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

Mercenaries – warriors hired to take part in armed conflicts, without being a formal part of a government’s forces – have played significant roles throughout much of history. Although their fortunes declined with the rise of national armies in the 18th century, mercenaries have continued to fill niche needs that enabled them to survive into the present. Indeed, mercenaries, known today as “private military contractors”, have experienced a revival since 2003’s Operation Iraqi Freedom.

Following are sixteen of history’s most significant mercenaries and mercenary bands.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Seljuk Turk warriors. Apricity

16 – The Abbasid Caliphs Discovered the Folly of Hiring Mercenaries Without Being Able to Control Them

The Abbasid Caliphate (750 – 1258) was the second of two hereditary dynasties that claimed suzerainty over the Islamic empire. At the height of their powers, the Abbasids ruled a realm stretching from the Atlantic Ocean to the borders of China, and from Central Asia to the borders of India. Their fortunes took a nose dive when shortsighted caliphs hired Turkish mercenaries, then failed to control them.

It began in the 9th century, with al Mu’tasim, a younger son of the dynasty’s most famous caliph, Harun al Rashid – a contemporary of Charlemagne and a recurring character in the Arabian Nights fables. Al Mu’tasim created a private army of Turkish mercenaries and slaves, and formed them into a Turkish Guard that helped him secure the caliphate in 833. However, the mercenaries engaged in widespread robberies and rapes that made them hugely unpopular with the civilian population. So in a bid to reduce the friction between his subjects and soldiers, al Mu’tasim relocated his capital in 835 from Baghdad to a new city, Samarra. That calmed things down for a while, but did not solve the core issue of controlling the Turkish mercenaries.

Things came to a head in 1861, in what came to be known as “The Anarchy at Samarra”. It began when the Turkish Guard murdered the caliph al Mutawakkil, and replaced him with his brother, al Muntasir. The new caliph lasted for six months, before the Turks did him in, then held a conference to appoint a successor, al Musta’in. He escaped in 865, but the mercenaries pursued, captured, and put him to death. They then appointed another caliph, al Mu’tazz, but when he bucked, they deposed and killed him in 869, replacing him with another puppet, al Muhtadi. He, too, tried to assert his authority, only to get murdered by the mercenaries and replaced in 870. The anarchy finally ended with the appointment of a caliph who accepted his role as a puppet.

The Abbasid Caliphate stumbled on for another four centuries, surviving as a shadow of what it had once been, with its caliphs as playthings of strongmen and sultans. It was finally put out of its misery in 1258, when the Mongols sacked Baghdad, and executed the last Caliph by rolling him inside a rug and trampling him to death beneath their horses’ hooves.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Black Army infantry in a castle, circa 1480. Wikimedia

15 – The Raven King and His Mercenary Black Army

The Raven King and his mercenary Black Army sound like something straight out of George R. R. Martin’s A Song of Ice and Fire. However, it refers to a real-life monarch and military unit, who became Europe’s most formidable warriors in the second half of the 15th century. To wit, King Matthias Corvinus of Hungary (1443 – 1490), whose name translates as “Matthew the Raven”, and a mercenary army he assembled to hold back the Ottoman Turks.

When Hungary’s king Ladislaus V died childless in 1457, the Diet of Hungary convened in January 1458 to elect a new king. It eventually chose 14-year-old Matthias Corvinus as a compromise candidate to avert a civil war between rival factions. The plan was for Matthias’ uncle to rule as regent until the new king came of age, but the teenager surprised everybody by administering state affairs independently from the outset.

Military matters were high on the list of state affairs that attracted Matthias’ attention, as he ascended the throne only 5 years after the Ottoman Turks had conquered Constantinople and extinguished the Byzantine Empire. The Turks, brimming with confidence, turned their attention to Hungary. Against all precedent, Matthias taxed Hungary’s nobles, and ignoring their howls of protest, used the funds to recruit 30,000 mercenaries, mainly from Germany, Poland, Bohemia, and Serbia, and after 1480, from Hungary.

