This series is devoted to the historical phenomenon known as "free companies," Vikings, pirates, freebooters or filibusters, all of which terms refer to voluntary stateless corporations that sprang up throughout history for the purpose of waging a sort of commercialized warfare in regions where established authority has collapsed or was weak. Often referred to as mercenaries because trading military service for pay was one of the methods such associations employed, they were open to any other method for turning violence into profit, including outright conquest, pillage, ransom of prisoners of war, civilians or even entire municipalities, slaving expeditions, and many other ingenious and amoral inventions.
The governance and dynamics of freely formed and member led anarchic military organizations, and their interactions with established powers provide unique insight into human psychology and the age during which they exist, while their exploits make for some great reading.
This particular installment focuses on a medieval European free company, known as the Catalan Grand Company, which overran the Byzantine Empire in the early 14th century, and its first leader Roger de Flor, a German-Italian pirate and disgraced Templar.
Rutger von Blum was born in 1267 in Italy, and was better known under his name’s Italian translation – Roger de Flor. He was the son of a high ranking German knight in the retinue of the Holy Roman Emperor Frederick II Hohenstaufen. By inheritance, Frederick, in addition to being the Holy Roman Emperor and the King of Germany, was also the King of Sicily, which kingdom included both the island and the southern part of the Italian peninsula. Frederick’s ambition aimed at nothing less than Imperial hegemony over all Christendom, but in his protracted fight with the Papacy and his own subjects, he failed to subdue even the endlessly warring city states of Northern Italy, which stood between his German and Sicilian territories. With Frederick’s death, the dream of a universal empire that could bring order and resurrect the glories of Rome was forgotten for a few more centuries.
The disintegration of Hohenstaufen power following his death led to decades of violent revision of the boundaries and wealth left by the crumbling dynasty. Sicily and Southern Italy were sold by the Pope to a French prince, Charles of Anjou, a very ambitious younger brother of the French King, who was then viewed as the most powerful monarch in Europe. Roger’s father fought for the Hohenstaufen cause until the end, but it was a hopeless struggle. The loyal knight was killed, and the possessions he accumulated in serving the Hohenstaufen were confiscated and distributed to the wave of French conquerors flooding into Italy. The alliance of the Papacy and French power seemed unbeatable, and the acquisition of Sicily was only the first item of the Angevin (the Anjou dynasty’s) agenda. The ports of Southern Italy were the gateway to the Orient, where many attractive targets presented themselves to an enterprising man such as Charles of Anjou.
Roger’s Italian mother took her children to live near her family in such a port, Brindisi. Roger grew up in relative poverty, in a land controlled by new masters hostile to his German lineage, though no one could strip him of his hereditary claim to knightly status or his burning ambition to improve his station in life. Living near the port, he became fascinated with the sea, and the promise of escape that it represented. The young boy spent most of his days climbing the rigging of the various ships in dock. His agility drew the notice of a Templar captain, who convinced Roger’s mother to give her boy to the care of the Order of the Temple, a military and religious order dedicated to fighting enemies of Christ, particularly in the Holy Land. This fight had been going badly for some time, with the Egyptian Sultanate successfully driving to extinguish the last footholds the Crusaders possessed on the eastern Mediterranean coast. However, the Templar organization, which functioned as an independent military and commercial organization organized along monastic lines and answerable only to the Papacy, still possessed considerable holdings in Europe and in the Crusader states, and served as one of the last bulwarks against the total collapse of the Crusader effort.
Roger quickly figured out a way to make this losing war pay, becoming the most successful pirate in the Templar fleet and growing wealthy preying on shipping and raiding coastal settlements in the chaos and power vacuum in the East. He was inducted into the Order and given his own ship to command by the age of 17. The 1291 fall of Acre, the last major Western fortress in Palestine, was a tragedy for medieval Christendom and a turning point in medieval culture, but it also made Roger a lot of money, since his ship represented the only hope for salvation for many of the city’s wealthiest residents, and salvation has never come cheaply.
The leaders of the Templar Order appreciated Roger’s talents for making the crusade a lucrative proposition. However, they too were skilled in the creative accumulation of wealth, and when they learned about Roger’s evacuation of Acre, which rumor had inflated into an enormously lucrative accomplishment, they moved to seize his purported treasures. Though he lost much of his wealth, Roger evaded arrest and was able to draw on his naval reputation and remaining credit to equip another ship. He then proceeded to shop his indisputable piratical talents around the Mediterranean.
