Buzz
Covert operations can fail in numerous unexpected ways. A small oversight, overlooked by planners, might cause the entire mission to collapse. Alternatively, a meticulously organized secret operation could be halted at the final moment due to political meddling or internal bureaucratic conflicts. As the examples in this list reveal, the reasons for such failures can sometimes appear utterly peculiar.
10. The CIA’s Poison Froze Solid in the Freezer
Mytour has previously explored the CIA’s numerous failed attempts to eliminate Fidel Castro, such as the exploding cigar, poisoned pen, and contaminated diving suit. The Agency’s closest effort to assassinating the Cuban leader involved an even more sinister tool—a toxic milkshake.
The CIA was aware of Castro’s fondness for stopping by Havana’s Hotel Libre to enjoy a refreshing milkshake. In 1964, they enlisted the Mafia to deliver a cyanide pill to a Cuban opposition group. The group had a mole working at the Hotel Libre (previously the Havana Hilton) who was tasked with slipping the pill into Castro’s drink. To ensure easy access, the assassin hid the pill in the freezer where the milkshake ingredients were stored.
Initially, the plan appeared to proceed smoothly. Castro arrived and ordered a shake from the insider, but when the assassin went to retrieve the pill, he discovered it had frozen to the freezer wall. Frantically attempting to free it, he accidentally tore the pill, spilling the poison. After a brief and futile effort to gather the poison from the freezer floor, the assassin, in a panic, aborted the mission. Castro’s security chief later estimated that over 600 attempts were made on his life before he resigned in 2008.
9. The British Believed Killing Hitler Might Benefit the Nazis
The strategy was both bold and straightforward. Under the cover of darkness, a small aircraft would soar over the Bavarian Alps. A British sniper and a Polish guide, dressed in German military uniforms, would parachute down and meet a local informant. Stealthily navigating the forest, they would penetrate a secluded Nazi base frequented by Adolf Hitler. As Hitler took his customary early morning stroll, the sniper, concealed in the foliage along the trail, would take a single, decisive shot.
This was the scheme devised by the British Special Operations Executive (SOE) after interrogating a former member of Hitler’s personal guard. The captive revealed details about Hitler’s morning routines and the minimal security at his Alpine hideaway. The SOE’s planning team proposed several assassination methods—ranging from a bazooka strike on Hitler’s preferred tea house to a full-scale parachute assault by an SAS unit—but ultimately chose the sniper approach, as it could be framed as the work of disgruntled German military factions.
However, the plan was never executed. Senior British officials concluded that eliminating Hitler would be counterproductive. They believed his incompetent leadership was more beneficial to the Allies than his removal. A high-ranking SOE official noted that Hitler’s “strategic missteps made him more valuable alive,” and Winston Churchill himself deemed assassinating him “detrimental.” Concerns also arose that killing Hitler might spawn a new “stab-in-the-back” narrative, transforming him into a martyr. The plan was discreetly abandoned.
8. An Anti-Nazi Assassin Became Trapped in a Restroom
An earlier attempt to assassinate Hitler took place in 1929, four years before he became Germany’s Chancellor. A disillusioned member of Hitler’s SS bodyguard, certain that the man he was sworn to protect would ruin Germany, planted a bomb beneath the platform where Hitler was set to deliver a speech. The bomb required manual detonation, which the guard, being close to Hitler, could easily manage. However, the anxious assassin decided to make a quick trip to the restroom before the event.
After finishing, the guard attempted to return to his position but found himself trapped in the bathroom. He yelled for assistance and banged on the door, but it was too late by the time he escaped. It’s unsettling to consider that the tragedies of World War II and the Holocaust might have been averted if not for a malfunctioning bathroom lock.
7. Washington Attempted to Seize Gunpowder Franklin Had Already Taken
In October 1775, a small fleet of American vessels quietly entered the waters near Bermuda. Sent by George Washington on a highly classified mission, their goal was critical. The Continental Congress was perilously low on gunpowder and essential supplies, but Washington was aware of a well-supplied British arsenal in Bermuda. He also knew the Bermudans were suffering under a British embargo on American goods, particularly food. Washington gambled that the locals would turn a blind eye while his men seized the gunpowder.
