Ferdinand Magellan was a proud and stubborn man, but he wasn’t an impulsive one. After his humiliation at the hands of King Manuel convinced him to break with Portugal, he remained in his homeland for well over two years, plotting that break carefully. He did, however, abandon Lisbon for his old childhood home of Porto, where he could do his due diligence away from the prying eyes of court gossips.

Magellan was wise to do so much planning, given that he wasn’t so much a sailor as a soldier who had happened to travel and fight on ships through most of his career. He had never commanded even a single vessel, much less an entire expedition like the one that was now gestating in his head. He had only a passing knowledge of winds and currents and stars, those bedrocks of a real sailor’s livelihood. So, he hit the books, trying to make up for lost time. And once he felt he had learned enough to ask intelligent questions, he began to quietly consult with experts in these matters. One of these was a mathematician, astronomer, and cartographer named Rodriguo Faleiro, with whom Magellan formed an unusual bond.

Faleiro’s reputation preceded him: he was so learned in so many fields that people said only half jokingly that he must have dabbled in the black arts, that his intellectual prodigality was the result of a “familiar demon.” And indeed, he was as erratic and temperamental as he was brilliant, qualities that had kept him from making a fine career for himself within the ivory towers of Europe’s universities and also kept him out of the post he coveted most of all, that of King Manual’s personal astronomer. He may have had no idea how to fire a musket or throw a grappling hook, but he was full of abstract knowledge about geography and navigation; the dingy loft in which Magellan found him was cluttered with maps, charts, globes, compasses, and astrolabes. When he told Magellan that he thought the idea which the latter had brought to him was very much within the realm of the achievable, it was a welcome validation. When he told him that he would like to join the enterprise as a full partner, Magellan quickly agreed. Almost comically different though they were in most respects,  they had one thing in common: each nursed a grudge against the king of Portugal, which grievance he channeled into this, his great hope for revenge.

But precisely what, you might be asking, was the scheme that had come to so obsess this odd couple? It was simply this: to approach the Spice Islands from the opposite direction of Magellan’s friend Francisco Serrão, by sailing directly west from Europe in the wake of Columbus rather than taking a roundabout course south and then northeast, as Portuguese seafarers had been doing for decades. In the broad strokes, then, it was no more than a slightly tweaked version of the old hope of reaching Asia from Europe by sailing west, the same hope that Columbus had cherished before becoming the Americas’ reluctant discoverer instead. It had merely been updated to fit the new picture of the world which Columbus had inculcated despite himself.

The plan was based on one correct and one mistaken assumption. Magellan and Faleiro concurred with the emerging consensus in Europe that the lands which Christopher Columbus had discovered, and which Spanish conquistadors like Hernán Cortes were already beginning to explore and claim for their king, were not some adjunct to Asia but a new continent or continents unto themselves. Yet they still clung to the notion of the Earth’s size which they had inherited from their hallowed ancient forebear Claudius Ptolemy, believing the planet to be about 30 percent smaller than we know to be the case today. The dimensions of the Atlantic and Indian Oceans were reasonably well charted by this point, leaving only one major expanse of water outside of the polar regions completely unknown to them: the biggest one of them all, the Pacific Ocean. It just so happens that, if one removes most of this improbably vast expanse of open water from a map of the Earth, one arrives at a planet of just about the size which Ptolemy said it ought to be. Magellan and Faleiro believed correctly, in other words, that North and South America were continents of their own, but believed incorrectly that mainland Asia lay a relatively short distance to the west of them, the Spice Islands even closer. Their core hypothesis, which could only be tested in the breach, was that it would be faster and easier to reach the Spice Islands and much or all of the rest of Asia by sailing between or around the Americas than by making the long, tedious trip down and then back up the coast of Africa.

