Silk Road

by Eileen Ormsby

It was the 'eBay of drugs', a billion dollar empire. Behind it was the FBI's Most Wanted Man, a mysterious crime czar dubbed 'Dread Pirate Roberts'. SILK ROAD lay at the heart of the 'Dark Web' - a parallel internet of porn, guns, assassins and drugs. Lots of drugs. With the click of a button LSD, heroin, meth, coke, any illegal drug imaginable, would wing its way by regular post from any dealer to any user in the world. How was this online drug cartel even possible? And who was the mastermind all its low roads led to? This is the incredible true story of Silk Road's rise and fall, told with unparalleled insight into the main players - including alleged founder and kingpin Dread Pirate Roberts himself - by lawyer and investigative journalist Eileen Ormsby. A stunning crime story with a truth that explodes off the page.

Genres: Nonfiction, True Crime, Crime, Technology, Drugs, Business, Journalism

352 pages, Paperback

First published November 1, 2014

About the author

Eileen Ormsby is a lawyer, author and freelance journalist based in Melbourne. Her first book, Silk Road was the world's first in-depth expose of the black markets that operate on the dark web.

Eileen's gonzo-style investigations have led her deep into the secretive corners of the dark web where drugs and weapons dealers, hackers, hitmen and worse ply their trade. Many of these dark web interactions turned into real-world relationships, entanglements, hack attempts on her computer and even death threats from the dark web's most successful hitman network as she researched Darkest Web. She now lives a quiet life off-grid as much as possible.

Reviews

[Nancy · Rating 3 out of 5]

Finished: 10 November 2017
Title: Silk Road
Genre: non-fiction
Score: C
Review: This was a quick read....but a real eye-opener! It tells the true story of Ross Ulbricht. He was the founder of notorious online drug market place Silk Road which rapidly grew to become the internet’s hidden one-stop-shop for all things illegal. The author fills in several chapters with stories about several bumbling traders who grew into slick professional business forces. Ultimate bad-boy and scam artist was not Ross Ulbricht -- aka Dread Pirate Roberts (DPR) -- but Tony76!
If you feel like reading something different....try this book about “the internet’s Pablo Escobar”
#AusReadingMonth

[Adrienne · Rating 5 out of 5]

Wow! This was SUCH a fantastic read!

I suspected with this story there would be a lot of computer-speak, and lingo (which there was...but it was really well explained). But above all it is written from so many different sources - distant to, as well as completely immersed in the world of the dark net, and specifically the Silk Road Marketplace.

It really does read like a Hollywood blockbuster...and I'm very excited to see that it is currently being worked into a movie! I imagine it might be a little way off, in that there are many legal proceedings pending against the alleged kingpin and other significant players within the SR market.

But regardless...the way it all played out from inception to its downfall, is a great story with many twists and turns.

I now follow DPR's legal proceedings with interest, and as mentioned...can't wait for the eventual film.

[Emy · Rating 4 out of 5]

I can't think of anything to say, just WOW !!!

[Olivia · Rating 3 out of 5]

So incredibly interesting however I felt that the book barely touched on who Ross Ulbricht is. It was worth listening to the Casefile podcast before reading this because the book didn’t cover everything the podcast did- I also felt some chapters maybe weren’t crucial to the book and maybe these chapters could have been replaced with more information about the investigation- the actual investigation was hardly covered at all.

[Andrew McMillen · Rating 4 out of 5]

A fine summary of the world's most popular online illicit drug marketplace, 'Silk Road' is the debut book by Melbourne-based journalist Eileen Ormsby, who reported on the website and its inner machinations from 2012 onwards. Silk Road offered a place for drug consumers around the world to trade high quality products anonymously, free from violence or police interference, and for a surprisingly long time, it fulfilled its promise of a borderless black market. It was an irresistible story for any journalist who heard about it – myself included – and early on, Ormsby established herself as a strong, non-judgemental voice in a crowded field. Her high visibility and balanced reporting earned her respect among the fickle, often paranoid people who frequented the site, and what Ormsby has set out here is the definitive longform summary of what went on there.

