Dread Pirate Roberts (Silk Road)
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Ross William Ulbricht (born March 27, 1984) is an American serving
life imprisonment Life imprisonment is any sentence of imprisonment for a crime under which convicted people are to remain in prison for the rest of their natural lives or indefinitely until pardoned, paroled, or otherwise commuted to a fixed term. Crimes for ...
for creating and operating the
darknet market A darknet market is a commercial website on the dark web that operates via darknets such as Tor or I2P. They function primarily as black markets, selling or brokering transactions involving drugs, cyber-arms, weapons, counterfeit currency, stole ...
website
Silk Road The Silk Road () was a network of Eurasian trade routes active from the second century BCE until the mid-15th century. Spanning over 6,400 kilometers (4,000 miles), it played a central role in facilitating economic, cultural, political, and reli ...
from 2011 until his arrest in 2013. The site operated as a hidden service on the
Tor network Tor, short for The Onion Router, is free and open-source software for enabling anonymous communication. It directs Internet traffic through a free, worldwide, volunteer overlay network, consisting of more than seven thousand relays, to conc ...
and facilitated the sale of narcotics and other illegal products and services. Ulbricht ran the site under the pseudonym " Dread Pirate Roberts", after the fictional character from ''
The Princess Bride The Princess Bride may refer to: * ''The Princess Bride'' (novel), 1973 fantasy romance novel by American writer William Goldman William Goldman (August 12, 1931 – November 16, 2018) was an American novelist, playwright, and screenwriter. He ...
.'' In 2013, the
Federal Bureau of Investigation The Federal Bureau of Investigation (FBI) is the domestic intelligence and security service of the United States and its principal federal law enforcement agency. Operating under the jurisdiction of the United States Department of Justice, t ...
(FBI) arrested Ulbricht and Silk Road was taken offline. In 2015, he was convicted of engaging in a
continuing criminal enterprise The Continuing Criminal Enterprise Statute (commonly referred to as CCE Statute or Kingpin Statute) is a United States federal law that targets large-scale drug traffickers who are responsible for long-term and elaborate drug conspiracies. Unlike t ...
, distributing narcotics, distributing narcotics by means of the internet, conspiracy to distribute narcotics, conspiracy to commit
money laundering Money laundering is the process of concealing the origin of money, obtained from illicit activities such as drug trafficking, corruption, embezzlement or gambling, by converting it into a legitimate source. It is a crime in many jurisdictions ...
, conspiracy to traffic fraudulent identity documents, and conspiracy to commit computer hacking. He was sentenced to a double life sentence plus 40 years without the possibility of parole. 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. He is incarcerated at the United States Penitentiary in Tucson.


Early life and education

Ulbricht grew up in Austin, Texas. He was a
Boy Scout A Scout (in some countries a Boy Scout, Girl Scout, or Pathfinder) is a child, usually 10–18 years of age, participating in the worldwide Scouting movement. Because of the large age and development span, many Scouting associations have split ...
, attaining the rank of
Eagle Scout Eagle Scout is the highest achievement or rank attainable in the Scouts BSA program of the Boy Scouts of America (BSA). Since its inception in 1911, only four percent of Scouts have earned this rank after a lengthy review process. The Eagle Sc ...
.Segal, David.
Eagle Scout. Idealist. Drug Trafficker?
" '' The New York Times''. January 18, 2014. Retrieved on June 10, 2015.
He attended West Ridge Middle School and Westlake High School, both near Austin, graduating from high school in 2002.Man with Austin ties charged with running vast underground drugs website

