Historic Schemes that Backfired in Catastrophic Fashion

29. The Would-Be Libertarian Founding Fathers Next Turned to Run Guns to a White Secessionist Movement in the Bahamas

The following year, Michael Oliver and his associates tried to create another libertarian tropical island paradise, this time closer to home: in the Bahamas. In 1973, as the then-British colony neared its independence, some white Bahamians objected to living in a majority-black country ruled by blacks. So they decided to secede, laid claim to the Bahamas’ Abaco islands as the nucleus for a white majority country, and formed the Abaco Independence Movement. That attracted the libertarians as swiftly as chum attracts sharks.

So they passed the plate to buy weapons and explosives for the secessionists. In exchange, they were promised that the white-ruled island would be run on principles that would make Ayn Rand proud. However, the plan backfired when the libertarians’ chosen gunrunner double-crossed them. Instead of smuggling the machine guns they had paid for to the secessionists, he tried to sell them in Costa Rica. He was caught, and in the ensuing scandal and legal mess, Oliver got deported from the Bahamas, and the plan for a libertarian Caribbean country was abandoned.

28. Next, the Phoenix Foundation Funded a South Pacific Cult

The Phoenix Foundation next took another stab at the South Pacific. This time in Vanuatu, where French planters, fearful of approaching independence and the threat to their land holdings by a native majority, plotted secession. They were led by a cult leader named Jimmy Stevens, who dubbed himself “Moses”. He wore long robes and grew a long white beard, and had a harem of twenty-three wives. The Foundation bought and smuggled guns to Vanuatu, and made passports, flags, and coins with Stevens’ face on them. All in all, the Foundation spent about a quarter-million dollars – serious money in a place as poor as Vanuatu, population of 115,000 at the time.

In 1980, Stevens led a rebellion and declared the independent Republic of Vemerana. Vanuatu had no military to suppress the rebels, so it seemed that third time was the charm for Oliver’s dream of a libertarian country. The scheme backfired, however, when Vanuatu sought aid from nearby Papua New Guinea, which did have an army. It sent a battalion, which swiftly crushed the rebellion. Oliver was deported and permanently banned from Vanuatu, and his libertarian coconspirators fled. Stevens was arrested, charged, convicted, and sentenced to fourteen years behind bars. Michael Oliver was a successful businessman, but as a libertarian would-be founding father, he was a three-time loser. The Phoenix Foundation did not rise from the ashes of its Vanuatu defeat and finally faded away.

27. This Plan to Spark a Communist Revolution in South America Backfired Badly

Marxist revolutionary Ernesto “Che” Guevara (1928 – 1967) rose to prominence during the Cuban Revolution. He gained international fame thereafter as a guerrilla warfare innovator, author, and diplomat. His image became a romantic icon of anti-imperialism, and after his death, he became a martyr to many worldwide. Things were going well for “el Che”, until he concocted an ambitious plan to spark a revolution in South America, that he would hoped would turn all of Latin America communist. It backfired on him, big time.

Born in Argentina in 1928, Guevara was raised in a progressive environment, and from early on, he developed an affinity for the poor and downtrodden. Despite being an asthmatic, he managed to excel in athletics. After graduating high school, he studied medicine, and as a young man in the 1950s, he spent his holidays motorcycling through South America. In his travels, he encountered conditions of dire poverty, inequality, and injustice, that radicalized and set him on the path to Marxism.

26. From Random Leftist to One of Latin America’s Most Famous Revolutionaries

As Che Guevara immersed himself in Marxism, he decided to abandon his study of medicine. As he saw it, only revolution could alleviate the suffering of the masses. In 1953, he moved to Guatemala, where the progressive government of Jacobo Arbenz was attempting land reform and redistribution. However, Arbenz’s land reforms – especially the part involving lands of the American United Fruits Company – backfired: his government was overthrown in a 1954 CIA-backed coup. That deepened Guevara’s radicalism and added anti-imperialism to his agenda. It also laid the foundations for a theory he later proselytized, about achieving socialism via worldwide revolution.