They were organized into a combined arms mix of light infantry operating around a base of heavily armored infantry, and supplemented by even more heavily armored knights. In a pioneering innovation that took advantage of recent firearms developments, every fourth soldier was armed with an arquebus. Matthias’ mercenaries, who came to be known as the “Black Army”, became a formidable force that dominated Central Europe and the Balkans, and held back the Ottomans for decades.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Artillery unit of the Ever Victorious Army. Emerging Civil War

14 – Frederick Townsend Ward and the Ever Victorious Army

As the Civil War raged in the US in the 1860s, an even more destructive civil war was raging on the other side of the globe in China: the Taiping Rebellion. It was a mixture of peasant uprising and millenarian Christian cult upheaval, led by an odd Chinese figure who, after failing the entrance exams into the Chinese civil service, had a breakdown, and upon recovery, declared himself Jesus Christ’s younger brother.

He amassed a following, and established the Taiping Heavenly Kingdom – an oppositional state that waged a brutal war from 1851 to 1864 against China’s ruling Qing Dynasty. By the time the Taiping were defeated, about 30 million people had been killed, making the rebellion the bloodiest war in history, until its toll was exceeded by that of World War II.

In the early runnings, the Taiping rebels repeatedly routed the armies of the Qing Dynasty. When Taiping armies drew close to Shanghai in 1860, the city’s business community pooled its resources to hire an American, Frederick Townsend Ward, to lead a mercenary force and protect the city. Officered by Westerners who led Chinese rankers drilled in modern warfare, Ward’s force, which came to be known as the “Ever Victorious Army” (EVA), turned the tide.

Although never exceeding 5000 men, the EVA’s well-trained mercenaries routed far bigger Taiping armies, and secured Shanghai. It then operated as a crack unit, spearheading the Qing Dynasty’s counterattack, and helping the imperial forces recapture Taiping fortresses and strongholds along the Yangtze River. Ward did not see the final victory, as he was killed in battle in 1862. His army was then taken over by a British officer, Charles “Chinese” Gordon, who led the EVA until the Taiping were finally crushed in 1864.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Varangian Guards. Pintrest

13 – Byzantine Vikings: The Varangian Guard

Mercenary units tend to be ad hoc affairs of adventurers from all over, gathered together under a captain for a specific mission, campaign, or war. As such, mercenary units seldom last for more than a few years before they are disbanded, once the conflict that gave rise to their creation is concluded. The Varangian Guard was an exception, and their history as a mercenary unit lasted for hundreds of years, stretching from the early 10th to the 14th centuries.

In the ninth century, Swedish Vikings penetrated deep into what is now Russia and Ukraine, and by 850, they had formed their own principalities in Kiev and Novgorod. From there, they dominated the surrounding Slavs as a ruling caste of a new civilization that came to be known as Kievan Rus. The princes of Rus tended to hire new fighters from Scandinavia, who were known as Varangians – a term meaning a stranger who had taken military service, or a member of a union of traders and warriors.

By the early 900s, some of these Varangian Vikings had ventured further south, sailed across the Black Sea, and raided Constantinople and the Byzantine lands. Some, however, took service with the Byzantine emperors as mercenaries, and as early as 902, contemporary records describe a force of about 700 Varangians taking part in a Byzantine expedition against Crete.

In 988, Byzantine Emperor Basil II sought military aid from his ally, Prince Vladimir I of Kiev. The Rus ruler sent 6000 of his most unruly warriors, whom he was having trouble paying anyhow. The emperor put Vladimir’s discards to good use against his enemies, then organized them into what became the nucleus of the Varangian Guard. As foreigners, the Vikings had no local ties, and thus few political links that could enmesh them in the Byzantine court’s intrigues and cabals. That made them suitable as bodyguards. They were not just palace soldiers, however, but accompanied the emperor on campaign, and formed the Byzantine army’s shock infantry.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Varangian Guards. Realm of History

