How One Mistake Took Down Silk Road Mastermind on Dark Web

Ross Ulbricht, who was born in Austin, Texas, in 1984, was the brains behind Silk Road, the largest online black market in history. Federal investigators detained Ulbricht on October 1, 2013, at a San Francisco public library where he was running the website.

Over the course of its two years and ten months of operation, Silk Road processed close to $214 million in sales utilizing Bitcoin as the method of payment. Ulbricht wanted to build a contemporary marketplace where people could shop anonymously and without leaving any digital footprints.

Regrettably, Ulbricht's actions on the dark web created a digital footprint that ultimately led to his capture and the collapse of his empire. On Ulbricht's computer, federal authorities discovered a notebook that detailed his plans to establish such a platform.

Ulbricht's upbringing was content despite his prosperity, and he continued his father's boy scout tradition by earning the highest rank of Eagle Scout.

Ross Ulbricht was a diligent student with a laid-back hipster persona who excelled on the SATs and was awarded a full scholarship to the University of Texas at Dallas to study physics.

Ross Ulbricht at 18 during an Eagle Scout speech.

Afterwards, he was awarded a second full scholarship to pursue a master's degree in materials science and engineering at Penn State, where he solidified his libertarian views.

Ulbricht founded Silk Road in January 2011 because he desired to build a world free from institutional or political control. The only way to access Silk Road, a secret online market for illicit products and drugs, was through the program Tor, which masks the real IP addresses of connected computers to protect users' identities and prevents government tracking.

Ulbricht used a jumble of random characters and numbers that ended in dot onion as the site's address, which he learned to code himself.

Julie Vie and Ross Ulbricht

Ross Ulbricht sought assistance from a buddy, Richard Bates, on a Bitcoin community forum to help him establish his online marketplace. Richard Bates provided coding assistance. Ulbricht also informed Julia Vie, his girlfriend, about the psychedelic mushrooms he was cultivating and offering for sale on his website.

In the end, Silk Road would provide a wide variety of substances for sale, including cannabis, cocaine, LSD, ecstasy, and heroin. Ulbricht advertised Silk Road as "an anonymous Amazon.com" via posts on forums like the Shroomery and a Bitcoin website under the alias "altoid."

Even though the drugs were concealed in CD and DVD cases and delivered with fictitious return addresses, officials were suspicious of the printed mailing labels. However, Ulbricht's decision to make his email public backfired on him.

A little package containing a single pink ecstasy pill was found in 2011 by Department of Homeland Security agent Jared Der-Yeghiayan traveling through Chicago's O'Hare International Airport. Der-Yeghiayan discovered that more parcels had arrived and that they had originated from the Silk Road website.

After doing some online investigation, he came upon a piece written by writer Adrian Chen that garnered millions of views and popularized Silk Road. Politicians like Senator Chuck Schumer, who demanded its closure, were interested in the website quickly.

The possibility that Silk Road could aid in other illicit operations like money laundering and terrorism also worried U.S. officials, in addition to drug sales. Till Ross Ulbricht's capture in 2013, Silk Road operated in spite of efforts to shut it down.

Richard, a buddy of Ulbricht, persuaded him to close Silk Road as it attracted attention. After relocating to Australia, "Variety Jones," who had messaged Ulbricht on the website, became his right-hand man.

A screenshot shown on November 11, 2014, at a press conference in the Land Office in Wiesbaden, Germany, shows Silk Road offering speed for sale.

Ulbricht made the decision to encrypt all of his files because Jones brought attention to the website's security flaws. Jones suggested Ulbricht’s alias, "Dread Pirate Roberts," and assisted him in realizing the potential scale of the website.

With around $214 million in revenues, Silk Road grew to over 100,000 customers in just two years. The Feds still didn't know, though, who was behind Silk Road.

Governmental organizations raced to pin down the notorious Dread Pirate Roberts, the brains behind Silk Road. Agent Der-Yeghiayan of Homeland Security went undercover as a customer, made 52 purchases, confiscated items, and detained a few persons.

He even assumed the identity of Cirrus, a Silk Road employee, and received instructions straight from the Dread Pirate Roberts. As a member of a task group, DEA agent Carl Force was also conducting research under the alias "Nob." Dread Pirate Roberts, with whom he had a cordial relationship, was unaware that he was communicating with a DEA agent.

Later, it was revealed that force was corrupt. Ross Ulbricht, often known as the Dread Pirate Roberts, was taken into custody in 2013 when Silk Road was shut down by the government. Ulbricht was given a life sentence in jail despite the defense's assertion that he had turned over the website to others.

The government thought it had defeated Silk Road, but since then, new darknet markets have appeared, showing that the fight against drugs is far from done.

DEA agent Carl Force and Security Service agent Shaun Bridges, two members of the Baltimore task team looking into Silk Road, were found to be corrupt. Force claimed to have "insider" knowledge from a government source to persuade Dread Pirate Roberts to give him $50,000 in Bitcoin.

