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

William Colepaugh

If his mission was to drink the bars of New York City dry, then William Colepaugh would have been the greatest secret agent the Nazis ever sent to the United States. But it wasn’t. Instead, the American-born spy was sent back to his homeland to try and learn – and steal – the Americans’ nuclear secrets. And, frankly, he wasn’t very good at it. In fact, he didn’t even come close to getting inside of the Manhattan Project, making him one of the most ineffectual spies in the history of World War Two.

Not the Colepaugh tried that hard. After all, when he decided to betray his country, he imagined fighting on the frontline, playing a brave and active role as the Third Reich assumed world domination. But the Nazi leadership had other ideas for the man who offered himself up to them in Lisbon, Portugal, in 1943. By that time, Colepaugh was a 26-year-old merchant sailor. He had already been to sea, serving in the U.S. Navy, from which he was honourably discharged. But he was no patriot. While a student at MIT, he embraced the German roots of his mother’s side of the family. Nobody knows quite why he was attracted to the Nazis, but, when his merchant ship docked in Portugal, he saw his chance to join their cause.

If they were suspicious of the young American, the Nazi spymasters in Lisbon soon overcame any reservations. Berlin saw in Colepaugh the perfect spy: He could blend back into American society and so help a fully-trained super agent in his mission to sabotage the nation’s war machine and find out its nuclear secrets. So, Colepaugh was paired up with full-on Nazi spy, 35-year-old Erich Gimpel. The mismatched duo were taken to the coast of America in a U-boat and they sailed ashore, making their way to New York City, carrying false documents, radio parts and a huge wad of cash – $60,000 to be precise.

The money was much too tempting for Colepaugh to resist. Rather than using it to finance his spying, the turncoat spent it in New York bars and lavished it on women. Unsurprisingly, Gimpel was not impressed with his partner’s lack of dedication to the cause, and the pair fell out. Undeterred, Colepaugh kept on boozing and womanizing, though soon he was more afraid of Kimpel than he was of the US government. So, sneaking away from his partner, he phoned the FBI and confessed all, including Kimpel’s whereabouts. Both men were apprehended and sentenced to death.

In the end, President Truman commuted their sentences. When the war ended, Kempel was sent back to Germany, though Colepaugh remained behind bars until 1960. After his release, he led a quiet life in Pennsylvania. While he was an active member of his community, he never did open up about his failed career as a Nazi spy.

Heinrich Albert

To everyone else riding the elevated train in Harlem, New York, on that afternoon in July 1915, he would have looked like every other commuter: smartly-dressed but weary and struggling to keep his eyes open. And in fact, the man in question did indeed start snoozing. Upon pulling into the 50^th Street Station, he awoke to find that his briefcase was missing. Normally, this wouldn’t be such a big deal. But, this was no ordinary man. It was a German diplomat by the name of Dr. Heinrich Albert and he had been in the Big Apple engaged in espionage. And the briefcase? Well, it was a treasure trove of information, and Dr. Albert’s carelessness had gifted the American authorities a huge diplomatic coup.

The lapse in concentration occurred at a point in time when the United States was still a neutral country, opting to keep out of the war that was setting Europe ablaze. The German High Command was committed to changing this. They knew that some Americans supported the German war effort and perhaps, with a push, the government could be encouraged to join in the conflict on their side. It was Dr. Albert’s job to provide that push. Ostensibly working as an assistant to Germany’s Ambassador to the United States, Johann von Bergstorff. With his boss, Albert was busy buying up shares in popular newspapers so as to get them to publish stories that could sway public opinion towards supporting American involvement in the war – not a cheap endeavour.

Albert was the money man in this scheme, receiving and spending huge sums. Unsurprisingly, this caught the attention of the fledgling Secret Service, and Albert was regularly tailed, including on that fateful day in July 1915. The agent tasked with shadowing the inept spy that afternoon was Frank Burke. It was he who noticed that Albert was dozing and, sensing an opportunity, he snatched the briefcase and the secrets in contained within. Finally, the Secret Service had proof that Germany was trying to manipulate the American people. They ‘accidentally’ leaked this proof to the press and the subsequent reports were met with outrage by the public. Any hopes of the country allying itself with the Kaiser were well and truly dashed – and all because a spy couldn’t stay awake.

