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The 6 worst spies of all time

Like any other profession, espionage is going to have its legends and its cautionary tales. Some spies are better than others. If you're truly a great spy, then chances are good no one will ever know what you did or why. This list isn't about effectiveness, this list is about methodology.


The six spies on this list experienced varying degrees of success or failure, depending on which side of the border the reader is seeing. How they went about their work is what's most suspect. There's a reason spy agencies check their employees' bank accounts, psychological profiles, and alcohol use. Then there's some spies who just can't wait to get spying, and they have to flag down the car of the local foreign intelligence agency chief.

1. Adolf Tolkachev

Tolkachev was a great American asset for ten years of the Cold War, after he made contact with the CIA, that is. He managed to do this by leaving hand-written notes on cars with diplomatic license plates that happened to be parked near the American Embassy in Moscow. He even banged on the car of the CIA's Moscow Station Chief.

This is how the KGB moves you once they find out you work for the CIA. (Melton Archive)

It's truly amazing that it took the KGB so long to catch Tolkachev in the act. In one day he was tried, convicted, and executed. In the end, it wasn't his open hatred of the Soviet government or the notes he left on cars a decade before, it was CIA agents (either Edward Howard or Aldrich Ames) who outed him to the KGB. Speaking of which...

2. Aldrich Ames

This guy is probably the reason federal investigators look for certain trouble warnings in their investigations for security clearances. Ames was more of a "bumbling boob" than a master spy. He kept being promoted despite a series of drunken incidents, poor performance reviews, and insubordination. Unsure of how the CIA could allow this to happen? Think about your own job. Is everyone there 100 percent effective? Right.

Ames also has a very punchable face.

In his nine years as a mole, Ames was able to ID at least twenty CIA operatives in the Soviet Union to the KGB. Many of those agents were executed as Ames lived a plush life on Soviet money, to the tune of some $4.6 million. This is why the Agency watches bank accounts, as Ames expenditures exceeded his monthly salary, he paid for a home and a Jaguar in cash, and started wearing very fine tailored suits. He is serving a life sentence with no parole.

3. Michael Bettaney

Bettaney was a British MI5 agent whose work was so awful and methods so crass, he was actually given up to the UK government by the Russians because they thought he was meant to be a crude sort of double agent.

Also, Bill Cosby needs his sweater back.

An alcoholic who would regularly try to avoid the drunk tank by telling everyone he was a spy, Bettaney photographed MI5 documents and stored those photos in his home. He was scheduled to leave for Austria to sell the stuff when the Russians betrayed him.

Basically, this guy was the English version of Archer if Archer never succeeded in a mission.

4. Anna Chapman

The laziest Russian spy of all time, Anna Chapman was part of a sleeper ring. She and her spies were so bad at espionage, the U.S. government just shipped Chapman back to Moscow because they didn't have enough evidence of actual secrets stolen to convict her.

Chapman in a Russian military video

That's not the worst of it. Chapman and the 11 others in the spy ring failed in a lot of espionage basics. They conducted monetary and other transactions in broad daylight, kept their communications guidebook instead of memorizing it and burning it, and met directly with sources instead of using an intermediary.

5. Unnamed CIA Lady

This is the person who is responsible for spreading the idea that "enhanced interrogation techniques" (aka torture) are an effective method for getting information from suspects with links to terror cells. Still at the CIA, her name remains a mystery to most, but an NBC investigator found documented evidence this woman not only defended the practice, but enjoyed taking part in its implementation, even on innocent people.

She inaccurately reflected intelligence to CIA leadership who continued a program she knew to be ineffective. Does this not sound so bad? This woman's name was also included in the 9/11 Commission's report for not sharing testimony about two of the hijackers with the FBI — which the reports say was one of the critical failures of pre-9/11 intelligence.

6. Stewart David Nozette

Nozette was a space scientist with a very high security clearance. He was arrested in 2009 for being an agent of Israel, spying on the U.S. for Mossad, the Israeli intelligence service. Unfortunately, the Israelis never talked to Nozette. He was actually talking to the FBI the whole time. And they got it on tape.

Nozette worked for a number of aerospace companies in Israel which shared defense contracts with the U.S. He practically announced his intention to become a spy and attempted espionage for $11,000 (a paltry sum, considering what other spies, like Jonathan Pollard, received for their services).

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