In movies and books, spies are always debonair and brilliant, pulling off the most complex schemes without getting caught (too badly.) But in real life, espionage is a messy, complicated business, and sometimes people screw up. Here are the 10 most jaw-dropping screwups in the history of real-life spies.

10. The Chief of Counter-Intelligence Had a Lunch Date With a Soviet Spy

James Jesus Angleton was a dedicated civil servant, and one of the most respected spy hunters in the non-communist world. He was the head of counterintelligence at the CIA for twenty-one years. The fact that he got that position after one particular incident is a testament to his talents.

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Kim Philby was a shining star in British intelligence, sent to Washington in 1949 to be the liaison between the CIA and MI6. Every week, the two men had lunch. They held court at Harvey's restaurant in Washington. Angleton was impressed by Philby's Cambridge background, and since felt proud that he could out drink the British spy, every lunch became a martini drinking contest.

In 1951, two of Philby's friends defected to Moscow. That didn't look good, but Angleton maintained belief in Philby's complete innocence. His claim was hollow, considering he burned all the documents pertaining to his long lunches with his friend. To be fair, after years of investigation, MI6 concluded that Philby was innocent as well. Were they right? Here's a hint - the portrait of Philby in this entry was taken from a Soviet stamp. Philby defected to Moscow and admitted he had been recruited by the USSR whilst at Cambridge. The revelation caused Angleton to become increasingly paranoid, believing that the CIA had been systematically undermined by the KGB, until he eventually left the agency.

9. Nazi Spies Forego Espionage for Spring Break

Nazi Germany landed at least three different groups of spies in America during World War II. Why do we not know about this? Because nearly every spy decided that sabotage and terror were a distant second to gambling, hookers, booze, and betrayal. The 1942 mission, dubbed Operation Pastorius, landed two groups of four spies in the United States. They had civilian clothes, money, weapons, and explosives. They were meant to take out American energy and manufacturing centers, plant bombs in Jewish-owned department stores, and spread terror by bombing public transportation. The group that landed in Long Island was immediately spotted by a member of the coast guard.

The coast guard officer who spotted the party got suspicious when George John Dasch, the leader of the group, tried to bribe him, and when another member of the group came up to the two of them and asked Dasch a question in German. Returning with a group of men to the abandoned scene of the landing, the officer saw a submarine disappearing into the water and found boxes of buried supplies, including German uniforms. The group was long gone, but that didn't matter. Dasch and another member, Ernest Peter Burger, decided that they weren't up to sabotage and terror, and decided to call the FBI and turn themselves in. But first, gambling! Dasch spent a day and a half playing pinochle, then took a long nap. He went to Washington, dumped all the leftover money on a poor FBI agent's desk, and asked to speak to J Edgar Hoover. Burger kept the rest of the team at a hotel, waiting for the FBI.

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As for the other team, two were arrested on Dasch's information. One of the team had been an American. He went home to his parents, and spent a lot of the money he got for the mission on a new car. Then he went to the FBI, explaining why he hadn't registered for the draft. They tailed him and arrested him. One spy went to the movies a lot, then got lonely so he went to see some friends, explaining to them that he'd come there on a German submarine, and was on a sabotage mission. They turned him in.

In 1944, two German agents landed in America. One was German and a loyalist. The other was American-born and an opportunist. They were sent to gather intelligence. They went to New York to do this. In one month, the American, William Colepaugh, had run through fifteen hundred dollars with drinking and gambling and ladies of ill-repute. (Though if they kept a Nazi sympathizer from focusing on bringing down America, those ladies rendered their country a valuable service and deserve the very best repute.) That spending spree was only a warm-up. Just before Christmas, Colepaugh took off with all the money the two spies were given - forty thousand dollars - and just after Christmas, the penniless Colepaugh turned himself in to the FBI, and told them where to find Gimpel.

The majority of the German spies during this time were given military tribunals and executed. The most cooperative received long sentences, which were commuted when the war was over.

8. American Intelligence Has Faith In a Nazi Spy

Doctor Ignatz Griebl came to America from Germany in 1925. He was a respected surgeon, a pillar of the community, a member of the Army reserves, and an ardent Nazi. He cultivated engineers and technology experts, convincing them to give Germany a peek at American technology. He organized a network of spies. He got himself a few mistresses (he had money to spend, thanks to the German government) who were secretaries or mistresses to American military officials. And he compiled a list of prominent Jews in America, for when Nazism caught on or took over the country. In 1938, one of his spies got caught by the FBI, and, during interrogation, named Griebl as his handler. The FBI brought Griebl in, and he confessed. He confessed everything he had, readily and amiably, as if he had been waiting for a chance to turn over the information. The FBI was so gratified that they released him until such time as he was needed at his grand jury hearing.

I'll say that again. They found a Nazi spymaster. And let him go, confident that he would happily come back to them so they could try him for espionage. Imagine their surprise when he did not come back. Instead, he went to Austria, where he practiced medicine for the rest of his life.