Later, he claimed he was never paid, but in reality, he transferred the Bitcoin to a personal account. Bridges stole 20,000 Bitcoin from user accounts on Silk Road using his admin access, and by the time he sold the money, it had grown to $820,000.

Dread Pirate Roberts wanted to rough up Silk Road customer service representative Curtis Clark Green after he was found in possession of a kilogram of cocaine, so he asked Nob (a.k.a. DEA agent Carl Force) to beat him up. But he had a change of heart. Dread Pirate Roberts was aware of Green's true identity because employees had to present their government identification in order to be hired by Silk Road.

Dread Pirate Roberts paid Nob to beat Green up for $80,000 in Bitcoin because he didn't want to take the chance that he would divulge any information to the police. Ulbricht later received images of Green's purported demise, but Agent Force manufactured it using Campbell's Chicken & Stars soup.

Although blackmailers and extortionists had targeted Silk Road, there was no proof that anyone had been slain, and Ulbricht was never accused of murder for hire. The DEA turned to the FBI's Cyber Crime unit in New York for help since the federal agencies were still unable to determine who Dread Pirate Roberts was.

When coding faults were discovered on the Silk Road website that allowed IP addresses to leak, it took nearly a year for FBI special agent Chris Tarbell to realize they needed to wait for Dread Pirate Roberts to make a mistake before they could eventually arrest him. This led to the identification of an Icelandic data center as the location of the Silk Road servers.

Agent Tarbell took a flight to Reykjavik, where he was given a disk containing data from the servers by Icelandic officials. The FBI had access to a variety of information, such as the total number of transactions completed, who logged in and out, and the "Frosty" name of the main computer that the Silk Road servers communicated with.

They also discovered that Dread Pirate Roberts had lately used a San Francisco cafe to check in using a VPN and had been using an encryption key that ended in frosty@frosty. Ulbricht relocated to San Francisco to reside with a boyhood buddy after coming back from Australia.

The FBI has since narrowed their search to San Francisco. Gary Alford, an IRS agent tasked with following the money, came across Ulbricht's online posts under the alias "altoid," where he requested Technical support and provided his personal email address. A query about Tor was also posted on Stack Overflow by a user going by the moniker Altoid.

The identity of Dread Pirate Roberts, who ran Silk Road, was revealed by Gary Alford, an IRS tax inspector. He came upon internet writings by "altoid," a person who later changed their name to "Frosty." Alford pointed out that "altoid" had also made a post on a Bitcoin forum requesting IT assistance and had supplied a private email address.

He ultimately put the pieces together and realized that Frosty was the name of the computer that the Dread Pirate Roberts was using. Federal authorities started to pursue Ross Ulbricht when Alford came to believe that he was the brains behind Silk Road.

Ulbricht finally acknowledged that he "hypothesized" ran Silk Road but insisted he was not the dreaded Dread Pirate Roberts. But later evidence gathered by federal agents demonstrated the opposite.

To make an arrest of Ross Ulbricht for operating Silk Road, authorities required solid proof. He had to be apprehended while signed in to the website as the Dread Pirate Roberts and with his laptop unlocked.

Dread Pirate Roberts logged on to the Silk Road on October 1, 2013, and Homeland Security agent Jared Der-Yeghiayan, acting as a staff member, began speaking with him. At the San Francisco public library, Ulbricht was present.

Der-Yeghiayan talked to him while signaling the other agents stationed in the library to approach Ross Ulbricht and arrest him.

Family and friends of Ulbricht expressed disbelief. How could the friendly, fun-loving man they were familiar with run a huge drug market? They were unable to believe it. Ulbricht was charged with seven offenses, including running a persistent criminal operation and selling drugs online. He entered a not guilty plea to every accusation.

The experiment lasted three weeks and started on January 13, 2015. Several of Ulbricht's supporters turned out because they thought a guilty verdict would be an injustice. Ulbricht's defense lawyer argued in court that Ulbricht wasn't the Dread Pirate Roberts and that he had handed Silk Road to another person.

The jury, however, didn't agree. A federal jury convicted Ross Ulbricht responsible for all seven charges on February 5, 2015.

Ulbricht had hoped that Silk Road would be so popular that he would become well-known. Yet perhaps not in the manner he had planned, his desire came true. Later, the FBI discovered that Roger Thomas Clark, a Canadian detained in Thailand in 2015, was Ulbricht’s mentor, Variety Jones.

Carl Force, a former DEA agent, was given a 6 1/2-year prison term for extortion, money laundering, and impeding the course of justice. Shaun Bridges, a former Secret Service agent, was found guilty of money laundering and obstructing justice and received a sentence of over 6 years in prison. Then, he received ANOTHER two-year term for stealing Bitcoin from the American government.