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In 1578, English adventurer Thomas Stukeley found himself embroiled in a Moroccan military intrigue with royal overtones and lethal results

By midafternoon on Aug. 4, 1578, three monarchs lay dead on a battlefield near the Moroccan town of Ksar el-Kebir. Two of the royals were Muslim, the third Christian, and the consequences of their deaths would resonate throughout Europe and North Africa for decades. At the heart of the regicidal misadventure was a theretofore irksome English opportunist who left his own legacy.

Best known in the English-speaking world as the Battle of Alcazar, the fight at Ksar el-Kebir is for obvious reasons also referred to as the Battle of the Three Kings.

Sebastian I. (Museu Nacional De Arte Antiga, Lisbon, Bridgeman Images)

The Christian monarch, Portugal’s King Sebastian I, was supporting deposed Moroccan Sultan Moulay Mohammed (Abu Abdallah Mohammed II), who had been ousted by his uncle, Abdelmalek (Abu Marwan Abd al-Malik). A son of Mohammed ash-Sheikh, founder of Morocco’s Saadi dynasty, Abdelmalek himself had fled to the Ottoman empire with his younger brothers in 1557 when their eldest brother, Abdallah al-Ghalib, became sultan and sought to eliminate them. Though Abdelmalek was the legitimate successor, on Abdallah al-Ghalib’s 1574 death from asthma his son Moulay Mohammed claimed the throne. The tribal country erupted in civil war. Supported by an Ottoman army, Abdelmalek invaded in 1576, forcing Moulay Mohammed to flee the capital, Marrakesh, and wage a guerrilla war against his uncle. It was then the sultan in exile sought Sebastian’s help in restoring him to the throne.

The Portuguese king, a dashing and childless 24-year-old with visions of a Moroccan crusade and outmoded ideals of chivalric kingship and feudal warfare, resolved to help Moulay Mohammed by raising an army and invading the Barbary realm. Especially eager to restore his nation’s fading martial glory, Sebastian chose to lead the expedition personally, despite having no prior combat or command experience.

Among those who chose to accompany the young king to North Africa was an English soldier of fortune named Thomas Stukeley (born circa 1520). Rumored to be a bastard son of King Henry VIII, Stukeley had been involved in all sorts of foreign escapades both for and against the Crown since the 1547–53 reign of Edward VI. Though engaged as a spy, pirate, mercenary, counterfeiter and all-round scoundrel since the early 1550s, he had always managed to escape any serious consequences for his shenanigans, while his confederates often met with execution. Stukeley’s repeated escapes from harm led many to suspect he may have had a claim on the English throne—a belief he fostered.

With the accession of Queen Elizabeth I in 1558, Stukeley continued to be a thorn in the side of the Crown, and in 1570 the reckless adventurer fled England for the Continent. There he became implicated in various schemes for Spanish-led invasions of England and Ireland, working with Spanish King Philip II and Popes Pius V and Gregory XIII. With the latter’s financial and materiel help, Stukeley set sail from Italy on Feb. 2, 1578, on a ship laden with arms, ammunition, supplies and provisions enough for 3,000 men. Also aboard were 600 Italian mercenaries. They were to join waiting Irish rebels in Spain for the long-planned invasion of Ireland. Fate put that plan on hold, however.

The ship was in very poor repair, taking more than two months to cover a distance that should have taken two weeks, and the provisions aboard were not enough for 600, let alone 3,000. By the time Stukeley’s ship anchored off Cadiz in mid-April, the Italians were on the verge of mutiny. While in port a messenger from shore brought a welcome missive to the beleaguered commander. In the letter Philip proposed Stukeley continue to Lisbon and join his forces with those Sebastian was gathering for the invasion of Morocco. The Englishman jumped at the chance—the pope, pardon the expression, be damned.

Stukeley’s snap decision to veer from the “divine” purpose of restoring Ireland to the Catholic fold rankled Gregory. When providing men and materiel for the invasion, the pope had instructed Stukeley to “do all the mischief that they may to that wicked woman”—a reference to the heretical Queen Elizabeth. Yet by summer Sebastian’s noble crusade had received Gregory’s blessing, both the papal nuncio and legate joining the royal train. And while Philip had remained on the sidelines when pressed by Gregory to help fund the invasion of Ireland, the Spanish king supported the Moroccan adventure, albeit with some trepidation over its trade implications, not to mention his nephew Sebastian’s rash nature.

Waving aside his uncle’s fears and committing his vast treasury to the campaign, Sebastian cobbled together a 17,000-man invasion force comprising some 9,000 raw peasant levies, 1,500 Aventuros (Portuguese noble volunteers who paid their own way), 1,000 cavalrymen (recruited from the noble ranks), 5,500 foreign mercenaries (Germans, Walloons, Spaniards and Stukeley’s Italians) and an artillery component. Such a multinational force inherently lacked cohesion. Stukeley’s Italians, resentful at having been “hijacked” under a foreign prince and forced by necessity to forage for provisions, proved especially unruly. While available firearms included three dozen cannons and some 7,000 muskets, most of the conscripts were armed with pikes, an outmoded weapon for use in formation that required significant training. But the Portuguese king was in a hurry. To his credit Sebastian held old-fashioned knightly ideals of leading from the front and exceeding his men in valor. But his lack of experience and headstrong refusal to accept advice would lead to disaster.

