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How the DEA tracked this doctor from the Silk Road to her front door

Oliva Bolles was a virtual mastermind. But she left some real-world footprints.


Aja Romano

Internet Culture

Posted on Nov 28, 2013   Updated on Jun 1, 2021, 12:59 am CDT

Every road has a destination—even the formerly vast and anonymous Silk Road. It’s not often that a journey through the Dark Web ends in broad daylight, but its shady network of illicit and illegal business transactions can’t exist without someone to provide the goods IRL. And in the case of a young Delaware doctor, the last leg of the trip is the one that proved her undoing.

In the latest instance of Silk Road scandals to reach real life, two OBGYN doctors, 32-year-old Olivia Bolles and her fiancée, Johns Hopkins instructor Alexandra Gold, were arrested last week on charges of providing prescription drugs like Xanax and other controlled substances to Silk Road consumers in over 17 countries.

Drug Enforcement Administration special agent Mark Trouville tracked transactions through numerous real-life channels, all of which ultimately pointed back to Delaware, and to Bolles, who now faces a 20-year sentence.

Bolles is accused of participating in Silk Road under the moniker “MDPro.” Although Gold faces allegations of helping her package the drugs, Bolles was the virtual mastermind, conducting over 600 sales through a variety of anonymous transactions in which she disguised Oxycotin and other pills by shipping them along with candy.

Like others on the Deep Web, Bolles used Bitcoins and participated in the anonymizing Tor network, which masks IP addresses and allows users to communicate in full anonymity.

But when it came to covering her tracks in real-life, as Forbes reports, Bolles made numerous slip-ups that led the DEA straight to her door. She made suspicious transactions on Ebay with the username “obolles,” which was also the handle she used for her Tormail account. She made transactions through her real-life bank accounts, and rented a P.O. box with her own name, email,  and identifying information—all to send packages with tracking numbers that listed her as their point of origin. Moreover, the supposedly anonymous postal drop she used, unbeknownst to Bolles, snapped her picture.

In some cases, Trouville’s criminal complaint claims, Bolles even sent packages listing a return address in Newark, Del.

The 54-page complaint gives a detailed description of the inner workings of Silk Road, which on the inside functioned like any other online commerce platform. Trouville describes how he simply clicked “add to cart” to purchase an assortment of substances from “MDPro”’s profile page, where she advertised Adderall, Xanax, and hash oil.

Trouville reports that Bolles did about $24,000 in illegal business between the time she created her profile in March and August. With the rising value of Bitcoin, the bitcoins she earned would be worth considerably more today.

Bolles’s arrest illustrates how much more difficult it is to hide a real-life footprint than a digital one. But the ease of tracking her may not necessarily signal the inevitable part of the fall of the Deep Web. Given the number of participants who have flocked to its other shadowy corners in the wake of the Silk Road’s demise, Bolles may well be a lone example of criminal clumsiness rather than a sign that law enforcement is expanding its reach. After all, even Ross Ulbricht, Silk Road’s founder, only got caught because he, too, used his legal name on the IRL end of his business.

Then again, if anonymity in the real world were as easy to achieve as it is online, the Silk Road might still be winding its way through the Internet.

And Bolles might not be looking at 20 years in prison.

Photo via deanslife/Flickr

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*First Published: Nov 28, 2013, 1:29 pm CST