By 1955, Guevara had relocated to Mexico, then a common refuge for leftists. There, he met and befriended a young Cuban lawyer and revolutionary, Fidel Castro, who was planning to overthrow the corrupt Batista regime in his home island. Guevara accompanied Castro and a small force to Cuba in 1956, in an ambitious bid to start a revolution. He became one of Castro’s chief advisors, and commanded revolutionary forces in guerrilla warfare, leading them to the final victory and seizure of the island in 1959.

25. Che Guevara’s Global Revolutionary Tour

Fidel Castro appointed Che Guevara to a variety of security, economic, and diplomatic posts in the new revolutionary government. The Argentinians played a key role in transforming Cuba into a communist state. He was instrumental in defeating the CIA-backed Bay of Pigs Invasion in 1961 and was a significant player during the Cuban Missile Crisis in 1962. He also traveled the world as a diplomat, and gave a notable speech before the UN in 1964, condemning America’s foreign policy and South Africa’s apartheid. However, Guevara’s greatest passion was for revolutionary warfare, and in 1965 he left to fight in revolutions around the world.

Read too: Cuban Missile Crisis of 1962.

He went first to the Congo, where he trained guerrillas. In 1966, he went to Bolivia, where he tried to spark a communist revolution that he hoped would sweep through South America. Things did not go well, and the attempt backfired. He was captured in 1967, and Bolivia’s president ordered Guevara’s execution. When the executioner entered the room where the prisoner was held, Guevara noticed that he appeared jittery and nervous. So he scornfully uttered his last words: “I know you have come to kill me. Shoot, coward! You are only going to kill a man!”

Read More:

• Freedom Fighter or Terrorist? The Life and Death of Che Guevara
• Nobody’s Hero: 9 Inconvenient Truths about Che Guevara
• Seven Key Moments in Fidel Castro’s Exceptional Life

24. A Sword Redesign That Backfired Dismally

It seems hard to screw up the design of something as simple as a sword, but the British Army did that when it introduced a new sword in the late eighteenth century. Officially termed the 1796 Infantry Officer’s Sword, and commonly known as the “1796 Spadroon”, it backfired dismally. It became the British Army’s standard-issue line regiment’s officer sidearm throughout the Napoleonic Wars and was heavily criticized. The 1796 Spadroon’s defects were especially problematic in an era when swords were still used in combat.

Back then, swords had not been relegated to mere decorative accouterments accompanying dress uniforms, as is the case today. Spadroons – straight-bladed, flat-backed, single-edged light swords of the cut and thrust type – were not bad weapons in themselves. However, the 1796 Spadroon’s designers managed to screw up the design of a simple weapon that had been around for millennia. They took a straightforward concept to the drawing board and came back with a weapon that was bad at cutting, thrusting, defense, and was poorly manufactured to boot.

23. A Sword That Could Not Slash, Stab, or Defend

The 1796 Spadroon backfired in all the ways possible for a sword. The first problem was the hilt: it was that of a small sword, a purely thrusting weapon such as a rapier. That made it ergonomically ill-suited for the handgrip necessary for cutting and slashing. If a user somehow managed to get a good grip for cutting, the blade was too light and flexible for a serious cut: it bounced off even naked skin. The excessive flexibility made it ill-suited even for the thrusting (stabbing) its hilt was best suited for. That was worsened by the lack of a profile taper – its point was not sharp and pointy enough to pierce well.

Another hilt problem was the guard. Instead of a solid saucer to protect the user’s hand, the guard was a folding clam shell secured by pins. They often broke under impact. Poor hand protection was exacerbated by a thin and weak knuckle-bow (the projecting piece on the hilt). It bent easily under impact or pressure, and frequently smashed into or pinched the user’s hand. As a contemporary British general summed it up: “Nothing could be more useless or ridiculous than the old infantry regulation [sword]; it was good for neither cut nor thrust and was a perfect encumbrance. In the Foot Artillery, when away from headquarters, we generally wore dirks instead“.

Also Read: History’s Deadliest Swords.

22. The Unluckiest Five Minutes in Japanese History

At 10:25 AM, June 4^th, 1942, Japan was mistress of the Pacific. She had the world’s most powerful naval aviation force, had been running roughshod over her enemies while marching from victory to victory, and was in the driver’s seat, dictating the terms of World War II in the Pacific Theater. By 10:30 AM, Japan had effectively lost WWII. The Japanese had experienced what was probably the unluckiest five minutes ever experienced by any country in the history of warfare.

