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IN THE YEARS following Christopher Columbus’s death, no one could agree on when and where (or in what order) he made his voyage proposals in hope of securing royal favor. The arguments were literally all over the map.

The sixteenth-century Spanish chronicler Anton de Herrara thought he tried his luck in Genoa first, in 1482. True or not, Columbus took the idea to the Portuguese court of João II in the early 1480s, probably exploiting connections he enjoyed through his in-laws. Jerome Münzer, a Nürnberg physician and humanist scholar who latinized his name as Hieronymus Monetarius, would meet João II at his castle at Évora in late November 1494. Münzer was in the midst of a tour of France, Spain, and Portugal on which he served as an envoy for Maximilian I, the King of the Romans (the German states) and the Holy Roman Emperor. João II was thirty-nine then, and Münzer found him “a very cultivated man, full of wisdom in everything, who rules his kingdom in peace and calm. He is very affable and has great curiosity in many subjects. He listens attentively to everyone who approaches him and boasts knowledge of the arts of war, navigation, and other sciences, then will make verifications and research proofs, and if he finds what someone says is true and useful, he gives everything necessary to make it possible.”

João II effectively had been ruling Portugal since 1477, after his father, Afonso V, retreated to a monastery during the war of the Castilian succession when his campaign began to falter, but the son was formally crowned only in August 1481. He was not yet thirty when Columbus approached him early in his reign; with both the Treaty of Alcáçovas and the bull Aeterni Regis in his favor, João II was fully engaged in expanding the Portuguese empire down the West African coast. In 1482, the fortified trading post of São Jorge de Mina, the first European settlement beyond the Mediterranean (which Columbus had visited, according to the 1492 journal abstract) was established on the Guinea coast in what is now Ghana; that same year, Diego Cão discovered the Congo River. Returning in April 1484 to Portugal, Cão set out again sometime in 1485 to push farther south and accommodate the sun-sight experiments.

Africa was the first true New World for Europeans, as the Portuguese continued to explore southward along its coast and began to send expeditions inland. Columbus was arguing for exploration in an entirely different direction. João II relied on the wisdom of scholars in ruling Portugal, and Columbus was told to present his voyage plan to a subcommittee drawn from the council the king had formed to solve the sun-sight problem.

The sixteenth-century Portuguese chronicler João de Barros said that Columbus proposed to sail west to reach Cipango, Marco Polo’s Japan, which the Venetian traveler’s account had assured was ripe with gold, pearls, and jewels. Relying on Polo’s estimations of distance and their impact on the Ptolemaic world, Columbus argued that Cipango was only one-quarter of the way west around the globe and the continental Indies one-third of the way.

João II was enthusiastic about the idea of a westward search for new landfalls. Licenses were issued periodically to adventurers from the Azores and the Madeiras, and Columbus probably knew about recent Madeiran efforts. One was the Martín Antonio Leme venture, which Fernando Columbus and Las Casas would say sighted three islands equated with Antilla around 1484 (although no royal concession survives). And in 1484, João II preemptively granted Fernão Domingues do Arco of Madeira the governorship of an Atlantic island that he intended to find.

The Las Casas abstract of Columbus’s 1492 voyage account traded in stories of landfalls and elusive sightings. Columbus gathered from “many trustworthy Spaniards” on the island of Ferro (Hierro) in the Canaries that every year they spied land to the west, which was affirmed for him by residents on Gomera. Las Casas probably was referring to the Arco grant when he then noted how Columbus recalled that in Portugal in 1484, a man from Madeira approached the king of Portugal “to ask for a caravel to go to this land which he had sighted, and which he swore he sighted every year and always in the same way.” Columbus recalled how in the Azores the same thing had been claimed, “with everyone seeing land in the same direction with the same aspect and the same size.”

João II’s subcommittee in any case rejected Columbus outright, deriding his knowledge. Relying on Barros, Las Casas recounted in his Historia de Las Indias how the subcommittee “perceived Columbus’s words to be vanities, founded on imagination and stories of the isle of Cipango” derived from Marco Polo’s travels. He was all but laughed out of court, an ill-educated fantasist who had managed to marry into the right family.

Columbus, dismissed as an unschooled dreamer, then fled Portugal for his life.

COLUMBUS WAS COMPELLED to flee Portugal by the terror arising from the Braganza conspiracies of 1483–84. João II was ruling with anything but the “peace and calm” Münzer would observe in 1494. The Duke of Braganza, Fernando II, was in legitimate succession to the Portuguese throne when João II had him executed for treason in 1483 after letters were intercepted between the duke and Isabel of Castile, asking her to intervene in João II’s consolidation of power. João II then personally stabbed to death Fernando II’s brother-in-law Diogo, Duke of Viseu, in 1484.

