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The Real Story Of How Dread Pirate Roberts Was Bagged

In Feb. 2015, a federal jury convicted the man they believed is the Dread Pirate Roberts — AKA the mastermind and ringleader behind the Silk Road online illegal drug trade website that used bitcoin as its currency.

That man, of course, was Ross Ulbricht, who was found guilty of seven criminal charges stemming from the site that the federal government says ran the massive online illegal drug trade that brought in billions of dollars for selling heroin, cocaine and crystal meth. What started as a small site selling homegrown illegal mushrooms soon turned into a giant bazaar for narcotics trafficking, illegal goods, computer hacking tools and money laundering to an audience in the thousands.

He was eventually sentenced to life in prison. Former Bitcoin Foundation board member and CEO of the now out of business BitInstant, Charlie Shrem, was sentenced to two years in prison in Dec. 2014 for his collaborator role and connection to activities aimed at helping Silk Road users swap their digital currency for cash.

But the case of Dread Pirate Roberts and the end of Silk Road began far sooner than that in June 2013 when Gary Alford, a tax investigator for the DEA in NYC, began on the case. Alford’s role in nabbing Ulbricht was featured in The New York Times late last week (Dec. 25) in a story that chronicles the tale of an investigator who discovered the case before anyone believed it had full merit.

According to the story, as told by NYT‘s Nathaniel Popper, the tax investigator had been reading through pages of chat rooms and blog posts and believed he had cracked the case with the ringleader of Silk Road, who would eventually be identified as Ulbricht.

When Alford first discovered him, he was still known only as Dread Pirate Roberts, the pseudonym that was created to mask his true identity. But even with the stack of evidence he believed was compelling, the others involved in the case weren’t ready to buy Alford’s report when it was first discussed.

As one of the most salacious cases of its kind for the DEA, it’s not shocking that no one was ready to buy that this investigator had actually cracked the case of the massive underground online drug marketplace. That’s why it took another three months to actually put together enough evidence for the government to gather a case worth tracking.

Eventually in the fall of 2013, at a NYC public library, Ulbricht was arrested and taken into custody after he was caught red-handed logging into the Dread Pirate Roberts account to make a deal on Silk Road. Finally, when he was arrested, Alford got an email that justified all his hard work.

“Congrats Gary, you were right,” the email said, according to Popper’s report.

While the Silk Road case took years of investigation to crack, it was Alford’s research that finally put the missing pieces together enough for the Feds to make their case. And even then, his work got brushed under the rug in the public spotlight as most focused on the FBI’s role in actually nabbing Ulbricht.

As Popper explains in his story, this follows the same path as Frank J. Wilson, the tax agent who helped nab Al Capone but never really received the proper credit. In his interview with Popper, Alford said, “That’s just how it is,” noting that “they don’t write movies about Frank Wilson building the tax case.”

And outside the interview with NYT, there may not be a movie that tells who Alford was in the Silk Road case either. But that doesn’t make his work any less relevant.

Popper’s narrative shows how Alford stuck to the case on whatever free time he had. And while it seems like it would have taken a tech genius to crack the case, the tax investigator said this case didn’t follow that path. That path included message boards and doing a lot of Google research.

“I’m not high-tech, but I’m like, ‘This isn’t that complicated. This is just some guy behind a computer,’” Alford recalled in a story to Popper. “In these technical investigations, people think they are too good to do the stupid old-school stuff. But I’m like, ‘Well, that stuff still works.’” 

That’s when he eventually learned what people were saying about Silk Road (the “anonymous Amazon”) on online forums. Eventually, Alford’s research led him down a deeper hole into more investigation policies that allowed him to start connecting the dots between Ulbricht and Dread Pirate Roberts, who Alford learned had very similar qualities to who would fit the bill to be the creator of such a site.

Despite the evidence that was stacking up, Alford wasn’t being taken seriously on the case for some time. As the case continued, Ulbricht’s name kept showing back up, and the tax agent couldn’t shake the connection. Had Alford shaken that inclination and what he believed to be strong evidence, it’s hard to know when Dread Pirate Roberts would have been caught.

And when it was all over? As Popper’s report shares, Alford was given a plaque from superiors with a Sherlock Holmes quote: “The world is full of obvious things which nobody by chance ever observes.”

How ironic for the case of Silk Road and Dread Pirate Roberts.

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