After the attack on Pearl Harbor, Japan went on a rampage and won a series of stunning victories. However, Japan’s war strategy was to win a battle of annihilation, like Tsushima, then negotiate a favorable peace. Pearl Harbor was a success, but no Tsushima. So the Japanese planned an invasion of Midway Island to lure what was left of the US Navy into showing up for a climactic showdown. Assuming that the US Navy had only one or two aircraft carriers in the Pacific, the Japanese launched their operation with four fleet carriers. It backfired, however, because American code breakers had cracked Japan’s secret codes and knew of the upcoming attack.

21. Japan’s Navy Thought it Was Sailing to Inflict a Crushing Blow Upon the US but Was Actually Sailing Into an Ambush

In addition to cracking Japan’s secret codes, the Americans had more aircraft carriers in the Pacific than the Japanese expected. One US carrier had been transferred from the Atlantic, and another that had been damaged in an earlier battle and was expected to take months to fix, was rushed back into service after 48 hours of repairs. Thus, the Japanese sailed out to meet three American carriers, and an alert enemy waiting in ambush, rather than one or two carriers caught off guard.

The Japanese launched a carrier strike against Midway on the morning of June 4^th, 1942. They inflicted significant damage, but a second strike was necessary. So the Japanese aircraft were recovered and readied. While doing that, the Japanese learned that American carriers were nearby. Midway wasn’t going anywhere, and destroying aircraft carriers was more important. So orders were given to switch bombs from ones intended for ground targets, to anti-ship bombs and torpedoes. That decision backfired spectacularly: while that was going on, the American carriers launched their own aircraft against the Japanese.

20. An American Lieutenant Commander’s Spur of the Moment Decision Doomed Japan

The first American planes to reach the Japanese fleet were Devastator torpedo bombers – slow planes that had to fly low, steady, and straight, to launch their torpedoes. 41 Devastators attacked the Japanese carriers without fighter escort. 35 were shot down, without scoring a hit. The Japanese carriers resumed refueling and rearming. While the American torpedo bombers were getting slaughtered, a flight of American Dauntless dive bombers was lost, trying to locate the Japanese. They neared the point beyond which they wouldn’t have enough fuel to return to their carriers, but their leader, Lieutenant Commander Wade McClusky, decided to keep going. He was rewarded by spotting a lone Japanese destroyer below. Guessing that it was heading to rejoin its fleet, McClusky used the destroyer’s wake as an arrow.

It led him to the Japanese fleet, which was caught at the worst possible time for an attack from dive bombers. The carriers were rearming and refueling, so bombs, torpedoes, and fuel hoses were all over the place. There was also no fighter cover: Japanese fighters had gone down to intercept and destroy the torpedo bombers that had attacked at low level. They hadn’t regained altitude when the American dive bombers showed up high above and dove down. Within five minutes, three of the four Japanese aircraft carriers were burning. The fourth was sunk later that day. Japan’s plan for a decisive victory had backfired. It turned the tide in the Pacific, and dealt the Japanese a defeat from which they never fully recovered.

19. A Study That Backfired and Became an Ivy League Scandal

One day in the late 1970s, an employee of Yale University unlocked a room on campus that had not been used in many years. Inside, there was one helluva surprise: thousands of photos of nude young men, showing their fronts, sides, and rears. To add to the oddity, there seemed to be metal pins sticking out of the naked men’s spines. What could it be? Was it the trove of some weirdo, with a niche fetish for BDSM voodoo porn? It turned out to be nothing so juicy, but it was still weird. From the 1940s to the 1970s, Yale and other Ivy League schools such as Harvard, Vassar, and Brown, had required their freshmen to pose nude for a photoshoot.

The goal was to furnish material for a massive study into how rickets developed. That involved sticking pins to the backs of male and female subjects. Although the goal was laudable, the failure to consider and protect the students’ privacy backfired. Generations of elites who attended the Ivy Leagues had posed, and the archives included naked photos of well-known figures ranging from George W. Bush to Hillary Clinton to Diane Sawyer to Meryl Streep. The photos were burned after news leaked, and the study was denounced. However, it is possible that some might have escaped the flames, and are still circulating out there, to potentially end up on the internet someday.

