Exclusive Q&A with Eileen Ormsby, Author of ‘The Darkest Web’

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Eileen Ormsby
Melbourne-based journalist Eileen Ormsby. Credit: Philip Gao Photography.

When investigating the depths of the dark web, the most effective way to fully understand and unpack its underpinnings is to dive into the scene completely.

This is precisely the commitment that writer Eileen Ormsby has held in her years of reporting on the darknet and all its subcultures. Much like how war correspondents work best when they embed themselves into the territory, Ormsby has opted to seek insights directly from the inside.

She has also been forthright about her role as a journalist in pursuit of perspective, and this choice to let her identity be known has gained her plenty of access to the subjects she wants to write about.

In 2012, Ormsby began recording these experiences on her website, AllThingsVice.com. She later wrote a book detailing the story of the Silk Road.

Hot off the presses is Ormsby’s latest work of nonfiction about the darknet, titled ‘The Darkest Web: Drugs, Deat, and Destroyed Lives…the Inside Story of the Internet’s Evil Twin.”

The book zooms in on three kinds of darknet communities. Fittingly, Ormsby presents these subjects in order—dark, darker, darkest.

Your TOR usage is being watched

Part I covers darknet markets, starting with the birth of the Silk Road, profiling the key individuals involved in illicit trades and chronicling the rise of other sites in SR’s place.

Part II then deals with the emergence of hitman-for-hire services, attempted and hoaxed assassinations, and the figures associated with the contract killing market.

Finally, Part III delves into the more horrific and extreme activities taking place in the dark web, covering atrocities from child exploitation to hurtcore.

In timing with the book’s recent release, Dark Web News landed an exclusive interview with Eileen. We talked about her reporting process, her relationships with sources, common darknet myths, her views on Bitcoin, her recommendations for staying secure and anonymous on the dark web, and more.

The Darknest Web book cover
The Darkest Web” by Eileen Ormsby

Here’s our Q&A:

How did you first gain interest in the dark web? Are you able to trace back your interest to a particular point in time?

I was a lawyer for a Magic Circle firm in London, working for the 1 percent, when the GFC hit. I had a bit of an existential crisis about working for the bad guys and eventually quit the law to become a writer. When my friend introduced me to Silk Road, they also introduced me to Bitcoin, which of course was developed partly in response to the GFC. It was the change and revolution I needed at the time.

The move from law to writing is quite the career shift. Do you think the knowledge base and skillset from your background in corporate law helps you better understand the dark web and how the markets are able to thrive in the digital ecosystem?

Maybe, not sure my particular law practice did. I do know that being a lawyer was a lot more lucrative than being a writer, but I’m much happier now.

Knowledge about the Silk Road became mainstream after a 2011 Gawker article. In interviews, you have mentioned being intrigued by the piece and wanting to further explore the SR market territory. How did you initially enter the dark web and research the market yourself? Were you hesitant?

I had friends using it and they showed me. I spent months getting to know the place before coming out as OzFreelancer, the username I used everywhere and which was connected to my real name.

I discussed the first news feature I wrote with DPR and other members of the community before I wrote it, then started AllThingsVice.com and became a really active member of Silk Road.

With every event you write about in ‘The Darkest Web,’ you seem to always make a point to offer some sort of historical context for the community or topic you’re discussing. What is this process like? Did you look to anyone for advice about which points to flesh out with contextual details?   

It was really organic. As I wrote what happened, it would occur to me to think about where the origins of things were. These things didn’t just appear out of nowhere, they all had some sort of historical context that brought us to where we are today.

It was for my own interest too. I find it fascinating to research the origins of hitmen, snuff films, etc.

What motivated you to make the choice to investigate the dark web’s more extreme subgroups in Part III of the book? Were they more sinister than you had previously thought? Or did their reputation meet up to your expectations of the reality?

