Ross Ulbricht

Palmertree, cofounder of Good Wagon Books with Ulbricht, eventually moved to Dallas, leaving Ulbricht to run the company by himself. Around this time, Ulbricht began planning Silk Road (initially he called it Underground Brokers).[17] 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."[17] 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."[18] 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."[15]

Silk Road ran on Tor, a network which implements protocols that encrypt data and routes internet traffic through intermediary servers that anonymize IP addresses before reaching a final destination. By hosting his market as a Tor site, Ulbricht could conceal its IP address.[4][5] Bitcoin, a cryptocurrency, was used for transactions on the site. While all bitcoin transactions were recorded in a public log called the blockchain, users who avoided linking their identities to their online "wallets" were able to conduct transactions with considerable anonymity.[19][20] Ulbricht used the "Dread Pirate Roberts" username for Silk Road, although it is disputed whether he was the only one to use that account.[21][22] Ulbricht attributed his inspiration for creating the Silk Road marketplace to the novel, Alongside Night, and the works of Samuel Edward Konkin III.[16]

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

Ulbricht was first 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.[23][24] 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.[23] In October 2013 Ulbricht was arrested by the Federal Bureau of Investigation while at the Glen Park branch of the San Francisco Public Library, and accused of being the "mastermind" behind the site.[25][26][27]

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,[28] according to Joshuah Bearman of Wired, the two agents then quickly moved in to arrest him while a third agent grabbed the laptop and handed it to agent Thomas Kiernan.[29] Kiernan then inserted a flash drive in one of the laptop's USB ports, with software that copied key files.[28]

Image placed on Silk Road after seizure by the FBI

On August 21, 2014, Ulbricht was charged with money laundering, conspiracy to commit computer hacking, and conspiracy to traffic narcotics.[30] He was ordered held without bail.[27] On February 4, 2015, Ulbricht was convicted on all counts after a jury trial that had taken place in January 2015.[31] On May 29, 2015, he was sentenced to double life imprisonment plus forty years, without the possibility of parole. Ulbricht was also ordered to pay approximately $183 million in restitution, based on the total sales of illegal drugs and counterfeit IDs through Silk Road.[32] [33] [34] [35]

Federal prosecutors alleged that Ulbricht had paid $730,000 in murder-for-hire deals targeting at least five people,[27] allegedly because they threatened to reveal Ulbricht's Silk Road enterprise.[36] Prosecutors believe no contracted killing actually occurred.[27] Ulbricht was not charged in his trial in New York federal court with any murder for hire,[27][37] but evidence was introduced at trial supporting the allegations.[27][38] 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 affirm the life sentence.[38]

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).[39] Prosecutors moved to drop this indictment after his New York conviction and sentence became final.[40][41]

Ulbricht appealed his conviction and sentence to the U.S. Court of Appeals for the Second Circuit in January 2016, centered on claims that the prosecution illegally withheld evidence of DEA agents' malfeasance in the investigation of Silk Road, for which two agents were convicted.[42] Ulbricht also argued his sentence was too harsh.[43] Oral arguments were heard in October 2016,[44][38][45] and the Second Circuit issued its decision in May 2017, upholding Ulbricht's conviction and life sentence in an opinion written by Judge Gerard E. Lynch.[38] In a 139-page opinion,[38][46] 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.[38][45]

In December 2017, Ulbricht filed a petition for a certiorari with the United States Supreme Court, asking the Court to hear his appeal on evidentiary and sentencing issues.[47][48] 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.[49] 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.[50] The U.S. government filed a response in opposition to Ulbricht's petition.[50][51] On June 28, 2018, the Supreme Court denied the petition, declining to consider Ulbricht's appeal.[52]

In 2019, Ulbricht attempted to vacate his life sentence, based on a claim of ineffective assistance of counsel by his defense lawyers. Though this attempt was initially rejected in August 2019 due to a procedural error,[53] the motion was refiled and is still pending.

In a 2020 Vanity Fair article Nick Bilton wrote that, according to investigators and attorneys involved in the case, Ulbricht had been offered a favorable plea deal which would have likely given him a decade-long sentence, but he turned it down. Bilton wrote, "(Ulbricht) believed that he was smarter than everyone in the room, and that he could beat them all."[54] Assistant US Attorney Timothy Howard, who was co-responsible for prosecuting the case, testified that the plea offer was made before Ulbricht's indictment and carried a mandatory minimum of 10 years to a maximum of life imprisonment, and that the United States sentencing guideline was life imprisonment.[55]

In 2020, President Trump reportedly considered commuting Ulbricht's sentence before leaving office,[56][54] but did not do so.[57]

During his trial, Ulbricht was incarcerated at the Metropolitan Correctional Center, New York.[58] Starting in July 2017, he was held at USP Florence High.[59] His mother Lyn moved to Colorado so she could visit him regularly.[60] Ulbricht has since been transferred to USP Tucson.[61][62]

In 2021, Ulbricht's prosecutors and defense agreed that Ulbricht would relinquish any ownership over a newly discovered fund of 69,370 Bitcoin ($3 billion in 2022) seized from a hacker in November 2020. The Bitcoins had been stolen from Silk Road in 2013. Ulbricht had been unsuccessful in getting them back. The U.S. government ultimately succeeded in tracing and seizing 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 ultimate custody over the bitcoins.[63][64]

Deep Web is a 2015 documentary film chronicling events surrounding Silk Road, bitcoin, and the politics of the dark web, including the trial of Ulbricht. 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.[65]

A film titled Silk Road was released on February 19, 2021. It was directed by Tiller Russell and follows Ulbricht's creation of the website, followed by the subsequent investigation by the FBI and DEA. Ulbricht was portrayed by American actor Nick Robinson.[66]

Ulbricht's family raised money for efforts to release him from jail via a decentralized autonomous organization FreeRossDAO which accepts donations from the public. In December 2021 the family auctioned a collection of his personal writings and artwork as an NFT, which FreeRossDAO bought for 1,442 Ethereum, or about $6.27 million at the time.[67][61]