18. This Ruler’s Rash Decision to Taunt One of History’s Scariest Conquerors Backfired Horribly

Genghis Khan (1162 – 1227) once said: “Life’s greatest joy is to rout and scatter your enemies, and drive them before you. To see their cities reduced to ashes. To see their loved ones shrouded and in tears, and to gather to your bosom their wives and daughters“. Somebody who says stuff like that is probably not the kind of person that a wise ruler should deliberately insult. Yet that is precisely what Shah Muhammad II, ruler of the Khwarezmian Empire from 1200 to 1220, did.

As if to double down on the stupid, Shah Muhammad then dared Genghis Khan to do something about it. Needless to say, it backfired. Genghis Khan founded the Mongol Empire, the world’s largest contiguous empire, and was one of history’s most terrifying figures. His conquests were often accompanied by widespread massacres, even genocide. As a percentage of global population, the estimated 40 million deaths of the Mongol conquests he initiated would be equivalent to 278 million deaths in the 20^th century.

17. Provoking the Beast

The beef between Genghis Khan and the Khwarezmian Empire of Shah Muhammad II began in 1218. At a time when the Mongol conqueror was busy fighting the Chinese, he sent an embassy and trade mission to Khwarezmia. In addition to diplomatic emissaries, the embassy included numerous merchants with valuable trade wares. Genghis had hoped to establish diplomatic and trade relations with the Khwarezmian Empire, which encompassed most of Central Asia, and whose borders stretched from present day Afghanistan to Georgia.

The Khwarezmian ruler, however, was suspicious of Genghis’ intentions. So when one of his governors halted the Mongol embassy at the border, accused it of spying, arrested its members, and seized its goods, he approved. Genghis tried to keep things diplomatic. He sent three envoys to Muhammad, requesting that he disavow the governor’s actions, and hand him over to the Mongols for punishment. Muhammad executed the envoys, and followed that up by executing all members of the earlier embassy and trade mission.

16. An Angry Genghis Khan Snuffed Out the Khwarezmian Empire and Its Ruler

Shah Muhammad II’s abuse and execution of Genghis Khan’s envoys, coupled with his refusal to make amends, turned out to be bad decisions. They backfired on him and his realm in horrible ways that he probably could not have imagined. An incensed Genghis interrupted his campaigning in China, and concentrated a force of over 100,000 men against the Khwarezmian Empire. It was smaller than Muhammad’s forces, but the Mongols struck in 1218 with a whirlwind campaign that caught him off balance.

The Khwarezmian ruler and his army never got a breather to regain their footing. The Mongol invasion was a military masterpiece that overwhelmed Muhammad’s empire, and extinguished it by 1221. As to Shah Muhammad, he fled and was denied any opportunity to recover and try a comeback. Genghis put two of his best generals, Subutai and Jebe, in charge of hunting the Khwarezmian ruler. Muhammad was chased and hounded across his domain to his death, abandoned and exhausted, on a small Caspian island as his relentless pursuers closed in.

15. This Ruler’s Rashness Backfired Not Only Upon Himself, But Upon His Subjects as Well

Shah Muhammad II’s insult to Genghis Khan backfired not only on him, but on his subjects as well. It was during their invasion of the Khwarezmian Empire that the Mongols gained their infamous reputation for savagery. Millions died, as Genghis ordered the massacre of entire cities that offered the least resistance, and sent thousands of captives ahead of his armies as human shields. By the time Genghis was done, Khwarezm had been reduced from a prosperous empire to an impoverished and depopulated wasteland.

At the grand mosque in the once-thriving but now smoldering city of Bukhara, Genghis told the survivors that he was the Flail of God, and that: “If you had not committed great sins, God would not have sent a punishment like me upon you“. The fate of Shah Muhammad, who brought catastrophe upon himself by insulting somebody he assumed was just another upstart barbarian nomad chieftain from the Steppe, was tragic. Even more tragic was the fate visited upon his subjects because of their ruler’s decision to insult one of history’s scariest conquerors.