But that’s not the whole story. Shortly after ‘War to End All Wars’ came to a conclusion, Albert returned to his native country. There, he set up a law firm representing American interests within Germany. Could it be that he was working with American all along? And that, instead of being one of the most inept spies of the First World War, he was a cool, calculating double agent whose subway car dozing was all for show? Ultimately, we’ll never really know the whole truth of this fascinating affair.

Michael Bettaney

In the movies, secret agents are often hard drinking, tough-living renegades, taking huge risks and getting away with it. In reality, men – or women – with a fondness for alcohol make terrible spies, as the case of Michael Bettaney was to prove. But, however useless Bettaney was himself, his superiors were just as bad at their jobs. After all, they cleared him to carry on working even when it was clear that he was hardly suited to keeping his head down. And so, when Betteney was finally convicted of treason, the British Security Service, or MI5, suffered one of the worst public humiliations in history. So, who was this bumbling agent?

Michael Bettaney was born in the English city of Stoke-on-Trent in 1950. Evidently smart, he attended the prestigious Oxford University, an institution that has long provided Britain’s spymasters with new talent. While at Oxford, Bettaney was something of a character. He was known for his hard-drinking ways. More shockingly, he was also open and extremely vocal in his admiration of Adolf Hitler and could often be heard drunkenly singing old Nazi songs in the quads of Pembroke College. Surely this was warning enough that Bettaney would make for a terrible spy? Evidently not as in 1974, he was recruited by MI5 (though, according to some accounts, this was only so that the spy agency could meet a quota on recruiting new agents from blue collar backgrounds).

By all accounts, Bettaney carried on drinking hard even after starting his career in espionage. Famously, he was once caught by police drunkenly singing offensive songs in public, only to shout out loud “You can’t arrest me, I’m a spy!”. Astonishingly, his bosses continued to overlook such indiscretions and, in 1982, they even promoted him to the Soviet desk, giving him access to highly secretive information. For Bettaney, this was an opportunity too good to resist. Soon, he was taking a camera to work, photographing sensitive documents and building up a collection to sell to Russia.

By 1984, Bettaney had amassed enough documents to earn himself a small fortune. He told his bosses he was going on holiday to Austria, bit instead set up a meeting with General Guk, the head of the KGB in London. Unbeknownst to both men, another high-ranking member of the KGB station, a certain Colonel Oleg Gordievsky, was an MI6 agent. Bettaney’s bumbling approach meant word got out, and Gordievsky informed his London handlers. It goes without saying that Bettaney had hardly covered his tracks well, so he had no chance of pleading innocence. He was ultimately sentenced to 23 years in prison, though was released on parole in 1998, his name becoming a byword for bad espionage and terrible management.

Nathan Hale

One of America’s very first spies – and, certainly, according to the CIA, the first to be executed for espionage – Nathan Hale was, to many, a true hero of the independence struggle. He was young, fearless and brave and is remembered with great admiration. Indeed, there’s even a statue of him, along with his famous last words (“I only regret that I have but one life to lose for my country”) at the CIA headquarters. But was he actually any good at spying? Sadly, it would appear not. In fact, according to some historians, he was completely out of his depth when he undertook his first – and last – mission as a secret agent.

That’s not to say he wasn’t enthusiastic about the role. Or even to doubt his bravery. Undoubtedly, he was both. At the age of just 21 and fresh out of Yale, he answered General George Washington’s call for volunteers to venture behind enemy lines and report on British army size and movements. Notably, Hale was the only man to step forward, a testament to his bravery. However, despite having been made a captain in the Continental Army, he knew nothing about the art of spying. Tragically, he didn’t receive any training in espionage or subterfuge either. Instead, in September of 1776, he was just given a set of civilian clothes and sent on his way across enemy lines.