Having secured testimonials from other prominent geographers and pilots to supplement Faleiro’s maps and charts and globes, Magellan prepared to seek patrons for their expedition in Seville, Spain. Fussily scrupulous as ever when it came to questions of honor, he went down to his lawyer’s office before leaving his homeland, to sign a formal testament renouncing his loyalty to King Manual I of Portugal, declaring in said document that said king had explicitly told him that he had no further need or wish for his services — a statement that was accurate enough in literal terms, although Manual had certainly not been aware of what Magellan would construe his words to mean for both of their futures. In his own mind, Magellan was now a free agent, who could peddle his ideas and abilities elsewhere without so much as a twinge of guilt.

With honor duly satisfied, Magellan, accompanied as always by the faithful Enrique, arrived in Seville on October 20, 1517, to seek friends and partners in the richest, most dynamic city in Iberia, arguably in Europe as a whole. Standing not directly on the southern Spanish coast but about 60 miles (100 kilometers) inland on the banks of the wide, deep, and easily navigable Guadalquivir River, Seville was the nerve center of the new Spanish mercantilism. By royal decree, it was the only port from which trading ships could sail for the New World and the only one to which they could return with holds full of gold and other expensive exotica. Its wharves and warehouses positively sang with the spirit of this burgeoning post-Medieval age of commerce, in which the accounts in the ledgers of the bookkeepers carried as much or more weight than the spiritual accounts kept by the priests.

Magellan stayed in the house of one Diogo Barbosa, whose own family were longtime friends or possibly distant relations of the Magellan family. The two men had much in common beyond this: Barbosa too had sought adventure in the Indian Ocean under the flag of Portugal as a young man, before renouncing his allegiance to that country and coming to Seville, where he had enjoyed modest success as one of the city’s new class of merchant princes. Barbosa was not, however, a big enough wheel to do much for Magellan’s cause on his own. He could only give his house guest the same advice that just about anyone else in Seville would have given: that he needed to go down to the Casa de la Contratación de las Indias, the “House of Trade of the Indies.” It was there that the agents of the Spanish crown authorized and sometimes funded new initiatives of all sorts involving the world beyond Europe.

Alas, Magellan was not warmly received there. Two of the three men who listened to his presentation were not at all impressed with this lame foreigner and his crazy ideas. Why roll the dice on a long shot like this when there was plenty of money already coming in from the established trading routes? Magellan’s application was voted down in short order.

But the third man on the panel was intrigued despite himself. Juan de Aranda was a merchant prince of a class far above the likes of Diogo Barbosa, with connections reaching all the way into the Spanish king’s inner circle. While Magellan was cooling his heels in the home of Barbosa, trying to decide how to break the news of his abject failure to Faleiro back home, Aranda made inquiries of his own back in Portugal to verify the supplicant’s bona fides. After learning that Magellan really was a soldier and adventurer of some note, and that his partner Faleiro really was a geographer and scholar of some standing, he asked to meet with Magellan again, this time in a private capacity.

He told him then that he smelled potential in the project, and that he had the power to bypass the bureaucracy of the Casa de la Contratación, which had been instituted for small, day-to-day business ventures, not for potentially transformative ones like this expedition. He could, he said, secure Magellan an audience with the king of Spain himself. But he hadn’t gotten rich by being a soft touch: he wanted 20 percent of the expedition’s profits as his fee for effecting this introduction. Magellan listened soberly, then replied that he would have to consult with his partner before talking further. Beneath the stoic façade, however, he was thanking the stars for this improbable shift in fortune. He dashed off a letter to Faleiro to tell him the good news.

But Faleiro did not take it as Magellan had expected. He declared himself to be shocked, appalled, and incensed at Magellan’s even entertaining the idea of letting one such as Aranda in on their action. Shocked and appalled in his own way upon receiving his partner’s indignant response, Magellan begged Faleiro to at least come to join him in Seville so that they could discuss the matter in person. Faleiro grudgingly did so, and, after much fraught negotiation, first between the partners themselves and then between the partners and their would-be entrée to the Spanish court, Aranda agreed to a 12.5 percent stake in return for the introduction. Faleiro capitulated with no good grace: even after the agreement was signed, he remained deeply embittered with Aranda, to the point of refusing to travel in the same carriage as him or sit with him at table.