14. Susceptibility to Enemy Ruses Caused the Boers to Miss an Opportunity to Win an Easy Victory

During the Second Boer War (1899 – 1902), the deck was overwhelmingly stacked against the Boers, who had to contend with the might of the British Empire. However, the Boers got off to a surprisingly good start and beat the odds that had predicted their defeat in a short campaign. Instead, they turned back invading enemy columns with a series of early upset victories that embarrassed the British and put them on the back foot. Then, incredibly, the Boers went on the offensive.

The Boers’ good start would have been even more incredible if they had not let an opportunity for an easy victory slip their grasp. It happened at the South African town of Mafeking, which the Boers besieged. They greatly outnumbered the defenders, but were taken in by a series of ruses and ended up believing that the town’s garrison was far stronger than it actually was. The adversary who gulled them was Colonel (later Lord, and founder of the Boy Scouts) Robert Baden-Powell, commander of Mafeking’s British garrison.

13. This Commander Seized a Town by Resorting to Trickery

Colonel Robert Baden-Powell, commander of Mafeking’s besieged British garrison, had initially seized the town by bluff during the runup to the war. He held on to it with a steady diet of bluffs during the subsequent siege after hostilities commenced. Baden-Powell, who had been ordered to raise two regiments of volunteers, began storing his supplies in Mafeking. However, he was prevented from openly marching into and garrisoning the town before the war started because doing so was deemed impolitic and provocative.

So Baden-Powell politely asked the townspeople for permission to send guards to protect his supplies. They consented, and Baden-Powell sent in his entire force of nearly 1500 men. When the townspeople protested, he responded that he had never specified the size of the guard. When the war began soon thereafter, the British colonel found himself besieged by a Boer force five bigger than his own. Those were dire odds, so Baden-Powell turned to trickery. The Boers’ failure to immediately attack and seize the town backfired by depriving them of an easy victory.

12. Having Seized Mafeking by Trick, Robert Baden-Powell Used More Trickery to Keep It

To keep the Boers wary of attacking Mafeking, Robert Baden-Powell began burying mysterious boxes around the town’s periphery. When asked, he responded that they were powerful new landmines, the latest in British technology. To demonstrate, he had a couple blown up within sight of Boer sympathizers, whom he then allowed to slip out of town to inform the enemy. In reality, the boxes blown up were stuffed with the town’s entire dynamite stores, while the other boxes buried around the defensive perimeter contained nothing but sand.

Another of Baden-Powell’s tricks revolved around barbed wire, of which Mafeking’s defenders had none. Barbed wire was known to be effective in slowing down a charge, and its presence in front of a defensive position was enough to give attackers pause. Mafeking’s British commander wanted to discourage the numerically superior Boers from charging and overrunning his defenses – something they could have easily done had they made a determined attempt. So he set out to convince them that he had plenty of barbed wire.

11. Ruses Kept the Boers From Capturing a Town That Had Been in Their Grasp

Colonel Robert Baden-Powell did not have any barbed wire at Mafeking. What he did have were plenty of wooden posts such as those from which barbed wire was strung. So he directed that the posts be hammered into the ground all around the defensive perimeter. From a distance, even with binoculars, barbed wire is difficult to see. However, the wooden posts from which barbed wire is usually strung are readily visible, and the sight of a line of such posts in the distance is indicative of barbed wire fences.

To further mislead Boer watchers, Baden-Powell had his men drop to the ground whenever they reached a line of wooden posts. They were instructed to then crawl “beneath” the imaginary barbed wire to reach the other side, before getting back on their feet, dusting themselves off, and carrying on. Such ruses, coupled with stubborn and bloody resistance when the situation warranted, worked. Baden-Powell fought off the enemy and withstood the Boer siege for 217 days. He held on to Mafeking until he was finally relieved by the arrival of a British army that chased off the Boers.

10. World War I’s Worst Weapon?

During World War I the French Army introduced an innovative new light machinegun, the Chauchat, but the new weapon backfired. The Chauchat gained infamy as one of the worst firearms to have ever gone into mass production and been inflicted upon an army as a standard-issue weapon. Introduced in 1915, it immediately began presenting problems stemming from both a defective design and poor workmanship. The defects were worsened by reliance on poor and low-quality metals during production.