Archive
. ''
Austin American-Statesman The ''Austin American-Statesman'' is the major daily newspaper for Austin, the capital city of Texas. It is owned by Gannett. The paper prints Associated Press, ''New York Times'', ''The Washington Post'', and ''Los Angeles Times'' internation ...
''. October 2, 2013. Retrieved on June 14, 2015.
Ulbricht attended the University of Texas at Dallas on a full academic scholarship, and graduated in 2006 with a bachelor's degree in physics. He then attended
Pennsylvania State University The Pennsylvania State University (Penn State or PSU) is a Public university, public Commonwealth System of Higher Education, state-related Land-grant university, land-grant research university with campuses and facilities throughout Pennsylvan ...
, where he was in a master's degree program in materials science and engineering and studied
crystallography Crystallography is the experimental science of determining the arrangement of atoms in crystalline solids. Crystallography is a fundamental subject in the fields of materials science and solid-state physics (condensed matter physics). The wor ...
. By the time Ulbricht graduated, he had become interested in
libertarian Libertarianism (from french: libertaire, "libertarian"; from la, libertas, "freedom") is a political philosophy that upholds liberty as a core value. Libertarians seek to maximize autonomy and political freedom, and minimize the state's e ...
economic theory; he adhered to the political philosophy of Ludwig von Mises, supported
Ron Paul Ronald Ernest Paul (born August 20, 1935) is an American author, activist, physician and retired politician who served as the U.S. representative for Texas's 22nd congressional district from 1976 to 1977 and again from 1979 to 1985, as well ...
, promoted
agorism Agorism is a social philosophy that advocates creating a society in which all relations between people are voluntary exchanges by means of counter-economics, engaging with aspects of nonviolent revolution. It was first proposed by American liber ...
, and participated in college debates to discuss his economic views.Dewey, Caitlin.
Everything we know about Ross Ulbricht, the outdoorsy libertarian behind Silk Road
". '' Washington Post''. October 3, 2013. Retrieved on June 15, 2015.
Ulbricht graduated from Penn State in 2009 and returned to Austin. He tried day trading and started a video game company; both ventures failed. He eventually partnered with his friend Donny Palmertree to help build an online used book seller, Good Wagon Books.


Silk Road


Creation and operation of 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 (initially called Underground Brokers). 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 Tor, short for The Onion Router, is free and open-source software for enabling anonymous communication. It directs Internet traffic through a free, worldwide, volunteer overlay network, consisting of more than seven thousand relays, to con ...
on the
Tor network Tor, short for The Onion Router, is free and open-source software for enabling anonymous communication. It directs Internet traffic through a free, worldwide, volunteer overlay network, consisting of more than seven thousand relays, to conc ...
, 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 Bitcoin ( abbreviation: BTC; sign: ₿) is a decentralized digital currency that can be transferred on the peer-to-peer bitcoin network. Bitcoin transactions are verified by network nodes through cryptography and recorded in a public distr ...
, a
cryptocurrency A cryptocurrency, crypto-currency, or crypto is a digital currency designed to work as a medium of exchange through a computer network that is not reliant on any central authority, such as a government or bank, to uphold or maintain it. It i ...
, was used for transactions on the site. While all bitcoin transactions were recorded in a public ledger called the
blockchain A blockchain is a type of distributed ledger technology (DLT) that consists of growing lists of records, called ''blocks'', that are securely linked together using cryptography. Each block contains a cryptographic hash of the previous block, a ...
, 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 ''Alongside Night'' is a dystopian novel by science fiction writer J. Neil Schulman intended to articulate the principles of Agorism, a political philosophy created by Samuel Edward Konkin III, to whom Schulman dedicated the work. It was first ...
'' and the works of
Samuel Edward Konkin III Samuel Edward Konkin III (8 July 1947 – 23 February 2004), also known as SEK3, was an American libertarian philosopher and Austrian school economist. As the author of the publication '' New Libertarian Manifesto'', he was a proponent of a polit ...
.


Arrest

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 use to be Pacific time, narrowing down his likely locatio

Law enforcement seized a Silk Road server in Iceland and gained a trove of chat logs, further enriching their knowledg

Ulbricht was connected to "Dread Pirate Roberts" by Gary Alford, an
Internal Revenue Service The Internal Revenue Service (IRS) is the revenue service for the United States federal government, which is responsible for collecting U.S. federal taxes and administering the Internal Revenue Code, the main body of the federal statutory ta ...
investigator working with the U.S. 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. In October 2013, the
Federal Bureau of Investigation The Federal Bureau of Investigation (FBI) is the domestic intelligence and security service of the United States and its principal federal law enforcement agency. Operating under the jurisdiction of the United States Department of Justice, t ...
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 quarreling lovers. When they had sufficiently distracted him, 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. 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.


