The late medieval period was a chaotic time in history. England and France were engaged in the Hundred Years’ War, and Italian city‑states were fighting one another for supremacy in the peninsula. In the absence of permanent standing armies, combatants relied on mercenary companies to do the fighting for them. The temporary peace brought about by the Treaty of Bretigny in 1360 unleashed thousands of unemployed men‑at‑arms looking to pillage to sustain themselves. Many coalesced around charismatic and intrepid leaders into what became known as “free companies.” In Italy, they were known as condottieri. This word is derived from condotta, meaning “contract,” the instrument by which they put themselves in the service of the highest bidder. These soldiers of fortune were the late medieval version of Mafia bosses, making their living with murder, extortion, and terror.
Why These 10 Swashbuckling Mercenaries Matter
Each of the ten figures below earned a reputation for ruthless efficiency, flamboyant bravado, and a willingness to switch sides for the right price. Their stories illuminate the chaotic world of medieval warfare and the shadowy economy of hired swords.
10 Roger de Flor
Roger de Flor was born in the then‑Catalonian province of Brindisi, Italy in 1267. As a boy he went out to sea and eventually became a Knight Templar. He took advantage of the Muslim capture of Acre in 1291 by robbing the refugees, and when his activities were exposed, he was expelled from the Templars. Fleeing to Genoa, he became commander of a force of Spanish mercenaries called Almogavares. Their name was derived from the Arab al‑mogauar, meaning “one who devastates,” and they were the descendants of the Iberians who accompanied Hannibal into Italy. In the seventh and eighth centuries they engaged in guerrilla operations against the Muslim invaders of Spain.
In 1303 the Byzantines recruited Roger, who was then in the service of the king of Aragon, to help fight the Ottoman Turks who had just wrested Bithynia from the Empire. In Constantinople Roger married a niece of Emperor Andronicus II Palaeologus and was made a grand duke. With 1,500 knights and 4,000 Almogavares called the Catalan Company, Roger won battles against the Turks, but he also pillaged and looted the Byzantine inhabitants of Anatolia in what is now Turkey. This led the authorities to denounce him as nothing better than a brigand, but success swelled his ego and he began dreaming of carving his own dominion in Anatolia.
Emperor Michael IX became convinced that Roger and his undisciplined Almogavares must be destroyed. In 1305 Roger was lured to Adrianople for a banquet hosted by Michael. There he was ambushed by another mercenary force and killed, along with 130 of his men. The remnants of the Catalan Company ravaged the countryside in revenge before settling in Greece and founding the Duchy of Athens in 1311.
9 Bascot de Mauleon
Bascot de Mauleon was captain of a group that marched into Burgundy with freebooters of various nationalities. Mauleon had his first experience of battle at Poitiers. Later he went to Prussia with the Count of Foix, crushing the peasant rebellion of the Jacquerie upon his return to France.
Mauleon estimated that about 12,000 men rode with him in the Loire region. This formidable force seized the castle of Brignais from the king and defeated the constable of France, amassing such wealth in ransoms and booty that the pope in Avignon feared for his safety.
Technically Mauleon fought for the king of England, but as an independent freebooter his main interest was money. Before he made it to the big time, Mauleon remembered, “Sometimes I have been so thoroughly down that I hadn’t even a horse to ride, and at other times fairly rich, as luck came and went.” His rags‑to‑riches tale was recorded by the French chronicler Froissart, who met him at a hostel in the Pyrenees. Froissart recalled, “He arrived with plenty of followers and baggage… He had as many pack horses with him as any great baron, and he and his people took their meals off silver plate.” Not a bad lifestyle for a highwayman.
8 Duke Werner von Urslingen
Taking upon himself the title of “Duke,” Werner von Urslingen stitched onto his doublet the motto “the enemy of pity, of mercy, and of God,” and lived up to it in the most horrific ways possible. Werner’s modus operandi was invading peaceful regions and robbing, raping, and killing the inhabitants before torching their property. He trumpeted his atrocities to authorities and threatened more unless he was paid, extorting vast sums from Siena, Perugia, Florence, and Bologna. In 1339 Werner and his band were denounced as “a plague of society.”
Werner founded the Great Company in 1342. At its height it numbered 6,000 men, mainly armored cavalry. He imposed strict discipline and a code of laws upon his men, including equal division of income. Later mercenary armies sought to model themselves after the powerful Great Company.
In 1347 Werner supported Queen Joanna I of Naples, sister‑in‑law of King Louis I of Hungary, after Louis invaded Naples to avenge his brother’s murder. Werner helped Joanna return to Naples and defended her against the opposing condottiere. On Joanna’s behalf Werner attacked the baronage of Meleto, raking in half a million florins’ worth of booty. Eventually both Werner and Wolfart were bought off, and Werner returned to Germany with his loot.