It was a busy time in Magellan’s life. Amidst all the rest, the lifelong bachelor was getting married as well, to a young woman named  Maria Caldera Beatriz Barbosa, the daughter of his host. Based on what we know of courtship customs of the time and on the swiftness of the wedding after Magellan’s arrival in Seville, the marriage was probably arranged beforehand. Being so supremely conscious of his aristocratic rights and duties, Magellan may have married in the hope of providing an heir to his estate, minor though it was, before going off on a supremely risky adventure. If so, his hope came to pass: his wife would bear him one son and became pregnant with a second child during the less than two years the couple would spend together.

Meanwhile Juan de Aranda had set to work on his part of the deal, proving as good as his word. Magellan and Faleiro soon received a formal letter from King Charles I of Spain, inviting them to join him at his court in the town of Valladolid, some 350 miles (550 kilometers) north of Seville. They set off immediately, arriving on February 16, 1518, just four months after Magellan had come to Spain with only the vaguest of hopes of finding a willing ear for their plan. Thanks to sheer luck as much as anything else, the two mismatched dreamers were on the cusp of pitching their scheme directly to the most exalted personage in Spain.

Still, the overall situation at court was not quite as that personage might have wished it. The fact was that the government of Spain was unsettled to an extent that it hadn’t been since the country was first unified decades before.

The power couple Ferdinand and Isabella — the one a prince of the eastern Iberian kingdom of Aragon, the other a princess of the large central kingdom of Castile — had laid the groundwork for the Spanish unification when they had married one another in 1469. In 1479, the work was completed, when Ferdinand, who was by then the king of Aragon, ascended to the throne of Castile as well by virtue of his marriage to Isabella. Their checkered joint reign — they were the authors of the horrors of the Spanish Inquisition as well as the backers of Columbus — ended with Isabella’s death in 1504, leaving Ferdinand to rule Spain alone.

Isabella had been an unusually strong queen, but she had failed to fulfill a queen’s most important duty: she had not provided her husband with a fit and healthy male heir. The couple’s only son was sickly throughout his life, dying at last of some illness in 1497 at age nineteen. Otherwise, there were only daughters, four of them in all. Ferdinand remarried after Isabella’s death in the hope of conceiving an heir with his second wife, but the only issue of that union, although a boy, died just hours after his birth. Thus when Ferdinand himself died, on January 23, 1516, the table was set for conflict — conflict that a fragile Spain, many of whose people were still decidedly skeptical about this notion of permanent unity, could hardly afford.

With no surviving males to be found in the generation immediately after Ferdinand, the throne should have descended to one of his grandsons. But this was made problematic by the fact that all four of his daughters had married other European royalty and moved elsewhere. His first daughter Isabella had been wed to none other than King Manual I of Portugal. She died whilst giving birth to her only son, who would have been the presumptive heir to the thrones of both Portugal and Spain had he too not died in infancy. (If the boy had lived, we might very well be speaking today of a single country called Iberia.) Ferdinand’s second daughter Joanna married Philip of the House of Habsburg, Duke of Burgundy and Lord of the Netherlands, with whom she had two healthy sons, the next in line for Ferdinand’s throne after the death of Isabella’s son. The third and fourth daughters are less relevant to our story — but, for the record: Maria became the second wife of King Manual of Portugal, while Catherine went to England to become the first of the six wives of King Henry VIII.

