Tag Archives: Culper Ring

The Founding Fathers of Cryptography?

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It’s Veterans Day, and on an occasion dedicated to giving thanks to all those who served the United States honorably during either war or peacetime, it seemed appropriate to turn our puzzly gaze toward at American history for today’s post.

In fact, let’s look to America’s formative days. We’ve written in the past about George Washington and his creation of America’s first spy ring, and how heavily they relied on encryption and codebreaking techniques to protect America’s earliest secrets.

But as it turns out, Washington was far from the only Founding Father who was a strong proponent of cryptography.

Second president John Adams used a cipher to send letters to his wife Abigail when he was traveling. That cipher was designed by James Lovell, a member of the Continental Congress Committee on Foreign Affairs.

President #3 also relied heavily on ciphers and secret methods of communication. Thomas Jefferson created special ciphers specifically for Meriwether Lewis to use during the Lewis and Clark Expedition to protect the intrepid duo’s findings.

He even developed his own method for encryption. Some call it the wheel cypher, but it’s more commonly referred to as the Jefferson Disk.

These 36 wheels, threaded onto an iron spindle, allow the user to twist them until a message reads out. Each wheel has the letters of the alphabet in a random order.

So how did it work? Well, according to Monticello.org:

As an example, the sender of the message shown in the picture, “COOL JEFFERSON WHEEL CIPHER,” spells the message out and then looks to any other line of text – possibly the one directly above, which on this version of the cipher begins with the letter “N.” The sender then copies the rest of the letters from that line into the correspondence to spell out “NKYG NSUS NXML CQYO TYUH HFTD.”

The man who succeeded Jefferson as president, James Madison, employed encryption for both official documents — like letters between himself and members of the Continental Congress — and communication with other key figures. For instance, he sent a partially encrypted letter to Jefferson that described his plan to introduce a Bill of Rights.

Madison’s fellow contributor to the Federalist Papers, John Jay (later the first Chief Justice of the Supreme Court) always employed ciphers for diplomatic correspondence when traveling outside the US.

[This wooden puzzle is known as Franklin’s Kite.]

And as you might expect, the influential inventor, statesman, and polymath Benjamin Franklin had his hands in codecracking and cryptography as well. He not only created some of the ciphers employed by the Continental Congress, but he also published a book about encryption in the 1740s: George Fisher’s The American Instructor.

The Continental Congress, for their part, passed a resolution ordering ciphers to be used for all messages that couldn’t be safely transmitted otherwise.

In the end, as in the beginning, America doesn’t just love puzzles, it’s founded on puzzly principles.

[For more content involving American history and puzzles, check out our multi-part series on the history of the NSA, as well as the story of how a Tap Code and other puzzly spycraft techniques kept a soldier’s love story alive.]

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George Washington: Commander in Chief (and Codes)

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George Washington was the first American president, the Father of Our Country, a general, a farmer, and an inventor. He invigorated and empowered the role of the president far beyond what the Framers of the Constitution originally envisioned, and is widely regarded as the standard against which all presidents are measured.

But did you know he also created America’s first spy ring?

The story is fascinating, and you get the full scoop in Brian Kilmeade and Don Yeager’s book George Washington’s Secret Six: The Spy Ring That Saved the American Revolution.

As the Revolutionary War raged on and America struggled to rout the British forces, Washington realized that British spycraft was heavily responsible for American losses. Determined to even the playing field, Washington marshalled trusted associates to form America’s first spy ring, known as the Culper Ring.

Originally, Washington and his agents employed code names and a few numerical substitutions for words in their messages. The two key agents, Benjamin Tallmadge and Abraham Woodhull, were designated Culper Junior and Culper Senior, respectively, while a still-unidentified female agent is known only as Agent 355. (355 was Tallmadge’s code for “lady.”)

10 stood for New York and 20 for Setauket, so that the recipient would know the source of the information contained in the reports. Two additional numbers, 30 and 40, were used to designate Jonas Hawkins and Austin Roe as post riders delivering the messages to their next destination.

But after two close calls with key agents and information endangered by the British, they followed the French model and developed a more elaborate code system.

Making a list from 1 to 763, he [Benjamin Tallmadge] … assigned each pertinent word, location, or name a numerical code. He became 721, Woodhull as Culper Senior 722, Townsend as Culper Junior 723, Roe 724, and Brewster 725. General Washington was 711 and his British counterpart, General Clinton, was 712. Numbers were often represented by letters, so that the year “1779,” for example, might read as “ennq.”

Could you decipher this message, a rudimentary version of the code eventually used by the Culper Ring?

[In this example of Tallmadge’s ever-evolving code,
“Setauket” went from “20” in the earlier code to “729.”]

They delivered their coded messages through some tried-and-true spying methods, including employing invisible ink and disguising vital communiques as bland family letters. And the Culper Ring had some stunning victories to its credit, including rooting out Benedict Arnold’s traitorous plot to hand over West Point to the British.

[An example of the more elaborate, French-inspired code system
employed later in the war by Washington and the Culper Ring.]

The Culper Ring even saved American aspiring cryptographers one heck of a headache. There was a standing order for agents to “learn as many of the British navy’s code signals as possible, so that the French fleet could decipher what the enemy ships were communicating to one another during naval engagements.”

As you might imagine, even skilled codebreakers would’ve had a nearly impossible time memorizing the codes AND deciphering them in the midst of battle. Thankfully, the Culper Ring obtained a copy of the entire British Naval Codebook, not only saving the eyes and sanity of numerous Americans, but delivering Yorktown to American Revolutionary forces.

In fact, British intelligence agent Major George Beckwith commented, “Washington did not really outfight the British, he simply outspied us!”

And he used some puzzly cryptography skills to do it.

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