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Dark Web Crimes: the Silk Road

Written by: Jenae

Trigger warning: drugs


The dark web is filled with the most deprived and awful things including hit men for hire, red rooms, and child pornography. (or the Cannibal Cafe like in episode 23) This portion of the web is not accessible to the general public, as there are many steps that must be taken to even access it. The dark web is categorized as anything that doesn’t show up on traditional search engines like Google. In order to access the dark web, you have to use specific software and Tor. Tor is a service that could be used to keep search anonymous, but with the right software, it can be used to hide your IP address and server location, making all types of illegal and awful activity possible. Essentially, websites use Tor to hide in the overlay network on top of the internet. This process only works if everything is configured correctly.

Now not all things on the dark web are awful or evil. The dark web can be used to access things like Facebook in countries where it’s not accessible or for whistleblower websites. The true draw of the dark web is the anonymity offered by the encryption. A piece of this anonymity includes cryptocurrency. Bitcoin is often used on the dark web because it allows you to buy whatever weird and illegal stuff you want without being traced. This was the perfect thing to be used on something like the Silk Road.

What is the Silk Road:

The Silk Road was an online marketplace where people could buy things like illegal drugs, guns, and other illegal goods, all anonymously. The site described as “the first big fuck you” to the war on drugs. And it was a huge money maker, raking in up to $1.3 million in sales per week never the end of its first run.

Essentially had two levels of protection, Tor and Bitcoin.

Though anyone could set up an anon account and buy/sell through the Silk Road, there were admins who would help with the site and it’s creation and keep it running. The head admin for the Silk Road called himself “Dread Pirate Roberts” (yes, like in Princess Bride. It’s a title passed down to noble criminals in the film).

The welcome page included a message that stated there were rules to the Silk Road, even if there were illegal goods being sold there. Some of the rules including a ban on selling certain things like child pornography, assassinations, or stolen property.

Some posts on the Silk Road including the reasoning for opening it from the Dread Pirate Roberts, stating that by making drugs available in an easily accessible way, they hoped to eliminate violence that can come from obtaining drugs in a traditional way.

The FBI describes the Silk Road as a large criminal conspiracy, but many believe it to be a large experiment in freedom.

The Beginning:

A few months into the Silk Road starting (2011), there was an article written about the site. While this did push traffic to the site, it also ensured that the site was now on the radar of authorities. The New York Cyber branch of the FBI took the lead on the investigation, hoping to shut down the site for good, there was collaboration across the country from law enforcement.

Then investigators found that there was a commission being taken from each seller by DPR. Somewhere between 3%-12% in its initial run, DPR was getting rich off the site.

All of the anonymity made DPR incredibly difficult to track, they had no idea where or who this person was. This would only go on for so long. One officer searched the web, looking for things to connect to the Silk Road. By limiting his search, he was able to find a post on a Bitcoin forum that predated all other posts about the Silk Road. The user, under the name altoid, advertised the Silk Road in that forum. Upon checking the users other postings, investigators found that the same user had posted that they were looking for some tech help to get a Bitcoin market up and running. In this posting, the user left their Gmail address for responses. This would be the Dread Pirate Roberts’ undoing, but the police would not take the investigator seriously in the beginning.

Founder of the Silk Road:

Ross Ulbricht or DPR

The email found by investigators was This email belonged to 27-year-old Ross Ulbricht. Ross was incredibly intelligent, graduating with a master’s degree in materials science and engineering from Pennsylvania State University in 2009. While he was in school, he became infatuated with Libertarian economic theory and political ideas. These ideas will ultimately lead him to creating the Silk Road. Ross had started a few businesses before and nothing had panned out. The Silk Road was a combo of his values, want to be an entrepreneur, and need to make money in a less traditional way.

During the process of the Silk Road, Ross kept an encrypted journal.

The End:

Near the end, DPR employed people for the Silk Road for simple things like settling disputes and password changes. One of those he employed was Curtis Green. Upon accepting employment, Ross asked for a copy of his driver’s license to verify who/where he was, Green sent this to Ross. Curtis Green was blindsided by the DEA and Homeland Security shortly after accepting the position. Green had been a user of the Silk Road, mostly for meds for his chronic pain. When taken into custody, they gave Green a clear ultimatum, cooperate or spend the next 40 years of his life in prison. During this process, they found that nearly $350,000 worth of Bitcoin had been stolen and placed in Green’s account. Green didn’t even know that this money had been placed in his account. DPR was unaware of the arrest.