Her chronological account covers the very first online promotion of Silk Road in early 2011 through to its seizure by the United States government in late 2013, and the arrest of its alleged founder, Ross Ulbricht, whose criminal trial took place in late 2014, months after this book went to print. This temporal quirk does not detract from Ormsby's narrative, as much of the book is about what the site represented, and how its users interacted with one another, rather than the typical 'whodunit' that many media outlets preferred to follow – which is understandable, really, as Silk Road was such a revolutionary concept executed so well that it took many people by surprise. The absence of an identifiable figurehead – the typical image of the 'drug kingpin' that we've come to expect – made it a difficult story for many to grasp.

Having used the website throughout its lifespan, and regularly visited its accompanying forums, I was already intimately familiar with much of what is covered in 'Silk Road', but it is to the author's credit that the facts are laid out in a straightforward manner, with little flair or dramatisation; the story is so compelling that it barely needs either trait. This book is already an enlightening historical document so soon after the site's creation and downfall; I imagine that it'll prove fascinating for future generations who wish to learn more about a unique community that married large-scale online technology with illicit drug consumption for the first time.

[Keen Reader · Rating 4 out of 5]

4.5 Stars!

“I’ve never killed a man or had one killed before, but it is the right move in this case.”

First of all kudos must be given for the nice use of 80s sci-fi font in the chapter headings, which works really well with the content. This is a really fascinating account Ormsby’s style is accessible and nice to read, its well-researched and it also has some delightful twists and turns that make for genuinely thrilling reading.

She dispels many of the sensationalist myths surrounding the dark web, Tor and Silk Road, like the hiring of hitmen or crowd funded assassinations. As well as the talk of live filmed torture sessions and organ selling, this is largely written off to the work of scammers and time wasters. She confirms that the reason for the vast majority of people using Tor is because they are tired of being tracked or pestered by ads.

Without doubt the biggest attraction for most of the traffic going to Silk Road was for people looking for drugs, and they seemed to find what they were looking for at a price they were happy with, but as the author shows us, the SR project and philosophy was about a lot more than that…or was it?...

Yes there are scammers and awful people on there, but you would find the exact same kind of people throughout society from high up in religious churches, to global politics and high finance. Ormsby’s reasoned approach allows us to see both sides of the coin and draw our own more informed conclusions by the end.

SR was headed up by the charismatic Dread Pirate Roberts, now unveiled as Ross Ulbricht and very much suffering the long term consequences for his actions. She also covers some of the other rival sites that appeared and disappeared on the dark web, the likes of Atlantis, Sheep Marketplace and BMR (Black Market Reloaded), though none of these could rival Silk Road in any meaningful way. We also learn about the short lived Silk Road 2.0 venture which was a poor imitation of its predecessor.

This was an excellent read from start to finish. Many of the topics explored in here have been updated and some investigated further in Andrew O’Hagan’s “The Secret Life” which makes an excellent companion to this book, for those interested in the subject and I would also suggest O’Hagan’s ghost written/doomed biography of Julian Assange as well.

[Koen · Rating 3 out of 5]