The mission appeared to falter immediately. Washington’s men discovered Bermuda, typically a quiet outpost, was teeming with British ships. Upon contacting locals, they learned the gunpowder had already been taken—by the Americans.
As it happened, while Washington was devising his plan, Ben Franklin had been orchestrating a similar operation. Collaborating with the father of Bermuda’s governor, Franklin arranged for food to be smuggled from South Carolina to Bermuda. In return, the Bermudans allowed Franklin’s men to plunder the arsenal. They secretly breached the armory roof, lowered an American sailor inside, and unlocked the doors. Washington’s gamble would have succeeded—he was merely a month behind.
6. MI5’s Fear-Detecting Gerbils Missed the Point
In the 1970s, MI5, the British counterintelligence agency, was often considered one of the least effective spy organizations globally. They failed to uncover Soviet agents independently and were riddled with moles. However, they stumbled upon a potentially game-changing tool—the sniffer gerbil. Researchers discovered that gerbils could detect human adrenaline, even slight increases in it. The plan was to use these small rodents as living lie detectors during interrogations.
An even more bizarre idea involved placing gerbil cages in airports and using large fans to direct passengers' scents toward them. The gerbils were supposed to identify spies and terrorists, who would presumably be more anxious than regular travelers. The Israeli Shin Bet agency implemented this system at Tel Aviv airport but had to scrap it when they realized the gerbils couldn’t distinguish between adrenaline from a nervous hijacker and that from someone with a fear of flying or carrying heavy luggage. MI5 also concluded that the gerbils responded to any adrenaline change, rendering them ineffective for interrogations. They reverted to traditional lie detectors.
5. A Corporate Spy Overlooked Deleting His Social Media Profiles
Environmental activist group Plane Stupid, which opposes UK airport expansion, gained a fervent new member in 2007 named “Ken Tobias.” However, the group grew wary of Tobias, partly because he “always arrived first to meetings . . . and was overly well-dressed,” which did little to challenge stereotypes about environmentalists.
Tobias consistently advocated for the group to adopt more radical and potentially aggressive measures, which began to leak to the media. He often bragged about his Oxford education, prompting the group to circulate his photo on campus. Eventually, someone recognized him as Toby Kendall. While using pseudonyms was common among members, a simple Google search uncovered a Bebo profile linking Kendall to C2-I, a corporate security firm specializing in aerospace. This mirrors another case where Vericola, a security company, infiltrated an environmental group, only to be exposed when the CEO mistakenly forwarded all her emails to the group's account.
4. Britain’s Attempt at Friendly Propaganda Backfired Spectacularly
During the Suez Crisis, Britain, France, and Israel launched an offensive against Egypt to reclaim control of the recently nationalized Suez Canal. The move was widely condemned as a colonial overreach, damaging the West’s reputation. U.S. pressure eventually forced a withdrawal. Britain’s efforts to frame the invasion as a peaceful, necessary act were further undermined by their propaganda team’s incompetence.
Led by Lieutenant Colonel Bernard Fergusson, who lacked experience in psychological warfare, the propaganda department aimed to sway Egyptian civilians to support or at least not resist the invasion. Fergusson ordered leaflet bombs to be dropped over villages, designed to explode high in the air and distribute messages claiming the intervention would combat communism and improve lives. However, the designers overlooked the barometric differences between Egypt and England, causing the bombs to explode just 2 meters (6 ft) above the ground—dangerously close to head level.
3. Russia’s Most Notorious Spy Was Unmasked Due to His Racist Views
Robert Hanssen stands as one of the most damaging spies of the Cold War era. After joining the FBI in 1976, he was tasked with surveilling a Soviet agent in New York. Instead, he approached the agent, introduced himself, and proposed espionage in return for payment. His treachery lasted 22 years, causing an estimated $44 billion in damages to the U.S. government and devastating human losses. Among his first betrayals was exposing Soviet Major General Dimitri Polyakov, who had been supplying intelligence to the CIA. Polyakov was subsequently arrested and executed.
