The Silk Road and the hunt for the elusive Dread Pirate Roberts

Drugs, weapons, poisons, computer hacking tools, murder! Welcome to The Silk Road, where just about anything you can think of was being bought and sold from all over the world, at anytime of the day or night. This is a review of the book ‘American Kingpin: The epic hunt for the criminal mastermind behind The Silk Road’ by Nick Bilton, which tells the story of the brilliant (and somewhat troubled) Ross Ulbricht a.k.a The Dread Pirate Roberts - the mastermind behind The Silk Road, and the attempts by the DEA and various FBI agents to bring him and his empire down.

The story starts of innocent enough with a young and carefree Ross living a very simple life - living in a basement and only having two rubbish bags of possessions - one of dirty clothes and one of clean clothes. From early on in the book Ross is a strong advocate for drug reform, and believes that all humans should have the right to ingest whatever they want. I actually wrote a separate post about this idea here. Being a bit of a drifter and after several unsuccessful attempts at running businesses he decided to have one last shot and start up what would end up being The Silk Road. Although not a coder Ross spent countless hours researching how this would work and worked on the initial code himself - this fact of his inexperience as a coder led to many problems and security issues throughout the book.

At the same time of coding the website Ross was secretly growing magic mushrooms so that he could sell these when The Silk Road was launched. What struck me at this early point was how methodological Ross was with everything he worked on around The Silk Road. I think from the beginning Ross knew not only the potential of The Silk Road, but also the danger if he was caught - that he might end up in prison for life. For this reason he made sure his every move was hidden, private and encrypted - from using TOR browser and implementing Bitcoin as the money for transactions on The Silk Road right down to encrypting (what he thought) was every last piece of evidence linking him to creating this drug empire.

After selling some of his mushrooms, word got around quickly and The Silk Road quickly ballooned in size, with drug dealers jumping on board and selling everything imaginable. As the size and scale increased so did the risk, and Ross (with some help from others he employed) decided to create an online moniker and do away with anything to to with Ross Ulbricht - and they came up with The Dread Pirate Roberts (taken from the book/movie ‘The Princess Bride’). From this point on this is what he was referred to on any forums. Any links to Ross suggested that yes he started The Silk Road but sold it on to the anonymous Dread Pirate Roberts.

Meanwhile, the DEA and FBI agents were finding and confiscating more and more drugs through the US postal service and were becoming fed up as they had little to no leads on who was behind all this and what they could do to stop it. One of my favorite quotes from the book was:

Your postman is a drug dealer. He just doesn't know it

With no other conceivable way they decided to go undercover (online) and interact with The Dread Pirate Roberts through the forums, to gain his trust and eventually bring him and The Silk Road down. DEA agents were able to gain direct contact with Ross - and some had corrupt intentions themselves. One of the agents, Carl Force a.k.a Nob, created several identities and sold insider information to Ross to keep him one step ahead of the law - and ended up extorting over $700k in Bitcoin. This really fascinated me that humans are so influenced by money and can become corrupt, even when trying to fight to bring down a huge drug empire.

The further the story goes on the more Ross had to lead a double life - one as the notorious drug kingpin Dread Pirate Roberts, and the other as a regular 20 something - often switching between the two on his laptop. Ross managed to keep the two lives separate but the strain of running a drug empire was beginning to take its toll. Having to be constantly near his computer, one step ahead of the FBI, and also living this double life.

At some point during the story there was a change in Ross - being the pirate and the leader of a revolution had led to Ross becoming a lot more ruthless. Around $300k of Bitcoin were stolen from him and he ordered a hit out on who he thought was responsible. It is thought that Ross ordered up to a dozen murders during his time as The Dread Pirate Roberts, although no bodies have ever been found. From the Ross we meet at the start of the book it doesn't seem like he is capable of such acts but running an empire where millions of dollars were at stake changed Ross, making him capable of ordering people to be killed.

Although Ross had done a good job at keeping his identity, his humble beginnings came back to haunt him. An FBI agent came across an early posting about this new online marketplace The Silk Road with the name Ross Ulbricht in the email address. Upon hours and hours more research the FBI were starting to put the pieces together and zero in on Ross as The Dread Pirate Roberts. In the world we live in where data is everything and companies such as Facebook and Google collect data on our every online interaction it amazed me that Ross did so well to keep his identities separate apart from a couple of mistakes that turned out to be huge.

Eventually the evidence against Ross built up strong enough for the FBI to swoop in and arrest him. The sting was carefully executed - they had to catch him ’red handed’, with his laptop open logged in to The Silk Road. After arresting Ross, he was finally sentenced to life in prison without parole.

The aftermath of The Silk Road and the ‘legacy’ of Ross Ulbricht has been huge - there has been many further attempts at illegal online marketplaces.

Thanks for reading and as always I would love to hear your thoughts!

All images downloaded from royalty free website www.pixabay.com