Biggest Losers In History

Biggest Losers In History

Khalid Elhassan - July 25, 2023

A loser John or Jane Average has far less to fall before face planting than a loser in a position of power, whose screwup and fall can be epic. The damage can be to a reputation, such as that of the record company head who passed on history’s biggest band. Or it could be more concrete and affect millions, as happened when a medieval ruler called out Genghis Khan, and ended up with his entire empire destroyed. Below are twenty five things about those and other historic losers and loser moments.

Biggest Losers In History
Lat Han China fractured into warlord-ruled mini states. Wikimedia

The Chaotic Collapse of Han Dynasty China, and the Last Ditch Attempt to Reunify the Empire

The Han Dynasty ruled China from 202 BC to 220 AD, and fell into serious decline in its last decades. Uprisings, such as the Yellow Turban Rebellion, swept the empire, and the imperial armies were powerless to put them down. In what turned out to be an unwise decision, the government issued a call for help that was answered by regional strongmen, who raised their own forces to fight the rebels. They crushed the rebellions, but now with private armies under their command, turned into warlords who posed an even greater threat to the Han government. The new warlords fought amongst themselves, and the imperial government was unable to control the chaos it had unleashed.

Biggest Losers In History
Tsao Tsao, as depicted in film. Duniako

China fractured into de facto independent fiefdoms ruled by warlords, and the emperors were reduced to figureheads and puppets. Eventually, a warlord named Tsao Tsao (alternatively, Cao Cao) came to the fore. Anything but a loser in the first part of his career, Tsao Tsao proved himself a ruthlessly capable general and politician. He defeated the warlords of northern China, and reunited it in the emperor’s name. That done, he turned his turned his attention to southern China. With a massive army that he claimed numbered more than 800,000 men, he marched to defeat his main remaining rivals, southern warlords Sun Quan and Liu Pei, and complete the reunification of China. As seen below, it ended in a shambolic defeat, as Tsao Tsao went from hero to zero, and from victor to epic loser.

Biggest Losers In History
A mengchong ship, of the type used in the Battle of Red Cliffs. Wikimedia

From Victor to Epic Loser

Tsao Tsao exaggerated his army’s size: modern estimates put his forces at around 250,000 men. It was still a massive host that greatly outnumbered his enemies, whose combined forces were no more than 50,000 men. With the deck heavily stacked in his favor, Tsao Tsao arrived at the Yangtze River, key waterway of southern China, where he assembled a fleet to assist his operations. The northern warlord and his men were unfamiliar with naval warfare, however. Like his army, his navy greatly outnumbered the southerners, but unlike his army, it lacked experience. His enemies exploited that at the Battle of Red Cliffs, 208 AD, and sent a secret agent to set him up for failure. He persuaded the northern warlord to chain his ships together to increase their stability, and reduce his men’s seasickness.

Biggest Losers In History
Tsao Tsao’s defeat at the Battle of Red Cliffs. Chen Kai

Next, a southern admiral offered to defect with his ships. Tsao Tsao believed him, and arrangements were made to welcome the defectors. Unbeknownst to Tsao Tsao, the “defecting” vessels had been converted into fire ships filled with flammable materials. Skeleton crews sailed them close to the northern fleet, set them alight, then escaped in small boats. The wind carried them to Tsao Tsao’s chained fleet, whose immobilized ships, unable to maneuver and escape, were destroyed in a massive inferno. He was forced into a retreat that soon deteriorated into a rout, in which most of his gigantic army was destroyed. That ended attempts to reunify China, which split into three kingdoms, and instead of a victor who reunified China, Tsao Tsao went down in history as an epic loser.

Biggest Losers In History
An ancient mosaic depiction of the precise moment when Alexander the Great’s charge at the Battle of Issus put Darius III to flight. Wikimedia

The King of Kings

On October 1st, 331 BC, Alexander the Great led 47,000 Macedonians and Greeks against 52,000-120,000 troops under the command of Persia’s “King of Kings”, Darius III. Two years earlier, at the Battle of Issus, Alexander had defeated the Persian monarch, who ignominiously fled the battlefield. In a high stakes rematch, the two rulers and their men faced off at Gaugamela, near the modern city of Dohuk in Iraqi Kurdistan, to decide the fate of the Persian Empire. Darius placed himself in the center of the Persian line, with cavalry on both flanks, and chariots in front.