Everything you ever wanted to know about the revolutionary darknet drug market. Well, everything known about it for now that is. There are many, many things i'd still like to know. A lot is still shrouded in mystery and the hard part is; we might never know the full story.
Since i became aware of the Silk Road early 2013 i've been fascinated about the website and it's proprieter Dread Pirate Roberts. There's so much to the story of the Silk Road (and it's competitors and copy-cats). At first there was amazement just about the existence of such a place and the technology behind it. Then there was this Dread Pirate Roberts, a fascinating character not at all like you'd expect the owner of the world's largest online market place for illicit goods to behave. He shared his interesting philosophical ideas in eloquent essays and gained lots of respect and love from the big community he build in rather a short time. Than came the drama. Lot's of drama.
And the drama continues to this day. The alleged DPR is behind bars for life and the Silk Road has long gone. But the genie was out of the bottle and new markets have come and gone. There are apparently more illegal goods listings now then there were at the hight of the Road. And there's drama almost on a weekly basis. The Darknet Markets subreddit is one of my favourites, especially at times when markets are seized or people get scammed. It's all just very entertaining.
But it all started with the Silk Road and that story alone is good enough for a book. Hell, there's a great movie in there ifg you'd ask me.
Eileen Ormsby gives a pretty complete, as far as i can tell, history of the Silk Road and DPR. The book is well researched and an easy read even if you've never heard of the Silk Road. It is a really good story with a lot of intrige. If you've been following the darknet markets over the years there might not be a lot of new information for you but it's nice to have the complete story in one convenient book.
The one problem of course are the questions still unanswered. I for one hope that at some time in the future a definitive memoir will surface from the real DPR. Wether that wil be Ross Ulbricht or someone else? I'm not at all sure.

[Sanjana · Rating 4 out of 5]

Was a quick and interesting read. I might say it delved a bit too much into bitcoin at times, but can’t argue about the links between that and Silk Road, so probably warranted

[Yee · Rating 5 out of 5]

I enjoyed reading this book because it consists of remarkably detailed research from the author. It was a great effort that she was able to explain such a complicated operation more straightforwardly to make it easier to understand. This book is one of the most mind-blowing books that I have ever read.

Book Review: Silk Road by Eileen Ormsby.

[Michael Livingston · Rating 3 out of 5]

A decent and thorough examination of the dark web and particularly its use as a home for innovative online drug markets.

[Mrchristoff · Rating 4 out of 5]

Fascinating and well-written.

[Preetam Chatterjee · Rating 5 out of 5]

There’s a strange pleasure in reading Eileen Ormsby’s Silk Road, because she writes like someone who has stared into the abyss long enough to sketch it from memory, but not long enough to let it redraw her moral compass.

She approaches the infamous darknet marketplace with a kind of pragmatic fascination, a “let’s not moralize too quickly; let’s first understand the architecture” energy. And honestly, that’s the exact tone you need for a book about a drug bazaar run by a libertarian idealist who believed he was building a utopia by selling heroin with customer feedback ratings.

What Ormsby captures so well is the surreal paradox of the Silk Road: a place where dealers used smiley emojis, customer service was impeccable, and buyers left heartfelt reviews for MDMA that made their weekend “transcendent”.

It reads like capitalism cosplay played by anarchists who wanted freedom without governance, trust without law, and community without identity. And yet Ormsby never slips into sensationalism. She keeps her feet firmly planted on the ground, even while describing events that feel like scenes from a cyberpunk novel.

Her narrative technique is crisp and journalistic but emotionally intelligent. She’s interested not just in the marketplace but in the ideals that built it.

The founder, known as the Dread Pirate Roberts (yes, very Princess Bride, very internet), envisioned the Silk Road as a digital experiment in libertarian ethics—no state, no surveillance, no coercion, just voluntary interaction.

You can feel Ormsby wrestling with the seductive charm of that idea. That tension—between idealism and criminality, between free markets and moral vacuums—is what gives the book its intellectual electricity.

And reading this during Covid, when the world was glued to the internet like a toddler to a tablet, the story hits differently.

The Silk Road feels less like a bizarre digital outlier and more like a prototype—an early blueprint for the decentralised, chaotic, trust-fragile online ecosystems we now take for granted. Ormsby shows how anonymity can be both liberating and lethal, how encryption can empower autonomy and violence in the same breath. It feels eerily prescient, like she’s handing us a diagnostic report for the decade that followed.

Her interviews with users, moderators, and law-enforcement operatives form a tapestry of clashing worldviews.

What you get is not a binary but a spectrum—idealists, criminals, philosophers, addicts, bureaucrats, and dreamers all orbiting the same digital planet. And because Ormsby doesn’t flatten them into caricatures, the book becomes weirdly human. You find yourself empathising with unexpected people and recoiling from others whose beliefs seem too slick, too convenient.

