Why The Deep Web Has Washington Worried

From: Time

From online drug bazaars to virtual currency tax shelters, the growing anonymous web has many corners of Washington concerned


Washington has no idea what to make of the Dread Pirate Roberts.

As Lev Grossman and I write in this week’s cover story, the Dread Pirate Roberts allegedly ran the Silk Road, the world’s most successful online drug bazaar, until the feds caught him earlier this month. His real name, according to a 39-page federal complaint against him, is Ross Ulbricht, 29. He supposedly took the pseudonym from a character in the movie and book, The Princess Bride. In the Silk Road, DPR, as his followers called him, created a business model for anyone wanting to sell illicit items online using free encryption software called Tor and the virtually anonymous crypto-currency Bitcoin. Though the feds have taken Silk Road offline, there are plenty of folks lining up to be the next Dread Pirate Roberts.

Lev and I examine the greater implications of the Deep Web, the massive and growing anonymous area of the Internet. But from the perspective of lawmakers and law enforcement in Washington, Silk Road presents a double conundrum. It’s a blueprint for criminals the world over at a time when FBI resources are stretched thin and political will to empower government snooping has cratered. And it has created a regulatory headache in figuring how to deal with whole new currencies, tax havens and virtual online markets.

While Tor is used by everyone from law enforcement to Syrian dissidents to protect valuable information, it is a double-edged sword. Many experts warn that groups ranging from the Russian mafia to international drug cartels are looking closely at the lessons learned from the Silk Road. It took the FBI more than two years of investigative work to find Ulbricht. They don’t have the resources to compete with Silicon Valley in hiring, or the tools—a long-hoped for modernization of the law governing online wiretapping is on ice in Congress thanks to Edward Snowden.

Developing technology to fight the Deep Web, or the anonymous non-searchable web, “is not adequately funded—it’s nowhere near adequately funded,” says Marcus Thomas, former assistant director of the FBI’s technology division and now on the advisory board Subsentio, which helps companies comply with online warranted wiretaps. “Historically it was well funded, but recently especially with sequestration, it’s been hard hit. It’s always been a difficult thing to build cost benefit analysis for. How much money should you spend building a technology you may not use for a year, if ever?”

Chester Wisnieski, a senior information technology security adviser at Sophos, adds that the FBI doesn’t have enough trained staff. “If you look at the FBI—how many agents do they have in cyber? Less than 200,” he said. “There’s been a very fast shift of traditional crimes moving online and don’t have skilled agents to deal with it.”

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