Alexander took his elite Companion Cavalry and most of the rest of his horsemen, and rode towards the right of the field, parallel to the Persian line. To keep the Persian chariots off his flank, Alexander took a scratch force of infantry, and placed them between his cavalry and the enemy chariots. As he rode to the right, Alexander was shadowed by Persian cavalry on that side of the field, to keep him from outflanking the Persian left. It was what Alexander wanted: to remove as much Persian cavalry from their initial position as possible. Alexander also had a surprise for the Persian horsemen: light infantry who kept pace with him, concealed by the dust stirred up by his cavalry.

Biggest Losers In History
Alexander the Great. Pinterest

The Unfortunate Loser Who Lost an Empire

Alexander the Great’s deployment of his troops at Gaugamela resulted in three parallel lines. Moving towards the right were the Persian cavalry, Alexander’s cavalry, whom the Persians could see, and his light infantry, whom the Persians could not see. The Persian cavalry eventually outflanked what they assumed was Alexander’s attempt to outflank them, then charged. It was what Alexander had hoped they would do. As the Persian cavalry shadowed the Macedonian monarch while he rode to the right of the field, a gap opened in the Persian line. Alexander had wanted to draw the Persian cavalry out of position in order to create that gap.

Biggest Losers In History
Alexander the Great changes direction and charges Darius’s position at the Battle of Gaugamela. Quora

With the Persian cavalry juked out of position, Alexander left the bulk of his cavalry, and the accompanying light infantry, to engage the Persian horsemen and keep them occupied. He disengaged his elite Companion Cavalry from the fray and rode off at their head, in a wedge formation, for the gap where the Persian cavalry had been at the start of the battle. A gap where Darius was stationed. It was a surgical strike that decided the battle. Seeing Alexander leading a furious cavalry charge straight at him, Darius twice a loser against Alexander, panicked and fled. Darius’ flight effectively ceded the Persian Empire to Alexander.

Biggest Losers In History
Dick Rowe, left. PBS

The 1960s’ Most Influential Music Executive

In the 1950s and 1960s, few wielded more influence in Britain’s music industry than Richard “Dick” Rowe. The head of Decca Records’ A&R (artists and repertoire), Rowe was in charge of finding new artists who showed promise. Although he became famous – or infamous – for an epically bad business decision, Rowe was overall pretty good at what he did. His signings included The Rolling Stones, Tom Jones, Cat Stevens, The Animals, and Them, the band that launched Van Morrison. Unfortunately, his name is forever tied with the one group he failed to sign.

It began on New Year’s Day, 1962. Brian Epstein, the manager of an unheralded group, took his young talents to audition with Decca Records at their studios in West Hampstead, North London. They were there at the invitation of one of Rowe’s A&R subordinates, Mike Smith, who had heard the band play a few weeks earlier. He liked what he heard, and asked them to do a session at Decca’s studio. The group drove to London all the way from Liverpool, in the middle of a snowstorm, and made it just on time for their 11 AM audition.

Biggest Losers In History
Brian Epstein, center at head of table, and his band. Biography Network

The Underwhelming Boys from Liverpool

After their long drive through a snowstorm just to reach Decca Records on time, the members of Brian Epstein’s group were understandably annoyed when the man who had invited them, Mike Smith, showed up late. Smith, who had apparently partied hard the night before, unnerved the young musicians even more when he refused to let the group use their own amplifiers. Instead, he demanded that they use Decca’s amplifiers, which he deemed to be superior to those used by Epstein’s charges.

