The Swashbuckling Tudor Mercenary Who Was Killed in a Battle That Claimed the Lives of Three 16th-Century Kings

Englishman Thomas Stukeley offered his services to various Catholic powers. He died while fighting for the Portuguese at the Battle of Alcácer Quibir on August 4, 1578.

The Loukkos River is wide and meandering, flowing from the foothills of Morocco’s Rif Mountains and emptying into the Atlantic Ocean near the present-day city of Larache. Its broad valley makes for a serene countryside, with bands of golden wheat punctuated by gray-green olive groves.

Few visitors realize that this spot was the site of one of the great battles in early modern history: the Battle of Alcácer Quibir, or the Battle of Three Kings, so named because three of the kings involved died on the day of the clash. The trio’s deaths on August 4, 1578, had powerful ripple effects across the early modern world and especially in the western Mediterranean corridor, where Morocco wanted to push the Portuguese and the Spanish out of their enclaves on the North African coast.

Since the early 15th century, Portugal had occupied Moroccan cities on the Atlantic and Mediterranean coasts, erecting fortresses and using the urban centers as trade depots. In 1497, Spain followed in Portugal’s footsteps, taking the city of Melilla, one of two enclaves on the Moroccan coast that the Spanish still hold to this day. The Ottomans had designs on Morocco, too, attempting various military expeditions and backing a variety of claimants to the kingdom’s throne.

Morocco’s leaders in the late 16th century, the Saadi dynasty, made their reputation through jihad, expelling Christian powers from Moroccan territory. The Saadis were on the edge of Europe, but they were very much aware of the power dynamics between the Islamic Ottoman Empire, the continent’s Catholic states and even Protestant England; they hoped to leverage their relationships with these power players to maintain Moroccan independence.

The Battle of Three Kings brought these tensions to a head, shifting the balance of power in Europe and North Africa. It also spelled the end of Thomas Stukeley (sometimes spelled Stucley or Stukley), one of the notorious rogues and mercenaries of the 16th century. A kind of Quixotic Forrest Gump of the early modern era, Stukeley fought for just about everyone in Europe over the course of his military career, joining up with major and minor Catholic states for their imperial and dynastic wars. He helped and manipulated kings and queens, staged naval parades on the Thames, raised an army to invade Ireland, and plotted an invasion of Florida. He was even rumored to be an illegitimate son of England’s Henry VIII, though this claim is extremely tenuous. But he is best known for his role in two of the biggest battles of the 16th century: the 1571 Battle of Lepanto and the Battle of Three Kings.

Stukeley was born in Devon, England, to minor gentry and made a name for himself in the service of two leading figures at Tudor court, the English dukes Charles Brandon and Edward Seymour. But his swashbuckling career only began in earnest in 1563, when Henry’s younger daughter, Elizabeth I, put Stukeley in charge of an expedition to establish a colony in Florida. That year, he set off with half a dozen ships and made it as far as the Bay of Biscay on the northern coast of Spain—in other words, not far at all—where he proceeded to turn his efforts to piracy. Stukeley blew all the resources given to him by the crown before even hazarding a trip across the Atlantic.

Out of favor upon his return, Stukeley eventually ended up in Spain, where he referred to himself without basis as the “Duke of Ireland.” In 1570 and 1571, he maneuvered around the Spanish court, lobbying Philip II for an army to invade Ireland and liberate it from heretical English rule (though, of course, he hadn’t objected so strongly to England’s queen when he was in her good graces). Elizabeth, like her younger brother, Edward VI, had embraced Protestantism, overturning the reforms of her Catholic sister and predecessor, Mary I, and angering those who, like Stukeley, still clung to the old religious traditions.

Philip had previously been married to Mary, but their union yielded no children, leaving the English throne open to Elizabeth upon her sister’s death in 1558. The Spanish king had courted Elizabeth after her ascension, but the proposed match failed, and the two had a volatile relationship thereafter. Philip recognized that Stukeley might be an asset in his power struggle against England, but he still kept the Englishman at arm’s length. Stukeley could talk a big game, but he could not be trusted with execution.