7 Conrad Of Landau
The German Conrad of Landau took command of the Great Company in 1354, operating in Tuscany, Umbria, the Romagna, and Lombardy. He held entire cities for ransom and reaped massive profits. As Conrad bluntly told a papal legate before invading church lands, “It is our custom to rob, sack, and pillage whoever resists. Our income is derived from the funds of the provinces we invade; he who values his life pays for peace and quiet from us at a steep price.”
On one occasion Conrad was ambushed by the Florentines on his way to Siena to fight Perugia. He was unhorsed and wounded, his force routed, and angry locals looted the remnants of the Company. It was a temporary setback, but Conrad continued to rake in vast revenues, enabling his father in Germany to buy back the family castle and lands lost to debt.
The Great Company was eventually hired by the Visconti rulers of Milan to drive away the rival White Company of Albert Sterz. In 1363 the two companies met at Canturino. Conrad held his line until his Hungarian contingents refused to fight fellow Hungarians in the opposing army. Their desertion tipped the scales to the White Company, and Conrad was killed in the ensuing battle.
6 Albert Sterz
The most infamous brigand group of all is the White Company, founded by the German Albert Sterz. It got its name from the white surcoats worn by its troops and the white banners they flew. Under Sterz, the Company was unmatched in efficiency. Its 3,500 horsemen and 2,000 infantry were impeccably organized and well equipped. Engineers even laid mines and built scaling ladders and siege towers within its ranks.
In 1360 Sterz moved the Company to Italy, the fertile field of constantly warring city‑states. Along the way he recruited an English knight named John Hawkwood, who swiftly rose through the ranks because of his negotiating skill. Sterz soon regretted his decision. Hawkwood’s men impressed him, deposed Sterz and gave command to the Englishman. The jealous Sterz sulked, biding his time for payback.
The Company drew up a contract with Pisa to attack rival Florence. The city was prepared, and Hawkwood’s attack stalled. Sterz seized his moment, switched sides, and carried his loyal men over to the Florentines. The White Company disintegrated, leaving Hawkwood with only 800 men. After the war Sterz merged the remnants with the German condottiere Hannekin Baumgarten, forming the Company of the Star, which enabled Sterz to crush Hawkwood.
5 Alberico de Barbiano
Alberico de Barbiano, a native of Cotignola in Romagna, began his career as a captain in the service of Milan. Later he was employed by Florence, Venice, Naples, and the papacy. Alberico’s most infamous moment came in 1377, when he participated in the horrific Massacre of Cesena, a town not far from his home, as captain of the forces under Cardinal Robert of Geneva (later anti‑pope Clement VII). Ordered by Pope Gregory XI to subdue the rebellious towns of Romagna, Cardinal Robert employed Breton mercenaries, “the most cruel and bestial seed of France.” Even after the townspeople surrendered their weapons, the inhabitants of Cesena were slaughtered in a three‑day bloodbath, their corpses left to be devoured by dogs.
In 1378 Alberico formed the Company of St. George, composed entirely of Italians who swore “hatred and eternal enmity” toward all foreigners. He turned against Clement VII and defeated his Breton force on behalf of Pope Urban VI, who proclaimed Italy “free of barbarians.” Yet the anti‑foreigner sentiment was empty bombast. After expelling the Bretons, Alberico began plundering Tuscan towns. His new band, the Company of the Hook, included Germans, Hungarians, and perhaps inevitably, Bretons.
At the close of the 14th century Alberico fought in wars between Florence and Milan, switching sides as it pleased him. He served Naples in the twilight of his career and died in 1409. Alberico is credited with military innovations such as improved armor and aggressive cavalry charges. His practice of recruiting troops from his own Romagnan feudatories, creating greater cohesion, is seen by some as a precursor to the eventual unification of Italy in the 19th century.
4 Muzio And Francesco Sforza
Muzio Attendolo was the first prominent member of the family that would later rule Milan. He hailed from Cotignola in Romagna and served under Alberico de Barbiano before striking out on his own. Alberico dubbed him Sforza, meaning “force,” and as an independent condottiere he made it his nom de guerre.
In 1398 Muzio entered the service of the Visconti rulers of Milan but soon departed to fight for Florence and then Ferrara. By 1412 Naples secured his services, and Muzio became constable of the kingdom. He endured a roller‑coaster career during the chaotic reign of Queen Joanna II, alternating between rewards of lands and offices and periods of imprisonment and torture. In 1424 Muzio drowned in a river while campaigning against a fellow condottiere.