It wasn’t long before Hale caught the attention of Major Robert Rogers. While Rogers, a Brit who had served with distinction in several previous conflicts, was a skilled and experienced outdoorsman, Hale was nothing of the sort. In fact, he looked so out of place in the open that Rogers immediately suspected he was up to something and decided to follow him. After a couple of days, he made his approach. The pair struck up an easy conversation, and soon the talk shifted to the war. Surely Hale, as a spy deep in enemy territory, would keep his mouth shut. Apparently not.

Despite having just met Rogers, the younger man willingly revealed himself to be a spy and told him of his mission. He even repeated his claims over dinner at Roger’s house. As one historian, writing for the Library of Congress’s Information Bulletin, noted: “How could anyone on a secret mission be so stupid, or to use more generous terms, so naïve or credulous, to be taken in by a perfect stranger and then to disclose, the next day, the object of his mission to several more perfect strangers.”

Tragically, such naivety was to be harshly punished. Hale was brought before the British authorities and convicted of spying. He was hung the next morning, right after saying his famous last words. History has been more forgiving, and Hale has long been considered a true American icon and is even the designated state hero of Connecticut.

Aldrich Ames

If you’re being paid to spy on your country, you might want to keep a low profile, right? Well, Aldrich Ames didn’t. In fact, it was the CIA man’s ostentatiousness which led to his downfall. After all, his bosses at the Agency, reasoned: how could a man on a (relatively) modest salary afford a top-of-the-range Jaguar car? And how come he was living in a mansion that the CIA Director himself would be happy to call home? The answer, of course, was that he was selling secrets for cold, hard cash. The only really shocking thing about the whole affair was how inept he was about it. Well, that and how he was able to get away with it for almost a decade.

Born in River Falls, Wisconsin, Ames was hardly a top scholar. But that didn’t stop him from joining the CIA. In fact, he started working for them in 1957, while still a sophomore at the University of Chicago. While he had big plans for his life, he got distracted from his studies and dropped out, choosing to work in a Chicago theatre for a couple of years before returning to the Agency to work full-time in menial clerical roles. After five years pushing paper, Ames went back to school. He graduated from George Washington University and then, to the surprise of some, was accepted onto the CIA’s Career Trainee Program. His spying career had begun – but so too had his career as a hard drinker.

Over the next few years, Ames bounced around the world. He worked in Turkey, then Washington and then New York City. His performances were consistently average at best and his superiors noted his thirst for whiskey with alarm. He even managed to get away with several sackable offences, including having an affair with a Colombian agent and even leaving a briefcase full of classified information on a subway train. He seemed untouchable. Could this be why, when he was moved to the Soviet Desk at CIA HQ in 1983, he decided to try and get rich? Or was he simply a desperate man, worried that divorcing his wife and taking up with the Colombian agent would bankrupt him?

Ames started off small. He sold essentially worthless information to the KGB for $50,000, establishing him with the Soviets. After this initial success, he arranged regular meetings with a KGB handler. He was paid $25,000 for each lunch meeting and is believed to have amassed $4.6 million in total. Soon, Ames was splashing the cash, claiming that his new Colombian wife came from a wealthy family. New, designer suits, cosmetic dentistry and constant home improvements made his colleagues and superiors suspicious. And, even though Ames passed two polygraph tests, his time was up. The CIA put him under round-the-clock surveillance and soon got enough to charge him with treason.

Ames may have been bungling, but he was far from harmless. His betrayals led to at least ten agents being uncovered and executed. That’s why, in 1994, he was convicted and sentenced to life imprisonment without the possibility of parole.

Werner von Janowski

During the Second World War, some secret agents went undetected for months or years. A select few spies even made it through the whole conflict without getting caught. But Werner von Janowski? Well, this bumbling Nazi only made it a few hours before he was caught. And, rather than being a victim of sheer bad luck or amazing counter-espionage, his cover was blown due to his own incompetence. Not for nothing has Werner been routinely dubbed ‘the worst Nazi spy’ of the whole war.

