Dread Pirate Roberts

Dread Pirate Roberts

Part of a series on Silk Road. [View Related Entries]

Updated Feb 04, 2015 at 07:15PM EST by Brad.

Added Oct 03, 2013 at 07:32PM EDT by Don.

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Dread Pirate Roberts is the pseudonym of Ross William Ulbricht, who was identified as the suspected owner of the Deep Web black marketplace Silk Road by the United States Federal Bureau of Investigation in October of 2013. The name is based on a fictional character from the 1973 fantasy novel and 1987 adventure film The Princess Bride.

Online History

On July 5th, 2010, Ulbricht posted a post on his Facebook[1] page titled “Thoughts on Freedom,” which included musings on what it means to be “free” and invited his Facebook friends to share their own thoughts on the subject.

“In light Independence Day, I have been inspired to write down my thoughts on freedom, about a page in length. I hope they will stimulate YOUR thoughts, which I would most enjoy hearing.”

What does it mean to be free? This word has been used to describe many things, including feelings, states of being, political and social arrangements, mental states, and physical states. Like something beyond the power of words to describe, freedom exists, but only as it occurs to someone experiencing it. Is it possible for someone locked in a cage to be freer than someone who isn’t? What if they are free from limiting beliefs and can imagine experiences without limits, while the other limits themselves to a prison of dull routines? Can freedom stand up to inter-personal comparisons, or is it a wholly personal experience?

Because of its vague nature, it is useful to make further distinctions. One way to identify freedom is by what one is free from. For example, social freedom could describe freedom from limitations imposed by others. Physical freedom could be freedom from physical restraint either imposed by others or by nature. Personal freedom could describe freedom from beliefs one may have about one’s self, others, and nature that limit what one believes is possible. Always, freedom arises in the absence of limitation. When someone is not limited by others, their physical environment, lack of knowledge or skill, or their own beliefs about what is possible; it is natural for them to expand how they express themselves in the world until the next barrier to their self-expression is reached.

One’s limitations can be difficult to identify because they are not always in plain view, especially the self-imposed ones but also the ones imposed by others and nature. For example, death and taxes are widely agreed upon to be inevitable, but are they? While one may have a choice in how they respond to external limitations, this does not negate their existence. Death and taxes are still real and observable, but inevitable? This is an interpretation. It is an extrapolation from the past in an attempt to predict the future, is not the truth and therefore limits what is possible.

That being said, it is my observation that far too much attention is directed, by people in general, toward limitations that arise out of a lack of skill or knowledge that could be better directed toward eliminating self-imposed limitations and one’s beliefs about seemingly inevitable external limitations. This is understandable because, for limitations in skill or knowledge, the problem, solution, and benefit are easy to see and predict. For example, I know I will have more freedom if I know how to play the piano and that all I need to do is learn to play and practice. However, the solution to and benefit of ridding one’s self of a belief such as “I’m shy” or “telepathy is impossible” are not so apparent. Imagine how rich and fulfilling your life could be, well beyond learning a new skill, if you could let go of the beliefs you have that limit you and live your life to its fullest potential. Imagine what could be accomplished and experienced.

Are you free? Yes and no. Freedom is a relative and unquantifiable thing. The question is, “How can I be freer?” and the answer to that depends on YOU. For me, I could be freer by letting go of beliefs like “life is hard,” “if you want something done right you should do it yourself,” “why try, I’ll probably fail” and so on. I could also be freer by creating and acquiring more resources that allow me to express myself in bigger and broader ways, both physical in form and in the form of relationships.

Let Independence Day be a reminder to us that we live in a most unique time, and are freer, as a generation, than any that has come before us. Let us be thankful for our freedom, and build a world where we, and the generations that follow us, will be freer than any that have come before!

Ulbricht began developing the Silk Road in November of 2010 and launched the website three months later in February of 2011. The site remained relatively unknown until June 1st, when Gawker[5] published an article about the site titled “The Underground Website Where You Can Buy Any Drug Imaginable.”


On October 2nd, 2013, the U.S. Federal Bureau of Investigations (FBI) shut down Silk Road and arrested Ulbricht on charges of narcotics trafficking conspiracy, computer hacking conspiracy and money laundering conspiracy. In addition, the authorities also seized $3.6 million worth of digital currency Bitcoin, the de facto currency used to complete transactions on the site. According to the court documents[2], the site allegedly facilitated more than 1.2 million illegal transactions involving 146,946 unique buyers and 3,877 unique vendors, generating more than 9.5 million bitcoins, or $1.2 billion, in total revenue. The files also revealed that Silk Road collected about $79.8 million worth of bitcoins in commission and site administrators received salaries of $1,000 to $2,000 weekly.

