Ross Ulbricht
Ross William Ulbricht is an American who created and operated Silk Road, the first modern darknet market, from 2011 until his arrest in 2013. Silk Road was an online marketplace that facilitated the trade in narcotics and other illegal products and services. Sales were anonymous, using bitcoin. It operated as a hidden service on the Tor network. Ulbricht ran the site under the pseudonym "Dread Pirate Roberts" after the fictional character from The Princess Bride.
In October 2013, the Federal Bureau of Investigation arrested Ulbricht and took Silk Road offline. In 2015, he was convicted of engaging in a continuing criminal enterprise, distributing narcotics by means of the internet, conspiracy to commit money laundering, conspiracy to traffic fraudulent identity documents, and conspiracy to commit computer hacking. He was sentenced to two life sentences plus 40 years without the possibility of parole, to be served concurrently. Many decried the sentence as excessive, most notably members of the Libertarian Party and the "Free Ross" movement. Ulbricht's appeals to the U.S. Court of Appeals for the Second Circuit in 2017 and the U.S. Supreme Court in 2018 were unsuccessful. After serving 12 years, he was released from prison in January 2025, when he received a full and unconditional pardon from U.S. president Donald Trump.
Early life
Ulbricht was born and raised in Austin, Texas. He was a Boy Scout, attaining the rank of Eagle Scout. He attended West Ridge Middle School and Westlake High School both in the Eanes Independent School District in the suburbs of Austin, graduating from high school in 2002.Ulbricht attended the University of Texas at Dallas on a full academic scholarship and graduated in 2006 with a bachelor's degree in physics. Ulbricht received an additional scholarship to attend Pennsylvania State University, where he was in a master's degree program in materials science and engineering and studied crystallography. By the time Ulbricht graduated from his master's degree program, he had become interested in libertarian economic theory and adhered to the political philosophy of Ludwig von Mises, supported Ron Paul, promoted agorism, and participated in college debates to discuss his economic views. Ulbricht graduated from Penn State in 2009 and returned to Austin. He tried day trading and started a video game company, but neither venture succeeded. He eventually partnered with his friend Donny Palmertree to help build an online used bookseller, Good Wagon Books.
Silk Road
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. 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". 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." 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."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. 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. Ulbricht used the "Dread Pirate Roberts" username for Silk Road, although it is disputed whether only he used that account. He attributed his inspiration for creating the Silk Road marketplace to the novel Alongside Night and the works of Samuel Edward Konkin III.
Arrest and trial
Initial arrest
Law enforcement broke Silk Road's cover in a number of ways. A drug agency investigator infiltrated the site and became an admin, gaining inside information about the site operations. He found Ulbricht's chats showed Pacific time, narrowing down his likely location. Law enforcement seized a Silk Road server in Iceland. Ulbricht was connected to "Dread Pirate Roberts" by Gary Alford, an Internal Revenue Service investigator working with the Drug Enforcement Administration on the Silk Road case, in mid-2013. 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. On October 1, 2013, the FBI arrested Ulbricht at the Glen Park branch of the San Francisco Public Library and accused him of being the "mastermind" behind the site.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 engaged in a quarrel to cause a commotion. Once Ulbricht was sufficiently distracted, according to Joshuah Bearman of Wired, several agents quickly moved in to arrest him while another agent grabbed the laptop and handed it to agent Thomas Kiernan. Kiernan then inserted a flash drive into one of the laptop's USB ports, with software that copied key files. Ulbricht was ordered held without bail.
Court proceedings
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. On August 21, 2014, a superseding indictment added three additional charges. The trial began on January 13, 2015.Federal prosecutors alleged that Ulbricht had paid $730,000 in murder-for-hire deals targeting at least five people, because they purportedly threatened to reveal the Silk Road enterprise. Prosecutors state that no contracted killing ever actually occurred. Ulbricht was not charged in his trial in New York federal court with this offense, although some evidence was introduced at trial supporting the allegations. The district court found by a preponderance of the evidence that Ulbricht probably sent messages inquiring about such orders. The possibility that Ulbricht might have commissioned hits was considered by the judge in sentencing Ulbricht to life and was a factor in the Second Circuit's decision to uphold the sentence. Ulbricht was separately indicted in federal court in Maryland on a single related charge, alleging that he contracted to have one of his employees killed. Prosecutors ultimately moved to drop this indictment as it was lacking in substantive evidence and after his New York conviction on other charges became final.
Conviction and sentence
On February 4, 2015, Ulbricht was convicted on all counts after a jury trial that had taken place in January 2015. On May 29, 2015, he was sentenced to double life imprisonment plus 40 years, without the possibility of parole, to be served concurrently. 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. Following his conviction, two of the federal agents who participated in the investigation were arrested and charged with wire fraud and money laundering. As the corruption was never mentioned at his trial, Ulbricht unsuccessfully used it as an argument when appealing for a new trial.Post-conviction
Incarceration
During his trial, Ulbricht was incarcerated at the Metropolitan Correctional Center, New York. Starting in July 2017, he was held at USP Florence High. His mother, Lyn, moved to Colorado so she could visit him regularly. Ulbricht was later transferred to USP Tucson.Appeal attempts
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. Ulbricht also argued his sentence was too harsh. Oral arguments were heard in October 2016, and the Second Circuit issued its decision in May 2017, upholding Ulbricht's conviction and sentence in an opinion by Judge Gerard E. Lynch. In a 139-page opinion, 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.In December 2017, Ulbricht filed a petition for certiorari with the U.S. Supreme Court, asking the Court to hear his appeal on evidentiary and sentencing issues. 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. 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. The U.S. government filed a response in opposition to Ulbricht's petition. On June 28, 2018, the Supreme Court denied the petition, declining to consider Ulbricht's appeal.
In a 2020 Vanity Fair article, it was asserted that Ulbricht had rejected a plea deal that would have potentially given him a decade-long sentence, stating that "According to more than a dozen investigators and attorneys involved in the case... Ulbricht's sentence could have been a lot less severe." However, while Assistant U.S. Attorney Timothy Howard, who was co-responsible for prosecuting the case, stated that a plea deal with a mandatory minimum of 10 years was "discussed at the final pretrial conference on December 17, 2014", the maximum sentence of life imprisonment was strongly recommended based on the sentencing guideline and testified that "no such plea offer was ever extended to Ross William Ulbricht, or conveyed to his then-counsel" before Ulbricht's indictment.