Hardly anything is known about von Janowski aside from his ill-fated mission to Canada in 1942. Despite the fact that the main theatre of war was many thousands of miles away, Canadians were on the alert for Nazi spies. In particular, people living close to the east coast were on heightened alert. They knew U-boats were patrolling the waters here and there were often rumours of sailors coming ashore or even spies landing in an attempt to infiltrate Canadian society. All the more reason for von Janowki to be extra cautious, right?

The secret agent came ashore on Canadian soil on the morning of 9 November 1942. He had been tasked with making contact with Canadian Nazi sympathizers and seeing if a popular rebellion in favor of Germany could be achieved. To begin with, von Janowski played everything by the book. He landed wearing a pristine German uniform, complete with Iron Cross. This way, if he was spotted, he could simply claim he was a sailor and so avoid summary execution. Undetected, he buried his uniform in the sand and assumed his false identity. According to his new papers, he was a Parisian-born traveling salesman who had been living in Canada for more than 20 years. So far, so good.

Sticking to the plan, Von Janowski walked into the quiet town of New Carlisle. His spymasters had instructed him to wait here until he could take a train to Quebec City. However, the spy had other ideas. He wanted a hot shower and a rest, so he found a hotel and tried to check in. Right away, the hotel staff knew something was up: The ‘traveling salesman’ claimed he had just arrived into New Carlisle by bus. But everyone knew the first bus of the day wasn’t due for another three hours. What’s more, he spoke with a strange accent, wore foreign clothes and smoked Belgian cigarettes. And then there’s the money. He attempted to pay with a Canadian bank note that hadn’t been in circulation for two decades!

Perhaps fearful for the safety, the hotel staff humored their guest and sent him on his way to the train station. They then alerted the authorities and a Mountie boarded the train. He asked von Janowski for his identity card. The rumbled not-so-secret agent replied simply: “I am caught. I am a German officer.” In all, he had been active for 12 hours, one of the shortest espionage careers of the whole war. The Canadian authorities tried to turn him into a double agent. The German quickly accepted the offer, but he was equally as inept at this, failing to provide any useful information about Nazi U-Boat movements. In the end, he was shipped off to a POW camp in England to see out the rest of the war.

Stewart David Nozette

Anyone granted Top Secret clearance in the United States is supposed to be smart, right? Certainly they would be expected to be smart enough to think twice if they receive a phone call from someone claiming to be from the Israeli secret intelligence agency, Mossad, and asking them to sell secrets. Apparently not. For this is exactly how Stewart David Nozette, referred to be some as ‘The Worst Spy Ever’ got caught.

While his own stupidity may have been his downfall, there’s no doubting that Nozette is a smart guy. Born in Chicago in 1957, he went on to study Geosciences at the University of Arizona before earning his PhD from the prestigious Massachusetts Institute of Technology (MIT) in 1983. With a stellar academic career behind him, Nozette then gained employment with the California Space Institute. He then led the design and development of the Clementine spacecraft, an ingenious device capable of testing for water on the lunar surface. Given his expertise, he was appointed to the National Space Council under President George H.W. Bush, a post that required Top Secret clearance and access to highly sensitive documents relating to national security.

All the while, however, Nozette was apparently taking more than a regular pay check from his employers. Over the years, he was submitting varied expense claims to NASA, including billings for several mortgages and even tennis club membership. Unsurprisingly, this attracted the attention of the Justice Department, who decided to investigate further. They stumbled across an e-mail in which Nozette warned he might divulge classified information to a foreign country, perhaps Israel. Alarmed, the investigators passed on the information to the FBI. The Feds decided to set a trap to see if this was mere bravado or if Nozette meant what he said.

