The Strange Tale of Enrique of Malacca

The first circumnavigation of the world.

Modern impressions of Enrique of Malacca Credit thescuttlefish.com

Once the world was proved round people wanted to circle it. Despite what is often said, it was not Columbus who disproved the hollow earth but mathematicians 2000 years earlier.

However Columbus did become the first person to to put spherical earth theory into practice was when in 1492, he failed to find the western route to India.

There is no evidence people in Europe thought he would sail off the edge of the world.

Columbus fell about 25’000 km short of India.

The discovery of America coincided with the final fall of the Byzantine empire, and the end of Moorish Spain.

The dual pressures of the loss of the lucrative silk road. And the need of the new kingdoms of Spain and Portugal to attain security lead the nascent states to push outwards like no states before.

Portugal under King Henry the navigator gambled on sailing south. Investing his nascent nations wealth in navigation, ship faring, mathematics and astrology.

To aid mapping and trading along the coast of Africa. This gamble led them to the gold coast, India, and finally the spice islands. Giving the Portuguese a monopoly on many luxury goods, most importantly spices in Europe for nearly a century. And turning them into one of the continents wealthiest nations.

Spain's monarchs meanwhile took a gamble investing on a penniless mad Italian twice rejected by the Portuguese crown. Who claimed Asia was 2400 km away across the Atlantic. Queen Isabella who took a liking to the mad Italian used her meager treasury to fund his expedition against the advice of… well everyone.

It’s worth noting, that Columbus was rejected over and over again,. Not because he was a visionary genius but because he was… kinda dumb. The 2400km claim was absurd even at the time. Where mathematicians already knew Asia couldn’t be that close if the world was a sphere.

But history is sometimes little more than a game of Roulette.

And so in 1492 Columbus accidentally embarked on one of the most monumentally important voyages of discovery and conquest in history.

It was in this great rush of exploration that a young man named Ferdinand Magellan was born in Portugal in 1480. Not much is known about young Magellan.

But we can imagine an impressionable 13 year old must have listened eagerly to the stories coming back from the new world, India and Africa. And looked greedily at the vast fortunes won and lost in this game of state.

Magellan was the son of a minor noble family. For minor nobles the glories and riches of the age of discovery offered a chance to improve their standing in ways domestic service never could.

In 1505 at 25 Magellan enlisted in the 7th Portugese India Armada. That established a series of forts to secure Portugese dominance of the Indian ocean.

By 1505, the Portuguese had well established their dominance over the new maritime Silk Road. And power structures had been developed. And Magellan for all his later ambition does not appear in histories of this time. He would remain in the Indies for several years until a new opportunity presented itself.

He would volunteer to sail with a diplomatic mission to Malacca, and in 1511 he would return with a fleet sent to conquer the city. Winning the trust of the fleets commander. He would be richly rewarded.

Around the same time Magellan took on an unassuming 14 year old Malay boy as slave, who was baptised Enrique.

Little is known about Enrique of Malacca who was Magellan’s personal slave and would follow him for the rest of their lives. Their fates would become irrevocably intertwined. And Enrique a slave child from the Malay archipelago would go on to make history. Though until recently he was all but written out.

Magellan Laden with plunder and riches could never have dreamed of in his native Portugal returned home accompanied by Enrique of Malacca.

As Magellan sailed for home further news of the America’s was filtering into Europe. The initial excitement for Columbus’ discovery had petered out when it became apparent, they had found neither India nor spices. And expedition by actual explorers like Amerigo Vespucci had quickly shown that the Americas was not in fact Asia. For a time it seemed like the continent of the America’s contained little of value compared to the riches of the spice islands

Magellan found life at home difficult and as often happened with the neuvo-rich of the age of discovery quickly fell out of favour with the court.

Magellans close friend Francisco Serrao had sailed west after the fall of Malacca and discovered the spice islands. And setting up a portugese embassy with the Sultanate of Ternate. He would send letters to his friend about the abundance of nutmeg, and cloves found on the islands.