The Varangians proved themselves in battle time after time, and their unit became an elite outfit whose members received higher pay than the rest of the army. In addition to higher pay, they were often granted the privilege of being the first to loot after victory. Another informal privilege, which fell into their lap as the main armed force in the imperial palace, was the privilege of plundering the emperor’s possessions after his death.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Swiss mercenary reenactors. Quora

12 – Swiss Mercenaries Were Europe’s Elite Infantrymen

During a roughly two-hundred-year stretch from the fourteenth to sixteenth centuries, everybody in Europe who could afford to wanted to hire Swiss pike-wielding mercenaries. Swiss infantrymen had developed a fierce reputation while defending their liberties against their Hapsburg overlords, with upset victories against heavily armed and armored knights in the battles of Morgarten in 1315, and Laupen in 1339.

Morgarten and Laupen secured the Swiss their reputation as elite foot soldiers, and their renown was furthered with further victories against their neighbors, as they expanded the boundaries of the Swiss Confederation. The Swiss peasants who filled the ranks were bound by no notions of chivalry, and felt no urge to capture enemy knights and aristocrats for ransom. Instead, they earned a terrifying reputation for giving no quarter, and reveled in slaughtering their foes.

Infantrymen who could routinely defeat knights – undisputed lords of the battlefield for centuries – and whose mere presence on the battlefield terrified their foes and sapped their morale, became a highly sought after asset. The French Valois kings, for example, virtually refused to offer battle unless they had Swiss pikemen at the core of their infantry formations.

The Swiss were more than happy to hire themselves out as mercenaries, but unlike most mercenaries, they did not hire themselves out as individuals. Instead, prospective employers contracted directly with local Swiss governments to hire their militias. That set the Swiss apart from run-of-the-mill mercenary companies, comprised of a motley collection of adventurers gathered from all over. Swiss mercenaries, hired as entire militia units, were ready-made trained contingents that had practiced together for years, and were knit together by ties of kinship, neighborliness, and personal acquaintance. That gave them strong unit cohesion and esprit de corps, and made them especially formidable on the battlefield.

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

11 – The German Landsknechts Displaced the Swiss as Europe’s Elite Mercenaries

The German Landsknechts began as a poor man’s version of the feared Swiss pikemen, but by the early 1500s, they had proved their worth in several battles, and displaced the Swiss as Europe’s supreme mercenary forces. Like the Swiss, Landsknecht units were comprised of squares of pikemen, but they improved upon the formation by flanking it with supporting troops armed with firearms, halberds, and swords.

The first Landsknecht units were formed in 1487, when Holy Roman Emperor Maximilian I directed a Swabian commander, Georg von Frundsberg, to form mercenary regiments. Frundsberg, who came to be known as the “father of the Landsknechts”, consciously modeled the new units on the Swiss pikemen, and hired Swiss instructors to train them.

By then, the Swiss formation and tactics, dependant on a tightly packed phalanx of pikemen and close hand-to-hand combat, were becoming outdated and increasingly vulnerable to firearms and artillery. The Landsknecht, assembled in pike blocks of about 200 men that were lighter, smaller, and thus more maneuverable than their Swiss counterparts, were intended to fight off the Swiss after their ranks had been depleted by arquebuses and cannon.

When Landsknecht and Swiss pikemen met on the battlefield, the result was like two fighting dogs unleashed against each other in a pit: no quarter was given or asked, in what was referred to as schlechten krieg, or “bad war”. The Landsknechts’ tactical innovations, fighting while supported by firearms, gave them an edge, and at the Battle of Marignano in 1515, they defeated the Swiss.

The Landsknechts thus earned a terrifying reputation on the battlefield, but it was eventually eclipsed by an even more terrifying reputation for their conduct off the battlefield. They were notoriously undisciplined and had no compunctions about going on rampages and taking what they were owed by force if they were not paid on time. Indeed, their reputation for unprincipled violence, rape, robbery, and massacre, led a contemporary chronicler to remark that the Landsknechts would not go to hell, because the devil was too afraid to let them enter his domain.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Celtic warriors of the ancient world. Ancient Origins

10 – The Ancient World’s Celtic Mercenaries

In the centuries before Julius Caesar’s conquest of Gaul and its subsequent pacification and Romanization, the Celtic peoples, who dominated most of Europe north of the Po and Danube river valleys, had a fearsome reputation that terrified many. The Romans in particular saw the barbarian Celts – whom they referred to as Gauls – as their greatest national threat, and for centuries, Roman mothers quieted down their fussy tots by warning them that the Gauls might hear them.

