It is a tale of paranoia, revenge, of kings and divided loyalties, and one family’s quest for honor. No, it is not the Wars of the Roses nor Julius Caesar’s civil war in Rome. It is the story of Spain’s Guzman family, and their epic generational mission to dominate the narrow peninsula of Gibraltar, slightly less than 3 miles wide, known popularly as “The Rock.”

Cue up the “Game of Thrones” theme song and envision a giant boulder in the middle of the ocean.

The Ancestor Who Started It All

Gibraltar, the tip of the Iberian Peninsula known for its iconic rock formation that shoots up 1,398 feet into the air, had been a traffic stop for a motley assortment of Romans, Phoenicians, Visigoths, Byzantines and whoever else happened to be floating around the coast of Spain at any given time. The Almohad Caliphate constructed a large fortress upon it—which might have contributed to the Rock envy that gripped various neighboring powers for the next several centuries.

Gibraltar eventually fell into the hands of the Marinid Sultanate and was basking in scenic isolation when King Ferdinand IV of Castile decided he wanted to claim it as part of Spain’s Reconquista in 1309.

The man chosen for this task was Alonzo Perez de Guzman, the king’s loyal retainer, known as Guzman “the Good.” But Guzman had not earned the epithet of “the Good” for his congenial personality. In fact he was notoriously ruthless. A loyal buddy of the king, Guzman had previously (in)famously refused to negotiate the release of his own son from captivity by one of the king’s rivals—instead Guzman is reputed to have offered his own knife to be used for the execution. The boy was murdered, and his head was allegedly catapulted into the midst of Guzman’s men to their great distress. Guzman however remained emotionless and is said to have informed his wife about the whole thing later. She is reported to have been, justifiably, horrified. In any case, the king considered “Guzman the Good” an ideal henchman. Guzman also had another son, who would carry on his legacy for years to come.

Guzman "the Good" is known for volunteering his own dagger to be used to kill his son rather than attempt hostage negotiations. (University of Zaragoza)

Arriving at Gibraltar in June 1309, Guzman attacked the peninsula by land and sea and bombarded the place with catapults. The Muslim garrison surrendered by September, and Gibraltar became a feather in Spain’s cap.

But Guzman’s success was short-lived. Although by then an older man over 50, he was ever eager to be in the thick of slaughter and mayhem. He sallied forth to Algeciras, where the king’s forces successfully ousted a Muslim garrison. Apparently Guzman failed to notice that enemy troops had not been ousted from the surrounding countryside, which he decided to “tour” with his troops. The tour was short-lived—Muslim forces annihilated Guzman along with his encampment.

In a show of generosity, the king awarded governorship of Gibraltar to Guzman’s son, Juan Alonso Perez de Guzmán y Coronel, thereby tying the family to “the Rock” for which they would battle for years to come.

Guzman 2.0 and Even More Sieges

Unlike his famous father, Juan Alonso Perez de Guzmán y Coronel proved to be an absentee warrior. He appears not to have been present on Gibraltar when the Emirate of Granada, unhappy that the Rock had been unceremoniously snatched by the Spanish, tried to reclaim it in 1315 but failed during the peninsula’s second siege.

This was far from the end of the story. The Marinid Sultanate hadn’t given up on the Rock and made a grab for Gibraltar in 1333. This time they took it—much to the despair of Juan Alonso Perez de Guzmán y Coronel, who finally showed up at Gibraltar. He arrived too late for the third siege, just in time to see victory go to the opposing side.

The Spanish decided they weren’t just going to accept this new score, so they immediately mounted a rematch—the fourth siege, also in 1333. Guzman wanted to make good on his name this time…or at least as much as he was able to. He is described as vigorously helping make preparations for the great reconquest. What he actually did during the battle is unknown, since there don’t seem to be many, if any, historical sources describing him doing any fighting during the siege. However he was at least in attendance for it.

A Stalemate

The end result of the fourth siege was that both sides exhausted each other, ran out of food, and became so miserable that they drew up a truce agreement. The Spanish sailed away without taking the Rock and the sultan of Granada was assassinated by indignant followers who, despite the fact that they were technically victorious, didn’t approve of the truce being signed.

A fifth siege took place afterwards, which ended with a fizzle after King Alfonso XI of Castile died of the Plague in 1350. Guzman—again—seems to have failed to appear for that engagement.

Gibraltar was out of Spain’s hands. A sixth siege took place between two opposing Muslim factions when the Spanish weren’t looking, with the victors being the Nasrid kingdom of Granada.

Drowned On Arrival

Two generations later the Guzman family was at it again—specifically, Enrique Pérez de Guzmán y Castilla, who launched an adventure in 1436 to take the Rock for his family honor once and for all…and failed with a freak accident.

After temporarily abandoning their conquest of the Rock, the Guzmans had married into Spain’s royal family. Their fortunes and standing had improved. Enrique intended to imitate his famous ancestor, Guzman the Good, and seize Gibraltar for honor and glory in a feat of military might. He organized a campaign and rallied men to his cause. They were going to launch assaults from both land and sea. They were going to take the Rock.

A Dutch map shows the rocky landscape of the Gibraltar peninsula. (Rijksmuseum, Netherlands)

Things quickly went askew. Enrique failed to take the high tide into account. When D-Day arrived, Enrique and his men washed up on the wrong side of the Rock below the sheer cliffs. Landing boats flipped over and men were tossed overboard. Among them was Enrique.

