Double Oh Fail: 10 of the Most Inept Spies in the History of Espionage

Double Oh Fail: 10 of the Most Inept Spies in the History of Espionage

D.G. Hewitt - May 10, 2018

Double Oh Fail: 10 of the Most Inept Spies in the History of Espionage
Brian Regan’s attempts to make money from secrets were undone by his own bad spelling. FBI.

Brian Regan

To be fair, Brian Regan was far from inept at espionage. In fact, he was really quite good at it. It was the treachery he wasn’t very good at. His was a classic tale: man gets job that allows him access to sensitive information but doesn’t pay too well, racks up big debts in his personal life, and then sees a chance to make a fast buck (or 13 million of them in this case). But despite having it all, Regan’s tale is hardly very well known. According to his biographers, the fact that he was caught just a few days before 9/11 happened means that his case was almost lost to history. Thankfully, his story has since come to light, showing how simple spelling mistakes helped uncover a potentially-catastrophic intelligence breach.

So, who was Brian Regan? Born in New York City in 1962, he joined the National Reconnaissance Office (NRO) as a signals specialist in 1995. Thanks to his position, he had access to Intelink, which is essentially a closed-off alternative internet just for spies. While his job may have been interesting, he felt unfulfilled and disrespected. At the same time, he was also spending way more than he earned, amassing more than $100,000 in credit card debts. By 1998, therefore, he had reached the obvious conclusion: Why not try and sell some of the classified information he had access to on a daily basis?

At the end of the work day, Regan would smuggle out hard copies of sensitive data, as well as CD-Roms and videotapes. He buried these in some woods in suburban Maryland and then started to reach out to other nations. In anonymous emails to, among others, Saddam Hussein as well as Libya and China, he offered to give up the GPS coordinates of his hidden stash in exchange for $13 million. Unbeknownst to Regan, the U.S. had a mole in one of these foreign regimes, and they warned that somebody was trying to sell information. And, while they didn’t know who it was, they did have one vital clue: whoever was writing these emails couldn’t spell.

From then on, it was a simple question of finding someone who both had access to such sensitive material and who was dyslexic. Before long, the finger was pointing at Regan. In August of 2001, the FBI made their move. Regan had booked himself onto a flight to Switzerland. No doubt tired of waiting for his anonymous emails to bear fruit, he was trying to get in touch with other nations in person. When agents arrested him, they found the contact information of the Iraqi, Libyan and Chinese embassies in Switzerland. The game was up. Regan was convicted of espionage. He avoided the death penalty but is currently serving life with no chance of parole. If only he’d used a spellchecker!

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