De Agostini (Getty Images)


The 500-ship invasion fleet sailed from the Tagus River off Lisbon on June 24 and landed at Asilah, on Morocco’s Atlantic coast, on July 14. The amateur nature of the Portuguese force was apparent from the start. Despite being in hostile territory, they erected no defensive perimeter, instead bivouacking in the open. Drills were sporadic to nonexistent. Furthermore, no one seemed to know his role, thus the men were prone to panic at the slightest disturbance.

The arrival of the invasion force prompted Abdelmalek to negotiate—a generous tract of coastal land in exchange for peace—but the king rebuffed the proposal. Feeling his oats, Sebastian then abandoned plans to march down the coast with the fleet in support. Convening a war council on June 23, he announced his intention to instead to strike inland for a rapid and decisive victory. Heedless of the dangers—e.g., abandoning the fleet, supply problems, inhospitable terrain—Sebastian refused to hear any advice from subordinates. Regardless, Stukeley and two other combat-experienced officers confronted the king, advising him to forgo any such hasty march against an unknown enemy force. Sebastian shut them down using “injurious terms.”

The army left camp on July 29 accompanied by thousands of camp followers—clerics, pages, prostitutes, musicians, servants, slaves and serving women, even wives and children—said to number as many as the fighting men. Some 1,100 wagons carried the nobles’ baggage, which included such “essentials” as ceremonial vestments, pavilions, sumptuous furniture and silver place settings and platters. Such processions had been commonplace on campaign in prior centuries, but war had become a far more serious and professional business by the 1570s. Despite their extensive baggage train, the Portuguese marched out short of water and food from the outset. En route to meet the enemy south at Ksar el-Kebir, they were shadowed by Moroccan light cavalry. It took Sebastian’s motley band six days to march those 33 miles. Abdelmalek knew where the invaders were the entire time.

During a war council on the night of August 3 Moulay Mohammed—who had added another 6,000 men to Sebastian’s army—advised the Portuguese king to delay his attack until late the following day, as spies had informed him Abdelmalek was seriously ill (perhaps poisoned) and might not live out the day. Were he to die, the enemy would be thrown into confusion, increasing the odds of a successful outcome. Stukeley seconded Moulay Mohammed’s advice but was again silenced by the king, who all but accused the Englishman of cowardice. Again Sebastian refused all counsel and ordered the attack to commence at first light. He selected the route of the Portuguese advance solely because it offered the opportunity for “beautiful cavalry charges and high feats of arms.” In a final folly he chose to attach his baggage train to the army in a large open square formation. By doing so, the king would squander many of his pikemen to protect little more than gilded carriages and silver baubles.

Stukeley and his Italians, along with the Spanish, would comprise the left wing of the infantry, the Germans and Walloons the right, with the peasant levies massed behind both wings. Likely out of mistrust, Stukeley split the Italians into small detachments sandwiched between Spanish contingents. The cavalry, led by Sebastian on the left and his Portuguese officers on the right, backed by Moulay Mohammed’s horsemen, protected the flanks of the square. Bringing up the rear were the musketeers.

Opposing Sebastian’s 23,000 march-weary troops were upward of 60,000 men in three long ranks under Abdelmalek, who had also deployed his cavalry on the wings. He, too, fielded cannons, and his arquebusiers outnumbered Sebastian’s musketeers.

As Sebastian wished, the Battle of Alcazar began at first light on August 4. It lasted just six hours and was a fiasco for the Portuguese almost from start to finish.

After drawing up in their respective formations and exchanging battle cries and largely ineffectual artillery and musketry volleys, the opposing infantry lines marched out and were soon engaged in savage hand-to-hand combat. With Sebastian leading from the front, the Portuguese cavalry charged into the enemy lines, opening large gaps, but they lacked the resources and reserves to exploit their gains. As Moorish reserves came forward to fill the gaps, Abdelmalek’s cavalry—outnumbering Sebastian’s by perhaps 10-to-1—chased the Portuguese riders back to their lines and soon decimated them. Numbers told the tale from then on, as the Muslims enveloped Sebastian’s square and cut down his army. Portuguese losses were estimated at more than 8,000 dead and 15,000 captured—all destined for slavery or ransom. Survivors who made it back to the fleet at Asilah numbered in the dozens. Moorish losses numbered some 4,000 dead. Among the heaped corpses lay those of the childless King Sebastian (who had fought courageously per his chivalric precepts and fallen late in the action), the ousted Sultan Moulay Mohammed (said to have drowned while attempting to flee across a river), the usurper Sultan Abdelmalek (who was indeed gravely ill and did not live out the day) and the adventurer Stukeley.