The group performed about fifteen songs for Smith and his boss Dick Rowe. They were nervous, what with the drive through a snow storm, the late arrival of their host, and the use of different amplifiers, and were not at their best. Nonetheless, they felt confident that had done well enough to secure a contract. Rowe, however, was underwhelmed. He passed on the group, with the airy remark that “guitar groups are on the way out, Mister Epstein“. As seen below, that forever marked Rowe as the biggest loser in the music business.

Biggest Losers In History
The Beatles. Pinterest

The Biggest Loser in the Music Industry’s History?

Epstein and his group left Decca’s studios dejected to start their New Year with a rejection. Not so Dick Rowe, who figured that 1962 had started great. That same day, he listened to another band that came in for an audition, liked what he heard, and signed up Brian Poole and the Tremeloes to a deal with Decca Records. As Rowe recalled later, he had told his A&R subordinate Mike Smith to decide between Epstein’s group and Brian Poole and the Tremeloes: “He said, ‘They’re both good, but one’s a local group, the other comes from Liverpool.’ We decided it was better to take the local group. We could work with them more easily and stay closer in touch.

Biggest Losers In History
Clockwise from top left, Dick Rowe, Brian Epstein, the Tremeloes, and the Beatles. Beatles 101

So they went with the Tremeloes. It was not a bad business decision in of itself, as the band had some success. In 1963, they entered the UK charts with a cover of the Isley Brothers’ Twist and Shout, and followed it up with a UK chart-topping cover of the Contours’ Do You Love Me. A year later, they did a cover of Roy Orbison’s Candy Man that pleased the Brits, and a cover of the Crickets’ Someone, Someone, which made it to number 2 on the UK charts. What branded Rowe as an all-time industry loser was his rejection of the other band that had auditioned the same day as the Tremoloes: the Silver Beatles, who soon shortened their name to The Beatles.

Biggest Losers In History
General Antoine Lasalle. Wikimedia

The Weak Commander of a Powerful Garrison

After the French victory in the Battle of Jena-Auerstedt in 1806, Napoleon ordered a vigorous pursuit of the retreating Prussians. He wanted to round them and capture their garrisons, before they got the chance to link up with and reinforce their Russian allies, who were still game for a fight. The once-proud Prussian army, less than two decades removed from its glory days under Frederick the Great, was now a demoralized loser mob after the disaster at Jena-Auerstedt. Against that backdrop, a French cavalry brigade under General Antoine Lasalle approached the port city of Stettin.

Lasalle had about 500 hussars under his command, and 2 light field guns. Stettin was a well-fortified port city with a garrison of nearly 10,000 men and 281 cannons, commanded by a General Friedrich von Romberg. A veteran with over 50 years’ experience, Romberg’s career stretched back to the Seven Years War, in which he fought under Frederick the Great. The city was well provisioned by the British Royal Navy, whose supply-laden ships sailed in and out of the port with no hindrance.

Biggest Losers In History
The capitulation of Stettin. Paris Musee Collection

The Loser General Who Got Snookered Into Surrendering to a Far Smaller Force

General Lasalle sent a subordinate under flag of truce on the afternoon of October 29th, 1806, to demand Stettin’s surrender. He promised to treat its garrison with all the honors of war. Von Romberg refused, and vowed to defend the city to the last man. An hour later, the emissary returned, this time with a more ominous message: “If by 8AM you have not surrendered, the town will be bombarded by our artillery and stormed by 50,000 men. The garrison will be put to the sword, and the town will be plundered for 24 hours“. An alarmed von Romberg consulted with the town leaders, who urged capitulation. That night, the details of the surrender were finalized.

Early the next day, the garrison marched out in perfect order, and filed past the French to throw their arms down at their feet. When von Romberg discovered just how tiny a force he had surrendered to, it was too late, and he had little choice but to stick to the negotiated agreement. Lasalle became a national hero, while von Romberg became a laughingstock loser. The Prussian general was tried by court martial in 1809, convicted, and sentenced to life imprisonment. He died two months later.

