evolved from reluctance to agreeing to kill a target's three roommates too [3]. In the conversation Tarbell acknowledges the dispute directly: "people argue back and forth that there was never murders on Silk Road" [3].

Two facts sit beside that. No one was actually killed [3]. And the murder allegations were never pursued in court [3]. Tarbell's explanation is a turf fight with a separate Baltimore investigation, including a "deconfliction" meeting full of talk about "sweat equity" that he found infuriating [3]. He says the Baltimore team's supposed photo of Ulbricht turned out to be an internet meme [3].

Tarbell: regret, and the war on drugs

Tarbell's lasting regret involves a father who spoke at Ulbricht's sentencing [3]. The man's son died from drugs bought on Silk Road in the window after investigators knew they could shut the server down and before the arrest [3]. Tarbell did the arithmetic himself: "We could have pulled the plug on the server and gone" [3]. His comment on it is short: "I still think about that father a lot" [3].

Asked whether the war on drugs has reduced suffering or caused it, he says the question is above his pay grade [3]. He understands the argument that buying online is safer than buying on street corners, but as a parent he is satisfied if drugs are harder for his children to get [3].

He also admits that the takedown may have backfired [3]. Before it, he says, Silk Road had thousands of users, and afterwards it was on the front page and millions of people knew about Tor and onion sites [3]. "It was an advertisement," he says [3]. He expected the case to hurt cryptocurrency, "I thought crypto was going to crash right after that," and concedes, "I'm obviously wrong on that one" [3]. Dark markets multiplied after the sentence, some of them scams that stole the money held in escrow [3]. Running Silk Road as a sting to catch dealers was never an option, he says, because no FBI manager would accept kids dying on an FBI-run drug site [3].

Tarbell: the man he arrested

Tarbell spent only five or six hours with Ulbricht, over two days [3]. His practice after an arrest was to put a hand on the person's chest, feel their heart and breathing, and speak to them honestly, because "be compassionate, be human" gets you further than being a hard-nosed cop [3]. Exhausted as he was, he went out and bought Ulbricht breakfast, and Ulbricht asked for granola bars [3]. Ulbricht had asked for a lawyer, so they talked as people and not about the case, though on the way to jail Ulbricht offered him $20 million to let him go [3].

"He was a human being," Tarbell says of the meeting, adding, "He was nervous when we arrested him" [3]. He believes Ulbricht was genuinely libertarian: "I don't think that was a front or a lie" [3]. His reading of what went wrong is that the money broke him [3]. Ulbricht started counting his growing fortune and, despite writing about walking away, could never give up control [3]. The conversation describes him as holding "dictatorial control" over the site, and Tarbell says of the diary that "he changed over time. You could see it in his writings that he changed" [3]. He imagines Ulbricht's life as deeply lonely [3].

Tarbell traces his own attitude to an earlier case. Sitting with the hacker Hector Monsegur taught him that criminals are human beings, which he says is why he treated Ulbricht with compassion [3]. He estimates that about 99% of the criminals he dealt with took a wrong turn and have good in them [3].

On the outcome he is matter-of-fact. Ulbricht received two life sentences plus 40 years with no parole, and Tarbell says only a presidential pardon could free him [3].

Michael Malice: a plea to Biden's staff

Michael Malice, the anarchist author, made his case on The Joe Rogan Experience in July 2024, days after Joe Biden withdrew from the presidential race [1]. He addressed it to President Biden's staff [1]. Donald Trump had promised at the Libertarian convention to free Ulbricht, Malice said, so Biden could beat him to it and win over tech-minded voters [1]. His slogan for the idea was "Republicans promised Democrats deliver" [1].

His argument on the merits is brief. Ulbricht is serving two life sentences plus 40 years, and Malice argues that he is nonviolent and that there is no concern he would reoffend [1].

Jamie pulled up the charges during the episode: they included narcotics conspiracy, money laundering and computer hacking conspiracy [1]. He also found that the murder-for-hire allegations were never charged but were considered at sentencing [1]. Rogan finds that indefensible, arguing that if prosecutors had the evidence they should have tried him for it [1]. Both men agree he should be released [1].

Earlier in the same episode, Malice and Rogan agree that making most drugs illegal is a mistake, though Malice raises what happened in Portland and Seattle [1]. Rogan's answer is that the problem there was leadership and not legalization: "You make drugs legal in a place run by maniacs" [1].

Dave Smith: an appeal to Trump

Dave Smith, the libertarian comedian, spoke the day after the 2024 presidential election [2]. He made a direct appeal to Trump to honor his promise at the Libertarian Party convention to free Ulbricht on day one [2].

Smith describes Ulbricht as a man who created a dark web marketplace and has served over a decade of a life sentence without parole [2]. The murder-for-hire accusation, he notes, was withdrawn and never led to a conviction [2]. He knows Ulbricht's mother, Lynn [2].