The Privy Council, Elizabeth’s royal advisory committee, once questioned “how this man, who had no penny, land or livelihood of himself, nor of any credit, could by fleeing into Spain be so esteemed there.” Indeed, Elizabeth was furious at the generous reception her subject had received in Spain. Her protests eventually convinced Philip to order Stukeley’s departure. Once again, he was on his way, this time to Rome, where he arrived by 1575.

Although Stukeley spent much of his time in Rome courting favor with church officials, “ambition and not religion guided his steps,” writes historian Juan E. Tazón in The Life and Times of Thomas Stukeley. He might have advanced the interests of Catholic powers, but he was happy to leave one for another and avoided situations where he did not stand to gain personally. In 1571, when Pope Pius V formed a Christian alliance known as the Holy League to combat Ottoman expansion in the Mediterranean, Stukeley reportedly jumped at the chance to join the naval expedition.

The October 7, 1571, Battle of Lepanto became one of the great epic military engagements of all time, pitting Spain, the Vatican and the Republic of Venice against the Ottoman Empire. “A lot of its importance came down to this idea of cross versus crescent,” the symbols of Christianity and Islam, says Emrah Safa Gürkan, a Turkish historian and the host of the popular “Historik” YouTube show about Turkish culture. “Any time in history,” he continues, “there’s always you and the ‘other,’ someone you’re afraid of, someone you can destroy. This kind of clash is always fashionable, especially to people in the 16th century.”

Lepanto also marked the last major battle in the Western world fought between galleys—ships rowed by huge teams of rowers. Popular lore suggests Stukeley commanded three galleys himself, but Tazón casts doubts on this claim, and perhaps even on the Englishman’s participation in the battle. Contemporary observers thought the Holy League’s victory would curb the Ottomans’ naval strength in the Mediterranean. In reality, the Ottomans quickly rebuilt their fleet and re-established control of the eastern half of the sea. “The story of the battle was always bigger than its strategic outcomes,” Gürkan says.

Stukeley undoubtedly did not know at the time that the Ottoman side included two men whose fates would intertwine with his own. Abd al-Malik and Ahmad al-Mansur of the Saadi dynasty had been forced to flee Morocco in 1557, when their older brother took the throne and sought to eliminate his rivals. They ended up in Algiers (then a province of the Ottoman Empire but now the capital of Algeria) and eventually joined the military.

Abd al-Malik was captured during the Battle of Lepanto and imprisoned by the Spanish, who hoped to use him for their own political purposes. But he escaped and fled back to the Ottoman Empire, where he gradually built support for an invasion of Morocco. In 1576, Abd al-Malik and Ahmad led Ottoman forces back into Morocco, where they took the city of Fez; deposed their nephew Abu Abdallah Muhammad II, who had succeeded their older brother as sultan in 1574; and installed Abd al-Malik on the throne.

Meanwhile, after Lepanto, Stukeley picked back up his mission to raise an army to invade Ireland and free it from English (and non-Catholic) rule. Philip of Spain wasn’t interested, but the new pope, Gregory XIII, agreed to provide men, money and ships, and Stukeley was once again on his way.

Keeping with form, Stukeley aborted the mission by the time he reached Portugal in the spring of 1578. His ship was in bad disrepair, and his men—almost all of them Italian—seem to have resented him and fought constantly among each other. While docked in Lisbon, Stukeley’s contemporaries guessed at his next move. As the 16th-century playwright George Peele later wrote of this moment, “St. George for England! and Ireland now adieu / For here Tom Stukeley shapes his course anew.”