Two traditions circulate regarding the latter’s death. One suggests he was killed early in the fighting when a Moroccan cannonball carried off his legs. The other claims he was murdered by his own Italians once it was clear defeat was imminent. The latter tradition was given life in two popular plays—English dramatist George Peele’s The Battle of Alcazar (published circa 1594) and the anonymous The Famous History of the Life and Death of Captain Thomas Stukeley (published circa 1600).

At first glance Stukeley’s death bears little significance. After all, the battle had claimed three monarchs, along with 40 dukes and earls (according to Richard Johnson’s 1612 ballad “The Life and Death of the Famous Thomas Stukeley”). Perhaps the greatest consequence was that the Portuguese throne, left without an heir, fell to Philip II of Spain within two years, and Portugal remained a puppet of the Hapsburg kings until 1640. In addition, as Sebastian had emptied the Portuguese coffers for his campaign, he’d left the country “naked of nobility, without heirs,” as one contemporary historian put it. It was Stukeley’s presence and death at Alcazar, however, that had lasting resonance in England, its implications no less complex than European court politics of the era.

In the context of the broader Moroccan saga Stukeley’s diversion to the invasion by Sebastian via Philip appears a rather unsurprising side note, one wholly in keeping with Stukeley’s expedient habit of shifting loyalties whenever it suited his own purposes. Yet his role in what marked his final adventure had greater underlying significance.

In her history Speaking of the Moor Rutgers University English professor Emily C. Bartels writes of the importance of trade with Morocco, notably in sugar but also saltpeter, an essential ingredient in gunpowder. In 1577 a trade mission from England had secured just that commodity from Abdelmalek. English merchants, agents and other representatives were present in Morocco at the time of the Battle of Alcazar, and Stukeley’s presence could only have undermined the Crown’s interests and activities. Concerned Italian and Portuguese merchants cataloged Stukeley’s actions, reporting back to William Cecil, Baron Burghley, Queen Elizabeth’s spymaster. Cecil and Stukeley had encountered each other early in the latter’s career, and Stukeley seems to have bested Cecil on that occasion—a slight the spymaster never forgot.

A romanticized 18th-century image depicts Sebastian’s imminent death at Alcazar. (Chronicle, Alamy Stock Photo)


In trading arms and ammunition with Morocco in exchange for sugar and saltpeter, Elizabeth sought to undermine Spain, ruled by her hated Catholic onetime brother-in-law, Philip. The Protestant queen, whom Pius V had declared “the pretended Queen of England and the servant of crime” when excommunicating her in 1570, openly ignored the papal ban on providing weapons to the “infidel.” Indeed, she had opened trade negotiations with both Moulay Mohammed and Abdelmalek, and in the wake of Alcazar she resumed negotiations with Ahmad al-Mansur, Abdelmalek’s brother and sultan of the Saadi dynasty until his death in 1603. The negotiations were shrouded in secrecy, extant state papers only alluding to them. Contact between the two countries wavered in the immediate aftermath of Alcazar, but by the time Peele’s play went into production, al-Mansur had sent ambassadors to England to cement an economic and political alliance.

Stukeley’s interference in Morocco, therefore, posed a diplomatic problem for England, jeopardizing a delicate, budding trade relationship. Recall that Pope Gregory had instructed the adventurer to “do mischief” to Elizabeth, and perhaps he was doing just that. The ongoing importance of the Anglo-Moroccan trade alliance may go some way to explain why Stukeley remained a featured figure in English drama into the 17th century. Though portraying him in largely heroic terms, the works also reminded contemporary audiences of Stukeley’s reckless nature and his vulnerability to manipulation through flattery.

Take, for example, Philip II, who cajoled Stukeley into joining Sebastian, thus using the English adventurer as a pawn in the Spanish king’s own plan to lash out at Elizabeth. It is a recurring theme throughout Stukeley’s career. Believing himself to be an integral cog at the highest levels of European government, he was in fact little more than a useful if dispensable tool, wielded by monarchs and their ministers in whatever schemes they had going at the moment. Though most visibly in the employ of the English and Spanish crowns, he’d also been engaged by two popes, Sebastian of Portugal, King Henry II of France, Holy Roman Emperor Charles V, Mary of Hungary, John of Austria and Emmanuel Philibert, Duke of Savoy. While he had entwined himself firmly in the Catholic cause in later life—a commitment he went to great lengths to prove—he’d apparently had no qualms about being a Protestant partisan earlier in his career. Stukeley was the epitome of the ambitious, upwardly mobile, pragmatic adventurer.

The Battle of Alcazar lays bare the intricacies of Christian European intervention in Muslim politics in the 16th century, as well as the importance of Barbary trade with regard to power struggles on the Continent. Its military outcome highlights the folly of rejecting advice from one’s more experienced peers. Finally, as the dramatists of old realized, the underlying story of Thomas Stukeley offers a remarkable, entertaining and cautionary glimpse into the life (and death) of a mercenary captain, adventurer and schemer of the first order.

New Zealander Murray Dahm is an Australia-based historian specializing in ancient and medieval topics. For further reading he recommends Roads to Ruin: The War for Morocco in the 16th Century, by Comer Plummer III, and Speaking of the Moor, by Emily C. Bartels.