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The Curious Cases of Ross Ulbricht's New Lawyer

A Guantanamo detainee who claimed he was tortured. A cabbie caught in a NSA wiretap. The Boston Bomber's widow. And now, the alleged founder of the Silk Road.
Dratel (middle) in 2011. Photo via CenterLine.

Joshua Dratel is no stranger to bad guys. The New York based lawyer and Harvard Law graduate has made a career out of defending what are arguably some of the most high-profile terrorism cases this side of 9/11. Now he's poised to defend a different sort of client: the alleged founder of the online drugs bazaar the Silk Road.

That would be the elusive Ross Ulbricht, the self-proclaimed "entrepreneur" detained in San Francisco earlier this month on grounds of drug-trafficking, money laundering, and computer-related fraud. The elfin 29-year-old has been riding out his days in solitary confinement ever since, making doodles and reading Master & Commander. He awaits imminent extradition to New York City, where he's expected to continue denying all charges.

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Ulbricht will then meet Dratel, who's been building the case against what he calls the "naked allegations" of the prosection's criminal accusations, Dratel told Forbes. Ulbricht's case, to say nothing of his story (that's if you believe he is—was?—the Dread Pirate Roberts, the Silk Road's founder-guru), couldn't be much different from those of Dratel's past. And yet he already seems, in something almost stranger-than-fiction, to be made for Dratel, whose subversive case history reads not only like a veritable Who's Who of Terror, but like a prophetic first draft of tomorrow's cybercrime litigations.

AN AL-QAEDA CONFIDANTE WHO HELPED BOMB TWO US EMBASSIES

Wadih el Hage helped conspire the 1998 bombings of US embassies in Kenya and Tanzania. The blasts killed 224 people. Dratel took on el Hage's case in 2001, and would see his client convicted on all counts to a life sentence without parole that same year. Wadih el Hage is currently locked up at the ADX-Florence supermax prison in Colorado.

AN ACCUSED TALIBAN FIGHTER WHO CLAIMED HE WAS TORTURED AT GUANTANAMO BAY

In 2003, Australian David Hicks found himself at the notorious American military prison, where he was tried as an enemy combatant and faced charges of aiding, abetting, and fighting alongside the Taliban in Afghanistan. Hicks would accept a plea bargain—something his Dratel-led legal team said was the only way to see their man escape the "duress" of Guantanamo, where Hicks said he was subjected to routine beatings and sleep deprivation, among other interrogation tactics that flouted basic human rights.

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Hicks' seven-year sentence would be shortened to just nine months, by all counts a win for the first ever Guantanamo case defended by a civilian attorney. Hicks now lives with his wife in Sydney.

AN IMMIGRANT CABBIE SNOOPED BY THE NSA

Baasaly Maolin is a Somali cab driver living in San Diego. He's become a sort of poster boy for dragnet surveillance by the National Security Agency: After it combed through Maolin's cell phone records, the NSA discovered that Maolin had reportedly wired $8,500 al-Shaabab, the Somali terrorist group behind recent attacks on a Kenyan shopping mall that killed 72.

Dratel is curently serving as Maolin's defense attorney. It's a case that Slate says could "destroy—or legitimize—mass NSA telephone surveillance."

A SCOTTISH SYSTEM ADMINISTRATOR WHO ALLEGEDLY HACKED INTO US MILITARY AND NASA COMPUTERS

Gary Mackinnon says he was just poking around for proof of "free-energy suppression" and of various UFO coverups. But his hacks into US military and NASA backends in 2002 were significant enough that the BBC pulled out the "biggest military computer hack of all time" card. In the end, Dratel saw Mackinnon's US-extradition order dropped—the same fate for Richard O'Dwyer, another British hacker and Dratel defendent who faced copyright infringement charges.

THE BOSTON BOMBER'S WIDOW

Katherine Russel, the widow of Tamarlane Tsarnaev, rang up Dratel in the wake of the worst domestic act of terrorism since Sept. 11. As of this writing, Russel faces no charges.

Even still, Dratel doesn't take just any old case. Defending terrorists and their known associates is almost always a surefire way to being labelled a pariah, or worse. In other words, Dratel has got to feel somewhat good about the odds. He's got to know he has a chance—even if that means getting up to speed with anonymizing software like Tor and cryptocurrencies like Bitcoin, a cool $80 million of which Ulbricht is believed to have earned by brokering deals on the Road.

To that point, Dratel told Forbes that from what's he's gathered thus far he feels "pretty good" about Ulbricht's case. “Part of the reward [of being a defense attorney] is taking a case that’s defensible. That’s one of the reasons this case is attractive.”

If you're wondering whether Dratel is taking on Ulbricht's defense pro bono, no, he is not. But does he accept Bitcoin?

@thebanderson