Tag Archives: cryptanalyst

Elizebeth Smith Friedman, Codebreaker and Scourge of Nazi Spymasters

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[William and Elizebeth Smith Friedman, hard at work.
Image courtesy of National Geographic.]

Last year, I rather ambitiously attempted to summarize the early history of American codebreaking and the NSA in a series of blog posts spanning World War II through the modern day. One of the names I cited in that series, William Friedman, is synonymous with American cryptography, thanks to his contributions to the cracking of the German ENIGMA code and his efforts to establish the National Security Agency.

Unfortunately, there is a gaping hole in the narrative I constructed. Because none of my sources made any reference to another crucial Friedman: Elizebeth Smith Friedman, William’s wife and partner in code-cracking.

Yes, she was name-dropped in my post about the book Code Girls: The Untold Story of the American Women Code Breakers of World War II, but she had to share those pages with a host of underappreciated women who were codebreaking geniuses.

[Image courtesy of HarperCollins Publishers.]

As The Woman Who Smashed Codes explains, she wasn’t just a talented codebreaker. She literally wrote the book on it. Eight of them, in fact. The Riverbank Publications — although often credited to her husband — covered new codebreaking techniques in rich detail, and they are still referred to today as part of the foundation of modern cryptography.

She also started the first and only American codebreaking unit ever run by a woman, serving as Cryptanalyst-in-Charge while jointly working for both the Treasury and the Coast Guard during and after World War II.

A history of American codebreaking without Elizebeth Smith Friedman is woefully incomplete, and in today’s post, I hope to rectify that oversight.

[Image courtesy of the Marshall Foundation.]

Elizebeth’s work with codes started in a most peculiar way. While seeking a job as a librarian after college, she was recruited by eccentric millionaire George Fabyan to live and work at Riverbank, his palatial estate that doubled as a self-funded research center for all sorts of scientific endeavors.

Elizebeth’s deep knowledge of Shakespeare was put to work attempting to prove Fabyan’s theory that there were secret messages encoded in the writings of Shakespeare. Although her work failed to uncover any hidden pattern in Shakespeare’s words or font choices, it did lead to two unexpected developments: a career in codebreaking and a budding romance with fellow Riverbank recruit William Friedman, whose own interest in codebreaking was sparked by the works of Edgar Allan Poe.

Thanks to the proliferation of radio, there was a seismic shift in how information was being passed between military units, governments, and other organizations, so the ability to listen in on one’s enemies (and allies) was not only a new strategic opportunity, but it was a relatively new science.

In short, America needed codebreakers who could crack the secret messages being transmitted (and intercepted). The military didn’t have them. The government didn’t have them.

But Riverbank did. And for the first eight months of World War I, the small group of William, Elizebeth, and those they trained handled ALL of the codebreaking for every part of the US government, from the State Department to the Army to the DOJ. William and Elizebeth began running a codebreaking school out of Riverbank, even embedding a secret message in a photo of the class taken on the last day of the course.

[Images courtesy of Elonka.com.]

In the aftermath of the First World War, codebreaking had become so important that countries were turning to machines to help develop uncrackable codes. And yet, at this point, American cryptography as a whole consisted of about 50 people. William went to work for the government, establishing the American version of Bletchley Park — Arlington Hall — and setting the stage for the creation of the NSA.

Elizebeth, on the other hand, cracked codes from home. And she did so for both the Treasury Department and the Coast Guard, who would send her sealed packages of intercepted encrypted intel and communications. In her first three months hunting down rum-runners during Prohibition, she solved two years’ worth of backlogged messages.

During World War II, Elizebeth’s Coast Guard Cryptography Unit turned their attention from smuggling (which waned during wartime) to cracking German codes. Under her tutelage, they would crack three different variations on the Enigma codes, each more complex than the last. (The British also cracked ENIGMA, independently of American efforts.)

Sadly, in the aftermath of the Pearl Harbor attack, the US military didn’t want civilians in charge of sensitive operations, so Elizebeth was demoted. Yes, she was no longer in charge of the group she started, trained, and cultivated, instead answering to a new boss of dubious cryptographic talents.

