A Countdown of History's 16 Most Influential and Formidable Mercenaries
A Countdown of History’s 16 Most Influential and Formidable Mercenaries

A Countdown of History’s 16 Most Influential and Formidable Mercenaries

Khalid Elhassan - October 20, 2018

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Francesco Sforza. Wikimedia

5 – Francesco Sforza, Renaissance Italy’s Most Successful Mercenary

Francesco Sforza (1401 – 1466), who led a fascinating life full of twists and turns, and capped it off by rising to the heights of power, was Renaissance Italy’s most successful condottiero, or soldier of fortune. A mercenary general, Sforza turned on his employers whenever opportune, switched sides multiple times, and eventually made himself duke of Milan, founding the Sforza Dynasty that influenced Italian politics for a century.

The illegitimate son of a mercenary commander, Sforza began accompanying his father on campaigns at age 17. He soon developed a reputation for toughness and strength, and became famous for his ability to bend metal bars with his bare hands. When his father drowned during a battle in 1424, Sforza took command, and proved himself a brilliant tactician and battlefield commander by leading his father’s mercenaries to victory.

Sforza then signed on to fight for multiple Italian rulers, including the Pope, the Neapolitans, and duke Visconti of Milan, whom Sforza fought for and against during the next two decades. In 1433, during one of the intervals when Sforza got along well with the Duke of Milan, he got engaged to Visconti’s illegitimate daughter and only child.

A year later, he switched sides and joined the Duke of Milan’s rival, Cosimo de Medici of Florence. In 1438, Sforza fought for Florence against his prospective father in law, and inflicted crushing defeats on Milan. In 1441, he patched things up with Milan’s duke, and finally married his daughter. Two years later, in 1443, he switched sides again, and fought against his father in law.

When the duke of Milan died in 1447 without a male heir, the Milanese rebelled, proclaimed a republic, and hired Sforza as their military commander. A three-sided struggle then ensued between the Milanese republic, the rival city of Venice, and Sforza. When the Milanese signed a peace with Venice in 1449 against Sforza’s wishes, he turned on his employers, besieged Milan, starved it into submission, and entered the city in 1450 as its new duke.

Francesco Sforza won his state by dint of his exceptional ability and skill rather than through luck or inheriting it by winning the lottery of birth. He then went on to consolidate his gains and secure them sufficiently to found a dynasty. His shrewdness, opportunism, and successful deviousness, made him the exemplar and model of Machiavelli’s Prince.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Romano-Briton nobleman Vortigern greeting Saxon chieftains Hengist and Horsa. Ancient Pages

4 – The Anglo Saxons Arrived in England as Mercenaries, Then Seized it For Themselves

Throughout much of the fourth century, Saxon raiders had been devastating 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, the Saxons complained that the Romano-Britons had skimped on the monthly supplies they had been promised. A conference meeting 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 resolving the dispute was to suddenly murder the Britons during the conference, sparing only Vortigern. Declaring the treaty void because the locals had failed to live up to its terms, the Saxons launched a massive onslaught against Britain, and forced Vortigern to sign a treaty that ceded them southeastern England.

The Saxons were not content, however, and continued attacking the Britons, launching 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 20 or 30 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 the stories of King Arthur, the heroic monarch who led the Britons against the Saxons.

Although King Arthur is a mythological figure, archaeology supports a Saxon setback around 500. The pattern of Saxon settlement steadily expanding westward and replacing the Britons, suddenly reversed, and Briton settlements began expanding eastwards, displacing the Saxons and reclaiming 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, and resumed their expansion at the expense of the Britons, eventually conquering and settling 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.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Execution of Jeanne de Clisson’s husband, Olivier IV de Clisson, 1343. Francais Chronique

3 – The Female Mercenary Pirate of the Hundred Years War

At the outset of the Hundred Years War, the French were terrorized by a bloodthirsty female mercenary and pirate who had a private vendetta against France. She was Jeanne de Clisson (1300 – 1359), also known as the Lioness of Brittany. After the French accused her husband of treason and executed him, de Clisson went on the warpath. She hired herself out to the English and turned pirate, preying upon French shipping in the English Channel, torturing and executing every French nobleman she came across.

