🌊 Trump's Big Day-One Decision

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Depending where you stand, Ross “Dread Pirate Roberts” Ulbricht is either a cold-blooded criminal or a political prisoner.

Donald Trump has promised to free him. Will he? Should he?

Ulbricht was born in 1984 in Austin, Texas. Known as a smart kid, a high SAT score helped him earn him a scholarship to the University of Texas at Dallas, where he dabbled in libertarian philosophy and psychedelics. After graduating, he received an engineering Master’s from Penn State – also on scholarship – and moved back to Texas.

Ulbricht first tried to trade stocks but failed; he then ran an unsuccessful online bookstore. But Ulbricht wanted to be an entrepreneur, and in 2010, as he posted on LinkedIn, he wanted to “use economic theory as a means to abolish the use of coercion and aggression amongst mankind.” The coercion and aggression he saw was the power of the government.

For him, that justified his business idea: The Silk Road, named after the ancient Asian trading route. Ulbricht learned to code and got to work designing a digital black market that would use the just-created bitcoin to allow people “to buy anything anonymously, with no trail whatsoever that could lead back to them.”

The site was part of the “deep” or “dark” web, a portion of the internet not visible via traditional browsers or search engines. It relied on Tor, an encrypted web browser that stands for “The Onion Router.” The Navy had launched Tor in 2002 with layers of encryption to make communication totally anonymous.

The site went live in January 2011 selling magic mushrooms Ulbricht grew himself. Quickly, though, other vendors and buyers signed on. Ulbricht announced a code of conduct: “Treat others as you would wish to be treated and don’t do anything to hurt or scam someone else.” All manner of drugs and fraudulent documents were available, but illegal materials and services available elsewhere on the dark web, like murderers-for-hire and child exploitation, were not.

The Silk Road became eBay for drugs, fake IDs, and hacking services. People left reviews and rated products and buyers; algorithms calculated recommended prices for goods. Drugs were shipped like anything else, often through USPS. That gave buyers plausible deniability: If the cops showed up, they could say, “I didn’t buy all that LSD!”

Ulbricht took the online name Dread Pirate Roberts, a mythical character with shifting identities from the movie The Princess Bride. He acted as both the Silk Road’s administrator and a prophet to his community, posting libertarian manifestos and organizing book clubs for its users. One representative comment left by a Silk Road user said Ulbricht ranked “among the greatest men and women in history.”

Ross was recorded as saying he wanted “to have a substantial positive impact on the future of humanity.” By age 27, he was certainly having an impact: The Silk Road had already become the world’s biggest online black market.

But it couldn’t last. Soon, Ross’s criminal enterprise would come crashing down.

Editor’s Note

A number of readers have been asking us if we can increase the number of these newsletters we send out. Good news: We’ll have a new reporter contributing starting next week and will now be looking to consistently publish at least two emails a week. We’re excited for that!

We’re curious to hear what you think about the case for freeing Ross. Will he be freed? Should he? Let us know by replying to this email.

Have a nice afternoon.

–Max and Max

RocaNews co-founders