I knew if I was going to write something called The Darkest Web, I would have to talk about the darkest topics. I did very little actual dark web exploring; the owner of Hurt2theCore, Lux, was from my home city of Melbourne, Australia and I was able to attend all his court hearings and read through the evidence. Most of the information I have comes from there.

I was careful to never go to any sites where I would view images or films—once you see that sort of stuff you can’t un-see it. The scene-by-scene description of Daisy’s Destruction is haunting enough and another description about a little disabled and mute girl still makes me sick to my stomach.

The one place I did go was the forums where predators would talk. That was sickening as they try to justify and normalize what they do.

The whole section was difficult to write. When people post on Reddit, etc. asking for the really dark stuff, the really gory stuff, they are not thinking of what is available on the hurtcore communities.

In the book, you describe in detail your relationship and communications with Yura of hitman-for-hire site Besa Mafia. Are you still in touch with him?

I haven’t heard from Yura in a few months now. We got to the point where we would chat about our families and used lots of smiley faces. I really hope he’s okay and using his millions wisely.

—Related Dark Web News coverage on Besa Mafia—

Do you think there’s any indication that Yura has acted on his stated intention to work with law enforcement since you submitted your manuscript?

There’s been a bunch of arrests of people ordering hits on Crimebay, so I guess LE is getting that information [from] somewhere.

—Related tweet—

In the Afterword, you talk about how your opinions of Yura shifted as time went on and you got to know him better. Have you had similar changes in opinion as you learn more about the subjects you write about? You talked a bit about this struggle when it became public that Dread Pirate Roberts had been ordering hits on people.

I was bitterly disappointed in how DPR went down that route. It made so much of what came before, what we could see publicly, seem like a sham. I still think Silk Road was an amazing, revolutionary endeavor, but I wish it had been able to survive as the violence-free utopia it was supposed to be.

Meeting Mongoose/Variety Jones—I liked him more than I thought I would.

Meeting the other three Silk Road lieutenants—they turned out to be very much how I expected they would be.

—Related AllThingsVice posts about Variety Jones—

What did you expect about Mongoose/Variety Jones before meeting him? How did you expect him to be and when did you come to the realization that he was different from what you thought?

I sort of thought he would be as he was—a little manic and fast-talking—but he was smarter and more charming than I expected.

In past interviews, you’ve brought up your thoughts on drug reform. In your initial stages in researching SR, were you ever skeptical about its potential to drive drug reform efforts? Has your opinion changed over time?

I thought Silk Road was going to change the face of drug dealing. I was naively thinking that we were really on the cusp of ending the War on Drugs and that people would actually take notice of a community like Silk Road and think that it was a little glimpse of what a post-prohibition world might look like: safer imbibing, support and health advice for those who need it, violence-free.

Obviously, the DNMs are not going to drive drug reform, but I am still optimistic that it will happen.

What are your thoughts on the Bitcoin boom that has taken shape over the last year or so? The mainstream media narrative in covering crypto’s history tends to miss the fact that the first real application of Bitcoin was on darknet markets. What do you think about this?

Yeah, a lot of people seem to want to deny how Bitcoin became what it is today. BTC was worth less than $1 when Silk Road started and its practical application was able to be tested and proven very convincingly. Would it have risen without the DNMs? What other application of it has been as phenomenally successful and in constant use as the DNMs?

Most people who “invest” in Bitcoin are bandwagon jumpers looking for a get rich quick scheme and don’t really understand what it is or was supposed to be.

—Related: The Evolution of the Dark Web with Bitcoin—

How do you judge the potential effectiveness of darknet crawling techniques used by law enforcement? Do you think they pose a real risk to darknet market users?

I actually did a show the other day with a federal officer/Ph.D. student who is right at the forefront of dark web crawling and categorization. They are more centered on finding child exploitation than DNMs. You don’t need crawlers to find DNMs—they advertise themselves! 

What are the primary myths of the dark web as it’s usually portrayed?

By far the biggest myth is that it’s 10 times larger than the internet. I mean, this should be common sense anyway, but it gets propagated by tabloid media all the time. Obviously, it comes from people using the terms “deep web” and “dark web” interchangeably when they are different things, as I’m sure your readers know. 

