Ross Ulbricht

Palmertree, cofounder of Good Wagon Books, eventually moved to Dallas, leaving Ulbricht to run the bookseller by himself. Around this time, Ulbricht began planning Silk Road (initially called Underground Brokers).[19] In his personal diary, he outlined his idea for a website "where people could buy anything anonymously, with no trail whatsoever that could lead back to them."[19] Ulbricht's ex-girlfriend said, "I remember when he had the idea ... He said something about ... the Silk Road in Asia ... and what a big network it was ... And that's what he wanted to create, so he thought it was the perfect name."[20] Ulbricht alluded to Silk Road on his public LinkedIn page, where he discussed his wish to "use economic theory as a means to abolish the use of coercion and aggression amongst mankind" and claimed, "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."[17]

Silk Road ran as an onion service on the Tor network, which implements data encryption and routes traffic through intermediary servers to anonymize the source and destination Internet Protocol addresses. By hosting his market as a Tor site, Ulbricht could conceal the server's IP address and thus its location.[5][6] Bitcoin, a cryptocurrency, was used for transactions on the site. While all bitcoin transactions were recorded in a public ledger called the blockchain, users who avoided linking their legal names to their cryptocurrency wallets were able to conduct transactions with considerable anonymity.[21][22] Ulbricht used the "Dread Pirate Roberts" username for Silk Road, although it is disputed whether only he used that account.[23][24] He attributed his inspiration for creating the Silk Road marketplace to the novel Alongside Night and the works of Samuel Edward Konkin III.[18]

The Glen Park branch of the San Francisco Public Library, where Ulbricht was arrested by the Federal Bureau of Investigation

Law enforcement broke Silk Road's cover in a number of ways. A drug agency investigator infiltrated the site and became an admin, thereby gaining inside information about the site operations, and finding Ulbricht's chats showed Pacific time, narrowing down his likely location.[25] Law enforcement seized a Silk Road server in Iceland[26][27] and gained a trove of chat logs, further enriching their knowledge.[28] Ulbricht was connected to "Dread Pirate Roberts" by Gary Alford, an Internal Revenue Service investigator working with the U.S. Drug Enforcement Administration on the Silk Road case, in mid-2013.[29][30] The connection was made by linking the username "altoid", used during Silk Road's early days to announce the website, and a forum post in which Ulbricht, posting under the nickname "altoid", asked for programming help and gave his email address, which contained his full name.[29] On October 1, 2013, the Federal Bureau of Investigation arrested Ulbricht at the Glen Park branch of the San Francisco Public Library and accused him of being the "mastermind" behind the site.[31][32][33]

To prevent Ulbricht from encrypting or deleting files on the laptop he was using to run the site as he was arrested, two agents pretended to be quarreling lovers. When they had sufficiently distracted him,[34] according to Joshuah Bearman of Wired, they quickly moved in to arrest him while a third agent grabbed the laptop and handed it to agent Thomas Kiernan.[35] Kiernan then inserted a flash drive into one of the laptop's USB ports, with software that copied key files.[34]

Ulbricht was ordered held without bail.[33]

Image placed on Silk Road after seizure by the FBI

On February 4, 2014, Ulbricht was charged with engaging in a continuing criminal enterprise, narcotics conspiracy, conspiracy to commit money laundering, and conspiracy to commit computer hacking.[36] On August 21, 2014, a superseding indictment added three additional charges.[37] On February 4, 2015, Ulbricht was convicted on all counts after a jury trial that had taken place in January 2015.[38] On May 29, 2015, he was sentenced to double life imprisonment plus 40 years, without the possibility of parole. Ulbricht was also ordered to pay about $183 million in restitution, based on the total sales of illegal drugs and counterfeit IDs through Silk Road.[39][40][41]

Federal prosecutors alleged that Ulbricht had paid $730,000 in murder-for-hire deals targeting at least five people,[33] allegedly because they threatened to reveal the Silk Road enterprise.[42] Prosecutors believe no contracted killing actually occurred.[33] Ulbricht was not charged in his trial in New York federal court with murder for hire[33][43] but evidence was introduced at trial supporting the allegations.[33][44] The district court found by a preponderance of the evidence that Ulbricht did commission the murders.[45] The evidence that Ulbricht had commissioned murders was considered by the judge in sentencing Ulbricht to life and was a factor in the Second Circuit's decision to uphold the sentence.[44]

Ulbricht was separately indicted in federal court in Maryland on a single murder-for-hire charge, alleging that he contracted to kill one of his employees (a former Silk Road moderator).[46] Prosecutors moved to drop this indictment after his New York conviction and sentence became final.[47][48]

