Analogue Players In a Digital World: How Silk Road Stumped the Justice Department

4 minute read

Posted by: DeepDotWeb November 20, 2013

It just so happens that the first Silk Road still has the feds stumped at best.  Even with all of their taxpayer-funded technological savvy, they still can’t seem to track drug traffickers through the Tor network, and are still hopelessly befuddled, as to why they can’t seem to follow the money trail in bitcoin transactions.

Indeed, the Silk Road was taken down, the drug bazaar’s ringleader imprisoned, and several others arrested for their activities; but the interesting aspect of this case is that the US Department of Justice had to flip their investigative methods upside down.  Usually, they would be able to track these lawbreakers right down to their computers and bank accounts –but because of Tor and the blossoming bitcoin [BTC], they had to resort to those long-forgotten methods of pounding the pavement.

Such as?

Undercover agents, seizing packages, busting in doors, capturing servers, and posing like contract killers.  However, even though the FBI is now the proud owner of Ross Ulbricht’s (the former Dread Pirate Roberts’) bitcoins, they can’t even access the account, because the sly captain decided to encrypt his wallet.  A shifty one, he is.

Operation Marco Polo

Perhaps the fed’s operational name had something to do with the old Silk Road being an obvious allusion to the ancient trade route to the Far East –the feds decided to name their little project, Operation Marco Polo.  How clever of them.

One of their tactics for taking down Silk Road members was keeping the operation quiet until they were ready to move in on ‘DPR’.  For instance, one of their first arrests was a top vendor on the site, Jacob Theodore George IV in Baltimore, Maryland, but didn’t report it to the press.  What tipped them off?  According to, George ‘the fourth’ wasn’t the savviest in keeping the feds off his trail:

“On July 6, 2011, shortly after authorities in Baltimore began looking at the drug emporium, digitalink revealed in a post to a Silk Road forum that a U.S. Postal inspector had contacted him about a package addressed to him that contained a suspicious white substance (that was in fact methylone) spilling from it. The postal authorities refused to deliver it. Fellow Silk Roaders warned George to ignore the agent and let the package go, but digitalink wouldn’t listen.”

However, many quip at the idea that George was considered a ‘top vendor’, as he was perhaps picked for being an easy target.  The comments below the Wired article tell another story.  On Reddit, poster, ‘badgrl2’ called George, “low hanging fruit”.

The Impossible Task of Hunting Invisible Pirates

It took the feds years to track down the infamous ‘DPR’, knowing that his arrest would just about bring a close to Silk Road’s operations.  However, they just couldn’t seem to do so through tracking transactions.  Instead, they had to rely on undercover buyers and sellers, and holding up contraband in transit:

“Investigators say there are at least half a dozen other arrests currently in the works. In addition, U.S. Postal Inspectors and Customs and Border Protection agents have seized at least 3,000 suspicious packages that authorities say can be tied to Silk Road.”

However, even the feds admit that they had to rethink their investigative strategies for tracking down the Silk Road lawbreakers.  Not only were they confined to wait until their prey made mistakes, overlooking their own operational security, but they had to seek out ‘suspicious packages’ in the mail.  Proving who was who, seemed to have been another matter entirely:

“Federal agents say the use of Tor and Bitcoin were major obstacles for them and that investigating the site was “uncharted territory” that involved a reversal of their usual investigative methods. Instead of starting with probable cause against a specific suspect who is already identified and then obtaining a search warrant to collect more evidence, the investigation of Silk Road involved collecting evidence from the site first and then trying to identify individuals.”

The feds admit that onion network has been stumping their efforts all along.  Ironically, this type of network was developed by US Naval Intelligence, but it is now being used to evade the same government that created it.

We can be fairly certain that the feds have realized they are sailing in ‘uncharted’ waters, a massive expanse of the sea that is owned by anonymous pirates –and it’s only the pirates who accidentally slip overboard, who are the ones that get burned.  The Tor network and the bitcoin, the two maritime gods of the deep (web) still appear to be keeping anonymous sailors safe.

Will the authorities soon be able to control these seas?  It’s a long shot.  But, in the meantime, Silk Road 2.0 is open for business.  These pirates sure don’t waste time.  There are drugs to be sold, and bills to be paid.


Updated: 2013-11-20