De Clisson was a Breton noblewoman from a prominent family. After two marriages, one which ended with her husband’s death and the other with an annulment, she married a wealthy Breton named Olivier Clisson in 1330. In 1342, Clisson was military commander of a town that was captured by the English, and he was taken prisoner. He was released soon thereafter in a prisoner exchange – the only Frenchman to be freed. Between that and an unusually low ransom requested by the English, Clisson was accused of treason. He was tried and convicted by a court of French nobles, and beheaded in 1343.

Jeanne de Clisson took her young sons to see their father’s head mounted on a spike, and vowed revenge. She sold her estates, and used the proceeds to raise a private force with which she began attacking the French. They did not take her seriously at first. Then she attacked and captured a French castle, and massacred its entire garrison, except for one man whom she let live to tell the tale. She was taken seriously from then on.

A determined French counterattack forced her to flee to England, where she accepted English backing to continue her war as a mercenary. She bought and outfitted three warships, and as a signal of her intent, painted them black and dyed their sails red. Then she led her black fleet into the English Channel, to fall upon French shipping. De Clisson soon gained a reputation for savagery, massacring nearly all who fell into her hands. French aristocrats in particular were in for a rough time if they were found aboard any ship captured by the mercenary pirate. There was good money to be made ransoming them, as the was custom of the day, but de Clisson wanted their lives, not their money. So she tortured her aristocratic captives, then personally beheaded them with an ax, before tossing their corpses overboard.

De Clisson continued her murderous rampage against the French wherever she could find them, for thirteen years, before her bloodlust was finally sated. Eventually, in 1356, she gave up the life of a mercenary pirate, and retired to her estates in Brittany. She remarried for a fourth time, and settled into a castle on Brittany’s southern coast, where she died peacefully in 1359.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Hernan Cortes and Montezuma II. Pintrest

2 – Hernan Cortes’ Conquistadores Were Among History’s Most Successful Mercenaries

Spanish conquistador Hernan Cortes and a small force of mercenaries landed on Mexico’s eastern coast in February of 1519. After subduing the region surrounding today’s Vera Cruz, they marched inland towards the Aztec capital of Tenochtitlan, defeating and allying with natives en route. Those who refused to join the Spaniards were massacred, as occurred in the city of Cholula. As Cortes described it, after capturing the city, he destroyed and burned it to the ground, while his conquistadors ran riot, killing about 3000 Cholulans in a few hours. Another Spanish eyewitness put the number of massacred Cholulans as high as 30,000. By the time Cortes reached Tenochtitlan, his core of mercenary conquistadores was surrounded by a large native army.

Montezuma II, the Aztec ruler, was indecisive. He invited the conquistadors into Tenochtitlan in November of 1519, hoping to better understand them. However, he foolishly plied them with lavish gifts of gold, which only excited their lust for plunder. The Spaniards treacherously seized Montezuma in his own palace, then ruled Tenochtitlan and the Aztec Empire through the captive emperor, whom they held as a hostage.

In April of 1520, Cortes had to return to Mexico’s east coast in order to ward off another Spanish expedition sent to oust him, and left 200 Spaniards behind under a trusted deputy. While Cortes was gone, his deputy massacred thousands of Aztecs in Tenochtitlan’s Great Temple, triggering an uprising. Cortes hurriedly returned to Tenochtitlan and trotted out the captive Montezuma in an attempt to placate the natives, but the livid Aztecs stoned the Spaniards’ puppet ruler to death.

