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.
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 (a former Silk Road moderator) 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.
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. 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.
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 $5.35 billion in 2025) seized from a hacker in November 2021. The Bitcoin had been stolen from Silk Road in 2013, and 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 Bitcoin.
In 2010, Ulbricht partnered with his friend Donny Palmertree to help build an online used bookseller, Good Wagon Books. Following the departure of Palmertree, he continued to operate the business as CEO until March 2011.
The son of Kirk and Lyn Ulbricht, Ross has a sister, Cally, who was residing in Australia at the time of his arrest, and a half-brother, Travis. His parents were reported to earn most of their income from renting out beachside vacation homes in Costa Rica. During his incarceration, his mother became a prominent campaigner for his release.
While studying at the University of Texas, Ulbricht reportedly became engaged. However, he ended the relationship after discovering that his girlfriend had cheated on him with a close friend. During his graduate studies at Penn State, he began a relationship with Julia Vie, then a freshman student at the university. Vie moved with Ulbricht to Austin after he received his master's degree, but she stated that his lack of interest in social activities while he was building Silk Road led to their breakup. In an effort to rekindle the relationship, she visited him in San Francisco shortly before his arrest.
Ulbricht is married. Following his release from prison, he expressed gratitude to his mother and wife for their efforts in campaigning for his freedom. Ulbricht identifies as a libertarian.
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