His political argument is that freeing Ulbricht would cost Trump no political capital [2]. He contrasts it with pardoning Edward Snowden, which he says would be harder because it would anger the NSA and the CIA [2]. Later in the episode Smith makes a wider claim: future generations, he says, will look back on war and on imprisoning nonviolent people the way we look at slavery and witch hunts [2]. Rogan, in the same episode, says the Nixon-era drug laws of 1970 were designed to target anti-war and civil rights protesters [2].

Where They Agree, and Where They Don't

The three accounts agree on more than their conclusions suggest. All of them say Ulbricht founded or created the marketplace [1][2][3]. Tarbell and Malice give the same sentence, two life sentences plus 40 years, and Tarbell and Smith both say there is no parole [1][2][3]. All three treat the murder-for-hire allegations as something that never went to trial: Tarbell says they were never pursued in court, Jamie's check in the Malice episode found they were never charged, and Smith says the accusation was withdrawn and never led to a conviction [1][2][3]. And all three see the way out as running through a president: Tarbell says only a pardon could free him, and Malice and Smith each address one [1][2][3].

They disagree about what the uncharged allegations should count for.

• Tarbell treats them as real and as the missing piece of the public story. The FBI believed six murders were ordered, he says, and he points to Ulbricht's diary and to Bitcoin payments [3]. He attributes the absence of a murder case to a fight between investigating teams [3].
• Malice calls Ulbricht nonviolent, and Rogan takes the absence of a charge as decisive: he objects that allegations which were never tried were still weighed at sentencing [1].
• Smith makes the same point in fewer words: withdrawn, and no conviction [2].

They also differ on what Silk Road was. Malice and Smith describe Ulbricht by his sentence and by the marketplace he created [1][2]. Tarbell says the site also offered hacking tools and hacking for hire, and he remembers the father whose son died from drugs bought there [3]. Tarbell himself declines to judge the drug war. He calls that question above his pay grade, says he understands the argument that online buying is safer, and as a parent is satisfied if drugs are harder for his children to get [3].

One difference is of kind. Tarbell describes what he saw and did over a long investigation [3]. Malice and Smith are advocates making a pitch to a president [1][2].

Why It Works

Why the investigation worked. Tarbell's account is that Tor and Bitcoin did their job, hiding both the IP address and the money, and that the case came from the person behind them [3]. The breakthroughs, in his telling, came less from exotic surveillance than from human mistakes [3].

Why the calls for freedom are made the way they are. The case made in the two Rogan episodes rests on the length of the sentence, on Malice's description of Ulbricht as nonviolent, and on the fact that the most serious accusation was never tested at trial [1][2]. Rogan's version of the principle is that prosecutors who had the evidence should have tried him for it [1]. The political pitch rests on cost: Smith says a pardon would cost no political capital, and Malice says it would win tech-minded voters [1][2].

Where It Applies, and Where It Doesn't

Tarbell's account is the view of the case agent. It is detailed on how Ulbricht was found and on what the FBI believed [3]. It is not a court's finding on the murder allegations, because, as he says himself, those were never pursued in court [3]. He also withholds how the Iceland server was located [3].

The calls for release are short passages in long conversations about politics [1][2].

Both pleas are tied to a moment. Malice spoke to a Biden White House in July 2024, and Smith to Trump the day after the election, each citing Trump's promise at the Libertarian convention [1][2].

What To Do With It

1. Separate what Ulbricht was charged with from what he was accused of. The charges read out in the Malice episode included narcotics conspiracy, money laundering and computer hacking conspiracy, and the murder-for-hire allegations were never charged but were considered at sentencing [1].
2. Before calling him nonviolent, read what Tarbell says the FBI found: diary entries about having people killed and large Bitcoin payments, with no one actually killed [3].
3. Before treating the murder allegations as proven, note that they were never pursued in court, and that Rogan's objection is to weighing untried allegations at sentencing [1][3].
4. Hold on to the father at the sentencing. Tarbell does, and the death he describes is part of what Silk Road was [3].
5. Ask what the takedown achieved. Tarbell says it advertised Tor to millions and that dark markets multiplied afterwards [3].
6. Take from the investigation what Tarbell takes from it: anonymity tools fail through habits, such as a reused name, a personal email address, kept logs and a diary [3].
7. Judge the person and the sentence separately. The agent who arrested Ulbricht believes his beliefs were sincere and treated him as a human being, while the two men who want him out argue about the length and basis of the sentence [1][2][3].

Sources

1. Michael Malice on Joe Rogan: Biden's Exit, Kamala Harris, Media Gaslighting, Japan and Deep-Sea Oddities · The Joe Rogan Experience
2. Dave Smith on Trump's 2024 Win, the Collapse of Media Trust, and Ending Endless Wars · The Joe Rogan Experience
3. Chris Tarbell: The FBI Agent Who Took Down Silk Road and Sabu · Lex Fridman Podcast