Trial

On February 4, 2014, Ulbricht was charged with engaging in a continuing criminal enterprise, narcotics conspiracy, conspiracy to commit
money laundering Money laundering is the process of concealing the origin of money, obtained from illicit activities such as drug trafficking, corruption, embezzlement or gambling, by converting it into a legitimate source. It is a crime in many jurisdictions ...
, and conspiracy to commit computer hacking. On August 21, 2014, a superseding indictment added three additional charges. 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 Life imprisonment is any sentence of imprisonment for a crime under which convicted people are to remain in prison for the rest of their natural lives or indefinitely until pardoned, paroled, or otherwise commuted to a fixed term. Crimes for ...
plus 40 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.


Murder-for-hire allegations

Federal prosecutors alleged that Ulbricht had paid $730,000 in murder-for-hire deals targeting at least five people, allegedly because they threatened to reveal the Silk Road enterprise.Alan Klasfeld
Silk Road Murder Threat Shown as Case Nears End
, Courthouse News Service (January 29, 2015): "Silk Road founder Ross Ulbricht is not charged with murder for hire in his New York trial, but federal prosecutors have long accused him of hiring a hit-man to kill those who threatened his underground online drug empire. Minutes before the second week of Ulbricht's trial ended on Thursday, a jury saw email records supporting this allegation."
Prosecutors believe no contracted killing actually occurred. Ulbricht was not charged in his trial in New York federal court with murder for hire, but evidence was introduced at trial supporting the allegations. The district court found by a preponderance of the evidence that Ulbricht did commission the murders. 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 sentence. 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). Prosecutors moved to drop this indictment after his New York conviction and sentence became final.


Attempts to reverse the trial outcome


Appeal

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,
United States v. Ulbricht
'', 858 F.3d 71 (2d. Cir. 2017)
and the Second Circuit issued its decision in May 2017, upholding Ulbricht's conviction and sentence in an opinion by Judge
Gerard E. Lynch Gerard Edmund Lynch (born September 4, 1951) is an American lawyer who serves as a senior United States circuit judge of the United States Court of Appeals for the Second Circuit. He was confirmed to that seat on September 17, 2009, after previo ...
. In a 139-page opinion,Cassye M. Cole & Harry Sandick
A Long Journey Through "Silk Road" Appeal: Second Circuit Affirms Conviction and Life Sentence of Silk Road Mastermind
, Patterson Belknap Webb & Tyler LLP, ''Lexology'' (June 8, 2017): "At trial, the government presented evidence that Ulbricht conspired to engage in multiple murders for hire to protect Silk Road's anonymity. Ulbricht was not charged with these offenses. ... At sentencing, in its Pre-Sentence Investigation Report, the U.S. Probation Office referenced the five commissioned murders, as well as six drug-related deaths connected with Silk Road. On May 29, 2015, the district court sentenced Ulbricht to life in prison, pursuant to the guidelines advisory sentence range, and based on the recommendation of the U.S. Probation Office. ... While the Court recognized that a life sentence for selling drugs was rare and could be considered harsh, the facts of this case involved much more than routine drug dealings—namely that Ulbricht commissioned at least five murders for hire and did not challenge those murders on appeal."
the court affirmed the district court's denial of Ulbricht's
motion to suppress Suppression of evidence is a term used in the United States legal system to describe the lawful or unlawful act of preventing evidence from being shown in a trial. This could happen for several reasons. For example, if a judge believes that the e ...
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 a ''certiorari'' with the United States 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 An ''amicus curiae'' (; ) is an individual or organization who is not a party to a legal case, but who is permitted to assist a court by offering information, expertise, or insight that has a bearing on the issues in the case. The decision on ...
'' 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.