Cortes fled Tenochtitlan, then returned with a powerful native army to subdue the city. After vicious street by street fighting that wrecked much of the Aztec capital, Cortes finally subdued the city, whose population had been decimated by Old World diseases against which the natives had no immunity. The Spanish built Mexico City and their colony of New Spain atop the ruins of Tenochtitlan and the Aztec Empire.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Pizarro and his men capturing the last Inca. Montgomery College

1 – Francisco Pizarro and His Men

Francisco Pizarro repeated against the Incas of South America what Hernan Cortes had visited upon the Aztecs of Mexico. Indeed, Pizarro’s dealings with the Incan emperor Atahualpa were even worse than those of Cortes with Montezuma a decade earlier. As with Cortes, Pizarro’s efforts also led to genocide, the destruction of a native empire, and its replacement by a new Spanish domain.

Pizarro landed in Peru in 1532, and after establishing a small colony, he set off to conquer with a small force of about 200 mercenaries. En route, he was met by an envoy from the Inca ruler, Atahualpa. The Inca invited the Spaniards to visit him at his camp, where he was resting with an army of about 100,000 men, having recently defeated a brother with whom he had briefly shared the empire.

A meeting was arranged for November 16th, 1532, in a plaza in the town of Cajamarca. Pizarro set off to meet Atahualpa with 110 infantry and 67 cavalry, armed and armored with steel, plus three arquebuses and two small cannon. On the eve of the meeting, Pizarro outlined for his men an audacious plan to seize Atahualpa, inspired by Cortes’ seizure of Montezuma. On the appointed day, Atahualpa left his army camped outside Cajamarca, and arrived at the town’s plaza on a fine litter carried by 80 high ranking officials. He was trailed by about 5000 Inca nobles and other courtiers, richly dressed in ceremonial garments, and unarmed except for small ceremonial stone axes.

The Spaniards were concealed in buildings surrounding the plaza, with cavalry hidden in alleys leading to the open square, and fell upon Atahualpa and his party at a signal from Pizarro. A massacre ensued. The unarmored natives proved no match for the Spaniards’ steel swords, pikes, bullets, or crossbow bolts, while the Incans’ ceremonial stone axes proved useless against Spanish plate armor.

Atahualpa was captured, and he sought to buy his life by offering to fill a room measuring 22 by 17 feet, up to a height of eight feet with gold, and twice with silver. Over the next eight months, the Incas gathered gold, silver, jewels, and other valuables to placate the Spaniards, who proved insatiable and kept upping their demands. After the payments were made, Pizarro reneged on the deal, and put Atahualpa through a sham trial. The Inca ruler was convicted of rebellion, idolatry, and murdering his brother. Atahualpa was sentenced to death by burning, but was spared that fate by agreeing to get baptized as a Catholic, and was executed by strangulation instead.


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

Ancient Origins – Exploring the Little Known History of Celtic Warriors in Egypt

Ancient Origins – Vikings in Byzantium: The Varangians and Their Fearless Conquests

Ancient Pages – Hengist and Horsa: Legendary Anglo-Saxon Warrior Brothers, and Leaders of First Settlers in Britain

Ann Bonny Pirate – Jeanne de Clisson Biography

Encyclopedia Britannica – Francisco Pizarro, Spanish Explorer

Encyclopedia Britannica – Sir John Hawkwood, Anglo-Italian Mercenary

History Extra – Cortes and Montezuma: The Conquering of Tenochtitlan

Listverse – 10 Fascinating Stories From Legendary Mercenaries

McLaughlin, Mark – The Wild Geese: The Irish Brigades of France and Spain (1980)

Military History Now – Meet the Landsknechts: 10 Wild Facts About the Most Murderous Mercenaries of the Renaissance

Military History Now – The Wild Geese History

Soldiers of Misfortune – The Taiping Rebellion and the Formation of the Ever Victorious Army

Soldiers of Misfortune – The Varangian Guard

ThoughtCo. – Albrecht Wallenstein in the Thirty Years’ War

Warfare History Network – The History of Swiss Pikemen

War History Online – Once the Greatest Army in Europe: The Black Army of Hungary

Wikipedia – Anarchy at Samarra

Wikipedia – Francesco I Sforza

Wikipedia – Phanes of Halicarnassus