Ulbricht appealed his conviction and sentence to the U.S. Court of Appeals for the Second Circuit in January 2016, claiming that the prosecution illegally withheld evidence of DEA agents' malfeasance in the investigation of Silk Road, of which two agents were convicted.[49] Ulbricht also argued his sentence was too harsh.[50] Oral arguments were heard in October 2016,[51][44][52] and the Second Circuit issued its decision in May 2017, upholding Ulbricht's conviction and sentence in an opinion by Judge Gerard E. Lynch.[44] In a 139-page opinion,[44][53] the court affirmed the district court's denial of Ulbricht's motion to suppress certain evidence, affirmed the district court's decisions on discovery and the admission of expert testimony, and rejected Ulbricht's argument that a life sentence was procedurally or substantively unreasonable.[44][52]

In December 2017, Ulbricht filed a petition for certiorari with the United States Supreme Court, asking the Court to hear his appeal on evidentiary and sentencing issues.[54][55] Ulbricht's petition asked whether the warrantless seizure of an individual's internet traffic information, without probable cause, violated the Fourth Amendment, and whether the Sixth Amendment permits judges to find facts necessary to support an otherwise unreasonable sentence.[56] Twenty-one amici filed five amicus curiae briefs in support of Ulbricht, including the National Lawyers Guild, American Black Cross, Reason Foundation, Drug Policy Alliance, and Downsize DC Foundation.[57] The U.S. government filed a response in opposition to Ulbricht's petition.[57][58] On June 28, 2018, the Supreme Court denied the petition, declining to consider Ulbricht's appeal.[59]

In 2019, Ulbricht attempted to vacate his life sentence based on a claim of ineffective assistance of counsel by his defense lawyers. This attempt was initially rejected in August 2019 due to a procedural error,[60] but the motion was refiled. The motion was denied in June 2022.[61]

In a 2020 Vanity Fair article Nick Bilton claimed that Ulbricht had rejected a plea deal that would have potentially given Ulbricht a decade-long sentence. Bilton writes "According to more than a dozen investigators and attorneys involved in the case who I spoke to for the book, Ulbricht’s sentence could have been a lot less severe..."[62] Assistant US Attorney Timothy Howard, who was co-responsible for prosecuting the case, testified that "...no such plea offer was ever extended to Ross William Ulbricht, or conveyed to his then-counsel..." before Ulbricht's indictment. Howard stated that a plea deal with a mandatory minimum of 10 years was, "...discussed at the final pretrial conference on December 17, 2014...", but that the maximum sentence of life imprisonment was strongly recommended based on the sentencing guideline.[63]

During his trial, Ulbricht was incarcerated at the Metropolitan Correctional Center, New York.[64] Starting in July 2017, he was held at USP Florence High.[65] His mother, Lyn, moved to Colorado so she could visit him regularly.[66] Ulbricht has since been transferred to USP Tucson.[67][68]

In 2021, Ulbricht's prosecutors and defense agreed that Ulbricht would relinquish any ownership of a newly discovered fund of 50,676 Bitcoin (worth nearly $3.4 billion in 2021) seized from a hacker in November 2021.[69] The Bitcoins had been stolen from Silk Road in 2013. Ulbricht had been unsuccessful in getting them back. The U.S. government traced and seized the stolen bitcoin. Ulbricht and the government agreed the fund would be used to pay off Ulbricht's $183 million debt in his criminal case, while the Department of Justice would take custody of the bitcoins.[70][71]

Deep Web is a 2015 documentary film chronicling events surrounding Silk Road, bitcoin, and the politics of the dark web, including Ulbricht's trial. Silk Road—Drugs, Death and the Dark Web is a documentary covering the FBI operation to track down Ulbricht and close Silk Road. The documentary was shown on UK television in 2017 in the BBC Storyville documentary series.[72]

The film Silk Road was released on February 19, 2021. Directed by Tiller Russell, it follows Ulbricht's creation of the website and the FBI and DEA investigations. Ulbricht is portrayed by American actor Nick Robinson.[73]

Ulbricht's family raised money for efforts to release him from jail via the decentralized autonomous organization FreeRossDAO, which accepted donations from the public. In December 2021 the family auctioned a collection of his writings and artwork as an NFT, which FreeRossDAO bought for 1,442 Ethereum, worth about $6.27 million at the time.[74][67]

Ulbricht's conviction became a cause célèbre in libertarian circles. In May 2022, Congressman Thomas Massie called for a commutation of Ulbricht's conviction.[75] The libertarian-oriented Reason Foundation attempted to raise funds, citing Ulbricht's case[76] without taking any legal action, and 2020 Libertarian presidential candidate Jo Jorgensen made a campaign pledge to pardon Ulbricht.[77]