Motion to vacate or reduce the sentence

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, but the motion was refiled. The motion was denied in June 2022. In a 2020 '' Vanity Fair'' article,
Nick Bilton Nick Bilton is a British-American journalist, author, and filmmaker. He is currently a special correspondent at ''Vanity Fair''. Life and career Bilton was born in Darlington, UK, and grew up in Leeds. He attended Marjory Stoneman Douglas Hi ...
wrote that, according to investigators and attorneys involved in the case, Ulbricht had been offered a plea deal that would likely have given him a 10-year sentence, but turned it down. In response to the article, assistant U.S. Attorney Timothy Howard, who was co-responsible for prosecuting the case, testified that no such plea offer existed. He further testified that the only plea offer had been made before Ulbricht's indictment. The plea offer had required Ulbricht to plead guilty to charges "carrying a mandatory minimum sentence of ten years and a maximum sentence of life imprisonment, with a recommended United States Sentencing Guidelines range of life imprisonment".


After the 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 has since been transferred to USP Tucson.


Restitution paid from seized assets

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. 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.


Documentaries and films

''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. The film ''
Silk Road The Silk Road () was a network of Eurasian trade routes active from the second century BCE until the mid-15th century. Spanning over 6,400 kilometers (4,000 miles), it played a central role in facilitating economic, cultural, political, and reli ...
'' 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 Nicholas, Nicky or Nick Robinson may refer to: * Nick Robinson (journalist) (born 1963), British political journalist * Nick Robinson (paperfolder) (born 1957), British origami artist * Nicky Robinson (rugby union) (born 1982), Welsh rugby player ...
.


NFT sale

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 A non-fungible token (NFT) is a unique digital identifier that cannot be copied, substituted, or subdivided, that is recorded in a blockchain, and that is used to certify authenticity and ownership. The ownership of an NFT is recorded in the ...
, which FreeRossDAO bought for 1,442 Ethereum, about $6.27 million at the time.


See also

* Variety Jones and Smedley: pseudonyms of people reported to have been closely involved with Silk Road's founding *
USBKill USBKill is anti-forensic software distributed via GitHub, written in Python for the BSD, Linux, and OS X operating systems. It is designed to serve as a kill switch if the computer on which it is installed should fall under the control of indiv ...
: kill-switch software created in response to the circumstances of Ulbricht's arrest * Kevin Mitnick


References


Further reading

*Greenberg, Andy.
Meet The Dread Pirate Roberts, The Man Behind Booming Black Market Drug Website Silk Road
. '' Forbes''. August 14, 2013. *Greenberg, Andy.
An Interview With A Digital Drug Lord: The Silk Road's Dread Pirate Roberts (Q&A)
. '' Forbes''. August 14, 2013. *Howell O’Neill, Patrick.
The mystery of the disappearing Silk Road murder charges
. '' The Daily Dot''. October 22, 2014. *
Bertrand, Natasha Natasha Bertrand (; born May 12, 1992) is an American journalist who is a White House reporter for CNN covering national security. Early life and career Bertrand attended Vassar College and the London School of Economics, where she double-ma ...
.
Eerie diary entries written by the Silk Road founder who just got a life sentence
. '' Business Insider''. May 29, 2015. *Mullin, Joe.
Sunk: How Ross Ulbricht ended up in prison for life
.
Ars Technica ''Ars Technica'' is a website covering news and opinions in technology, science, politics, and society, created by Ken Fisher and Jon Stokes in 1998. It publishes news, reviews, and guides on issues such as computer hardware and software, sci ...
. May 29, 2015. *Bearman, Joshuah.
Silk Road: The Untold Story
'' Wired Magazine''. April/May 2015. *Bilton, Nick, American Kingpin, 2017. * Doherty, Brian.
Ross Ulbricht's Murder-for-Hire Charges Dropped by U.S. Attorney
. '' Reason''. July 25, 2018. {{DEFAULTSORT:Ulbricht, Ross 1984 births Living people 21st-century American criminals American computer criminals American drug traffickers American libertarians American money launderers American prisoners sentenced to life imprisonment Dark web Penn State College of Engineering alumni People associated with Bitcoin People from Austin, Texas Prisoners sentenced to life imprisonment by the United States federal government University of Texas at Dallas alumni Westlake High School (Texas) alumni