So, it was to the two sons of Ferdinand’s second daughter Joanna that the eyes of Spain turned following the death of the aforementioned king. The eldest of these, whose name was Charles, was by all law and tradition the rightful heir. Yet there was a wrinkle here. Charles had grown up speaking Dutch in the Netherlands, while Joanna’s second son, whose name was also Ferdinand, had been sent to Spain to live at court with his namesake grandfather. The latter had in fact taken a strong dislike to Charles, even as he had lavished affection upon his other grandson. After the old king’s passing, Spain was thus left with two princes to weigh — one of them a known quantity who was plainly, deeply Spanish in culture and outlook, the other a foreign stranger with only the traditional order of succession working in his favor. And there was something else to think about besides all this: Charles already stood next in line to become Europe’s next Holy Roman Emperor, which would give him sovereignty over Germany and many of its adjoining lands. If he became ruler of Spain, Germany, and the Netherlands together — he had officially been Lord of the Netherlands since the death of his father when he was just six years old — he would be the most powerful single monarch in Europe, on paper at any rate, since the time of Charlemagne. But was it really in Spain’s interest to become a part of such a sprawling collective of subject lands? Seen from the perspective of today, the debate stands at a fascinating juncture in history, in which the old ways of dynastic rule met a budding new spirit of nationalism, by whose lights loyalty to country would eventually come to trump loyalty to bloodline. The younger Ferdinand knew where he stood on the matter, aggressively pushing his own claim to the Spanish throne, saying that the title of Holy Roman Emperor alone ought to be more than enough for his brother, and that it was entirely too much to get tangled up with the proudly independent country of Spain.

It was a close-run thing for a time, but it turned out that the old ways still had enough juice to win the day for a little while longer. Francisco Jiménez de Cisneros, the archbishop of Toledo and a longtime trusted advisor to the old King Ferdinand, pushed through the letter of the law of the succession, putting Prince Ferdinand under house arrest for some months to keep him from stirring the pot any further. It would prove one of the last such victories for the Medieval mindset on this fast-changing continent.

The new King Charles I of Spain, just seventeen years of age — his presumptuous younger brother was just fourteen when he was making his play for the Spanish throne — didn’t set foot in his kingdom until September 19, 1517, more than a year and a half after his grandfather’s death. He proceeded to do almost everything wrong, beginning with the private army of German mercenaries he brought with him, an all too blatant signal of the precise level of trust he had in his new subjects. The painful fact was that Charles knew almost nothing of Spain, could speak only a few words of Spanish. By way of compounding his travails, the wily old Archbishop Cisneros, the man to whom he largely owed his throne, had fallen ill; he died on November 8, 1517, depriving Charles of a vital ally and advisor.

The young Charles V, as painted in 1519 by Barend van Orley. (Public Domain)

At a glance, one might not have given much for Charles’s long-term chances in the great game of European politics. This boy upon whom so much status and expectation had descended cut a thoroughly unprepossessing figure in person. He was short of stature, pale of skin, awkward of mien, and homely of visage, with an equine nose and lantern jaw. His voice was hesitant rather than commanding, his lack of facility with Spanish easy to mistake for a more generalized dull-wittedness. It isn’t hard to understand why so many Spaniards would have preferred to cast this fish out of water back where he came from in favor of his handsomer, glibber younger brother. Yet in time Charles would show himself to be made of stronger, cleverer stuff than anyone might have guessed, such that his reign as king of Spain would last even longer than that of his grandfather.

But those qualities had yet to show themselves when Magellan and Faleiro arrived in the bucolic little town of Valladolid, the very spot where Ferdinand and Isabella had held their auspicious wedding in 1469. Even with the letters of recommendation of Juan de Aranda and their formal invitation to court in hand, they weren’t allowed to simply walk in and present themselves to King Charles. First they had to get through the so-called “Privy Council,” made up of his four closest advisors. Three of these men were foreign imports like their king. (One of them would go on to become Pope Adrian VI.) This trio was not overly interested in foreign adventures, being more concerned with consolidating their liege’s shaky position in Europe than the Americas or Asia. They listened to Magellan and Faleiro’s earnest presentation with half an ear at best.

The partners quickly realized that the key man was the elderly but sharp-witted Bishop Juan Rodríguez de Fonseca, who, despite his ecclesiastical robes, had long been the chief advisor to Ferdinand and Isabella on all matters to do with overseas exploration and empire. It had, for example, been Fonseca who had listened to Christopher Columbus’s idea for a westward voyage to Asia and finally, after much hard interrogation, passed the Genoese navigator on to his sovereigns with his seal of approval. He was less hard on Magellan, who did most of the talking for the partners. He listened raptly as the old salt walked him through the pair’s plan, pulling one visual aid after another from a seemingly bottomless chest of trinkets as he did so: maps of the world that they thought they knew, newfangled navigational instruments, and finally the coup de grâce, that original life-changing letter which Magellan had received from Francisco Serrão, wrinkled and faded now from long handling but exuding a patina of promise, like a secret treasure map to a pharaoh’s tomb. The presentation struck Fonseca with all the force of a divine revelation. This expedition could change the great game of overseas empire forever, he realized.

