In 2011, a 27-year-old man, known as “Pirate,” had a vision. He despised government intervention and regulations, and he wanted to create a platform where people could engage in trade without interference. That idea led to the birth of Silk Road, an anonymous marketplace on the dark web where users could buy and sell anything, drugs, fake passports, illegal weapons, all using Bitcoin, making transactions difficult to trace.
The website quickly gained traction. It was essentially Amazon for illegal goods, complete with a rating and review system. Within a year, Pirate had ten employees, half a million dollars in weekly sales, and a rapidly expanding user base. He took a commission on every transaction, amassing tens of millions of dollars. Despite his wealth, he was too engrossed in running the site to spend much of it.
However, Silk Road’s success attracted the attention of the U.S. government. Law enforcement agencies launched investigations, and among those leading the charge was DEA agent Carl Force. Going undercover, he became an active user on Silk Road, embedding himself within the community. His team eventually identified one of Pirate’s employees, known online as “Chronic Pain.”
The feds set up a sting operation, arrested Chronic Pain, and Pirate became concerned. He feared that his employee would cooperate with the authorities and that his empire would crumble. Additionally, Pirate believed that Chronic Pain was stealing Bitcoin from the site. In 2013, he allegedly made a drastic decision to hire a hitman to eliminate Chronic Pain.
The supposed hitman? None other than Carl Force. Working undercover, Force staged a fake execution, even producing photos to convince Pirate that Chronic Pain had been taken out. However, Chronic Pain had never stolen from the site, and he was very much alive.
Pirate allegedly commissioned five more hits over time, further entrenching himself in criminal activity. Meanwhile, government agencies were closing in. They finally traced Silk Road’s IP address to multiple locations, one being an internet café in San Francisco, near Pirate’s residence. Piecing together evidence, authorities identified Pirate as the mastermind.
Yet, arresting him wasn’t straightforward. His electronic devices were encrypted, meaning that if the feds couldn’t access his laptop while it was open, convicting him would be difficult. A plan was devised.
Agents surveilled Pirate, learning his routines. They followed him to the San Francisco Public Library, where he often worked. Undercover officers staged a loud argument, with one agent playing an enraged spouse who physically lashed out at their “partner.” The distraction worked. As Pirate turned to watch the commotion, another agent swiftly snatched his open laptop. Within moments, he was apprehended and arrested.
Silk Road had facilitated an estimated $1.2 billion in sales, with Pirate himself profiting around $184 million. The trial was intense. Families of individuals who had overdosed on drugs purchased from Silk Road testified, their emotional accounts deeply influencing the case. The prosecution also referenced Pirate’s alleged attempts to order assassinations, though he was never formally charged for those incidents.
Ultimately, Pirate was convicted and sentenced to life in prison without the possibility of parole. Many found the sentence extreme, after all, he had merely created a website. However, the case took yet another shocking turn when it was revealed that Carl Force had been extorting Pirate for Bitcoin throughout the investigation. Pirate had unknowingly handed over $750,000 to the corrupt agent. Force was convicted and sentenced to six years in prison. Another federal agent was also caught stealing Bitcoin from Silk Road while working on the case and received a five-year sentence.
Then, in an unexpected twist in 2025, after serving approximately ten years in prison, Pirate was pardoned. He walked free, marking the conclusion of one of the most infamous cases in internet history.