Columbus may have been left dangerously exposed to the king’s wrath through his in-laws. Columbus’s wife, Filipa, was a cousin of Isabel’s, and Diogo Gil Moniz was a member of the murdered duke’s household. The exodus to Castile was led by Don Alvaro de Portugal, brother of the Duke of Braganza and a cousin of Isabel, who became president of the Council of Castile and a close advisor to the queen. Many members of Columbus’s wife’s family sought refuge in Isabel’s kingdom, and Columbus followed them. When Columbus left Portugal, Filipa likely was already dead of unknown causes. Las Casas volunteered that God took her from Columbus so that he would be free to do the work of the Lord in spreading Christianity.

Filipa’s sister, Violante (Brigolanda) Moniz Perestrello, resettled in Huelva with her husband, Miguel Muliart, in 1485; they would relocate to Seville in 1493, when Muliart joined Columbus for his second voyage. With son Diego in tow, Columbus is believed to have arrived at the Franciscan monastery of Santa María de La Rábida around 1485 as well. La Rábida was part of the harbor complex at the confluence of the rivers Odiel and Tinto that included the towns of Palos (de la Frontera) next door, Huelva, across the Tinto, and Isla Saltés sheltering the estuary from the Bay of Cadíz. The monastery was well known to sailors who called at the Andalusian port from different nations and made donations to the Franciscans to pray for them.

Columbus had been “deprived of all human aid, and because of both the faithlessness of his associates and his desperate poverty, he fell on such hard times that he went to [Santa María de La Rábida].” So claimed Alessandro Geraldini, the humanist scholar who would provide crucial support to Columbus in his arguments for making a westward voyage during the debate that led to his initial capitulation, secured at Santa Fé in April 1492.

The Columbus timeline is contentious: He may not have been taken in at La Rábida until 1491, long after arriving in Spain. Nevertheless, the Palos physician García Fernández also would vividly recall the aspiring explorer’s forlorn arrival at La Rábida “on foot with son don Diego. . . . And at the entrance he requested that they give the little boy, who was a child, bread and water to drink.” The Franciscans were known for their love of learning, and according to Geraldini, the friary’s cosmographer and astronomer Antonio de Marchena “took pity on Columbus there.”

Marchena supported Columbus in his voyage ambitions, but the most important figure in this influential circle was Juan Pérez, prior of the La Rábida monastery, who had served as Isabel’s accountant and then as her confessor after entering the Franciscan order. Pérez tended to the protocol of securing Columbus an audience with Isabel and would represent Columbus in the negotiations for his capitulations in 1492.

Notwithstanding Las Casas’s idea that God took Columbus’s wife away so he could do the Lord’s work, Columbus found a new companion, Beatriz Enriquez de Arana, who bore him the illegitimate Fernando around 1488. Columbus evidently dealt in maps and perhaps books as well, perhaps alongside Bartolomé, while trying to convince the Spanish monarchs to back a voyage. The Venetian Angelo Trevisan, who met Columbus in 1501, recounted how Columbus “followed for a long time the most serene sovereigns of Spain wherever they went, seeking their help to fit out some vessels, for he offered to find islands in the west in the neighborhood of India, where there is an abundance of precious stones, spices, and gold, which could easily be obtained. For a long time the king and queen and all the prominent men of Spain made fun of the idea, but finally, after seven years and many hardships, they conceded to his will.”

Columbus’s voyage pitch apparently was focused on Isabel, his late wife’s cousin. The Treaty of Alcáçovas of 1479, which had secured so much of the known Atlantic realm for Portugal just as Columbus was marrying into the Perestrello and Moniz families, had also concluded the war of the Castilian succession in Isabel’s favor. She had been contesting the right to Castile with her niece Juana, spouse of Portugal’s Afonso V and daughter of her half brother, the late Enrique IV of Castile. Enrique had been shopping Isabel all over Europe when Isabel took matters into her own hands and married Fernando, heir to the neighboring kingdom of Aragon, in 1469.

Isabel and Fernando ruled Spain as coregents, equally powerful, under the motto Tanto monta, monta tanto—Isabel como Fernando (as much as the one is worth so much is the other—Isabel as Fernando), while their kingdoms of Castile and Aragon continued to operate under their own laws and civil administrations. The duo sought every opportunity to expand their realm through conquest and diplomacy. In 1487, they were about five years into an intermittent ten-year military campaign to secure Al-Andalus, the emirate of Granada on Castile’s southern frontier, and end the centuries-old reconquista to eliminate the Muslim presence on the Iberian Peninsula. They were also beginning to arrange marriages for their five children, to secure dynastic alliances with England, Portugal, and the Holy Roman Empire. Their eldest, Isabel, who was seventeen when Columbus had his first audience with the queen, had been betrothed as a child to the Portuguese crown prince, Afonso, son of João II, as a means of healing the Iberian rift.