In September of 2009, then, Nozette started receiving phone calls from an anonymous person claiming to be a Mossad agent. Would he be willing to exchange classified information for money? Nozette said he would. What’s more, he provided answers to some questions ‘Mossad’ posed to test his reliability and access to sensitive material. Having seemingly gained the spies’ trust, Nozette then left a folder full of data relating to US early warning systems in a post office box for agents to pick up. At this point, the FBI decided to swoop. They arrested Nozette and his espionage career was over before it had really begun.

In the end, Nozette was convicted of just a single charge of espionage and sentenced to 13 years in prison. Quite why he was so willing to spy on his country remains something of a mystery. Certainly, it wasn’t for the money. In the first instance, he asked for $11,000 in exchange for information, a tiny sum compared to what most traitors ask for. It’s more likely that he was a genuine Israeli sympathizer and volunteered to help the country. He genuinely wanted to be a Mossad mole in the American space program. If only Mossad had actually been interested…

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!

Carl Meier and the Nazi spies of Operation Lena

In September of 1940, Nazi Germany sent 12 spies to the UK. Their mission was simple: to report on British troop movements, civilian morale and, where possible, sabotage the enemy’s preparations for war. In short, the Nazi secret agents were to pave the way for a German invasion of the British Isles, to be codenamed Operation Sealion. However, these men were far from super spies. In fact, the dozen men of Operation Lena were really quite inept, making errors so basic and stupid that their British captors were convinced the Germans were playing some kind of trick.

Carl Meier was one of the first to land on enemy soil. The 23-year-old Nazi Party member had rowed ashore alongside three other men, landing on the south coast. His spying career was to last a matter of hours. Upon coming to shore, Meier strolled into the nearest village and found the pub. He went in and ordered a pint of cider. The only problem was it was 9 o’clock in the morning and, as every Brit knew, landlords weren’t allowed to serve until 11. What’s more, the mysterious customer was taller than the average Brit – he hit his head on the wooden beams of the old pub – and spoke in a funny accent. The landlady, a woman by the name of Mabel Cole, immediately called the police and Meier was arrested. His three comrades were also quickly rounded up and convicted of spying.

At the other end of the country, a pair of Nazi spies were also given away by their lack of preparation. Landing in Scotland, they found a pair of bicycles and set off on their mission – riding on the wrong side of the road! They were caught with German sausages in their pockets. Their war was over. Clearly, these men were incompetent and inept spies. But historians of the period think there may be more to the story. Could it be that the head of the German intelligence services deliberately chose young men who were passionate Nazis but terrible intellects, knowing they would fail on their mission?

Undoubtedly, there’s plenty of evidence that some spy chiefs, along with army heads, were far from convinced in Adolf Hitler as a leader. What’s more, some disagreed with the plans to invade Great Britain. Could it be that attempts at espionage were sabotaged from the inside? Or were the spy chiefs every bit as incompetent as the men they sent on Operation Lena in 1940?

Where did we get this stuff? Here are our sources:

“Nazi Saboteurs and George Dasch”. The FBI.

“William Colepaugh, The Connecticut Spy Who Went Out in the Maine Cold”. New England Historical Society.

“Spy Out of Jail”. BBC News, May 1998.

“Nathan Hale Blundered Into a Trap, Papers Show”. The New York Times, September 2003.

“How the F.B.I. Finally Caught Aldrich Ames”. The New York Times, January 1995.

“The world’s worst Nazi spy: The German agent caught by Canada in a matter of hours”. Tristin Hopper, The National Post, April 2016.

“The Socialite Spy Who Played So Dumb She Outsmarted the Nazis”. Christopher Dickey, The Daily Beast, September 2016.

“The Worst Spy Ever”. Martin Sieff, The Daily Beast, October 2009.

“The spy who couldn’t spell: How the biggest heist in the history of US espionage was foiled”. Yudhijit Bhattacharjee, The Guardian, October 2016.

“Secrecy and firing squads: Britain’s ruthless war on Nazi spies”. Ian Cobain, The Guardian, August 2016.