On the positive side, the Chauchat was revolutionary. It was the world’s first truly light (20 lbs) portable automatic firearm, that did not require a team of machine gunners and a heavy mount or tripod. It was light enough to be carried around the battlefield by a single soldier. It could be fired from the hip during assaults in suppressive marching or walking fire to pin down enemy defenders while the attackers closed in. It was also inexpensive and featured a detachable magazine and a selective fire capability. From that perspective, the Chauchat set the template for subsequent light machine guns, from the BAR to the SAW.

9. Yes, the Chauchat Was WWI’s Worst Weapon

WWI’s battlefield conditions exposed serious defects in the Chauchat. Among sundry problems, the worst was the detachable magazine, which was designed with one side open. That backfired by allowing the entry of loose earth, mud, dirt, and grit with which WWI’s trenches abounded. The particles made their way into the chamber, barrel, and firing mechanism, resulting in stoppages and malfunctions. The magazines were flimsy and easily dented, resulting in jamming and stoppage. The ejection port lacked a cover, which allowed dirt and other particles to enter from there as well and cause malfunctions.

When the Chauchat did not cease firing because it was jammed with dirt and mud, or because the magazine got dented, it ceased firing from overheating. The sights were misaligned, which wreaked havoc with aiming. The plate assemblies were secured by screws that often came loose and fell off when the weapon was fired. Moreover, the bipod was loose. That, coupled with poor ergonomics, made it impossible to keep the weapon on target other than with short bursts. By 1918, only three years after its introduction and with months still to go before the war ended, the Chauchat was gradually withdrawn from service, to be replaced by the M1918 Browning Automatic Rifle (BAR).

8. Overconfidence Backfired Upon Islam’s Last Caliph

Arrogance and overconfidence are bad traits. They are even worse when deployed by somebody in a weak position against an opponent who is overwhelmingly stronger. That was a lesson learned – too late – by Al Musta’sim Billah (1213 -1258), the last ruler of the Abbasid Caliphate, and Islam’s last Caliph. Towards the end of his reign – and as it turned out, the end of his dynasty – Al Musta’sim decided to engage in a medieval version of a flame with the Mongols, led by Hulagu, one of history’s most terrifying generals.

It backfired badly upon Al Musta’sim, a weak ruler ruling a weak rump of what had once been a mighty empire. Worse, it backfired upon his subjects, who paid dearly for their ruler’s failure to accurately assess the situation and act accordingly. The last Caliph had the misfortune to be surrounded by ineffectual advisors, who offered him conflicting advice when the Mongols demanded his submission. He rejected some demands, ignored others, and answered others with bluster and empty threats. However, he failed to prepare adequate defenses against what was sure to follow.

7. The Mongols Turn Their Attentions to the Abbasid Caliphate

The Mongols first erupted into the Islamic world in the 1220s. As seen above, that was when Genghis Khan destroyed the Khwarezmian Empire and conquered as far west as western Persia up to the edges of Mesopotamia. That outburst was followed by a decades-long lull, as far as the Middle East and the Islamic world were concerned. In the meantime, the Mongols directed their energies elsewhere, against China, Kievan Rus, Eastern Europe, and in internal squabbles amongst themselves. The lull ended in the 1250s, when a new Mongol ruler, Genghis’ grandson Mongke, turned his attention to the Middle East and sent his brother, Hulagu, to assert Mongol power over the region.

Hulagu began his campaign of conquest by first destroying the Assassins. A murderous cult led by a shadowy mystic known as The Old Man of the Mountain, the Assassins operated from a string of mountain holdfasts and had terrorized the Middle East for over a century and a half. Hulagu completed their suppression by 1256, then turned his attention to the Abbasid Caliphate, based in Baghdad. He ordered its Caliph, Al Musta’sim, to submit to Mongol suzerainty and pay tribute.