The Romans had good reason for alarm. Throughout much of Rome’s early history, Celtic/ Gaulish tribes dominated Italy north of the Po River and along much of Italy’s Adriatic coast – not that far as the crow flies or as the barbarian marches. That was driven home in 387 BC, when Gaulish tribesmen, led by a chieftain named Brennus, defeated a Roman army, then marched on to capture and sack Rome. It was a feat no foreigners would repeat for another eight centuries.

The era’s Celtic warriors were famous for the quality of their weapons, their courage and ferocity in battle, their frightful battle cries, and their terrifying, butt-naked, headlong charges. That reputation made them highly sought after as mercenaries. Starting in the 4th century BC – and especially after the fragmentation of Alexander the Great’s empire into feuding Hellenistic states – Celtic mercenaries became all the rage from Sicily to Asia Minor. In addition to fighting for the various Greek kingdoms, Celts also fought for Carthage, and formed a significant part of Hannibal’s army when he invaded Italy in the Second Punic War.

Celtic mercenaries were also a bulwark of Egypt’s Ptolemaic Dynasty in the third century BC, and were included in the Egyptian army’s order of battle. For example, Ptolemy II Philadelphus hired 4000 Celtic mercenaries, recruited from the Balkans with help from the Anigonids of Macedon. They played a decisive role in beating back a challenge from a half-brother who made a bid for Ptolemy’s throne.

However, the Celt mercenaries then made a bid of their own to dethrone Ptolemy and seize Egypt for themselves. After crushing their rebellion, Ptolemy dumped them into a small island in a Nile, to die of starvation. Notwithstanding, the Ptolemies continued to hire Celts mercenaries – their lack of local roots made them particularly useful in putting down uprisings by native Egyptians. They remained in Ptolemaic service until the end, and the dynasty’s final ruler, Cleopatra, was known to have employed Celtic mercenaries.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Wild Geese of the Irish Brigade. Daisy Roots Books

9 – The Wild Geese and France’s Irish Brigade

After England’s “Glorious Revolution” of 1688-1689, the newly crowned Protestant king William III took an army to Ireland to subdue the island and mop up the last Jacobite supporters of his Catholic predecessor, King James II. After losing to William in the Battle of Boyne in 1690, James fled to Europe, leaving his most Irish Catholic supporters to try and retrieve the situation. Despite their best efforts, the Irish Jacobites were decisively defeated at the Battle of Aughrim in 1691, and forced to capitulate.

Peace was concluded with the Treaty of Limerick, signed in October 1691. It offered favorable terms to Jacobites willing to swear allegiance to William III. Those unwilling to do so were allowed to leave Ireland en masse, and join the exiled James II in France. In what came to be known as “The Flight of the Wild Geese”, roughly 14,000 men, accompanied by 10,000 women and children, left Ireland for France.

Upon arrival, the Wild Geese took service as mercenaries, and for the next hundred years, the French army would include an Irish Brigade, whose nucleus was the exiles of 1691. During that period, their ranks were constantly replenished by new arrivals from Ireland. French ships smuggling brandy and wine into Ireland usually smuggled out new recruits for the Irish Brigade, who were often listed in the ship’s log – in a nod to the first batch of recruits from 1691 – as “Wild Geese”.