Hanssen, a grim and peculiar individual, often raised suspicions among colleagues but managed to evade detection multiple times. Once, he was caught hacking into a fellow agent’s computer but claimed it was to highlight security vulnerabilities. On another occasion, he was found installing a password-cracking program on his FBI computer. Astonishingly, his excuse—that he was attempting to connect a printer and had forgotten the admin password—was believed. When the FBI realized a mole was among them, Hanssen was even assigned to the investigation. It seemed he might never be caught—until his peculiar racist behavior gave him away.
By 2000, the FBI mistakenly suspected Brian Kelley of being the mole but lacked evidence to confirm their theory. In a desperate move, they sent an agent with a fabricated Russian accent to Kelley’s home, warning him his cover was compromised. They hoped he would flee and incriminate himself, but Kelley, baffled and innocent, reported the encounter to authorities instead.
The agency finally caught a lucky break when a former Russian spy offered to sell them a recording of the mole’s voice. The voice on the tape didn’t match Brian Kelley’s, temporarily stalling the investigation. However, the voice soon launched into a tirade, using the odd racial slur “purple-pissing Japanese,” a phrase famously associated with George Patton and often repeated by Robert Hanssen. This led to Hanssen’s arrest, and he was ultimately sentenced to 15 consecutive life terms with no chance of parole.
2. British Intelligence Executed a Plan So Covert It Went Completely Unnoticed
In World War II, the British Special Operations Executive (SOE) devised a cunning strategy to weaken the German war machine. They recognized that Heinrich Himmler, the SS leader, was deeply disliked compared to other Nazi figures and viewed as overly ambitious. Rumors circulated that Himmler might attempt to overthrow Hitler, and the SOE aimed to exploit these fears to incite internal conflict within the Nazi hierarchy. To succeed, they had to execute their plan with such subtlety that it would evade detection entirely.
The strategy they devised involved creating counterfeit German stamps featuring Himmler’s portrait instead of Hitler’s. The idea was that people would interpret the stamps as evidence of Himmler’s ambition to seize power, mistakenly released ahead of schedule. Britain’s top forgers meticulously replicated the stamps to match authentic German designs. These fakes were circulated across Europe, and the SOE eagerly anticipated the fallout. However, nothing happened.
No one paid attention. The stamps were used as if they were entirely normal. Frustrated, the SOE instructed agents to visit German stamp shops and highlight the unusual stamps. Even then, collectors simply assumed the stamps were issued to honor Himmler, completely missing the intended implication.
One government was thoroughly deceived—unfortunately, it was the U.S. government. The American embassy in Switzerland sent a sample of the mysterious stamps to Washington for analysis. Since the British hadn’t informed their allies about the operation, American officials wasted resources investigating the fabricated “stamp mystery.”
1. The Soviet Union’s Greatest Strength Lay in Their Inexpensive Staples
In World War II, German intelligence believed infiltrating Soviet ranks would be straightforward, given the Soviet military’s vast size and inefficiency. However, their spies were consistently captured shortly after crossing into Soviet territory. This led to speculation: did the Soviets possess an exceptionally effective counterintelligence system?
The truth was far simpler. The Germans had meticulously crafted counterfeit Soviet passports for their agents, but they overlooked a critical detail. Authentic Soviet passports were assembled with low-quality iron staples that rusted over time, leaving noticeable brown stains on the documents. The German forgeries used stainless steel staples, which didn’t rust, making the passports stand out immediately to any vigilant border guard.
Remarkably, this oversight was never identified—and post-war, the Americans repeated the same error. In the 1950s, the CIA recruited Soviet refugees, primarily Ukrainians, as sleeper agents. These operatives were parachuted into the USSR with missions to conduct sabotage and organize resistance. However, their CIA-issued forged passports also featured stainless steel staples, leading to their swift arrests upon arrival.