Jerome Münzer would meet the queen Isabel at Madrid in January 1495. He judged her plump—an impression upheld by her wedding portrait—but with a handsome face, and while he thought she was forty-eight (she was actually forty-four), he decided she could pass for thirty-six. He praised her capabilities as a ruler in both peace and war, possessing almost all virtues, “beyond what one would expect to find in someone of the female sex.” Like other commentators, he noted her devotion to Christ and generous support of churches and monasteries: “She is profoundly religious, very pious, full of indulgence.”

Piety did not save her from suspicions of infidelity, which had caused such chaos in the succession schemes of her forbears. (Fernando himself was no shining example of fidelity, as he sired at least a half dozen illegitimate children, some of them before his marriage to Isabel.) “Up to now,” Münzer observed after meeting Isabel at Madrid, “when the king was not here, she always slept in a common chamber with her young servants, male and female. But now, she sleeps with her children and several noble women, so as not to risk being stained by the infamy of adultery. It must be said that the people of Castile are very mistrusting and always think the worst.”

Whether it was because of her personal inclination, the connections to her and the Castilian court that could be leveraged at La Rábida, the links between Isabel and Columbus’s late wife’s family, or the fact that Castile rather than Aragon fronted on the Atlantic, it was Isabel rather than Fernando who took the lead role in the Spanish monarchy’s consideration of Columbus’s plan.

Columbus would praise Isabel’s support of his plan, to the exclusion of all others (including Fernando), in a letter in 1500: “In all men there was disbelief, but to the Queen, my Lady, [God] gave the spirit of understanding, and great courage, and made her heiress of all, as a dear and much loved daughter. I went to take possession of all this in her royal name. They sought to make amends to her for the ignorance they had all shown by passing over their little knowledge and talking of obstacles and expenses. Her Highness, on the other hand, approved of it, and supported it as far as she was able.”

Juan Rodríguez Cabezudo of Palos, who would claim to have watched over young Diego while Columbus was away on the first voyage, recalled renting to Columbus a mule so he could send “a friar of St. Francis” to court to negotiate on his behalf. He testified how “many people made jest of the admiral about the enterprise he undertook in going to discover the Indies and they laughed about it and even reproached this witness because he had given the mule, and that publicly they made jest of him and held the enterprise as futile, which he heard many people say publicly in this town [Palos] and even outside it.” Like others to give evidence, Rodríguez Cabezudo insisted “if the old admiral had not discovered what he discovered, no one would have gone to discover.”

Dr. Fernández too recalled the mule. Secretly before midnight, the prior Pérez climbed onto the animal at La Rábida and headed to court to confer with Isabel, who soon assented to the voyage. The physician also recalled how Isabel sent twenty thousand maravedis “in florins” to Diego Prieto of Palos, to provide to Columbus “so he could dress respectably and buy himself a good mount and appear before her majesty” and secure his capitulation. Rented mules would not do.

Columbus had also sought a noble patron, attempting to insinuate himself with the dukes of Medina-Sidonia and Medinaceli, both of whom had coastal power bases in Andalusia. He may have joined the staff of Luis de la Cerda, first Duke of Medinaceli, who, like Enrique de Guzmán, the second Duke of Medina-Sidonia, was active in the war for Granada.

Although Columbus’s 1492–93 voyage journal suggests that his initial proposal was made on January 20, 1486, he is believed to have appeared at the siege of Málaga in 1487 at the behest of Isabel, as the Castilians began the final push to starve out the inhabitants of the port city in Granada and sell the Muslim residents into slavery around the Mediterranean. The initial voyage discussions, however, amounted to nothing. A learned council similar to the one formed by Portugal’s João II found Columbus’s proposal full of conceptual faults, among them an Earth too small in diameter and an Asia too close to the West. In any event, the proposal could not be entertained properly until Spain had completed its conquest of Granada. And that was more than four long years away.

SOON AFTER CHRISTOPHER COLUMBUS fled Portugal and the wrath of João II, John Cabot too was on the run. He bolted Venice as an insolvent debtor at some point prior to November 5, 1488, when the Venetian government issued a license recognizing a fairly significant debt, of 212 ducats, before court costs, owed by Johannes Caboto and his brother Pietro (Piero) to Tommaso Mocenigo and Paolo Rizzardo. The license would allow agents of the creditors to pursue the Cabot brothers beyond the bounds of the Venetian republic.

Virtually nothing is known about Rizzardo, beyond the fact that he was a steward of the procurators of the sestier or district of San Marco in 1509. Tommaso Mocenigo had a more extensive and intriguing curriculum vitae. He may have been from the same branch of the Mocenigo family that spawned three doges, and he would be elected mayor and captain of Treviso in 1494, mayor of Padua in 1501, and serve as one of three procurators, or patrician administrators, of the foremost Venetian sestier, San Marco, during which duties he was served by Rizzardo, his co-creditor of Cabot from 1488. His family had been active in merchant affairs in England; about one-third of goods transported by the Flanders Galleys from England in the early 1480s were directed to Marin Mocenigo, the son of the creditor pursuing the Cabotos. In April 1486, Tommaso Mocenigo acted on behalf of his deceased son in a legal case involving business in London.