Magellan took these letters to King Manuel of Portugal. Eagre to sail west around the newly discovered tip of South America and into Asia to open a new route to the spice islands for Portugal. Manuel declined.

Magellan would repeatedly petition the court and would be declined again and again. By this point the trade route to the spice islands was well established. What use did the crown have for another route disrupting their existing power balances.

Frustrated in his desire to lead Magellan departed for campaigns against Morocco where in 1514 he was accused of illegal trading with the Moors.

Magellan continued quarreling with the King until finally in 1517 he left for Spain, accompanied by his trusty slave Enrique and armed with the letters from Serrao detailing the riches of the spice islands.

He offered his services to King Charles the first. Who gladly seized the opportunity to break the Portuguese spice monopoly.

As Magellan crossed the border it is likely he would have known he would never be able to return.

Once the voyage was sold to the Spanish he would renounce his citizenship be branded a traitor in his home country and his properties seized. He was alone in the world. But for his trusty servant Enrique.

The Spanish were extremely eager to retain Magellan, despite coming from a nation they viewed as their chief rival. Up to this point the Portugese had run circles round the Spanish at sea. And the Spanish gamble on the America’s was not paying off. Despite claims by some in the America’s stories of gold laden cities were at this point just stories.

For this reason Charles was eager to set up a Spanish presence in the spice islands. And Magellan was quickly provided with five ships, 270 men and two years of supplies, as well as a contract promising 10% of any returns the voyage made.

Magellan slaved away over charts in Seville, consulting explorers, and cartographers to map a route to the America’s and beyond. From Seville to Brazil and from Malacca home he could rely on maps, and logs. But from the tip of South America to the straits of Malacca he was blind.

Unfortunately, despite his experience. He would make a fatal error in his calculations.

Despite threats from the Portuguese the Spanish were determined and so on the 20th of September 1519 the San Antonio, the Victoria, the Conception the Santiago, and the flag ship the Trinidad set sail for the new world.

39 year old Magellan commanded the Trinidad and with him sailed as always his trusty servant Enrique of Malacca now 21 years old and Antonio Pigafetta, an Italian chronicler who worked as Magellans personal assistant, and whose account of the voyage is where most of our knowledge of it comes from.

Enrique was actually far more important to this voyage than is sometimes realized through the simple fact he spoke Malay. The trade language of the Malay archipelago.

With trade routes monopolized by the Portuguese, the Spanish had no one but Enrique who could communicate with locals on arrival. And cooperation with locals was going to be necessary given the Portuguese had a policy of treating any foreign ship East of the Cape of good hope as pirates.

Magellan kept a simple and unadorned captains log. And on the 20th he wrote very simply:

"The journey to the great riches of the Spice Islands has begun. More Spanish crewmen have been added for the voyage as they suspect me of betraying them, but this will not slow down the truth of this voyage. We have left the port at Spain.”

The fear of betrayal would come back to haunt Magellan. Of the five leaders of the expedition 3 were Spaniards. And the Spanish crown seemed to treat Magellan more as a useful tool than a loyal ally.

The simplicity of Magellan’s entry seems surprising given the enormity of the expedition. And possibly speaks to an ignorance of its dangers.

Though Europeans had sailed 15’000 km east, and found the spice islands. None had tried to cross the pacific. Its size was a complete unknown, by some accounts rough calculations used by Magellan had estimated the size of the globe. And had suggested the Pacific would only take a few days, or weeks to cross. After all how big could it be?

The fleet would make average time crossing the Atlantic. And sail down the coast of Brazil. And Argentina. Reaching the edge of the known world.

However in the harsh region of Patagonia the flee would become trapped by winter storms. And would eat through much of their supplies.

Having spent only 6 months at sea, and having barely left known waters the 3 of the fleets captains mutinied.

The insurrection was short and bloody. One captain would be killed another beheaded, and a third marooned on an island in the inhospitable Patagonian coast.

However worse was to come, on the 20th of April the Santiago was sent to find a passage and was struck by a storm and sunk. All it’s crew members but one rescued. And it took the fleet another month to rescue all the crew and set out once more.