Biggest Losers In History
Nelson Bunker Hunt, right. America’s Best Racing

The Silver-Mad Siblings

With a lock on much of the East Texas Oil Field, one of the world’s biggest oil deposits, H.L. Hunt (1889 – 1974) was one of the world’s richest men. His sons Nelson, William, and Lamar – the last a founder of the American Football League and Major League Soccer – were also quite wealthy. Especially Nelson, who drilled for oil in Libya and made a fortune. However, Nelson Hunt became a crackpot who feared a US government conspiracy to steal his wealth. So to protect it, he decided to buy a lot of silver, and hoard it in Switzerland. Then he decided to buy all the silver, and persuaded his brothers to join him in a bid to corner the global silver market.

The Hunt brothers went on a silver buying spree in the 1970s. When they ran out of money, they borrowed heavily to buy more silver. By 1979, they had accumulated about 100 million troy ounces – almost 7 million pounds – of the stuff. That was almost half the world’s transportable supply. That speculation caused the price of silver to spike by over 800%, from $6 an ounce in early 1979, to over $50 by early 1980. The brothers made about $4 billion in paper profits, but in reality they had simply created a huge asset bubble, that was bound to burst sooner or later. When it did, they lost big, and Nelson Hunt in particular went from visionary genius to crackpot loser.

Biggest Losers In History
Silver prices, and the 1979 spike caused by the Hunt brothers’ speculation. Wikimedia

From Crank Genius to Crackpot Loser

As silver prices spiked, people around the world melted silverware. Thieves went on a silver-stealing spree. Tiffany’s ads attacked the Hunt brothers’ speculation for making silver unaffordable to consumers. The brothers ended created a bubble market for silver. It was a bubble in which the Hunts themselves, as the world’s biggest silver hoarders, were most at risk. The Federal Reserve, which aims to avert such bubbles, stepped in and issued a rule specifically targeted against the Hunts. It banned banks from lending to precious metal speculators. That burst the Hunts’ bubble market burst on March 27th, 1980, which came to be known as “Silver Thursday”. Prices collapsed, and the Hunts almost immediately lost over a billion dollars. They pledged most of their assets as collateral for a rescue loan package. However, the value of their assets declined steadily throughout the 1980s.

Biggest Losers In History
The Hunt brothers, from left to right, William, Lamar, and Nelson. New York Daily News

By 1985, their net wealth had fallen from over $5 billion just before Silver Thursday, to less than a billion. Then things got worse, especially for the genius behind the silver hoarding plan, Nelson Hunt. The brothers hung on for much of the 1980s, but their luck ran out in 1988. That year, they lost a lawsuit that accused them of conspiracy related to their silver speculation. They were hit with hundreds of millions in liability and fines. Nelson Hunt was hardest hit, and he broke the record for the biggest personal bankruptcy in US history. From visionary businessman, he was now seen as a crackpot loser. His assets were seized and sold to satisfy creditors, including his oil fields, house, bowling alley, and a $12 million coin collection.

Biggest Losers In History
Vortigern welcomes Saxon chiefs Hengist and Horsa to Britain. Ancient Pages

The Loser Ruler Whose Mercenaries Turned on Him

The recent Wagner Group mutiny in Russia is hardly the first time a ruler hired mercenaries, only to have them turn on him. Throughout much of the fourth century, Saxon raiders devastated the Roman province of Britain. Then, in one of history’s worst “it takes a thief to catch a thief” brainstorms, the Romano-Britons struck a deal to hire the Saxons as mercenaries, and settle them on British soil. In exchange, the Saxons promised to defend Britain from other barbarians. Once they had settled in, however, the Saxons complained that the Romano-Britons had skimped on the monthly supplies promised them.

A conference to resolve the dispute was arranged between native nobles led by a Vortigern, and the Saxons led by two chieftains named Hengist and Horsa. However, the Saxons’ idea of dispute resolution was to suddenly murder the Britons mid-conference. Only Vortigern, who went down as the biggest loser in Romano-Briton history, was spared. The Saxons declared the treaty void because the locals had failed to live up to its terms, and launched a massive onslaught against Britain. Vortigern, reduced to their puppet, was forced to sign a new treaty that ceded them southeastern England.