That said, he was smart enough to see that the partners were glossing over a lot of aspects of their proposal. The most obvious of these was how they would actually get past the Americas, what with no one having yet discovered any sign of any water route stretching from east to west across those land barriers. Nor did anyone know how far south the land mass stretched. If Magellan and Faleiro were obliged to sail all the way down and around the bottom of South America, would their route really end up being any faster or safer than sailing around Africa in similar fashion?

And then there was another concern: of late, there had been a rapprochement between Spain and Portugal, which was to be cemented, as such things usually were, through the mechanism of royal marriages. King Ferdinand’s third daughter, the one who had become the second wife of King Manual, had recently died, leaving the Portuguese king once again a widower. Having exhausted the late Spanish king’s supply of marriageable daughters, he was to start on his granddaughters, by marrying Charles’s sister Eleanor. Meanwhile Charles himself had agreed to marry Manuel’s fifteen-year-old daughter Isabella at some future date. The détente had been predicated on an understanding to which the pope in Rome had given his spiritual imprimatur: that Asia and the most easterly outcropping of South America — a part of the nation of Brazil today — would be Portugal’s to exploit, while Spain built its empire in the rest of the Americas. If Spain now blatantly encroached on Portugal’s sphere of influence, as Magellan and Faleiro were proposing, all of the diplomacy would be at risk of coming to naught.

Yet Fonseca decided the expedition was a gamble worth taking in light of the potential rewards. Its effect on Spain’s relations with Portugal, he judged, need not become a worry unless and until the venture panned out. He talked the rest of the Privy Council into voting with him to pass the proposal on to King Charles. Then he told Magellan and Faleiro to prepare to address the king. He regarded this as a mere formality; having no higher an opinion of Charles than most of the rest of the young king’s new Spanish court, Fonseca assumed he would simply sign off on whatever “suggestions” the Privy Council deigned to send him.

Those suggestions entailed approving the venture, but with one important caveat. Bishop Fonseca didn’t tell Magellan and Faleiro that he didn’t actually intend to let them lead the expedition. He had learned to dislike and distrust all Portuguese in general, and, even when he tried to set aside that prejudice, he saw little reason to place much faith in these two amateurs in particular. He didn’t appreciate Magellan’s aristocratic airs any more than he did Faleiro’s abstracted intellectual ones. There were better men — loyal Spaniards born and bred — to place in charge of the voyage. At most, Magellan and Faleiro might be sent along as advisors. Or, better yet, they could just be sent on their way with a few bags of gold as their thanks for bringing the possibility of such a voyage to the Spanish crown’s attention.

Of course, Magellan and Faleiro knew none of this when the day came to make their pitch to the king of Spain, who had just celebrated his eighteenth birthday. We can picture the slender youth sitting there on a massive throne which threatens to swallow him whole, his mouth moving a little as he strains to follow the Spanish words that are being spoken. Having laid out the hard facts of the case to the sober-minded Bishop Fonseca, Magellan and Faleiro leaned more on spectacle before the king and his courtiers. Enrique was trotted in, announced as a native of the Spice Islands rather than Malaysia. Samples of fragrant spices, which may or may not have come to Magellan with one of Serrão’s sporadic shipments, were passed around the room. And then the letter from Serrão was read aloud, filling the throne room with images of a tropical paradise bursting with untold pleasures and riches, just waiting for the taking.

