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Prince Henry the Navigator (d. 1460) is one of those Portuguese guys you spend a few minutes on in high school history class in the rush to get to Columbus. Which is unfortunate, because he’s an important figure. The explorations Henry sponsored were the first Portuguese voyages along the Atlantic coast of Africa, and later explorers like Bartolomeu Dias and Vasco da Gama built on the progress those trips made, eventually getting all the way around Africa and on to India. Henry can thus be considered the father, or one of the fathers, of the Age of Discovery.
Prince Henry (Wikimedia Commons)
Frankly, it’s lucky for Henry that he’s known for his contributions to European exploration, because he also had a considerably less successful career as a soldier. It started off promisingly enough—he was an active participant (wounded in battle, in fact) in Portugal’s 1415 conquest of the North African city of Ceuta (which belongs to Spain today, but that’s another story). But his escapades in the 1437 Battle of Tangier were disastrous enough to really be a legacy-killer for most people.
It was Portuguese dissatisfaction with their conquest of Ceuta that led to Henry’s attempt to capture Tangier. King John I of Portugal (d. 1433) had desired Ceuta because it was the main terminus of the north-south Trans-Saharan trade route, which meant that Ceuta was constantly receiving gold from Mali and other points south. John wanted very badly to tax that gold, and he also believed that having a big North African port would give him a leg up in comparison with the other Iberian kingdoms, Castile and Aragon. However, things didn’t quite work out the way John had hoped. Given the choice between continuing to bring their caravans into Ceuta, thereby enriching the Portuguese, and simply shifting the trade route a short distance west to Tangier, the Marinid Empire—which at the time ruled Morocco—opted for Tangier. So Ceuta quickly became a big fat albatross for the Portuguese crown.
This map should help orient you
John delegated responsibility for Ceuta to one of his sons, Henry. Resisting a growing chorus in the Portuguese court to simply abandon Ceuta, Henry convinced the king to let him lead an army against Tangier and thereby put Portugal in control of both of the port cities. Then John died and was succeeded by one of Henry’s brothers, Edward (d. 1438), who wasn’t so keen on the idea. But Henry persisted and managed to convince their younger brother, Ferdinand, and Edward’s wife, Eleanor of Aragon, to support him. Henry even agreed to adopt Edward’s younger son, Infante Ferdinand, and name him his heir (relieving Edward of the burden of providing for him) to get Edward on board.
In Henry’s defense, this wasn’t a bad time for another attack on the Marinids. Sultan Abd al-Haqq II (d. 1465) was just entering his mid-teens (he’d inherited the throne at the age of one in 1420) and tensions were rising between him and his regent/vizier, Abu Zakariya Yahya al-Wattasi (d. 1448). Henry argued that the internal discord would prevent the Marinids from organizing a defense and allow a smaller Portuguese army to take Tangier was well as a few other towns in the area. He further reasoned that he could get Pope Eugenius IV (d. 1447) to declare the expedition a Crusade, which offered the promise of soldiers from all over Europe signing on and bolstering Portuguese manpower.
Eugenius did declare the expedition a Crusade, but thanks in part to a diplomatic dispute with Castile that almost escalated into war, very few foreigners showed up to participate. Henry set sail with somewhere around 7000-8000 men, tops, which was barely as large as the Tangier garrison, who had the benefit of being behind their defensive walls. Worse, Wattasi made a grand appeal for national unity in the face of the invasion that by this point the Marinids all knew was coming, and it succeeded. So that whole bit about not being able to mount a defense went right out the window.
At this point you can probably see where we’re heading. An army of 7000 men might have been able to take Tangier and defeat whatever large relief army the Marinids were forming if, I don’t know, they’d suddenly invented helicopters or something, but that wasn’t in the cards. The cannons Henry’s army took to Tangier weren’t even powerful enough to break down the city’s walls. And he certainly didn’t have enough men to successfully assault those walls. Making things worse, as it turned out, Henry decided to fortify his siege camp against a relief army. What may have seemed like a solid defensive plan actually had the effect of anchoring the Portuguese army in place when the attack came, making it less likely that they would or could hightail it out of there—which is what they should have done.
Henry’s army—part sailing from Ceuta, part marching overland—besieged Tangier on September 13. His first attempt to take the city by assault, on September 20, failed in part because his siege ladders weren’t tall enough—which, dude, what the hell are you doing? On September 30, the first Marinid relief army showed up. We don’t know how large it was—the Portuguese claim it was 100,000 men strong, but as we’ll see they tended to exaggerate. Henry moved his army to meet this force, but it refused to engage. Instead, the Marinid army was hoping to distract Henry to allow the Tangier garrison to march out and attack the Portuguese camp, which it did, but the camp guards were able to hold them off and so Henry was able to keep his army in the field. By this time, the Portuguese had brought in a couple of larger guns and built a siege tower, so they decided to make another go at taking the city on October 5. They failed again.
Wattasi’s main relief force showed up on October 9. The Portuguese put the size of this army at upwards of 800,000 men, which is comically exaggerated to help explain the defeat they’re about to suffer. But it’s certainly true that Henry was now badly outnumbered, and between the two relief armies Wattasi may have had over 100,000 men at this point. Henry knew it, too, so he ordered a retreat to his ships. Wattasi decided to attack quickly so as not to allow him time to withdraw. The Marinid/Wattasid (we’ll get to that in a moment) army overwhelmed the Portuguese and besieged their camp.
Surrender talks began on October 12, and the terms were not good for the Portuguese. Henry not only agreed that Portugal would leave Tangier alone (along with the rest of Morocco) for at least 100 years, he also agreed to return Ceuta to the Marinids, and as insurance he was required to leave Prince Ferdinand, his (and Edward’s) brother, behind as a hostage. Henry fled to Ceuta and basically locked himself in his room and refused to see anybody. He dispatched some other poor schlub to break the news to Edward that he’d lost Tangier and Ceuta and their little brother.
When he finally snapped out of it, Henry wrote a letter to Edward advising him to abrogate the terms of the deal he’d signed and keep Ceuta. He argued that a minor skirmish his men had fought with the Marinids after signing the surrender deal amounted to a treaty violation and gave Portugal the right to tear the deal up. Just about every other noble in the Portuguese court was urging Edward to give Ceuta—which, remember, was actually costing Portugal money—to the Marinids and get Ferdinand back. Edward, inexplicably, agreed with Henry. In response, the Marinids moved Ferdinand from relatively posh accommodations as a royal hostage to a regular old jail, complete with regular torture sessions.
After Edward’s death in 1438, the regent for his son and heir, Alfonso V, tried to reopen talks with the Marinids to trade Ceuta for Prince Ferdinand. This is a whole other story, including a bit where the Portuguese fleet sent to negotiate the deal was raided by Genoese pirates, but the upshot is that the Marinids refused to let Ferdinand go until they had the city, and the Portuguese refused to surrender the city until they had Ferdinand. So they called the whole thing off. Ceuta, obviously, never went back to Morocco, and Ferdinand died in captivity in 1443. He’s called “the Holy Prince” now, basically because he died in Muslim custody.
As for the Marinids, their victory at Tangier actually helped usher in their demise. Since the victory really belonged to their vizier, Wattasi, it swung the balance of power in the empire toward him and his descendants, who eventually took power in their own right and ruled Morocco as the Wattasid dynasty from 1472 through 1554. Henry, desperate to find the source of the gold that kept coming north across the Sahara and thus bypass Tangier altogether, sponsored naval expeditions that made it all the way to modern Sierra Leone. Because of those, his embarrassing failure at Tangier barely warrants a footnote in his biography nowadays.