MANHATTAN (CN) — Like the storied Silk Road of old, its namesake in the deep-web narcotics trade had many furtive dangers, including hit men, heroin, and the constant threat of arrest.
In one of the Second Circuit's most-anticipated appeals this year, lawyers for the website's now-incarcerated leader Ross Ulbricht highlighted a threat kept hidden from a federal jury at his client's trial: corrupt federal agents.
Ulbricht, a 32-year-old unmasked as the site's mastermind "Dread Pirate Roberts," has been living out the rest of his young life in prison since May 29, 2015, when a federal judge dealt him the maximum-allowable sentence for operating an online drug bazaar on the so-called deep web.
Then the largest case of its kind, Ulbricht's prosecution generated intense controversy about the government's digital War on Drugs, along with its corruptions and casualties — not only among dealers and addicts, but also the law enforcement officials seeking to discourage a booming online trade.
To his supporters, Ulbricht is a symbol of a prosecutorial overreach, and at least one judge appeared troubled that a young man has been condemned to spend the rest of his life behind bars for running a website.
"It is unusual for a young man in his early 30s with no criminal record, who himself was not dealing drugs, except some mushrooms at one point, at least there was some evidence that suggested that, to receive a life sentence," U.S. Circuit Judge Christopher Droney said in one blockbuster remark at Thursday's Second Circuit hearing.
The now-defunct Silk Road was once a billion-dollar marketplace as the largest online shop for selling a variety of illicit wares, primarily drugs, through highly encrypted transactions of bitcoin, a then-underground online currency.
Business was so good, Ulbricht's attorney Joshua Dratel noted, that even federal investigators wanted to get in on the action.
Months after Ulbricht received his life sentence, Secret Service agent Shaun Bridges and Drug Enforcement Agency official Carl Force admitted swiping hundreds of thousands of dollars in bitcoins for themselves.
Both men had been part of Baltimore's Silk Road Task Force before New York federal investigators took over.
Force, in particular, tried to extort Dread Pirate Roberts — not knowing he was Ulbricht — by threatening to expose his identity if he did not receive $250,000, according to his criminal complaint.
"They hijacked accounts," Dratel said, referring to the officers. "They changed passwords. They stole money. They were inside the guts of this website."
Questioning how far this intrusion went, U.S. Circuit Judge Gerard Lynch asked, "Were they inside the guts of Mr. Ulbricht's laptop?"
"No, but that's another issue that we were not allowed to explore," Dratel replied.
The contents of that laptop, snatched during Ulbricht's arrest almost exactly three years ago, were crucial to the case against him.
An FBI team swiped Ulbricht's Samsung 700Z computer moments before handcuffing him at San Francisco's Glen Park Library on Oct. 2, 2013.
Its hard drive contained mountains of evidence identifying Ulbricht as Silk Road's leader Dread Pirate Roberts, including Silk Road's business plans, Excel spreadsheets of the website's sales, detailed diary entries, and the site's passcodes.