Biggest Losers In History
Saxon raiders. The Book Palace

From a Mercenary Mutiny to a Massive Invasion and Conquest

The Saxons soon grew dissatisfied with Vortigern’s concessions. They launched a war of conquest that sought to seize the entire province, displace the locals, and replace them with Germanic settlers. They were joined by Angles, from today’s Schleswig-Holstein, between Germany and Denmark, plus Jutes, from today’s Jutland in Denmark and Lower Saxony in Germany. The onslaught lasted for about thirty years, until the Britons won a crucial victory at the Battle of Mons Badonicus, sometime around 500. That temporarily stopped the invaders, who by then had overrun about half of what had been the Roman province of Britain. It was this period of warfare that gave rise to stories of King Arthur, the heroic monarch who led the Britons against the Saxons.

Biggest Losers In History
Anglo-Saxon migration to Britain. Wikimedia

Although King Arthur is mythological, archaeological evidence supports a Saxon setback around 500. The pattern of Saxon settlement steadily expanding westward and replacing the Britons, suddenly reversed. Briton settlements began to expand eastwards, displace the Saxons, and reclaim previously lost lands. Thus, accounts of a major Briton victory sometime around 500 are probably true. The Britons’ reprieve proved only temporary, however. The Anglo-Saxons recovered, resumed their expansion at the expense of the Britons, and eventually conquered and settled nearly all of what is now England. The indigenous Britons lost their most productive lands, and their last independent remnants were pushed into the peripheral regions of Cornwall and Wales.

Biggest Losers In History
A 1940s Pepsi ad aimed at African Americans, a target ignored by Coca-Cola at the time. The Economics Detective

The Coca-Cola CEO Who Declined to Buy Pepsi

Pepsi was created in 1893, and for decades, it was a niche drink with a tiny market. It went unnoticed by Coca-Cola, and stood no chance of challenging the soft drink giant. In the 1920s, Charles Guth, president of candy manufacturer Loft Inc., asked Coca-Cola for a discount on its syrup, which was used in the soda fountains of some of his retail stores. Coca-Cola refused, so when Pepsi entered bankruptcy in 1923, Guth bought it for $10,500 (equivalent to about $190,000 in 2023), and had chemists rework its formula to come as close to Coke as possible. Over the following decade, Pepsi-Cola was offered to the Coca-Cola Company for purchase on various occasions, but the soda giant declined the offer each time. It was a loser decision that Coca-Cola came to regret.

Charles Guth turned Pepsi around within two years, and made it a profitable enterprise. By 1936, Pepsi was the second largest soda company, behind only Coca-Cola, with sales of half a billion bottles a year. It was right around then that Loft Inc. sued Guth for breach of fiduciary duty, and took Pepsi from him in 1939. Loft focused on Pepsi, and spun off its non-soda businesses in 1941. The brand continued to grow, and eventually merged with Frito Lay in 1965, to become PepsiCo. That new company went on to finally eclipse Coke in sales in the 1980s, and in 2005, PepsiCo surpassed the Coca-Cola Company in market value.

Biggest Losers In History
Genghis Khan statue at the Mongolian Parliament building in Ulan Bator. ABC News

The Loser Sultan Who Called Out Genghis Khan

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” – Genghis Khan. The kind of person who drops chilling quotes like the preceding is not somebody a wise ruler would go out of his way to insult. Yet that is precisely what Shah Muhammad II, ruler of the Khwarazmian Empire from 1200 to 1220, did.

Not only that, but as if to double down on the stupid, Muhammad II then dared Genghis Khan to do something about it. He did, and in the process, transformed the Khwarazmian ruler into an epic loser. Genghis Khan (1162 – 1227) founded the Mongol 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 forty million death toll of the Mongol conquests initiated by him would be equivalent to 278 million deaths in the violent twentieth century – far more than total fatalities of both world wars.