One ship down the fleet wanders aimlessly through Patagonia. It will take them 7 months to find a passage through to the pacific. A distance of less than 1000km.

Six months later the fleet is still wandering through the islands of Patagonia. The San Antonio the largest ship in the fleet is sent to explore and never returns.

The fleet searches for the ship for two weeks, venturing as far back as the Atlantic ocean. Six months later the San Antonio will sail back into Seville. It’s captain, Magellan’s cousin in chains.

A trial was ordered, Mazquita Magellan's cousin insisted the mutiny was unfounded, however he had signed a confession that Magellan had tortured Spanish sailors… after being tortured.

Unknown to Magellan the mutineers would be exonerated and Mezquita imprisoned.

After two weeks Magellan decided the three ships now more crowded and under supplied than ever had to set out into the pacific. And in November 1520, a strait today named the straits of Magellan finally led them into the Pacific ocean.

Not knowing the extent of the Pacific, some estimates at the time suggested it would take 4 days of sailing to reach the other side.

Nearly 4 months later they landed in Guam. 30 men had died of scurvy and their supplies were almost exhausted.

Though in desperate need of rest the fleet was forced on after raiding the local villages. 10 days later they arrived in the Philippines. Where they at last recuperated.

At this point Magellan was just 3000km away from becoming the first person to ever circumnavigate the world. Unlike Columbus who jointly discovered America with the crew of three ships. This would have been an achievement of just two men in the fleet.

No one but Portuguese sailors had reached the spice islands. So not a sailor on board had been to the East Indies.

In what is today the Philippines the Spanish encountered large war ships, and trading ships, their leaders laden with gold. And the usefulness of Enrique of Malacca became apparent as he used Malay to communicate with these strangers, who invited the small fleet to their cities.

Magellan no doubt interested in the large amounts of gold he saw. Tried to hard to win the locals trust And would eventually be granted an audience with a powerful local ruler, the Raj of Cebu.

Now the story of Magellan and the Raj of Cebu is unfortunately only told from the Spanish perspective.

And so the story goes:

Arriving at the palace on Cebu, the Raj made clear he demanded tribute from all boats that passed through his waters.

Magellan through Enrique convinced him to make an exception, as he was the emissary of a vast and powerful empire. Magellan then impressed the locals with their steel, gunpowder, ships, and gifts.

He then healed the sick through the power of christ and so awed by his personality says the chronicler Pigafetta that the Raj of Cebu converted to Christianity and swore fealty to Spain along with his wife and most of his chiefs.

“If I and my vassals all belong to your sovereign, how much more ought the land.” The raj said when Magellan requested use of some land.

The Raj then ordered all his client chieftains to convert to Christianity and aid the Spanish with resupplying.

However, within the Rajanate, there was division among the chiefs and one local client chief Lapulapu of Mactan refused to swear fealty to Spain.

Another Chief of Mactan sends an emissary to the Raj apologizing and asking for help to suppress Lapulapu who does not speak for him. And so the Raj asks Magellan to accompany him on his expedition.

Magellan offers not just to join the battle but to conduct it alone to prove to them the might of Christianity and of Spain.

Now… it seems highly unlikely the ruler of a powerful trading empire would just immediately role over at the site a couple of hundred emaciated Spaniards. And maybe someone in this story had an agenda either Pigafetta or the Raj. For let’s say… telling some porkies.

However, using outsiders to control troublesome internal quarrels is a strategy as old as history. And sometimes people record what they wanted to hear and not what was actually being said.

On the 14th of April the Spanish sacked a town called Bulaia on Mactan Island. However the Lapulapu was not subdued.

So on the 27th of April 1521. Magellan landed outside the main town of Mactan, to confront the local Lapulapu’s forces.

Magellan’s next decision is baffling. On Mactan there were two chiefs. One, Zula who wished to swear fealty to Spain, or stay loyal to the Raj. And requested one boatload of men to help him fight Lapu lapu about 20 or 30 men.

Magellan’s next move is baffling for historians.