7. The Dreyfus Affair Rips Apart a Country

Let's go a little farther back. It's 1894, Germany and France are not getting along, and French military intelligence knows that someone is leaking information to the Germans. Alfred Dreyfus, a French military officer is not well-liked. He is also Jewish. These are two big mistakes on his part. Officers do suspect him of being the leak, but they don't have proof. Perhaps if they forge a few papers, and make up a few meetings. It works, and Dreyfus gets sent to Devil's Island, off the coast of South America.

This incident did not sit well with certain fringe periodicals, which wouldn't have been a problem, except the French public loved their fringe periodicals. Papers proliferated, and The Dreyfus Affair, as it came to be known, facilitated the rise and fall of quite a few of them. J'accuse, the title of an article condemning the fraud committed by the "anti-Dreyfusards" has come to be a popular phrase, reused many times in many different contexts. Zola was right. The evidence was faked. But when people began examining the fake evidence, officials responded with more fake evidence, concocted in secret and passed from one person to the next during clandestine meetings. All the evidence, real and false, was hashed over in the press, until a case could be made for nearly any point of view, depending on what point of view a person wanted to take. And so a counterintelligence operation became a trial, which became a culture war.

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The anti-Dreyfusards were the old guard, traditional, religious, and of the opinion that if the military had passed judgement on Dreyfus, their judgment should be respected, to preserve the honor of the nation if nothing else. The Dreyfusards were, for the most part, cantankerous progressives with a grudge against the establishment. The affair caused riots, marches, and a shift in international politics - and not just between France and Germany. There were riots in Italy over the Dreyfus Affair, and it wrecked relations between France and Italy until it was resolved. How was it resolved? Dreyfus was tried again, convicted again, and then exonerated of all charges and returned to his post in the military. He served in World War I.

6. The British Insist on Sending a Spy to the Manhattan Project

General Leslie Groves was the American commander in charge of the "Manhattan Engineer Project" in 1942. He was in charge of every phase of the project, worked with some of the most celebrated military officials, politicians, and scientists in the world, and made zero friends. This was fine by Groves. What wasn't fine by him was the fact that the British allies refused to allow America to thoroughly vet and clear every scientist they chose to send over. How dare he, the British asked. How very dare he. At last, the American brass backed down, and the British sent their esteemed, and cleared, scientists over to work on the atomic bomb.

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One of the scientists they sent was Klaus Fuchs. He spent the next six years passing detailed information on the atom bomb, and then the hydrogen bomb. He went back to England in 1949, where he began work Harwell Atomic Energy Research Establishment. By that time, he was disenchanted with the Soviet system. It must have come as a disappointment when intelligence officers cracked a Soviet cypher, and uncovered his work. He spent ten years in prison, had his British citizenship revoked, and went to East Germany. Fuchs had an even more prestigious career in communist countries than he did in capitalist ones. He even consulted with Chinese scientists on how to build an atomic bomb.

5. The Venona Code Gets Broken Because of a Printing Error

In 1943, Gene Grabel, of the US Army's Signal Intelligence Service, started a little project known as Venona. It was meant to decipher the fiendishly difficult Soviet encryption system. Soviet messages were encrypted into numerical code using books that were given to the sender and the receiver. These books were used only one time. The "one-time pads" made the code impossible to decipher, but they presented practical problems. The numbers in the books had to be random, and, since there was a war going on, the volume of messages sent required the government to produce massive amounts of books.

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The books were reused. Sometimes they were reprinted. Sometimes they were used by operators who didn't or couldn't acquire new ones. But they were reused, more and more, towards the end of the war. Eventually, codebreakers working on Venona managed to spot the patterns of reuse. The messages didn't come easily, or quickly. Some weren't decrypted until the 1950s. But once some messages were decrypted, others came easier and faster. The Venona project alerted officials to the presence of double agents - although Kim Philby knew about Venona and got regular updates on its progress. It unmasked Klaus Fuchs and Julius Rosenberg.

4. Communist Spies Took Advantage of the Both CIA and the Spirit of the 1970s

Karl and Hana Koecher had a tough time getting by in Czechoslovakia, despite Hana's parents being fairly high up in the Communist party. Karl was a comedy writer for a local radio station, and he often wrote satirical broadcasts mocking the political state of affairs in his country. This did not sit well with local officials, so Karl and Hana came to the United States. Karl earned a doctorate in philosophy, but his skills cried out for a use more practical than comedy or philosophy. His language proficiency and history of opposing Communism, made him perfect for the CIA. He was hired in 1973, and was nearly immediately granted access to high level security information.

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The Koecher incident wasn't a screw up because he turned out to be a double agent. His cover was carefully constructed. His seemingly subversive broadcasts had been approved by Czechoslovak intelligence service. His oppression by and hatred for the party was sustained for years. His civilian identity in the United States was well constructed. And who could know his wife was in on it? In fact, multiple times during his career as a mole in the CIA, even the KGB was doubtful as to who he was actually was working for. What made the Koechers a screw up for the intelligence community was the fact that they gained a lot of their information not at Karl's job, but at orgies and wife-swapping parties with other officials in New York and Washington. This not only got them more information, but made their acquaintances hesitant to expose them and the CIA hesitant to go after them, since exposing them meant exposing a culture within the agency that no one wanted to make public. As it was, the couple wasn't arrested until 1984. They were eventually sent back home as part of a prisoner exchange.

