Silk Road's Dread Pirate Roberts vs. The Princess Bride's

The Princess Bride, Robin Wright, Cary Elwes (as Dread Pirate Roberts), 1987 Photograph by 20th Century Fox Film Corp./Everett Collection

In the Princess Bride, the Dread Pirate Roberts is fearsome, ruthless, and unfailingly polite. Even when his true love tells him she doesn’t care if he dies, his response is, “as you wish.” (Spoiler alert: He doesn’t die, they end up kissing, and Fred Savage’s character learns to appreciate the mushy parts of love stories. It really is a great movie.)

The Dread Pirate Roberts of the online black market Silk Road, allegedly aka Ross William Ulbricht, bears some resemblance to his fictional namesake. The FBI complaint against him describes a man who is easy to please as he gives instructions how to seal drugs properly or offers a consumer support option through which the site’s employees “will take care of you personally.”

Photograph by David Colbran/Demotix/Corbis
This pirate is especially gracious when offering to pay someone to kill a man with a wife and three children. Ulbricht seems almost to be reciting from the movie’s script as he puts out a hit on a man extorting him, beginning by saying that he “wouldn’t mind if he was executed.”

“I would like to put a bounty on his head if it’s not too much trouble for you,” he continues, according to the complaint. “What would be an adequate amount to motivate you to find him? Necessities do happen from time to time for a person in my position.” (Law enforcement officials aren’t convinced the murder ever actually happened.)

But the most relevant parallel is how the Dread Pirate Roberts of the movie refers not to a person, but to a job. In the Princess Bride, the men holding the title periodically decide to retire, secretly passing the torch down to their successors while helping obscure the fact that a change has taken place. With Ulbricht indisposed, such an orderly handoff seems impossible. Still, this Dread Pirate Roberts seems to have fallen victim to his own sloppiness, not some inherent weakness in Silk Road or the technologies that make it possible. All the essential elements remain in place: a worldwide web of computers, software for obscuring identities, and a healthy desire to buy and sell drugs. A sequel is likely in the works.

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