Cryptonomicon is the quintessential hacker novel. The author, Neal Stephenson, describes a story that is set around the intersection between the discovery of world-changing math insights and the incipient designs of our computer science founding fathers. Stephenson delights in explaining how all of these things go together. His collection of fictional and nonfictional characters orbits each other across a thousand pages and propels the reader through dual timelines of World War II and the dot-com startup decade of the 1990s. The result is a multigenerational treasure hunt worthy of an Indiana Jones adventure, but unlike Indiana Jones, this is not a light read. It is dense with ideas. You do not skim through this looking for the good parts, but if you take the time to savor the journey, you will not be disappointed. You will be fed cyber security history, rollicking adventure, heartbreaking tragedy, the pleasures and perils of a multigenerational family, and the awkwardness of several geek love stories all told from the hacker perspective. There is something for everyone here, and you owe yourself the pleasure of finding your favorite part. In other words, it is part of the canon. You should have read this by now.
Stephenson published Cryptonomicon in 1999, and it is the best hacker novel I have ever read. I use the word “hacker” here from the old-school definition -- not computer trolls who spend their time breaking into systems for fun and profit but technological wizards who have a genuine passion for learning about how things work and making the world a better place with that knowledge.
I admit it: I am a fan-boy of Mr. Stephenson. He has written several of my favorite hacker novels over the last two decades:
- Snow Crash (1992) – A classic in the cyber punk genre
- The Baroque Cycle (2003) – A three-volume collection of historical fiction that weaves in some old-school hackers like Sir Isaac Newton and Gottfried Wilhelm Leibniz and whose fictional characters are related to the characters in Cryptonomicon
- Reamde (2011) – A modern-day hacker novel that touches upon many of the same themes as Cryptonomicon
As you could expect, it is a dense read. One fan and author, Charles Yu, describes the book this way:
"A copy of Cryptonomicon has more information per unit volume than any other object in this universe. Any place that a copy of the book exists is, at that moment, the most information-rich region of space-time in the universe." 
You get the idea. It is not a novel you are going to get through in a weekend.
One of Stephenson’s great gifts is his ability to juggle many seemingly unrelated and interesting characters within a story and then surprise the reader about how they are all connected. He does it in Snow Crash, The Baroque Cycle, and Reamde. He crafts four main narrative arcs in Cryptonomicon and uses a parade of major and minor characters that intersects at key moments to propel the story. Three of the arcs happen during WWII, and the fourth happens during the Internet boom of the 1990s.
Team Bobby Shaftoe: Shaftoe is a US Marine who starts the story in the Philippines just before WWII begins, loses his Filipino fiancé because of the ravages of war, becomes one of the operating arms of the Allied code breakers at Bletchley Park, and spends a good portion of the book working his way back to the Philippines to find his lost fiancé.
Team Goto Dengo: Dengo is a Japanese military engineer. He gets caught behind enemy lines, escapes & evades his way across New Guinea, and eventually ends up as the primary engineer to design and build one of the tombs in the Philippines that the Japanese leadership plans to use to store large amounts of pilfered gold. The tomb is the object of the treasure hunt that binds the entire book together across multiple generations.
Team Lawrence Waterhouse: Lawrence is a US cryptologist in the Pacific theater of operations who spends his time breaking Japanese codes. He is friends with Alan Turing, and Stephenson uses this relationship to explore code breaking in general and the nuances of information theory during a world war. The nuance here is diabolical. Because the Allies had broken the German Enigma encryption scheme and pretty much knew the orders of the German field commanders before they did, how many times could they act on that intelligence to save lives before the German’s figured out that their system was broken? The implications of that question are heartbreaking. The word “Cryptonomicon,” from the book’s title, is a collection of code-breaking techniques that Lawrence inherits and develops throughout the story.
Team Randy Waterhouse: Randy is Lawrence’s direct descendent in the present day (1990s). He and a group of college buddies, who played Dungeons and Dragons during their school years, have banded together to form a start-up. They want to build something called the “Vault” in the Philippines, which is a sort of data haven that anybody can use to store whatever kind of digital information they want free and clear of government intervention. Along the way, Randy partners with the Shaftoe family (related to Team Shaftoe) who runs an underwater salvage company, helps build the vault, and becomes an essential partner in the treasure hunt.
Just so you don’t think that this book is only about men and math and computers and commando operations, Cryptonomicon has three fairly decent love stories. I already highlighted Bobby Shaftoe’s epic journey to find his fiancé, but both Waterhouse boys get their share of romance too, especially Randy. It is amusing to watch these two brainiac math and computer wizards try to reduce the world to binary equations on one hand and, on the other, become completely befuddled with the mysteries of the opposite sex. It is sweet and funny and spot-on for how the Dungeons and Dragons crowd approaches girls. Well, at least I recognized myself in their bewilderment.
While these orbiting characters bounce off of each other through the nearly 1,000 pages, Stephenson also tosses in a mix of some groundbreaking math ideas from the likes of Kurt Gödel and his incompleteness theorems, Alfred Whitehead and Bertrand Russell and their re-imagining of the math ecosystem in a book titled “Principia Mathematica,” Alan Turing and his Turing Machine Thought Experiment that changed the world  and Bernhard Riemann and his zeta function. Stephenson also dips his toes into modular arithmetic, probability distributions, information theory, and cryptanalysis. But don’t let the math scare you away. His intent here is to introduce these subjects to the uninitiated, and he is a pretty good teacher.
Cryptonomicon is the quintessential hacker novel. It is unique in that it qualifies in two different categories: “books for important historical context” and “novels that don’t exaggerate the genre.” For historical context, Stephenson describes a story that is set around the intersection between the discovery of world-changing math insights and the incipient designs of our computer science founding fathers. That intersection is ground zero for my chosen profession—cyber security—and the hacks that we see Team Randy Waterhouse perform are interesting and well within the realm of “the possible.” But with all of that, Cryptonomicon is not an easy read. It is dense with ideas. You do not skim through this looking for the good parts, but if you take the time to savor the journey, you will not be disappointed. There is something for everyone here, and you owe yourself the pleasure of finding your favorite part. In other words, you should have read this by now.
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