3. Oh, Canada

America is not the only country that blundered, crotch-first, into disaster. In 1966, Pierre Albert Sévigny, the Canadian Associate Minister of National Defense had the unenviable job of explaining why his name was on the citizenship application of a Soviet spy. Gerda Munsinger was a playgirl who got a lot of playing in. She bagged at least two cabinet ministers. Then American intelligence agencies and the Royal Mounted Police put a few things together, talked to Prime minister John Deifenbaker, and deported Munsinger. Deifenbaker had a word with Sévigny, who resigned a little while later.

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That's nothing, some might argue. That's not even a blip, they would say. And they would be right. And then they would shut up about it. And they would refrain from taunting the opposition government about the handling of people deemed a security risk. In 1966 Deifenbaker learned a hard lesson in not throwing stones. Deifenbaker was publicly berating Lucien Cardin, a member of the opposition party, about his handling of a suspected spy. Cardin got angry, and retorted that Deifenbaker shouldn't talk tough after the "Monseignor case." The press was immediately on the track, and after a few days during which it was rumored that "Monsignor" was a gangster in the government, Canada had its first ever political sex scandal. The spy lesson to be learned from this case? Do not push your luck.

2. Pearl Harbor Happened Because No One Wanted to Share (Or Maybe Not)

In December 1941, a military attache got word that the Dutch had broken a Japanese diplomatic code. The Japanese were planning an attack on Hawaii, the Philippines, and Thailand. The attache reported it, but was dismissed. Meanwhile, in Washington, analysts intercepted a message to the Japanese embassy - burn the code books and destroy the cipher machines. But meanwhile, the Japanese fleet seemed to be moving southwards, towards the Philippines. Nobody noticed a few ships coming too close to Hawaii.

The attack on Pearl Harbor will probably be the most controversial item on this list. While some historians argue strongly that, if the disparate people collecting the information were willing to share their information, either with one central agency or with commanders in the field, the attack could have been prevented or ameliorated. The Central Intelligence Agency has also made the claim. Then again, they would. They were established in 1947, to do the job of collecting and overseeing intelligence information like this.

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Other analysts argue that the United States was getting a lot of conflicting messages, and that people did the best they could with them. ( For example, the US was warned about an attack on Pearl Harbor in January of 1941. This was a false message, as no attack was being planned at the time.) One thing that most people agree on is, whether or not this was a failure of intelligence, it was a failure of understanding. The United States underestimated its opponent's abilities and motivations, and so enjoyed a false sense of security.

1. Heinrich Albert Was Either The World's Worst Spy or the World's Best Spy

If you've been paying attention, you'll notice that one nation's humiliating mistake is always another nation's brilliant intelligence success. Espionage is as close to a zero-sum game as it is possible to get. What's bad for one nation is great for the other. Which is what makes the Heinrich Albert Nap so confusing. Heinrich Albert was a German diplomat in New York in 1914. He was serving the ambassador, Johann von Bergstorff. And he was doing some things that Americans might have found questionable. Some Americans supported the German cause in World War I, and even wanted to join the German army, but most Americans were against Germany. Then again, most Americans did not care to get involved in "foreign" war. Von Bergstorff was trying to shape public opinion by buying shares in newspapers reporting on the front and running stories favoring the German cause. Von Bergstorff was also in charge of creating, buying, or stealing passports so that German sailors could move freely in and out of the United States. Albert was the paymaster, raising money for all these activities and paying it out.

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United States intelligence officials suspected Albert was involved in something shady, and so they monitored his activities. One of those activities turned out to be a taking a nap on a warm subway car, being startled awake, and leaving that car without his briefcase. It proved to be a costly little snooze. American agents leaked the papers in the briefcase to the press. Many citizens were German-American and felt sympathy for their homeland, and even some of those who had no ties to Germany supported the German cause. Not anymore. Although it wasn't the defining moment that tipped America into the war, US citizens started seeing Germany as a country actively working against American interests. So Albert was clearly a terrible spy.

Or so it seemed. After the war, Albert started a law firm that represented American interests in Germany - just as before the war he had represented German interests in America. Which leaves us with the question: Who the hell was he actually working for?

[Sources: The Kim and Jim Show, Before the Fallout, The Detonators, 9 Tiny Mistakes, Inside the CIA, The Lives of the Cambridge Spies and the Project Known as Venona, German Saboteurs Invade America, The Star Spangled Screen, Griebl Gets a Nazi Welcome, The Proud Tower, The Canadian Encyclopedia, Canadians React to the Munsinger Affair, Biggest American Intelligence Failures, The Intelligence Failure of Pearl Harbor, Pearl Harbor: Estimating Then and Now.]