Many of the new recruits sought adventure, others simply wanted to make a living, and most were looking for an opportunity to fight Ireland’s ancient enemy, the English. Thousands of Irishmen thus served France in the century after the Treaty of Limerick. They fought for the French in numerous wars, and proved instrumental in some notable victories against the British, such as at the Battle of Fontenoy in 1745. After the French Revolution, the unit’s existence as a separate entity came to an end, when foreign regiments were integrated into the French army’s line infantry.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Albrecht Wallenstein. Wikimedia

8 – The 17th Century’s Greatest Mercenary General

The 17th century’s greatest mercenary was probably Albrecht Wenzel Eusebius von Wallenstein (1583 – 1634), a soldier from Bohemia who approached warfare and soldiering as business moves and financial transactions. Although a Protestant, he rose to command the armies of the Holy Roman Empire during the Thirty Years War, fought for the Catholics, switched sides to fight for the Protestants, then switched once more to fight for the Catholics.

Wallenstein was born a Lutheran, but took service with the Catholic Hapsburgs in 1604. He ingratiated himself with his employers and with the influential Jesuits at their court with a nominal “conversion” to Catholicism. Like most moves in Wallenstein’s life, the conversion was a profitable one: his Jesuit confessor arranged for him to marry a fabulously wealthy elderly widow with huge estates. His wife’s vast wealth and lands, which Wallenstein inherited after her death in 1614, instantly vaulted him into the ranks of the powerful in the Habsburg realms.

Wallenstein fought in numerous campaigns and battles, and earned a reputation for military brilliance. When the Thirty Years’ War broke out, the Habsburgs feared that they would end up facing the Protestant-born Wallenstein, but he calculated that serving the wealthier Catholics would prove more lucrative. So he offered his services and an army of 30,000 to 100,000 to the Holy Roman Emperor, Ferdinand II.

The Protestant-born Wallenstein then proceeded to destroy Protestant armies and the Protestant cause in his native Bohemia. He did such a thorough job of it, particularly at the Battle of White Mountain in 1620, that he eradicated two centuries of a strong Protestant tradition, dating back to Jan Hus’ uprising in the early 1400s. From a Protestant bastion in Central Europe, Bohemia was transformed into a Catholic stronghold, and it remains Catholic to this day.

Having wrecked the Protestant cause in Bohemia, Wallenstein then proceeded to wreck the Protestant cause in Western and Northern Germany. However, his successes and ambition, plus fears that he was preparing to switch sides, led Emperor Ferdinand to remove him from command in 1630. It was the break the Protestants needed to recover and led by Sweden’s king Gustavus Adolphus, they won a series of stunning victories. The Emperor, reasoning that a potentially treasonous general was better than incompetent ones, recalled Wallenstein. He stabilized the situation by defeating Gustavus Adolphus at the Battle of Alte Veste in 1632, and killed him at the Battle of Lutzen later that year.

However, Wallenstein grew increasingly resentful of his treatment by Ferdinand. In a rare bad move, he did little to hide his intent to switch sides and defect to the Protestant cause by joining the Swedes, as soon as he negotiated an agreeable deal. Word got back to the Emperor of Wallenstein’s planned defection, so he nipped the problem in the bud by having the problematic general assassinated in 1634.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
John Hawkwood fresco. Traveling in Tuscany

7 – John Hawkwood and the White Company Wreaked Havoc in Italy

Europe’s greatest mercenary of the 14th century was Sir John Hawkwood (1320 – 1394. An English soldier of fortune, he is best known for plying his trade as a condottiere in Italy, where he was known as Giovani Acuto, meaning “John the Astute”. As captain of a powerful mercenary band, Hawkwood played a significant role in the wars and politics of fourteenth-century Italy, switching sides on numerous occasions between the peninsula’s competing states and factions.

He began his military career in France during the Hundred Years War in the armies of England’s king Edward III, who knighted Hawkwood for exemplary military service. However, that war was temporarily interrupted by a peace treaty in 1360, so Hawkwood left France for greener pastures in Italy at the head of a company of mercenaries.

Upon arrival in Italy, he joined an English mercenary unit known as the White Company. Hawkwood rose through its ranks, and in 1364, he was elected captain-general. He swiftly put his stamp on the White Company by adopting the English longbow and tactics successfully used in France. He also instilled strict discipline and lightened his men’s armor and equipment, which made them famous for the rapidity of their movements. Hawkwood’s reforms transformed the White Company into an elite and highly sought-after mercenary unit.