Legend says he was trying to save his men when the accident happened. No one knows for sure. In any case his boat was overloaded with men from another boat who didn’t want to drown and thus inevitably sank, drowning their commander.

Thus Enrique Pérez de Guzmán y Castilla died before the seventh siege even began. We can only wonder what the Muslim garrison, looking down from the cliffs, must have thought as they watched the Spanish floundering in the water below.

In any case, the Muslim defenders recovered Enrique’s body from the surf, posthumously decapitated him and hung his body in a basket from the fortress walls, presumably as a warning to would-be besiegers.

A Son’s Revenge—Siege No. 8

Meanwhile, on another side of the Rock, Enrique’s son, who was supposed to be commanding the land forces, fell into despair at his father’s drowning. He pulled back his troops and is said to have tried to negotiate with the Muslim garrison to return his father’s body, but was rebuffed. The young man withdrew in anger and humiliation…but, in classic Guzman fashion, he would definitely return. His name was Juan Alonso de Guzmán y Suárez de Figueroa Orozco. He was determined to avenge the accidental death of his father.

Guzman came back to Gibraltar to roost 26 years later in 1462, resolved that the Rock would be his at last. He had spent years fuming about the failure to possess Gibraltar and his father’s ignominious demise. An informant brought news to Spain that the Muslim garrison at Gibraltar had been slacking off in terms of its defenses.

Forces led by Alonzo of Arcos were the first to get there, but couldn’t do the job without help and asked for aid from Spanish nobles. Guzman decided it was the right time to settle scores and jumped into the fray. The eighth siege was soon underway.

Rodrigo Ponce de Leon, Duke of Cadiz, got into a dispute with Juan Alonso de Guzman when it came to taking the surrender of Gibraltar after the eighth siege. (City Council of Seville)

However, if Guzman had inherited the iron pride of his ancestor Guzman the Good, he also seems to have been plagued by the curse of another ancestor—he arrived late. The siege was pretty well over and Rodrigo Ponce de Leon, Duke of Cadiz, was already in control of the city gates, ready to accept surrender, when the indignant Guzman finally arrived on the scene.

There was a spat such as could only have happened between two proud Spanish noblemen. According to lore, Guzman and Ponce de Leon narrowly avoided a physical fight over which one of them would be allowed to actually take the Rock. To avoid an all-out duel, they worked out a deal to walk into the fortress together and politely set up their banners at the same time. Thus the siege ended and the families hated each other ever since.

Rebelling against The Crown

To add insult to injury, King Enrique IV of Spain gave Guzman the boot after the siege was won. Ordering Guzman to leave the Rock’s premises, the king awarded himself the title of “King of Gibraltar.” Of course Guzman would have none of it. Guzman launched the ninth siege of Gibraltar, against his own king, on July 26, 1467—and actually achieved his life’s goal of taking the Rock for his family.

However, after all of that trouble, his son Enrique Perez de Guzmán y Fonseca didn't seem to have been very passionate about the Rock or building up family roots there. He was more interested in money than war. Reputed to have been the richest man in Spain, he was known for crooked dealings and treating those who engaged in business with him unjustly.

Queen Isabella of Castile

Queen Isabella I of Castile gave him the title of Marquis of Gibraltar, but changed her mind after he died and took the title away from the family. Seemingly it was Isabella’s chance to rectify the fact that the Rock had technically been stolen from the crown previously.

In the style of his ancestors before him, the late nobleman's son, Juan Alonso Pérez de Guzmán y de Ribera, was furious that the Rock had been taken away from him and dared to write to the queen exactly what he thought about it. It seems that Isabella ignored him. She removed the Guzman family banners from Gibraltar and decorated the place with Spanish royal emblems.

After Isabella died in 1504, Guzman decided he was going to reverse this redecorating project and restore the Rock to Guzman family ownership. Gathering an army, he mounted the tenth siege of the Rock with the help of his son, named Enrique.

The Fate of Gibraltar

Guzman expected that the city would welcome him with open arms. The opposite occurred. Royal troops in the fortress barricaded themselves inside and local Gibraltarians rallied to Spain’s cause. The Guzmans sat outside the city for four months before eventually realizing that victory just wasn’t going to happen.

Counseled by the church, the Guzman family finally gave up on Gibraltar—temporarily. Juan de Guzman firmly believed that the Rock was his rightful property and was actually planning to launch an eleventh siege before he perished at age 40 in 1507.

A member of the Guzman family was the reluctant commander of the Spanish Armada, defeated by the English. The British would also ultimately take control of Gibraltar. (Royal Museums, Greenwich)

After having shed blood, sweat and tears for Gibraltar from 1309 to 1507, the Guzman family ceased to besiege the Rock. However it definitely wasn’t the last time the family would leave an unusual footprint in Spain’s military history.

A Guzman descendant, Alonso Pérez de Guzmán y de Zuniga-Sotomayor, was placed in charge of the doomed Spanish Armada in 1588—against his wishes. In contrast to his fierce ancestors, Guzman protested against being given command, pleading ignorance of naval matters and an alleged tendency toward seasickness.

Nevertheless Guzman got the job despite expressly not wanting it. Needless to say the Spanish Armada was soundly defeated by the English, who would also ultimately take ownership of the Guzman family treasure, Gibraltar.