Magellan took three boats of 60 men and refused any help. Insisting on fighting Lapulapu alone.

Lapulapu had 1500 men.

Lapu lapu’s forces were not a rag tag group of hunter gatherers. The Rajanate of Cebu was a wealthy trading district. Their warriors armed with iron, steel, and experience.

According to Pigafetta, the officers begged Magellan not to go ahead with his plan. Magellan ignored them.

But Magellan did have guns, crossbows and canons. Things which against unprepared forces can be devastating.

With just 300 men Pizarro toppled the Incan empire by luring the Inca into a trap and kidnapping the Emperor..

Magellan landed with 60 men. Sending an emissary to Lapulapu he demands surrender. The reply was no, and a request the Spaniards wait till morning so that they could gather more men.

The Spanish attempt to attack but find the path to the town littered with traps and retreat.

The next morning the 60 sailors land again, Lapulapu has gathered his full force around the beach 1500 men. Magellan leads 49 to the beach while 11 armed with crossbows and muskets guarded the boats. The Trinidad sits out to sea watching the battle with the ships of the Rajanate of Cebu. No doubt eagerly watching to see how these vastly outnumbered Spaniards are going to fare.

Let’s leave Magellan on the Mactan beach for battle a moment to fly back across the Pacific to Mexico. Where at this exact moment Cortez is assembling his forces for a march on the great Aztec city of Tenochtitlan.

Cortez had begun his conquest of Mexico just four months before Magellan set sail. Just 3 days after Magellan left Spain, Cortez marched victorious into Tlaxcalan with just 600 men where he Allies with their leaders against the Aztecs and marches on Tenochtitlan now backed by over 30’000 hardened warriors.

And at the exact moment Magellan lands on Mactan dreaming of glory. Cortez is on the otherside of the world preparing to bring an empire to it’s knees.

The comparison between Cortez and Magellan is a fascinating one. Both minor nobility, both desperate for glory, both on risky quests to bring wealth and territory to Spain.

In many ways they are very similar men. But in one they seem different.

The story of the rise of colonialization often runs: Europeans arrive, are so technologically superior, no one can stand against them.

But the reality of the world at this point was not that. And even against a stone age society Cortez understood this. When Cortez set to conquering the Aztec’s he used all his wit, and cunning. Turning local allies, seizing their god emperor, lying, deceit, cunning, and only fighting when he had to.

Magellan when put in a similar position, did the exact opposite. Pitting 60 Spaniards, against 1500. Despite his bravado Cortez understood, 500 Spaniards could not overcome 100’000 Aztecs. His cousin Pizarro would understand this during the conquest of Peru. Resorting to kidnapping and ambush.

But Magellan, seemed to believe that 60 Spaniards with steel swords were the match for 1500 Matcans… who also had steel swords.

Now let’s get back to Mactan beach.

The Matcans surround the Spanish, as Magellan wades to shore there is no doubt confusion and apprehension in their ranks.

This must be a trap they must think. But no one comes. Magelan stands their alone.

Perhaps they look nervously out to sea at the great sailing ship the Trinidad. Having heard stories of the great destructive thunder it can make. But nothing happens.

Magellan chose a beach that was too shallow. And the canons of his fleet are well out of range.

The Mactan's charge, and the guns and crossbows open fire. The locals are held back for a time. But the muskets are too far back to be effective.

Worse they run out of ammunition within half an hour.

The Spanish steel protects them for a time and Magellan sends a small party of men to burn their houses hoping to draw off part of the force, but it fails. And the Mactan's suddenly notice that Spaniards undefended legs and begin targetting these

.

The Spanish steel protects them for a time and Magellan sends a small party of men to burn their houses hoping to draw off part of the force, but it fails. And the Mactan's suddenly notice that Spaniards undefended legs and begin targeting these.

Magellan a handful of men are surrounded and cut off. Where they fight on for an hour. Finally Magellan loses his spear, and grasping for his sword is struck in the leg by a terciado, a type of triangular sword from the region. Magellan collapses and is killed.

Local tradition usually represents this fatal moment with Lapulapu striking the deadly blow. However no details of Lapulapu other than his name survive.