(Of course, the sexist dimwits making decisions like this had to grin and bear it when numerous other organizations and agencies continued to asked for Elizebeth’s assistance by name.)

And stealing Elizebeth’s credit was practically a cottage industry over at the FBI. We have them to thank for erasing Elizebeth’s role in particular — and the Coast Guard’s role in general — in hunting down, exposing, and compromising Nazi spy networks in South America, even though the FBI’s hamfisted blundering actually served to expose codebreaking operations in the past, forcing Elizebeth to crack new codes in order to regain the advantage the FBI had squandered.

Oh, yeah, did I mention that both during AND after World War II, Elizebeth continued to hound the Nazi forces in South America who sought to destabilize the region?

As one historian put it, referring to the thousands of pages of decryptions Elizebeth produced:

These pieces of paper saved lives. They almost certainly stopped coups. They put fascist spies in prison. They drove wedges between Germany and other nations that were trying to sustain and prolong Nazi terror. By any measure, Elizebeth was a great heroine of the Second World War.

The British knew it. The navy knew it. The FBI knew it. But the American public never did, because Elizebeth wasn’t allowed to speak.

[Image courtesy of Find a Grave.]

Even in their retirement, the Friedmans continued to contribute to the world of cryptography. They returned to the subject of Shakespeare with The Shakespeare Ciphers Examined, thoroughly debunking the whole idea of hidden codes in the Bard’s works.

When William died, Elizebeth even hid a secret message on his tombstone, for those who knew how to look. (It was Bacon’s cipher, something they both studied extensively during their time at Riverbank.) What a touching tribute to how she met her partner and husband.

And although the accolades and appreciation for Elizebeth’s incredible contributions have been slow in coming, they are trickling in. In the 1990s, the NSA renamed its auditorium from the William F. Friedman Memorial Auditorium to the William F. Friedman and Elizebeth S. Friedman Memorial Auditorium. A Justice Department building also has an auditorium bearing her name.

More information about the massive expansion of codebreaking worldwide is coming to light with every passing year. Hopefully that will mean greater attention for minds like Elizebeth, who used her puzzly mind to protect the world. That’s someone worth celebrating.

[Much of the information in this post comes from a wonderful book on Elizebeth, The Woman Who Smashed Codes by Jason Fagone, and it’s well-worth your time to check out her story in full.]

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Puzzles Endanger, Then Save, a Nation: The Spy Who Couldn’t Spell

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While working on our multi-part series of posts about the history of codebreaking in America during the 20th century, I mentioned that some of the recent revelations about the National Security Agency were the result of Edward Snowden’s actions during his time as a government contractor.

What you might not know is that he has not been the only contractor to sneak information off of government computers in that fashion: a decade before Edward Snowden, there was Brian Patrick Regan.

Regan was a career soldier in the Air Force who eventually reached the rank of Master Sergeant and worked in signals intelligence.

Buried under hundreds of thousands of dollars in credit card debt, Regan decided his only way out of financial ruin was to try to sell US government secrets to a foreign government. He copied page after page of sensitive documents from national defense systems and snuck them out of his office, eventually amassing more than 15,000 pages, CD-ROMs, and other material in his home.

He would later bury bundles of these documents in various locations, including state parks, concealing the GPS coordinates of these valuables caches through a complicated series of encryptions where letters and numbers became three-digit sets.

You see, Regan had spent a fair amount of time studying cryptography, and fancied himself a top-shelf codemaster.

Regan used another set of encryptions of lesser complexity when he attempted to contact agents of the Libyan, Iraqi, and Chinese governments in order to sell off the treasure trove of secrets he’d amassed during his time at the National Reconnaissance Office.

One of these packets — a collection of three parcels intended for Libya — ended up in the hands of an FBI agent named Steven Carr.

From The Spy Who Couldn’t Spell by Yudhijit Bhattacharjee:

In the first envelope was a four-page letter with 149 lines of typed text consisting of alphabets and numbers. The second envelope included instructions on how to decode the letter. The third envelope included two sets of code sheets.

