Like any other profession, the world of espionage has its legends and its cautionary tales. Some spies are just better than others. If you’re truly a great spy, then chances are good no one will ever know what you did or why. If you somehow got famous in the course of your espionage career, you’ve probably made a serious (and potentially deadly) vocational error somewhere along the way.
Related: That time the CIA shot down a bomber with an AK-47
The six spies on this list experienced varying degrees of success or failure, depending on which side of the border the reader is on. 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 are 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 to tell them about it.
This list isn’t about effectiveness; this list is about methodology.
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.
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 specific trouble signs 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.
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 and Rolexes. He finished serving a life sentence with no parole in January 2026.
3. Michael Bettaney
Bettaney was a British MI5 operative 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.
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 James Bond without any of the women, style, or espionage skills.
4. Anna Chapman
The laziest Russian spy of all time, Anna Chapman was part of a Russian sleeper ring. She and her spies were so bad at espionage that the U.S. government just shipped Chapman back to Moscow because they didn’t have enough evidence of actual secrets stolen to convict her.
That’s not the worst of it. Chapman and the 11 others in the spy ring failed at many 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.
Real spies call this “tradecraft.” Chapman’s sleeper ring apparently thought it was a waste of time. Look where that got her.
5. Unnamed CIA Lady
This is the person who is responsible for spreading the idea that “enhanced interrogation techniques” (also known as “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 that this woman not only defended the practice, but enjoyed taking part in its implementation, even on innocent people.
James Mitchell and Bruce Jessen – The CIA's $1000 a Day Torture Specialists
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.
Essentially, this person is so bad at her job that it literally helped 9/11 happen.
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 and spying on the U.S. for Mossad, the Israeli intelligence service. Unfortunately for Nozette, the Israelis never actually talked to him. He was really talking to the FBI the whole time. And they got it on tape.
FBI surveillance video of Stewart Nozette – Released under FOIA 3/4/2013
Nozette worked for a number of aerospace companies in Israel, many of which shared defense contracts with the United States. 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).