Magellan's suicidal charge into 1500 Mactans without his canons is one of the strangest episodes in colonial history. His inexplicable decision to leave his gunners so far away. To land on a beach where his canons could not help him. And worse to deny assistance from local chieftains. It beggars belief. How could such a competent sailor, and leader, make such an insane decision.

Perhaps Magellan truly bought into the idea of his voyage and victory as something ordained by god.

Enrique of Malacca injured alongside Magellan took to his bed to recover and refused to come out from under a heavy woolen blanket.

Magellan’s will is opened, and it is found that he has granted freedom to Enrique for his years of loyal service.

It is impossible to say what Enrique was thinking at this point. He had been bound to Magellan for 10 years from the age of 14.

Had Magellan told the young man he would free him? Did they have a good relationship? Magellan seems to have put a lot of faith in him and he was often sent alone to treat with the locals.

Pigafetta, who gives us some of the only records of this young man simply says he refused to come out from under a blanket.

It must have been frightening for the young man who had been bound to Magellan for so long to realise he finally had his freedom.

This realization would have been short lived however as he earned the wrath of the new commander of the flag ship Duarte Barbosa. Who informed him he was still a slave and would be taken to Spain and presented to Dona Beatrice, wife of the Magellan, who unbeknownst to them had died that same year.

Enrique was roused from his recuperation and ordered to resume his duties as servant and interpreter else he would be flogged. Before being sent alone to negotiate with the Raj of Cebu. He returned with a message.

The king had tribute he wished to send to the King of Spain and asked them all to come dine with him. So on the 1st of May 1521 24 men two of the three fleet captains and the expeditions astrologer and priest went ashore with 24 year old Enrique of Malacca.

Pigafetta the chronicler was not one of them. He had been struck by a poisoned arrow in the forehead and was recovering. 2 men returned to warn the ship to keep alert. As they arrived there was a commotion in the city. The ship weighed anchor, and fired it’s guns.

A little while later Joao Serrao appeared on the shore bound. Begging them not to keep firing. Serrao told them everyone but he and Enrique of Malacca were dead. He said the Raj of Cebu would let him go if they ransomed his life.

The ship set sail without Joao Serrao. Before they left Serrao said on judgement day he would demand the soul of his friend Joao Carvalho who had refused him. Neither he nor Enrique nor any of the others were seen again.

It is often said they were poisoned. However, given no one returned from the feast, there is no record of Serrao being poisoned or claiming poison and there are no records from the people of the island. This is complete speculation that is often reported as fact.

Pigafetta puts the blame for the massacre squarely on the shoulders of Enrique. Claiming he organized a scheme to seize the ship and its merchandise.

Given Carvalho said only he and the interpreter were alive this seems credible. However no one gives any evidence for this.

Three ships and about 110 men remained after the massacre on Cebu too few to crew all three ships so Concepcion was burned and they set sail west with two ships remaining.

The ships continued to explore. But unbeknownst to them their troubles have not ended.

After engaging in acts of piracy they are attacked by a Brunaeian fleet. Losing more men. The fleet sails south and finally encounters the rumored spice islands.

Unfortunately for the crew, Magellan had many contacts and experience in South East Asia from his campaigns as a young man. His friend Francisco Serrao had still been positioned in the Spice islands though he had coincidentally died around the same time as Magellan.

No one else in the crew had any experience, or spoke Malay. There was also another danger. The Portuguese. Who had no problem attacking other Europeans who tried to break their spice monopoly.

The ships finally found a safe port in Tidore in modern day Indonesia. Whose leader was more than happy to relieve the Europeans of their trade goods in exchange for spices.

Finally back in areas mapped by Europeans. And in the home stretch they loaded down with cloves and nutmegs. The Trinidad however was damaged so the two ships decided to head back seperatley.

The Victoria commanded now by Juan Sebastian Elcano sailed west. For the cape of good hope. 20 men died of starvation before they could resupply Because they had filled their cargo with 20 tons of cloves instead of… you know food.