In the 1370s, the White Company and Hawkwood served the Pope, but when the Holy Father stiffed them on payment, the mercenary bided his time. When the Pope sent him to put down a rebellion in Citta di Castello, Hawkwood captured and kept the city in order to compel payment. Strapped for cash, the Pope was forced to invest in Hawkwood with the city, granting it to him in return for uncompensated services.

Between 1372 and 1378, Hawkwood repeatedly switched sides, alternately serving the Pope and his rival, the Duke of Milan, whose illegitimate daughter Hawkwood married in 1377. In 1378, after quarreling with his new father-in-law, Hawkwood switched sides and signed a contract with Milan’s rival, the city of Florence, and was appointed its captain-general. He remained in Florence until he finally decided to sell his Italian properties and retire to England to spend his last years, but died in 1394 before he could do so.

A Countdown of History’s 16 Most Influential and Formidable Mercenaries
Image extracted from a 6th century BC seal, depicting Cambyses II of Persia capturing Egyptian pharaoh Psamtik III. Wikimedia

6 – Ancient History’s Most Influential Mercenary

Phanes of Halicarnassus (flourished 6th century BC) was a Greek mercenary general who served Egyptian Pharaoh Amasis II (570 – 524 BC). During a war between Egypt and Persia, Phanes switched sides and joined the army of King Cambyses II of Persia, and played an instrumental role in helping the Persians defeat his former employers and paymasters.

The war was supposedly instigated by the intrigues of a disgruntled Egyptian eye doctor, who had been sent to the Persian court by Pharaoh Amasis when Persia’s king Cambyses asked for a physician to treat his sight. Angry at the Pharaoh for separating him from his family and sending him all the way to Persia, the physician got his revenge by advising the Persian king to ask for Amasis’ favorite daughter. He knew that the request would put Amasis in a bind: accept and grow wretched at the loss of his daughter, or refuse, and offend Cambyses.

The Pharaoh did not want to send his beloved daughter to Persia, especially because he knew that Cambyses did not want her as a wife, but as a mere concubine. However, he was also intimidated by Persia’s power. So he fudged, and sent the daughter of a former Pharaoh. It backfired: soon as she reached Persia, the former princess told Cambyses that Amasis had tried to fob him off with somebody else’s daughter. Cambyses, who had been itching for an excuse to conquer Egypt, declared war.

Amasis chose that precarious time to offend Phanes, and the disgruntled Greek general set out to join the Persians. Amasis sent assassins to kill or capture Phanes before he reached Cambyses, but after harrowing adventures, including an escape from captivity by getting his guards drunk, Phanes reached the Persians. He promptly advised Cambyses about the best invasion route into Egypt, through Arab tribal lands, bribing their chieftains into granting him safe passage with generous gifts.

By then, Amasis had died, and he was succeeded by his son, Psamtik III. Enraged at Phanes, Psamtik tricked the Greek general’s sons into meeting him, took them captive, and had them executed. He then had their blood drained and mixed with wine, which he quaffed down along with his subordinates. Phanes got his revenge by leading the Persian army into Egypt, acting as Cambyses’ guide and military advisor. With the mercenary general’s assistance, the Persians defeated and captured Psamtik. Phanes then engineered the execution of his sons’ murderer by uncovering and informing Cambyses of a plot by the captive pharaoh to stir up a revolt.

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 to 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 cannons. 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.

Treachery paid off for Pizarro, who amassed considerable wealth and power after his slimy move against Atahualpa, until some measure of karmic justice caught up with him in 1541. On June 26th of that year, heavily armed supporters of a rival stormed Pizarro’s palace. In the ensuing struggle, Pizarro was stabbed in the throat. Falling to the ground, he made a cross with his own blood while gurgling cries for help from Jesus to no avail, and bled to death.


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

History Collection – Historic Betrayals that Shocked the World

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