Like a medieval Michael Corleone, Muzio’s son Francesco took up his father’s mantle and became the most successful mercenary captain of the 15th century. Francesco served the Visconti against Venice, then Venice against the Visconti, attacked the pope, then defended him. To bind Francesco permanently to Milan, Duke Filippo Visconti married him to his only daughter in 1441. Expecting to inherit the dukedom, Francesco was thwarted when Milan declared a republic. He besieged Milan and seized the title by force in 1450 – the Sforza name was earned.
3 Rodrigo de Villandrando
Many mercenaries were not averse to robbing their own employers. This was the case with Rodrigo de Villandrando, one of the greatest mercenaries of his era. Rodrigo was born in Castile in 1380. Seeking a military career he traveled to France and first joined the mercenary army of Amaury de Severac and the Burgundians.
Rodrigo formed his own mercenary company in 1420 and offered his services to the French Dauphin Charles. He extorted money from the cities and estates of Languedoc and pillaged the countryside, all within Charles’ realm. When Charles ordered him to attack the English, Rodrigo refused and instead went to Toulouse, recruiting more men. He eventually attacked English‑held Bordeaux and was pardoned by Charles. In a later battle at Anthon his 400 men defeated the Burgundians; one enemy soldier hid in a hollow tree, only to be crushed by his own armor. The tree was cut down in 1672, revealing his skeleton.
At his peak Rodrigo commanded 10,000 men, exacting ransoms from nobles and demanding “protection money” from locals who wished to avoid murder and pillage. His violent forays in Gascony earned him the title “Emperor of Pillagers.” Enriched, he retired in the 1440s, returned to Castile, willed his wealth to a monastery, and died in 1457.
2 Arnaud de Cervole
Born into a minor noble Gascon family, Arnaud de Cervole was the archpriest of Vélines in the diocese of Périgueux. Being a man of God didn’t stop him from mixing with brigands and men of base extraction. Deprived of his benefice by the bishop of Bordeaux, he turned to full‑time brigandage, specializing in stealing castles. At one point Arnaud and his band seized three castles in Angoulême as security until their employer paid their wages. The French crown charged him with theft when he took over a castle in Normandy, though he was then in the service of King Jean II.
After Jean II’s capture at Poitiers, Arnaud lost his patron and turned to pillaging, establishing a protection racket in the wealthy, peaceful region of Provence. He approached Avignon, terrifying the pope into a shakedown. Froissart records, “He entered Avignon with most of his followers by friendly agreement, and was received with as much respect as if he had been the king of France’s son, and dined several times with the pope and the cardinals. All his sins were remitted and when he left he was given 40,000 crowns (20,000 gold florins) to distribute among his companions.”
Shifting operations to Burgundy, Arnaud seized castle after castle until the count bought him off for 2,500 gold francs. In 1365 Pope Urban V recruited Arnaud to lead a crusade against the Turks, but the true aim was to move the freebooters away from the Rhône. Arnaud’s army reached Lyon but refused to march on. Unfed and unpaid, his men quarreled with him, which ended in his murder.
1 Sir John Hawkwood
Despite leading the murderous White Company, Sir John Hawkwood died a fairly rich man and was even honored by an equestrian fresco in the Florence Cathedral. The memorial was a personal affront to Victorian author Ferdinand Gregorovius, who lamented, “Florence, who denied Dante a resting place, erected a noble monument to a robber.”
Born to a minor Essex landowner, Hawkwood left for France to fight for Edward III at age 18. He was knighted for his role in the English victory at Poitiers, but after the Treaty of Bretigny he was left a poor knight without a job. He joined the Free Companies to support himself.
As a soldier of the king Hawkwood was an unknown, but as a freelancer he achieved astounding success. Seeking his fortune in the medieval snake pit of Italy, he became leader of the White Company, which terrorized Italy and earned a reputation as “perfidious and most wicked.” The only consolation was that “they did not mutilate or roast their victims like the Hungarians.” The locals called Hawkwood’s force “devils in human shape.”
Over the next thirty years Hawkwood’s business of murder, pillage, and blackmail prospered. His fighting skill was coveted by the pope, Florence, Milan, Pisa, and Perugia. Because his loyalty was only to money, he betrayed each client when a juicier offer appeared. Florins flowed so freely into his coffers that he rivaled banks and trading houses. The White Company employed lawyers and notaries to keep records of bribes and ransoms, accountants and secretaries to divide the plunder, and brokers to sell each soldier’s share.
Hawkwood became so influential that he arranged the marriage of Edward’s third son, Lionel, to the daughter of the Duke of Milan. He himself married the duke’s 17‑year‑old daughter when he was 57. Florence offered the richest rewards, and he ended his days as a general of the Florentines, instrumental in creating their republic. When he died in 1394, he was remembered as “the ablest military commander of the Middle Ages.”