Forced to land. The ship stopped in Cape Verde, a Portuguese colony off the west coast of Africa.

This wouldn’t have been a problem… if the ship wasn’t loaded down with spices. The Portugese detained 13 crew members. And the ship had to beat a hasty retreat.

Finally on the 6th of September 1522 the Victoria limped battered and bruised into San lucar Spain, almost three years to the day that they had left. Of 277 men who had set sail just 18 returned. 12 more would be freed by the Portuguese a few months later.

And of the men on the Trinidad?

Well, the Trinidad would be captured by the Portuguese. And the ship lost. Only 5 would return between 1525 and 1526

The men of the Victoria would be given a royal audience, received a share of the spice profits, a clap on the shoulder and were promptly forgotten.

The Aztec empire collapsed in 1521 and by 1522 the first boatloads of Mesoamerican gold began to arrive in Seville.

Of all the characters of the age of discovery Magellan is arguably the least romanticized. In the English world Sir Francis drakes circumnavigation 50 years later is better known. And not just in the English speaking world according to the first biography of the explorer written in English in 1890. There were no biographies of the man outside of Spain and the first translated into Portuguese was in 1881.

This may be partly for the untimely end of the man, however Magellan was just an inconvenient character for Spain.

He was Portuguese. He was a lesser noble. And he had already had his name tarnished by the trial of the crew of the San Antonio. It is likely had he returned alive things would not have gone well for him.

For all its gild the age of discovery had a habit of consuming its children.

Pizarro was assassinated, Columbus died impoverished and ridiculed. And even the great Cortez would become an inconvenient embarrassment to the crown. And is said to have once leapt onto the kings carriage and on not being recognized cried out “I am the one who has given your majesty more countries than your ancestors left you cities.”

Out of 270 sailors that set off with Magellan One ship load deserted. 40 successfully circumnavigated the world. 35 survived the journey. And 4 disappeared into the mists of history.

The fates of Juan de Cartegena, and Pedro Sanchez, last seen marooned on a Patagonian island, and of Joao Serrao last seen begging for his life on Cebu is unknown.

As is that of Enrique of Malacca who was never seen after he left for the feast on Cebu on the 1st of May but who Joao Serrao insisted was still alive.

Enrique of Mallaca was named such because he had been taken as a slave 10 years earlier in the straits of Malacca by a young Magellan, taken west around the world to Portugal, taught Portuguese and Spanish. Before being taken with Magellan to Spain, and then onto the Trinidad as his personal servant and translator. Enrique could speak Malay the trade language of the Malay archipelago.

Where he would sail East with his Master. Through the icy waters of Patagonia, and across the endless expanse of the Pacific. To the islands of the Philippines and the Rajanate of Cebu, to a land where once more he was surrounded by people speaking his native tongue.

Enrique fought for Magellan, was injured in his service, and after his masters death, was still treated as a slave. The Spanish believed he was the one who betrayed them. If he did what was his price? Did he walk into the Palace of the Raj, burning with furry and sell out his comrades for nothing but the pleasure or revenge? Or did he have something else in mind.

The island of Cebu is just 2400km from the Straits of Malacca where he was born. A long distance. But certainly not insurmountable in the well interconnected archipelago.

And so though Enrique of Malacca disappears from the historical record. Let us imagine a young man standing alone in the Palace of the Raj finding himself for the first time in his life terrifying alone.

Perhaps he boards a ship south to find if any vestige of his old life remains in the tropical peninsula of Malay.

And if he did then it is entirely possible that a humble slave boy became the first person to ever circumnavigate the world.

Unfortunately it is also possible he was killed. If he did indeed betray the Spanish the failure to capture a ship might have cost him his life. Or he might not have betrayed them. Maybe he was just left alive for negotiations.

Unfortunately, we don’t know. His life will forever be one of those great historical mysteries.

But personally… I like to imagine a 25 year old Enrique. Sitting on deck, his eyes craned for the first site of land. Closing his eyes, and breathing deeply the sea breeze that carries the unmistakable smell of home. And knowing he was finally free.