Biggest Losers In History
Genghis Khan’s territory, right, and Muhammad II’s Khwarazmian Empire, left, circa 1215, before the Mongols invaded. Wikimedia

The Wrath of (Genghis) Khan

In 1218, Genghis Khan was busy with the conquest of China, when he sent an embassy and trade mission to Muhammad II. In addition to diplomatic emissaries, it included numerous merchants with valuable goods. Genghis wanted to establish diplomatic and trade relations with the Khwarazmian Empire, which encompassed most of Central Asia, and stretched from today’s Afghanistan to Georgia. Shah Muhammad, however, was suspicious of Genghis’ intentions. So he had one of his governors halt the Mongol embassy at the border, accuse it of espionage, arrest its members, and seize its goods. Despite the insult, Genghis sent three more envoys, in an attempt to keep things diplomatic.

They requested that the Khwarazmian ruler disavow the governor’s actions, and hand him over to the Mongols for punishment. Muhammad executed the envoys, then executed all members of the earlier embassy and trade mission. In response, Genghis interrupted his campaign in China, and concentrated a force of over 100,000 against the Khwarazmian Empire. It was smaller than their foe’s forces, but the Mongols struck in 1218 with a whirlwind campaign that caught Muhammad off balance, and he never got an opportunity to recover. Genghis’ invasion was a military masterpiece that overwhelmed Muhammad’s empire, and extinguished it by 1221.

Biggest Losers In History
Mongols in action in Central Asia. PBS

Don’t Make the Mongols Mad

Muhammad II fled, but the Mongols never gave him a chance to find sanctuary and recover for a comeback. Genghis ordered two of his best generals, Subutai and Jebe, to hunt down the Khwarazmian ruler. Muhammad, reduced to a pitiful loser, was chased and hounded across his domain to his death, abandoned and exhausted, on a small Caspian island as his relentless pursuers closed in. It was in this invasion that the Mongols gained their 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.

Biggest Losers In History
Ruins of Shah Muhammad II’s palace in Urgench, modern Turkmenistan. Wikimedia

By the time Genghis was done, Khwarazm had been reduced from a thriving and wealthy 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“. Muhammad II ended up as a tragic loser who brought catastrophe upon himself and his realm when he insulted somebody he assumed was just another upstart barbarian nomad chieftain from the Steppe. He discovered, too late, that he had challenged history’s greatest conqueror.

Biggest Losers In History
Colorized photo of Franz Reichelt’s parachute suit. Pinterest

A Parachute Pioneer With More Courage Than Sense

Franz Reichelt (1879 – 1912) was an Austrian-born French tailor who was fascinated with flight since childhood. After the invention of the airplane, he sought to invent a device that would allow pilots to parachute safely to the ground if they ran into trouble aloft. His efforts were spurred on when, in 1911, the Aero Club de France offered a 10,000 Franc prize to the first inventor of a successful parachute. Reichelt’s design was a suit that featured a cloak with a big silken hood. It weighed about twenty pounds, and had a surface area of around 340 square feet.

Reichelt tested his design several times on dummies thrown out of his fifth floor apartment, but without success. Despite the repeated failures, he petitioned the Paris police for permission to test his invention on a dummy from the Eiffel Tower. Once a permit was secured, he proceeded to drum up interest among journalists and the public to witness the test at 8AM, February 4th, 1912. On the appointed day, Reichelt arrived clad in his parachute suit. He was met by a crowd of onlookers gathered at the Eiffel Tower, outside a cordoned off drop zone.

Biggest Losers In History
Franz Reichelt’s jump from the Eiffel Tower. Imgur

Rather Than a Hero, Reichelt Went Down (Hard) as a Clownish Loser

Accompanied by journalists, Franz Reichelt ascended the Eiffel Tower. Two film crews positioned themselves, one on the ground to catch the drop from the tower, and another at the tower to film the dummy being thrown. People were perplexed, however, because they saw no dummy. It gradually dawned upon them that Reichelt had not brought a dummy, but planned to test his design by jumping off the tower in person. A guard stopped him initially, but Reichelt convinced him to let him proceed. Friends and journalists also tried to talk him out of it, but to no avail.