Charles sat and took it all in without saying much, as was his wont. Yet as was also becoming his habit already, when he did speak up he did so as every inch a king. He wished to fund the expedition, he said. And so it would be funded. But then, much to Fonseca’s surprise and dismay, he ignored the bishop’s advice not to promise any more than that, saying that he wished as well for Ferdinand Magellan and Rodriguo Faleiro to lead it personally. And so they would lead it. Perhaps the young king felt some affinity for the old soldier and his brainy companion, fish out of water here in Spain just as much as himself, who likewise spoke Spanish in the halting accents of a second language. Perhaps he hoped that, if the voyage should pan out, some of its glamor would rub off on him, leaving his Spanish subjects more fondly disposed toward their foreign-born king.

At any rate, on March 22, 1518, Magellan and Faliero received their contract from His Majesty. It promised them five ships, “two each of 130 tons, two each of 90 tons, and one of 60 tons, equipped with crew, food, and artillery.” In an effort to create a degree of plausible deniability with Portugal, the contract was purposefully vague about the goal of the expedition, saying only that it would involve sailing westward from Europe over a great distance. The terms were quite generous toward Magellan and Faleiro. In addition to an ample salary for each, which was to start immediately and continue for the duration of the expedition, they would each be entitled to 5 percent of the profits from any new trading lanes that they opened up for Spain, in perpetuity. If everything worked out and the king honored all of his promises, Magellan and Faleiro stood to end up fabulously wealthy as well as famous. It was an amazing turnaround for these two laughingstocks of the Portuguese court; it had taken them less than six months in Spain to get everything they could possibly have imagined from the Spanish king. Indeed, King Charles seemed almost more excited about the venture than its inventors. He wished, he said, for the ships to sail before the year was out. Magellan and Faliero were living their dream.

Unfortunately for them, Bishop Fonseca was not a man who took it lightly when his advice was ignored. The odd couple was about to learn that even Charles was not omnipotent — about to learn what it meant to be caught between a monarch and his powerful lieutenant scorned.

Did you enjoy this chapter? If so, please think about pitching in to help me make many more like it. You can pledge any amount you like.

(A full listing of print and online sources used will follow the final article in this series.)

7 Comments for "Chapter 3: The Plan"

  • Leo Vellés

    Very intrigued by this cliffhanger, can’t wait to know how this is going to continue. Great work as allways, Jimmy!

    • Martin

      Yeah. My money is in they call the whole thing off and forget all about it. 🙂

      I have always been poor…..

  • Lee Hauser

    Typo: one of your Barbosas is Barbossa:

    “While Magellan was cooling his heels in the home of *Barbossa,* trying to decide…”

    Otherwise excellent, as always.

    • Jimmy Maher


  • glorkvorn

    “Almost comically different though they were in most respects, they had one thing in common”
    Very interesting! I feel like there is a deep lesson here. The more academic “thinkers” tend to get stuck in a bad cycle where we just sit there, thinking, doing nothing real. Meanwhile the pure “doers” just go out and try thing, but either fail or die in the attempt. The really interesting stuff happens from collaborations between the two, where a thinker meets a doer and they can both leverage each other’s strengths.

    See also: that W Bush quote about the “Reality-based community:”'We're%20an%20empire%20now,how%20things%20will%20sort%20out.

  • Ilmari Jauhiainen

    “(If the boy had lived, we might very well be speaking today of a single country called Iberia.)”

    Spain and Portugal were eventually ruled by couple of shared rulers (interestingly, all were named Philip), but still the union did not last. Do you think the case would have been different if the union had occurred earlier?

    • Jimmy Maher

      My feeling is indeed that the union might have proved more lasting if it had come earlier. The beginning of the fifteenth century was still a time of kingdoms, whereas by 1580, the time that the 60-year Iberian Union that we know began, Europe was fast transitioning into nation-states; the monarch no longer *was* the country, as during Medieval times. Additionally, the Iberian Peninsula was a far more unsettled, febrile place 80 years earlier. The addition of Portugal to the kingdom, coming fast on the heels of the unification of Castile and Aragon and the conquest of Granada, would perhaps have seemed a more natural or even inevitable development.

      Counter-factuals are of course always dangerous in history, but that’s my two cents, anyway…


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