What makes this book work so well for a 21st-century reader is its refusal to offer easy closure. The Silk Road’s demise doesn’t resolve anything; if anything, it intensifies the ambiguity around digital morality. And Ormsby subtly nudges you toward the uncomfortable truth: innovation often grows first in the soil of illegality.

The early internet, fintech, and encryption tech—so many “respectable” technologies began at the margins. The Silk Road may have been a criminal haven, but it also pushed forward conversations about censorship, privacy, crypto-economics, and digital sovereignty in ways lawmakers still haven’t caught up to.

And you, with your love of narrative complexity and transgressive spaces, will appreciate this deeply. Silk Road reads almost like a philosophical thriller disguised as investigative nonfiction.

It’s fast yet thoughtful, dark yet strangely idealistic, and grounded yet pulsing with the chaotic energy of human desire.

[Paul Quick · Rating 4 out of 5]

well researched. Fitting that Dread Pirate Roberts was himself victim to numerous scams. Also, his libertarian philosophy failure is a expose of others who have similar beliefs.

SR was created to be accessed thru the TOR browser (onion website that does not retain a cookie audit trail). It was coded using PHP/CURL where PHP is script-like (w/embedded HTML) to be interpreted on the web server. CURL is simply a library of useful PHP objects. Obviously, the client has its own codings (unsure of language for SR). The security method PGP. Fiancial transaction were made using BitCoin so the browser, currency and scripting is all geared to make communications hidden.

Some of the features of SR were a Tumbler to facilitate money laundering, an escrow-system to insure the buyer can verify goods received before selle is paid. SR admin holds the funds in escrow and releases it on buyers verification.

SR started in April 2011 initial marketing done in REDDIT threads. The founder philosophy seemed to be agorist (Libertarian) i.e. trading markets free of government oversight and taxes. The original owner seemed to operate from Apr-2011 until Oct-2012. At that time , website taken down, new admin/moderators were assigned and probably Ross Ulbricht took the reins. It is unknow who the the original DPR was (Dread Pirate Roberts - character from Princess Bride). In Sept-2013 Ulbricht admitted he was not the founder on a blog. By oct-2013 SR was brought down by a sting orchestrated by government agencies.

SR operated pretty smoothly until 2013 when scammers started appearing as users/dealers on their website. Also, around that time competitive Black market Sites came and went BMR(Black mark reload) SHEEP, Atlantis (media-hungry, possibly a government HoneyPot).

Part of the government sting was FriendlyChemist user pretending to be in-debt to the RedandWhite User(aka hells Angels). DPR paid to have FriendlyChemist murdered which would be very contrary to the philosophy the original DPR.

The reader is left with the impression that the original DPR is probably still at-large and that Ross Ulbricht was possibly a partner or probably knew him since when they were hring admins Ross Ulbricht email address was used. This actually supports the position that mr. Ulbricht was not the original DPR.

[Mike · Rating 5 out of 5]

Excellent account of the history regarding the Silk Road, the drug-selling website and the legendary online community that surrounded it.

If you just want a cursory overview of the Silk Road, look elsewhere. (Wired magazine wrote an excellent long-read article about the Silk Road story, can be found online.)

But for those who want to go balls-deep in the lore of SR, this is the place. This book pulls no punches in providing all the details necessary to paint a complete picture of how SR began, what it was like in its heyday, and ultimately its epic downfall.

The author even goes so far as to include many excerpts of text straight from the SR message boards to help flesh out this mostly online story. If it weren't for 90% of the story being about people sitting behind computer screens, this would make prime material for a Hollywood blockbuster. (It worked for Facebook!)

Well-researched, documented, and interestingly told.

[Joe · Rating 3 out of 5]

Inconclusive.

I understand that it explores the world of the Dark Web and so by nature, most of the book will point to inconclusive facts. However, I found this "feature" an annoying flaw. I would understand if the author had discovered concrete facts worth reporting. Most of the chapters ended with an air of uncertainty or obvious speculation.