6. Defiance Coupled With Weakness Turned Out to be a Deadly Mix

The Abbasids had once been a powerful dynasty that ruled the world’s strongest, wealthiest and largest empire. In Al Musta’sim’s era, however, they were centuries removed from their heyday. By the 1250s, the Abbasid Caliphate’s writ did not go far beyond Baghdad. As to the Caliph, he had been reduced to a ceremonial figurehead, a puppet of Turkish or Persian sultans wielding real power and acting in his name. What the Caliph still had was some spiritual and moral authority, and enough pride to refuse Hulagu’s summons to submit. However, he was not prepared to face the Mongols, who had conquered bigger and tougher opponents than the small rump that still remained to the Abbasids.

Al Musta’sim believed that the Mongols would not be able to seize Baghdad, and that if the city was endangered, the Islamic world would rush to its aid. That belief backfired upon the Caliph. Hulagu marched on Baghdad, the Islamic world did not rush to its aid, and after a twelve-day siege, the city fell. The Mongols sacked Baghdad, massacred its inhabitants, burned its vast libraries, and put the city to the torch. Al Musta’sim was captured, but the Mongols had a taboo against spilling royal blood. So they executed him by rolling him in a carpet, over which their army rode when it marched off to further conquests, their horses trampling the last Caliph to death.

5. An Ancient Athenian Scheme That Backfired Spectacularly

Few plans in history have backfired more spectacularly than that concocted to bring down controversial Ancient Athenian general and politician Alkibiades (450 – 404 BC). He was a relative of Pericles, Ancient Athens’ most prominent politician, and the one who took the city to the pinnacle of its Classical Era glory and prestige. However, Alkibiades did not share his famous kinsman’s probity or commitment to democracy. Instead, he was perhaps the most dynamic, adventurous, fascinating, and catastrophic Athenian leader of his era.

With Athens at the height of her power, Alkibiades’ rivals tried to take advantage of a murky scandal to prosecute him while most of his supporters were away at war. However, instead of obeying a summons to stand a trial, he was bound to lose, Alkibiades fled. He defected to Athens’ enemy, Sparta, and helped it turn the tide of war against his home city. What followed next was a decade of twists and turns, betrayals and counter-betrayals. As seen below, it all ended with a humiliating Athenian defeat, and a spectacular fall from which the city never recovered.

4. A Pretty Boy Spoiled Brat

Alkibiades was born into a wealthy family. His father had made a name for himself during the Persian War – the one in the movie 300 and its less impressive sequel, 300: Rise of an Empire – both as a fighter and by subsidizing the cost of a trireme. The father was killed when Alkibiades was a toddler, and his relative Pericles became his guardian. However, Pericles was too busy with his duties as a statesman to provide the boy with the necessary guidance. Fortunately for Pericles, he did not live to see how the failure to properly raise his ward backfired so badly that it wrecked Athens.

Alkibiades developed into a dissipated young man, whose gifts of brilliance and charm were counterbalanced by self-centeredness, irresponsibility, extravagance, and debauchery. In his early years growing up, Alkibiades was considered Athens’ most beautiful youth. In an era when pederasty was widespread and acceptable, he was passionately pursued by many and was showered with gifts and flattery. Even Socrates was among his admirers. That kind of pursuit, admiration, and being the center of attention boosted Alkibiades’ ego through the stratosphere and solidified his sense of entitlement.

3. A Deft Political Maneuver to Isolate Alkibiades From His Supporters

When the Peloponnesian War (431 – 404 BC) between Athens and Sparta began, Alkibiades quickly gained a reputation for courage and military talent. That went hand in hand with his rise as a charismatic and persuasive speaker in the Athenian Assembly. A hawk, by 420 BC Alkibiades had become one of Athens’ generals, and he strongly opposed reconciliation with Sparta. In 415 BC, he convinced the Assembly to send a massive expedition to invade Sicily and conquer Syracuse. On the eve of sailing, however, statues of the god Hermes throughout Athens were desecrated. Suspicion immediately fell upon Alkibiades, whose dissolute clique had a reputation for impiety and drunken vandalism.

There was no concrete proof, however. Alkibiades demanded an immediate trial, but his enemies realized that he would be acquitted if a trial was held at the time. Instead, they allowed the expedition, whose ranks were disproportionately comprised of Alkibiades’ supporters, to sail, with the charges still hanging over him. Then, after the city had been largely emptied of his partisans, a ship was sent to Sicily, summoning Alkibiades to return to Athens and face trial before an Assembly in which his enemies were now a majority. It seemed like a deft political maneuver, but it backfired spectacularly.