By this time, the once dominant French Angevin dynasty, which Roger’s father had died fighting, was itself on the defensive, having lost control of Sicily and much of Southern Italy to an embarrassing popular rebellion, something almost unheard of in the Middle Ages. The French overlords had overreached themselves, and their ambitions engendered a reaction as had the Hohenstaufen ambitions a generation before. The Sicilians did not appreciate being the tax base for Charles of Anjou’s aspirations to make himself Emperor at Constantinople and to reconquer the East. During Easter services in the year 1282, provoked by the arrogant behavior of the foreign elite, the Sicilians turned on their occupiers, slaughtering them by the hundreds, burning the war fleet Charles had waiting in port for departure to the East, and proclaiming a Free Commune under the Pope’s protection.
Because it started during an Easter service, the rebellion became known as the Sicilian Vespers, and quickly spiraled into a general European war. When the Free Commune idea was not well received by the Pope and it became clear that they were about to be subdued by the most brutal measures, the Sicilians offered their throne to Peter the Great of Aragon, who just happened to be floating a few hundred miles offshore with his own war fleet, trying to look innocent. The Pope reciprocated by excommunicating Peter and launching an unsuccessful Crusade against Aragon. The frustrated Angevins mounted invasion after invasion into the rebellious provinces. The new round of wars, coming so quickly after the previous conflicts, made Southern Italy a magnet for adventurers and professional soldiers, who flooded in from every corner of Europe looking for employment, advancement and loot. Aragon was then at the height of its power, flush with a surplus of veteran soldiers freed up by the success of the Reconquista, who now poured into Sicily.
Cast out from the Temple, Roger joined this flow. At the particular moment when Roger found himself on the market, the Angevin fortunes appeared to have revived, and it was to them that the ever pragmatic Roger offered his services first, notwithstanding the fact that his father had fallen fighting their cause. This choice, more than anything else in this story, illuminates the mentality of the adventurer class which is the subject of this work. Entirely unsentimental, immune to appeals of religion, patriotism or morality, these people were guided solely by obscure personal reasons. Their motivations cannot be reduced to a simple search for profit, because the life of a freebooter was a very dangerous one, full of hardships and much more likely to lead to an ugly death than to a wealthy retirement. It seems that the primary motivation was provided by the possibility of existence outside all established social constraints, forging one’s own destiny through a mixture of war and banditry. It made this life very attractive, in particular to the lower classes and those displaced by war or social instability, and it provided an avenue for advancement when all other opportunities were closed off by the rigid medieval social hierarchy.
While the focus of the historians is on the men who chose this life, the participation of women in these enterprises cannot be overlooked. A freebooter army was usually accompanied by a greater number of camp followers, traders, prostitutes, wives and mistresses, children, dependents. As a Free Company passed through a devastated land (rendered even more so by its very passage), the dislocated natives flocked to join the Company in some capacity, as soldier or camp follower. While the majority of the victimized population remained hostile and horrified toward the invaders, a certain proportion appeared to have little difficulty overcoming their natural hostility toward people who were ravaging their homeland, and opted for this chance for survival and escape. This constant infusion of adventurers kept Company ranks growing so long as a Company enjoyed success in its undertakings.
Although Roger appeared to have no qualms about serving the dynasty which had destroyed his father and his patrimony, the Angevin Duke did not equally forthcoming. He rejected the offer, not because of Roger’s lineage, but because Roger was now a disgraced fugitive from the Templars and by extension the Pope, whose allies the Angevins were. At this time, the Angevins were allied with Aragon against a renegade branch of the Aragonese royal line. The coalition of world powers had a nearly complete control of the seas over the Sicilian insurgents, and had no need of this petty pirate. Roger then made his way to Sicily, where the beleaguered Aragonese renegade prince Frederique was happy to employ Roger on the condition that Roger would have to provide for himself, as no pay was forthcoming from the empty rebel treasury. Since all Roger really needed was a few safe harbors and recruiting stations for his pirate operations, he accepted the offer.