—Related video: The Dark Web Vs. The Deep Web—

When it comes to myths of what can be found on the dark web, it is the whole idea that there is a further, deeper, darker section of the dark web, called Mariana’s Web or the Shadow Web, where only a select few discover the key to unlock the greatest horrors or government secrets and alien abductions.

The most popular myth of all is Red Rooms, where people—usually women—are tortured to death live on camera while those who have paid to watch type in torture commands in a chat box. Think the movie Hostel, with webcams. There is some truth to this rumor, but the execution is not like you see in the movies. Most notably, because it involves children, not adults.

What are your go-to resources for finding accurate information about the dark web?

I go to the source. I’m not going to name my onion sites, but there are several forums that have consistently high quality information.

But without sounding like too much of a dick, I want to *be* the go-to resource for accurate dark web info.

In a world where our privacy is increasingly compromised on the clearnet/surface web, do you think more average internet users will be flocking to the dark web in search of anonymity?

I think the dark web technologies will be coming to our computers as more people seek to claw back their right to privacy. It is not feasible to simply live our lives offline, so I think people are really going to start demanding genuine control over who can take our information and what they can do with it.

—Related: Resources for safeguarding your anonymity online—

As you know, several DNM subreddits have been banned over the past few weeks. What are your thoughts on Reddit’s ramped up content moderation tactics? Any effective alternatives you can recommend?

I’m not that concerned about it. There was always far too high noise-to-signal ratio in Reddit and it produced a lot of crap posts about the aforementioned myths. There are plenty of forums on the actual dark web where people can chat.

—Related coverage: Dread, A New Reddit-Like Service for the Dark Web—

I’ve noticed in some of your posts (example) that you recommend IPVanish as a good VPN. What other tips or recommendations can you give for maintaining your security and anonymity on the dark web?

The Tails/Tor combo is more than enough for most people. However, to truly be secure and anonymous on the dark web you need to:

  • Learn all you can from reliable sources. Use critical thinking when weighing up the accuracy of information. Make educating yourself an ongoing commitment.
  • Learn and use PGP encryption. It is by far the strongest security weapon we have, yet hardly anyone uses it.
  • If you don’t know someone in real life, you don’t know them. Many people forget this and imagine themselves to be “friends” with others because they chat online. It’s much easier to hack a human than to hack a computer and social engineering is the strongest weapon available to anyone who wants to de-anonymize you.

What’s next for you? I assume you’re super busy touring and speaking to the press at the moment. You mentioned you aren’t particularly interested in writing another book about the dark web. Are there any other types of projects on tap for when things settle down?

I’ve started writing a series of novels – “ripped from the headlines” thriller fiction (dark web based of course). Also I’m in talks with a couple of different TV networks/production companies about being a dark web consultant on their shows. There are some things going on in the Bitcoin/crypto space that could possibly have a book in them.

My biggest problem is choosing a project and I am a master procrastinator.

What do you take away from the experience of writing ‘The Darkest Web’?

Honestly, it has been so much a part of my life for the last five years, that it’s become almost normal to me. I find it hard to believe that there’s so many people who have no idea about the dark web, when I’ve been in it and talking to people within it almost every day. I do think I’ve done all I need to now though. I can’t imagine there is another dark web book in me.


‘The Darkest Web’ is available on Amazon Kindle and in print. You can also find it on the publisher’s website.

Eileen Ormsby’s first book, ‘Silk Road: The Shocking True Story Behind the World’s Most Notorious Online Drug Market,’ is available here.

You can find Eileen on Twitter, Reddit and on her website at AllThingsVice.com.

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The articles and content found on Dark Web News are for general information purposes only and are not intended to solicit illegal activity or constitute legal advice. Using drugs is harmful to your health and can cause serious problems including death and imprisonment, and any treatment should not be undertaken without medical supervision.


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