As he climbed the stairs, Reichelt paused to give the crowd a cheery “A bientot!” He then continued on to the tower’s first deck. There, as the cameras rolled and people shouted at him to stop, he climbed on a stool placed atop a table adjacent to the guardrail, and jumped at 8:22AM. The suit was a flop, literally and figuratively. Reichelt fell about 200 feet to his death on the frozen ground below, with an impact that left a six inch crater and crushed his spine and skull. Unbeknownst to him, just two days earlier, an American had successfully parachuted 225 feet from the Statute of Liberty, with what became the standard half-spherical backpack parachute.

Biggest Losers In History
Napoleon crowns himself emperor in 1804. Imgur

From Spectacular Winner to Spectacular Loser

In 1812, just before he invaded Russia, Napoleon bestrode Europe and was at the height of his power. By year’s end, he had suffered an epic defeat, and began a downward slide that culminated two years later in his exile to St. Helena. His first misstep was his poor choice of subordinates. Napoleon wanted to decisively defeat the Russian army as soon as possible, in order to bring the Tsar to heel. However, he appointed his unqualified stepson, Prince Eugene, to a major command, and the inexperienced youth allowed the Russians to retreat. Napoleon then plunged into Russia, and followed the Tsar’s army for hundreds of miles as it retreated, refusing to give battle and scorching the countryside.

The French emperor had planned to halt at Smolensk, go into winter quarters, and resume the campaign in 1813. Once in Smolensk, however, he decided to continue on to Moscow. Near Moscow, the Russians finally offered battle at Borodino, and Napoleon won a hard-fought engagement. At the decisive moment, however, he wavered and held off from his usual tactic of sending in the elite Imperial Guard, kept in reserve, to finish off the reeling enemy. That prevented the victory from becoming decisive, and allowed the battered Russians to live to fight another day.

Biggest Losers In History
Napoleon retreats from Moscow. ABC

From the Sublime to the Ridiculous

When he reached Moscow, Napoleon assumed that the Russians would sue for peace. So he waited for their peace feelers, as winter drew near. The Russians strung him along, but no more than he strung himself along with hopes of peace negotiations long after it became obvious that the Russians were not interested. By the time he gave up and marched back to Smolensk, it was too late, and his unprepared army was caught by winter. That was exacerbated by his choice of route.

Napoleon had two options, and picked the far worse one. He chose a route that was struck by severe winter storms, while the one he didn’t take saw little snow that year. Most of his army starved or froze to death, while more were killed by Cossacks who harried the rear and flanks of the retreating columns. Napoleon had marched into Russia with 685,000 men – at the time, the largest army the world had ever seen. He came out with only 35,000 Frenchmen still under his command. The rest had died (over 400,000), deserted, or switched sides. Reflecting upon the debacle, Napoleon commented: “From the sublime to the ridiculous, it is only one step“.

Biggest Losers In History
Captain Kidd in New York Harbor. Library of Congress

The Unfortunate Captain Kidd

One of New York City’s most charismatic socialites and leading citizens, William Kidd (circa 1645 – 1701) was a personal friend of at least three colonial governors of New York. A philanthropist, he played a major role in building New York City’s now historic Trinity Church. There was little to indicate that he would end up a tragic loser, hanged as the notorious pirate, Captain Kidd. His first sea command was as a privateer. In 1689, the governor of Nevis commissioned him to fight the French, and gave him a letter of marque that authorized him to prey on French vessels. His mission was expanded in 1695, when he received a roving commission to attack pirates in the Indian Ocean.

Things got off to a bad start. As he sailed out of London in a newly equipped ship, the 34 gun and 150-man-crew Adventure Galley, Kidd offended a Royal Navy captain when he failed to salute his warship. In retaliation, the captain stopped the Adventure Galley, and pressed half of its into the Royal Navy. Kidd crossed the Atlantic short-handed, and replenished his crew in New York with whatever unemployed seafarers he could find. Most them were hardened criminals and former pirates. As he sailed to the Indian Ocean, a third of Kidd’s crew died of cholera by the time they reached the Comoros islands. To top it off, he was unable to find any of the pirates he had been sent to hunt down.