Roger found the situation in Sicily desperate. The islanders themselves were as resolute as ever in their opposition to foreign domination, but they were not a match for the military might that the coalition of France, Aragon and the Papacy could muster. The only hope for victory against the opposing coalition lay in the veteran Catalan soldiers who remained with Prince Frederique despite the fact that their feudal overlord, the King of Aragon had ordered them to return to Spain, and the large numbers of mercenaries who had been fighting on alternating sides of the conflict for decades and were only looking for a chance to fight and to get paid for it. With the island was under blockade by the French and Aragonese fleets, Frederique lacked the funds to pay these soldiers, and their military effectiveness tended to decrease in direct proportion to their lack of compensation. A large army of French knights was expected imminently to invade the island, and the outlook was grim.
Roger set out to raise these funds by waging an indiscriminate campaign of piracy from the Italian coast to Africa, seizing all ships that came his way, regardless of their affiliation. Given Sicily’s diplomatic isolation at the time, indiscriminate naval warfare was unlikely to exacerbate the situation, but for those captains who protested that their ships were not involved in the conflict, Roger issued receipts for all property seized, which the captains could redeem after the end of hostilities if they could prove their non-belligerent status. But for the present moment, Roger viewed all ships as valid targets, and his campaign began to accumulate wealth at a rapid pace. H added the ships he captures to his fleet, and used the captured booty to hire soldiers to man them, and as his fleet grew, his targets became more ambitious.
Educated perhaps by his sad fate with the Templars, Roger now went out of his way to share his bounty, using the money to pay the wages of the mercenaries stationed all over the island, and the provisions seized to resupply besieged fortresses. When the French army finally landed and besieged Messina, a fortress dominating the strait between Italy and the island, Roger loaded his ships, which at this point basically constituted the entire Sicilian navy, with grain and moved to break the blockade and resupply the garrison. The strait of Messina, known for its violent storms, immortalized by Homer as Scylla and Charibdys, had been the graveyard of many a fleet from the earliest days of human navigation in the Mediterranean. Waiting for a powerful storm to confine the blockading squadrons to their ports, Roger’s fleet, with Roger personally captaining the lead vessel, sailed through the storm in the dead of night to enter the port of Messina without losing a single ship. The siege was broken and the tide of war turned. At least that is how Roger told the story a few years later to his friend, the chronicler Ramon Muntamer whose history is the source for most of what we know abut Roger’s career.
In recognition of his services, Roger was quickly appointed vice admiral of the Sicilian navy. Moreover, by paying the mercenaries personally, and selling the provisions he brought in at below market rates (a pirate cannot be expected to simply give away valuable commodities, even to people fighting formally on his side), Roger began to win the loyalty and affection of the polyglot international army fighting against the Angevin assault. His reputation for success and profitable undertakings drew men to him, while his wealth allowed him to maintain a growing personal retinue within the larger Sicilian army, in addition to his personal naval squadron.
In 1302, the Angevins were forces to concede that they could not hope to regain the island of Sicily against the stubborn opposition of its population and the veteran Catalan soldiers, who remained loyal to Prince Frederique, in part due to Roger’s efforts. Frederique was recognized as ruler of the island of Sicily, with the title King of Trinacria, while his Angevin competitor Charles gained control over all of Southern Italy and retaining the formal title King of Sicily. The outbreak of peace left the thousands of mercenaries on the island in a precarious position. King Frederique lacked the money to pay them the wages owed, and the cessation of hostilities meant that there would be no chance to recoup their losses by plundering captured territories or ransoming prisoners. Unable to maintain themselves in Sicily, the Catalans who made up the bulk of the army were also reluctant to return to Aragon, since they had technically spent the last few years fighting against their rightful lord, the Kong of Aragon. Roger was in an even worse situation, his native city of Brindisi lay within the territories of the Angevins whom he had fought for the past several years, and he also feared that as King Frederique became reconciled to the Pope and eager to regain the Papacy’s favor, the Master of the Templars through the Pope might request that Roger be extradited to face justice.
The captains of the various armed bands comprising the Sicilian army now approached Roger with the suggestion that he use his personal navy and amassed wealth to transport their forces somewhere where their talents were in demand and might prove lucrative, and offered him command of such an expedition. Roger jumped at the proposal – he had the perfect client in mind. But before we talk about the client, we must first discuss the product being offered, the Catalan Grand Company. The hard core of veterans was the Catalans, who gave the Company its distinctive character. They numbered as many as ten thousand men, though not all could be expected to join the company. The eventual number of fighting men would be more than doubled by the various camp followers which could be expected to follow the fighters. Over the decades of war in Italy, the soldiers had acquired wives, children and mistresses who could not be left behind.