I gave it three stars because it was interesting to read about Silk Road. It gave a good description of the community and how Silk Road represented an ideology. As an outsider, I thought it was about drugs and hitman. I only came across the sensationalist media reports. This book cleared that up and gave a non-biased account of the dark web marketplace.

[ANGELA PETRIE · Rating 5 out of 5]

I dreaded finishing this

This is without a doubt, one of the best books I have ever read. I first found out about Silk Road not that long ago. I’m always late to the party! I was very intrigued and wanted to find out more, after doing some research I figured that, this book had been given such positive reviews, I would start here. Silk Road takes you from the beginnings of the site right through to the end. This book doesn’t exactly give an opinion on Silk Road one way or the other but just advises the facts and let’s you make up your own mind. Read it if you’re interested in the site and find out a bit of the dark web to boot.

[Brenna · Rating 5 out of 5]

I will be honest, I accidentally read this book. I meant to read Ormsby's other title "The Darkest Web". Despite having a basic knowledge of Silk Road's history, Ormsby's writing kept me engaged to the last page. Multiple quotes and perspectives were woven into the timeline with ease helping readers understand many perspectives, issues, and characters that created Silk Road. Excited to read the right book next after this amazing read!

[Yanty Chen · Rating 5 out of 5]

Really love on how the author presented Silk Road,the game changer of online drug trading. Her comprehensive review covered from the birth of Silk Road,the charismatic leader Dread Pirate Roberts,the lively community,the scam,its fall and the shadow left behind,not forgetting the bitcoin and Onionland,the two basic foundation that made the whole things existed

[Jan · Rating 5 out of 5]

The book is well researched and well written. It's a good read.

I have become interested in the rise and fall of the silk road since "The Untold Story of Silk Road" in the WIRED Magazine 2015-05 (https://www.wired.com/2015/05/silk-ro...)

[Jill Meyer · Rating 5 out of 5]

Darknet.onion

Great, easy to read book which provides the history and downfall of the original Silk Road. Read this in two day, exciting, interesting and fast paced. Highly recommend.

[Jarrod Brown · Rating 3 out of 5]

An easy and quick read. I was able to read the book cover to cover on a flight from Houston to LA. Very informative on the darkweb market place Silk Road and how it developed and was eventually taken down.

[Brianna Moulton · Rating 4 out of 5]

Very well written! Learned a lot about the dark web and bit coin’s role in the online drug trade. Very interesting how the community of Silk Road was so tight knit and supportive of one another. Highly recommend!

[Ellen · Rating 3 out of 5]

A diverting dip into the dark web, with colourful characters doused in alternate ideas.

[Reader · Rating 5 out of 5]

Holy cow.

[Camerer Marsh · Rating 4 out of 5]

Very informative. The structuring of chapters was odd, things would be brought up and not elaborated on, but other than that its probably rhe best book out there on the topic

[Francis Telegadas · Rating 5 out of 5]

Interesting book about the rise and fall of silk road. Very well written

[Donna B · Rating 5 out of 5]

Well written & understandable account of Silk Road from its beginnings to its end.

[Ross Warren · Rating 5 out of 5]

Good read

Good overview of market and how it operated. Fascinating to read how concept caught on and scale relative to how little of a “workforce” it took to operate

[Hussain · Rating 1 out of 5]

Although it wasn't a total waste of my time, you get nothing useful from reading this book, sure it describes the Silk Road community in detail but there is (0%) information about the investigation and take down which the only reason you would want to read a book of this kind, my recommendation is to go online and search the magazines, newspapers, forums and blogs for any real information.

[Joel · Rating 4 out of 5]

Three-and-a-half stars. An easy and interesting read, but Ormsby's writing isn't fantastic. Her editor ought to have been a lot tougher on her, as she repeats herself several times and outs herself as a bit of a square, almost but not quite understanding the technology and associated jargon.