2. The Plan to Isolate Alkibiades Backfired on Athens in a Major Way

Rather than obey the summons to face trial in Athens, Alkibiades fled, and defected to Sparta. He advised the Spartans to adopt a strategy that led to the near-complete annihilation of Athens’ Sicilian expedition – the force he had organized, convinced Athens to send to Sicily, and whose men he had once led. It was the most catastrophic defeat suffered by Athens during the war. Of the tens of thousands of Athenians who took part, only a relative handful ever saw Athens again. Those not killed in combat or massacred afterward were enslaved, and sent to Sicilian quarries were they were worked to death.

Alkibiades also convinced the Spartans to abandon their strategy of marching into Athens’ home region of Attica each campaigning season, burning in looting, then retreating and repeating the cycle the following year. Instead, he had the Spartans establish a permanent fortified base in Attica, which allowed them to exert direct pressure on Athens year-round. He also went to Ionia, where he stirred up a revolt against Athens by her allies and subject cities in Asia Minor. However, Alkibiades was notoriously unable to keep it in his pants, and it backfired on him when he was caught in bed with the wife of Sparta’s King Agis II.

1. After Betraying Everybody, Alkibiades Went Down, and Took Athens With Him

Fleeing from Sparta, Alkibiades made a beeline for the Persians. He convinced them to adopt a strategy to prolong the war as long as possible, to keep Athens and Sparta too busy fighting each other to challenge Persia’s interests. Back in Athens, which was reeling from the string of catastrophes that Alkibiades had helped inflict upon his city, political turmoil led to an oligarchic coup. However, the Athenian fleet remained pro-democracy. Alkibiades stepped into the chaos and used his charisma to persuade the fleet to take him back. From 411 to 408 BC, he led the Athenian fleet in a dramatic recovery, winning a series of stunning victories that turned the war around.

Suddenly, it was Sparta that was reeling and on the verge of collapse. Alkibiades returned to Athens in 407 BC, and received a rapturous welcome. His earlier treasons were forgiven and temporarily forgotten, and he was given supreme command in conducting the war. However, the Athenians turned on him a few months later, after a minor naval defeat when he was absent from the fleet. He fled again, and having burned bridges with all sides, holed up in a fortified castle in Thrace, before fleeing even further away to Phrygia. A Spartan delegation traveled to Phrygia, and convinced its Persian governor to have Alkibiades murdered in 404 BC. That same year Athens finally collapsed beneath the load of disasters heaped upon it by Alkibiades, and surrendered.

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Where Did We Find This Stuff? Some Sources and Further Reading

Anderson, Jon Lee – Che Guevara: A Revolutionary Life (1997)

Cornelius Nepos – Life of Alcibiades

Cracked – 6 Grand Mastermind Coups (That Fell Apart Immediately)

Encyclopedia Britannica – Al Musta’sim, Abbasid Caliph

Encyclopedia Britannica – Siege of Mafeking

Forgotten Weapons – The Worst Gun Ever

History Collection – Terrible Schemes That Governments and People Have Tried

Hopkins, Pat, and Dugmore, Heather – The Boy: Baden-Powell and the Siege of Mafeking (1999)

Lord, Walter – Incredible Victory (2012)

Morgan, David – The Mongols (1986)

Naylor, R.T. – Hot Money and the Politics of Debt (1987)

New York Times Magazine, January 15^th, 1995 – The Great Ivy League Nude Photo Posture Scandal

Parshall, Jonathan, and Tully, Anthony – Shattered Sword: The Untold Story of the Battle of Midway (2005)

Philosopher of the Boudoir – Grim History: Michael Oliver, the Phoenix Foundation and Three Failed Attempts at Starting a New Nation

Plutarch – Parallel Lives: Alcibiades

Strauss, Erwin S. – How to Start Your Own Country (1999)

Thucydides – History of the Peloponnesian War, V – VIII

Wikipedia – 1796 Pattern British Infantry Officer’s Sword

Wikipedia – Che Guevara

Wikipedia – Mongol Conquest of the Khwarezmian Empire