That same day, The Daily Dot[8] published a summary digest of the FBI’s official complaint filed against Ulbricht. According to the files, the investigation began in January 2011, around the same time Silk Road was launched, with an individual who used the handle “Altoid” to advertise a Tor-protected anonymous black market on recreation drug forums and BitCoin discussion sites. Then in October, Altoid posted a job listing on BitcoinTalk forum in search of “an IT pro in the Bitcoin community,” adding his personal e-mail account “rossulbricht at gmail dot com” as the reply address. After examining his records from Google, the FBI was soon able to determine that “Altoid” wass an account used by Ulbricht. According to the Associated Press,[7] Ulbricht also made the mistake of ordering fake identification documents from a Canadian vendor that were intercepted during a customs search.

Hit Purchases

According to the criminal complaint,[2] Ulbricht offered 1,670 bitcoins (approximately $150,000) to have the site user FriendlyChemist assassinated, after the user sent messages threatening to publish the names and addresses of Silk Road customers unless he received $500,000.

Ulbricht contacted user redandwhite to place a hit on the alleged blackmailer, who responded that he had taken care of the problem after receiving payment:

“Your problem has been taken care of … Rest easy though, because he won’t be blackmailing anyone again. Ever.”

On November 20th, 2013, the Ross Ulbricht YouTube channel uploaded a video narrated by his close friends and family, pleading for support and donations for Ulbricht’s legal defense (shown below).

Ties with BitCoin Inventor

On November 24th, 2013, Dorit Ron and Adi Shamir, two Israeli computer scientists at the Weizmann Institute of Science, published a research paper titled “How Did Dread Pirate Roberts Acquire and Protect His Bitcoin Wealth,”[11] which estimated that only about 22 percent of the total commissions earned by Ulbricht had been seized by the F.B.I, leaving the majority of the $80 million unaccounted for. In the paper, the researchers also noted their discovery of a particularly large transfer in the amount of 1,000 Bitcoins to Ulbricht’s account from from one of the first Bitcoin accounts created in January 2009, which is believed to belong to “Satoshi Nakamoto,” an alias used by the secretive founder of the digital currency (shown below). While Ron and Shamir admitted that their assertion remains speculative at best and cannot be proven, they suspected the sheer volume of the one-off transfer may represent either a large-scale transaction on Silk Road, or some form of investment or partnership, between the accounts belonging to Ulbricht and Nakamoto.

Trial and Conviction

On January 13th, 2015, Ulbricht’s trial began at the Federal District Court in Manhattan, New York. At the onset of the proceedings, Ulbricht admitted to having founded the website, though he claimed to have relinquished control of the site to others soon afterwards. Furthermore, Ulbricht’s lawyers argued that the defendant had been set up as a scapegoat by Mark Karpelès, the former CEO of Bitcoin exchange Mt. Gox, whom they say has retained control of the site’s operations under the pseudonym Dread Pirate Roberts. During the second week of the trial, prosecutors countered the defense team’s argument with a series of evidences, including documents and chat logs that were found on Ulbricht’s seized computer, to demonstrate how Ulbricht had administered the site for several months, in direct contradiction to the defendant’s claim that he had transferred the control of site’s operations soon after its launch.

On February 4th, the twelve-member jury found Ulbricht guilty and convicted him on all seven charges: distributing or aiding and abetting the distribution of narcotics; trafficking narcotics or aiding and abetting distribution over the Internet; conspiracy to violate narcotics laws; operation of a “continuing criminal enterprise”; computer hacking; distributing false identification and money laundering. Ulbricht faces up to a life sentence in prison. That same day, a small group of Ulbricht’s supporters staged a rally outside of the court in protest against the jury’s verdict (shown below).

Personal Life

According to his LinkedIn[3] profile, Ulbricht studied physics at the University of Texas at Dallas before earning a master’s degree at Penn State in materials science and engineering. Ulbricht moved to San Francisco in 2012, where he lived with two roommates under the fake name “Josh” and paid $1,000 per month to rent a room.[6] On December 6th, 2012, Ulbricht was interviewed by his friend Rene Pinnell, in which he revealed that he wanted to “start a family in the next five years” and wanted to have had a “substantial positive impact on the future of humanity” in the next two decades.

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