One set contained a list of ciphers. The other, running to six pages, listed dozens of words along with their encoded abbreviations: a system commonly known as brevity codes. Together, the two sets were meant to serve as the key for the decryption.

Some of the document had already been decrypted by FBI agents, and it revealed a member of the US intelligence community — claiming to be CIA, which was unverified, but definitely someone with top secret access — was trying to sell government secrets.

And this person had terrible spelling.

Brian Patrick Regan suffered from severe dyslexia. And, despite concerted efforts to perfect both his encryptions and his plan to net millions by selling government secrets, that dyslexia would be one of the clues that led Steven Carr to Regan’s doorstep.

It took Carr six months to connect Regan to the Libyan package, but once he did, surveillance on Regan began immediately.

When Regan attempted to board a plane to Zurich in 2001 — intending to meet with Iraqi and Libyan embassy officials — he was nabbed by the FBI and taken into custody.

Again, excerpted from The Spy Who Couldn’t Spell:

On searching Regan, officials found a piece of paper tucked between the inner and outer soles of his right shoe, on which were written addresses of Iraqi and Chinese embassies in Europe. The other materials they found on him and in his belongings were more mystifying. In a trouser pocket, Regan was carrying a spiral pad containing a page with 13 words that didn’t add up to anything: like tricycle, rocket and glove.

He had another 26 random words scribbled on an index card. Among the contents of Regan’s wallet was a piece of paper with a string of letters and numbers that read “5-6-N-V-O-A-I …” And in a folder he was carrying in his duffel bag were four sheets with handwritten lines of three-digit numbers.

FBI cryptanalyst Daniel Olson decoded some of the messages found on Regan when he was captured, but he had failed to unravel the multi-stage encryptions that concealed where Regan had buried his secret parcels. The government knew which state parks, but with acres and acres of possible hiding places, they needed more precise information.

And those parcels were the key, because they weren’t just packages to be sold to the highest bidder. No, those parcels doubled as a ransom in order to secure a better deal for himself with the US government. He wanted to blackmail the government for a reduced sentence.

They were his insurance plan.

As Thomas G. West said in Seeing What Others Cannot See, a book about visual thinking and dyslexia, “It’s not hard for a dyslexic to think ‘out of the box’ because they have never been in the box.”

Thankfully, Regan eventually realized that cooperation was in his best interest, and he revealed that each of the elaborate three-digit codes concealed a backdoor key built into the code itself.

Regan designed them this way so that, if he forgot the actual details of the encryption, all he would need is the starter word, a spark that would unlock the built-in key and help him decode the entire message.

This backdoor key system worked in a similar fashion to the Vigenere cipher, where a keyword or key phrase served as the entry point for a longer string of encrypted text. The trouble is… you need to know the cipher word or source in order to crack the code.

For example, during World War II, German agents in Europe used Daphne du Maurier’s Rebecca as the basis of a code for transmitting intelligence from Cairo to support a campaign by the Axis powers against the Allies in North Africa.

The discovery of the book among the possessions of two German radio operators who didn’t read English ultimately led to the breaking of the code, which in turn led to the capture of the German spies in Cairo.

Regan revealed the cipher words for the various hiding spots in state parks — which used cipher words from sources as peculiar as Regan’s own high school yearbook — and soon, the FBI recovered all but one of the buried parcels.

But Regan couldn’t remember the cipher word for the last one.

Daniel Olson would then step in, having learned some of Regan’s techniques as they uncovered the other parcels, and partially decrypting the remaining message enough to spark Regan’s memory. Regan finally came up with the last cipher key, and the final parcel was recovered.

Yes, once again, puzzly perseverance had saved the day!

Regan was found guilty on two counts of attempted espionage and one of gathering national defense information, and sentenced to life imprisonment with parole. Which, quite honestly, is getting off easy, considering that prosecutors were seeking the death penalty for his treasonous acts. (If prosecutors had gotten their way, he would’ve been the first person executed for espionage since the Rosenbergs in the ’50s.)

For the full story, including more in-depth explanations of Regan’s elaborate encryptions, check out The Spy Who Couldn’t Spell by Yudhijit Bhattacharjee.

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