The fighters included heavily armored knights, the cream of medieval society, including a few high born Aragonese noblemen who would maintain their own personal armies within the larger body. The knights fought in combination with many sorts of support troops, from mounted sergeants, expert cavalrymen who were not of the knightly rank, to squires, pages and crossbowmen. But the main strength of the army was the Almogavers, ferocious lightly armed troops who fought primarily as infantry.
The nature of the Almogavers is still in dispute, with some historians considering them to be a general term for light Spanish infantry of the age, while others believe it refers to hardscrabble northern Spanish mountain tribesmen who fought in a particular manner and supplemented their tribes’ income by taking service as mercenaries. Since nearly all references to Catalan infantry in the sources of the age refer to them as Almogavers, it seems to this author unlikely that the bulk of the infantry was composed of only particular tribes, and appears much more likely that the reference is to a particular type of equipment and fighting style, which might have at one time been associated with a particular group, but had since become generally practiced by the soldiers of the region. The best argument against this theory was made by the 17th century historian Moncado, who reasoned that they must have been tribesmen, for what other person would voluntarily choose this sort of life?
The Almogavers wore little or no armor, relying on the speed and ferocity of their onslaught to provide them protection. They were armed with several javelins and a short sword, equipment which resembled quite closely that of the early Roman legionnaires. It is possible that both the Roman legion and the Almogaver descended from the same prototypical early European warrior. While their lack of armor and light weaponry seemed to place them at a distinct disadvantage in fighting heavily armored opponents, the Almogaver technique was adapted precisely to oppose the armored knights who then dominated European warfare. Before the battle, the Almogavers pounded their javelins on the ground and shouted "Desperta Ferro!" – "Irons, awake!," to focus their weapons on the task ahead. Then they would typically charge in one mass toward the standards of their enemies, hoping to destroy the command centers and disorder the enemy ranks. As they closed with the enemy they threw their javelins, which they would retrieve as they advanced, and in this they were remarkably and consistently successful against overwhelmingly superior enemy numbers. Although their javelins could not be expected to pierce the armor of a knight, the horses proved easy prey. Once a knight was unhorsed, his armor became more a hindrance than an aid in fighting a light and nimble opponent who darted in and out, using speed and agility to attack the weak spots in the armor with the short sword. Though they preferred fighting as infantry, when mobility was required, they fought in mounted formations, as jinetes, light cavalry which discharged its javelins to disorder the enemy ranks and then retreated before their heavily armored opponents could counterattack.
To a veteran Almogaver, a confrontation with a knight was more of a coveted opportunity to capture a lucrative target for ransom than a danger to be feared. This confidence, and the greed for potential ransoms fueled the ferocity of their onslaught, they pounced on the cream of European chivalry like hunters upon a fox, which obviously unsettled their opponents. A similar technique to turn the disparity in equipment and wealth into an advantage was employed a century later by lightly armored English bowmen in their victories over the French knighthood during the battles of the Hundred Years’ War. Both the Spanish and the English innovations gave lightly and cheaply armored commoners an advantage over heavily and expensively armed elites, and spawned the rise of successful free companies. Finally given the tools to defeat the ruling classes in battle, soldiers from the lower strata of society used their power to seize some of the wealth accumulated by these ruling classes. They learned to prey on their former rulers, pillaging their lands and taking the knights themselves prisoner for hefty ransom. The defeat, capture and ransoming of the fearsome elites became a habitual moneymaker for many men, who were expected under the medieval caste system to live in awe of their betters.
Led by outcasts, criminals, and status-less but ambitious adventurers such as Roger de Flor, the Free Companies formed by such men became the bane of Europe’s nobility, inflicting humiliating losses on the crème of medieval chivalry and overrunning region after region. Faced with this new reality, the knightly class quickly found itself eclipsed as Europe’s dominant military power by infantry formations composed their social inferiors. At the end of the Hundred Years’ War, the French Kings, who were unable to eradicate them by force, hired the remaining Free Companies to form the nucleus of a new French professional national army, which replaced the knights and nobles as the source of French military might. In time, all European warfare became dominated by the Swiss peasant pikemn, the landsknechts, drawn from the dregs of German society, the Spanish tercios which fought very much in the Roman legionnaire/Almogaver style, with the formerly elite cavalry being relegated into irrelevance.
In the next installment, we will find out where Roger took his newly formed company and how they fared.