Biggest Losers In History
William Kidd. Pinterest

From Manhattan Socialite to Loser Rotting in a Gibbet

Kidd’s enterprise seemed a failure, so his crew urged him to attack some passing vessels in order to make the voyage worth their time. They threatened to mutiny if he declined. Under pressure, Kidd reluctantly began to attack ships not covered by his privateer commission. He overcame his early scruples, and by 1698, he was a full blown pirate. That year, he sealed his fate when he attacked a British East India Company ship. The powerful company exerted its influence in London, and Kidd was declared an outlaw. By the time he returned to the American Colonies, Kidd’s public image had gone from charismatic socialite and philanthropist, to that of an infamous pirate.

Biggest Losers In History
Captain Kidd gibbeted near Tilbury, Essex, after his execution. History Today

Worse for Kidd, attitudes towards piracy had hardened in his absence. When he began his voyage, things had been lenient. Now, crackdown was in the air, and the authorities were eager to make an example of somebody. So Kidd was seriously unlucky to return when he did. He was arrested as soon as he docked in Boston, was clapped in chains, and shipped across the Atlantic for prosecution in London. There, his powerful contacts abandoned him. He was swiftly tried and convicted, then hanged on May 23rd, 1701, with his corpse left to rot in a cage on the Thames for all to see.

Biggest Losers In History
Dinar coin struck during the reign of Al Musta’sim. Numis Bid

The Other Muslim Ruler Who Called Out the Mongols

One would think that the fate of Shah Muhammad II, above, would have the made contemporaries wary of calling out the Mongols. One ruler who did not heed the lesson was Al Musta’sim Billah (1213 -1258), the last ruler of the Abbasid Caliphate, and Islam’s last Caliph. A weak ruler of the weak rump of what had once been a mighty empire, Al Musta’sim was surrounded by ineffectual advisors who offered poor advice when the Mongols demanded his submission. He rejected the demands, ignored some and answered others with bluster and empty threats. What he did not do was prepare adequate defenses against what was sure to follow such rejection. He should have known better. The Mongols had first erupted into the Islamic world in the 1220s, when Genghis Khan destroyed the Khwarazmian Empire and conquered as far west as western Persia up to the edges of Mesopotamia.

That outburst was followed by a decades-long relative lull, as far as the Middle East and the Islamic world were concerned. 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 Khan’s grandson Mongke, turned his attention to the Middle East and sent his brother, Hulagu, to assert Mongol power over the region. To kick things off, Hulagu destroyed the Assassins, a murderous cult led by a shadowy mystic known as The Old Man of the Mountain. It had operated from mountain holdfasts, and terrorized the Middle East for over a century and a half. Hulagu completed that task by 1256, then turned his attention to the Abbassid Caliphate, based in Baghdad.

Biggest Losers In History
Medieval depiction of the Mongol siege and seizure of Baghdad. Wikimedia

The Loser Caliph Who Invited the Demise of the Caliphate

Hulagu ordered Caliph Al Musta’sim to submit to Mongol suzerainty and pay tribute. The Abbassids had once been a powerful dynasty that ruled the world’s largest, strongest, and most prosperous empire. However, it was a loser realm, centuries removed from its heyday by the time Al Musta’sim became Caliph. By the 1250s, the Abbasid Caliphate’s sway did not stretch far beyond Baghdad. As to the Caliph, he had been reduced to a mostly ceremonial figurehead loser, a puppet of Turkish or Persian sultans who wielded real power while they acted in his name. What the Caliph did have left was a remnant of spiritual and moral authority, and enough pride to refuse Hulagu’s summons to submit.

The Abbasids were not prepared to face the Mongols, who had conquered bigger and tougher opponents than the small rump that remained of the Abbasid Caliphate. However, 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. 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. To execute him, they rolled him in a carpet, and their army rode over him when it marched off to further conquests. Thus, the last caliph was trampled to death beneath Mongol hooves.


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