Curtis Green, employee for DPR

After the arrest, one of DPR’s closest workers (inigo) noticed that $350,000 was missing from the Silk Road account. Upon hearing about the theft, DPR turned to a trusted dealer on the Silk Road (nob). Inigo was able to track down who had stolen the money, Green. DPR then sent the home info to nob to carry out a hit on Green. What Ross didn’t know was that nob was actually a DEA agent. In order to keep his cover, nob and Green created some waterboarding like photos of torture to send to Ross to keep his trust.

That night Ross reached out to another worker and told them the whole situation and that Green had been arrested (found out through a Google search). Green had been arrested on 1/17 but the Bitcoin was not stolen until the 26th. This timeline wasn’t adding up and it had Ross on edge.

By this time, the FBI had been searching for the IP address attached to the server that was hosting the Silk Road for over a year. Eventually, the FBI were able to locate the IP address of the Silk Road server, however it was located in Iceland. With the help of authorities in Iceland, the FBI was able to create a mirror copy of the server and bring it back to the US. By doing this, they were able to see where targeted people (like DPR) were logging in. The FBI traced this IP address to a cyber cafe in San Francisco, just down the street from Ross’s home. After this, the FBI obtained a search warrant for Ross Ulbricht.

In a local San Francisco library, the FBI caught Ross Ulbricht while still logged into the Silk Road. In order to prevent Ross from encrypting his files upon arrest (this can be done with just a few keys), two agents pretended to be a couple in an argument. When Ross looked in their direction, another agent grabbed his computer and one agent placed his arms behind his back.

After his arrest, police determined that Ross had executed hits on 5 other people and no bodies were ever found. Many of the people who knew Ross personally don’t believe this to be accurate.


The charges brought against Ulbricht included money laundering, hacking, and conspiracy to commit drug trafficking. He was never charged for the hits he “took out”, but they were used as evidence in his case. Ulbricht was convicted of all counts, with a jury deliberation time of only 3 hours. He was given two sentences of life in prison without the possibility of parole. On the final day of the trial, the prosecutor stated that the six murder-for-hire cases never occurred.

Ulbricht’s lawyer filed an appeal in 2016, stating that the prosecution had withheld evidence of wrongdoing on the part of DEA agents throughout the investigation, although they convicted. At this time, Ulbricht and his lawyer argued that the sentencing was too harsh for the crime. In 2017, Ulbricht’s appeal was denied and the court upheld his original sentence.

Near the end of 2017, Ulbricht filed a petition for a writ of certiorari (orders a lower court to deliver its record in a case so that the higher court may review it), stating that his 4th Amendment rights (prohibiting unreasonable search and seizure) and his 6th Amendment rights (right to due process, knowledge of charges being brought against you, the right to an unbiased jury, and right to counsel) were violated. In 2018, the US government responded to the petition, stating that a decision couldn’t be made on the first portion until another case with similar concerns around collection of communications data but tossed out the second concern that Ulbricht brought up. In 2018, a clemency petition with 55,000 was sent to the President. Nothing was done with this thus far.

The Silk Road 2 and 3:

Blake Benthall, founder of Silk Road 2.0

The arrest of DPR was not the end of the Silk Road. In 2013, indigo and another member of the former Silk Road re-launched the site under the name Silk Road 2.0. 2.0 had a multitude of problems, including vulnerability in Bitcoin protocol. The site stayed up, but the $2.7 million worth of Bitcoin in the site’s escrow accounts was stolen. It was discovered that this was a problem with a button on the site. In 2014, the FBI and other agencies arrested the owner of Silk Road 2.0, Blake Benthall. He cooperated with investigators and was released. The creator of the Silk Road 2.0, Thomas White, was also arrested but it was unknown to the public until recently. As part of the charges included White admitting to creating child porn and attempting to launch a site to share it on. He was only given a 5 year sentence.

After the downfall of Silk Road 2.0, another dark web market called Diabolus Marketplace renamed itself Silk Road Reloaded in 2015. This site has also been pulled down.

Other than Ulbricht, the sentences for admins, drug dealers, and creators/operators on all versions of the Silk Road received sentences that spanned between no jail time-10 years.

By the time of his arrest, Ulbricht was making nearly $20,000 a day from the site and his net worth was estimated at $105 million. Ultimately, Ross believed he was doing the world some good, by allowing people to freely decide what they could and couldn’t put in their bodies without any legal repercussions. In the end, he broke his own rules and let the corruption get to him, ordering a hit on his own workers.


Silk Road: Drugs, Death, and the Dark Web


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