The only real certainty was that Stukeley would “procure for himself the means of living more handsomely in accordance with his character, which is that of a great spendthrift, than to do other sort of service to Christendom,” according to a contemporary. That’s when Sebastian, the 24-year-old king of Portugal, came calling. Abdallah Muhammad, the ousted sultan of Morocco, had taken refuge in Portugal; Sebastian wanted to invade Morocco and install a friendlier ruler than Abd al-Malik in power. Here was another chance for glory, and Stukeley snatched it.

Hundreds of Portuguese ships sailed out of the Tagus River in June 1578, bound for the North African coast. Sebastian’s uncle, the Spanish king Philip, had agreed to support only a limited coastal attack; the pope, meanwhile, tried to convince Sebastian not to attack at all. As Tazón writes, this was a “medieval crusade that was completely outmoded,” and a badly organized one at that. Sebastian and Abdallah Muhammad eventually disembarked at Asilah, on the northwest tip of Morocco, with some 16,000 troops, including many members of the Portuguese nobility, as well as thousands of assorted priests, servants, sex workers, entertainers and spouses. Abd al-Malik waited patiently with his forces, which were superior to Sebastian’s in number, just outside the town of Ksar el-Kebir (sometimes known in Spanish as Alcácer Quibir), in northern Morocco.

The fighting was bloody and brief. Near a bend in the Loukkos River, Moroccan forces, supported by thousands of Ottoman janissaries and armed with ammunition supplied by the English, demolished the beleaguered invaders. Abd al-Malik died either just before or during the battle, falling victim to poisoning, tainted water or some pre-existing illness, so his younger brother Ahmad was proclaimed sultan on the spot. Sebastian and Abdallah Muhammad were both killed during combat—hence the moniker the Battle of Three Kings. Moroccan forces recovered Abdallah Muhammad’s body, which they flayed, stuffed with straw and displayed around Morocco as a warning sign. Moroccan historians of the period referred to the former sultan simply as “al-Maslukh,” or “the flayed one.”

Stukeley died in the fighting, too. One theory posits that his own men killed him after he was wounded in battle; such was their dislike. Another, more conventional, explanation is that he was taken out early in the fighting. The cruel irony of Stukeley’s death is that he spent much of his life trying to get back at the English, and it was likely an English cannonball that killed him. For all Stukeley’s successes as a high-profile con man, the other irony is that he was duped by Sebastian’s recklessness.

Stukeley’s mischievous wanderings pointed to bigger connections between Europe and Africa. “Lepanto was an important battle because of the size and scope,” Gürkan explains, “but if we’re talking about strategic outcomes, Three Kings was far greater.”

The death of Sebastian—along with key members of the Portuguese nobility—eventually led to a succession crisis, as the king was only 24 years old and had no children. Philip took advantage and invaded Portugal in 1580, adding it to the Spanish Empire.

In Morocco, Ahmad emerged from the battle as a hero, thereafter going by “al-Mansur” (“the victorious”). He was innovative in charting a middle path between the rival power blocs and even expanded Morocco’s borders deep into the Sahara. “The battle offers Ahmad al-Mansur a critical lesson in statecraft,” says Samia Errazzouki, a historian at Stanford University. “In order to maintain Moroccan sovereignty, [he had] to navigate the testy waters of diplomatic rivalries.”

The Battle of Three Kings actually brought Morocco and England closer together. As Errazzouki describes it, “For Catholic Europe, it was a stinging defeat.” In 1588, Philip’s mighty Spanish Armada attempted to invade England, only to suffer an even more catastrophic loss. In the aftermath of Spain’s defeat, Ahmad struck up a long correspondence with England’s queen as he tried to situate Morocco as an emerging imperial power in the Atlantic world, too.

Despite Stukeley’s reputation as a charlatan and traitor in Elizabeth’s court, his legacy lived on in the popular imagination in England, where several successful plays and broadsides boosted the memory of “brave Stukeley” as evidence, however historically inaccurate, of an Englishman rising above his station and finding success and fortune abroad.