There is no clue as to how or why the Cabot brothers fell afoul of a Venetian noble as prominent as Tommaso Mocenigo, although it could have had something to do with trade in English wool or hides. Nothing further would be heard of Pietro Cabot, but John Cabot was in for even stormier weather. On November 18, a “letter of recommendation to justice” was countersigned by a notary of the Venetian court in the name of the doge, Agostino Barbarigo, in favor of another daunting creditor of John Cabot alone. The letter empowered local authorities beyond Venice to act on the creditor’s behalf to bring the fugitive debtor to justice.

The letter was given to a young noble, Vincenzo Cappello di Nicolò, to carry to Milan on behalf of his father, Nicolò Cappello. The elder Cappello was an important figure in Venetian maritime affairs and trade. In 1480, he was caught up in a short-lived trade dispute between Venice and England. As captain of the Flanders Galleys, he had been barred from loading English wool at Southampton, when Edward IV tried to restrict the export to Florentine vessels. The surprising news generated a diplomatic protest to Edward IV from the Venetian doge, Giovanni Mocenigo, who was quite likely a relative of Tommaso Mocenigo, Cabot’s 1488 creditor.

In May 1488, Nicolò Cappello was commissioned as one of two directors of the Venetian fleet at Cyprus under the captain-general of the sea, Francesco Priuli. He moved to the Aegean that October when Priuli was recalled by the senate, just before the letter was secured from the Venetian court to pursue Cabot for bad debts. His son Vincenzo, dispatched to hunt down Cabot, would be a captain of the Flanders Galleys in 1504 and a supplier for the Venetian fleet in the eastern Mediterranean in 1512.

Nicolò Cappello was claiming from Cabot a considerable obligation of 981 ducats, which included his court costs. The debt may have arisen from a business Cappello had helped form in September 1487, in which Cappello was obligated to import wool from a northern source, probably England. Cabot may have been an intermediary or a merchant expected to provide the wool, and the size of the debt would suggest he had received funds to make a purchase he did not actually complete.

Vincenzo Cappello was to present the letter to the Venetian ambassador in Milan, Ermolao Barbaro, to bring to the attention of the duchy’s authorities. Should Cabot not be found within the duchy, an additional letter was to be taken to Turin to present to Charles I, Duke of Savoy (which didn’t have a Venetian ambassador), in the event that Cabot had fled to his realm.

Above and beyond the specific debts owed to Rizzardo, Mocenigo, and Cappello, military unrest in the Levant already may have pressed Cabot into dire straits by forcing the end of his usual merchant activities or inflicted a debilitating financial loss. Although the Ottomans had withdrawn from a campaign into northern Italy in 1481, they were at war in the Levant with the Sultan of Egypt from 1485 to 1491.

The Scuola Grande of San Giovanni Evangelista was supposed to take care of members who had fallen on hard times. If he still belonged in 1488, Cabot was either above asking for such charity or beyond hope. He surely left the republic with his wife and children. His status as an insolvent, possibly bankrupt debtor made him liable to arrest and imprisonment and the confiscation of his possessions.

Being incarcerated in Venice could be less mortifying than in many European jurisdictions. The Holy Land pilgrim Felix Fabri of Ulm, who passed through Venice twice in the early 1480s, wrote of prisons that were “beneath the walkway of the [Doge’s] Palace, looking out towards the public square, and are lit by open windows barred by iron grilles, through which the prisoners can look out.” In one he saw “rich men of business confined, but dicing and playing chess, and their wives and maids and servants stood talking to them through the bars. . . . They deliberately guard many prisoners with less care and allow them the chance of flight, especially where they think the opposing party has been unduly harsh, and so they mind little when such people break out and make off—as a few years ago a merchant of Ulm broke through the vaulting and escaped from custody.” In another he saw “imprisoned artisans sitting and working with their hands at their trades and earning money.”

But unless you were the right sort of prisoner who had committed the right sort of crime, being locked up in Venice was nothing to be envied. In still another prison Fabri saw “more than forty poor creatures going about and crying out for charity; in another I saw poor women calling for alms.” Cabot was not going to chance such a fate for himself or his family. The letters issued for his creditors suggest that he was believed to have escaped overland through northern Italy to the duchy of Milan, which also ruled the republic of Genoa, or to Savoy, on Genoa’s frontier. But as early as 1490, John Cabot had moved on to Spain, specifically to Valencia, most certainly with his family. He surfaced in a letter written on September 27, 1492, as “Johan Caboto Montecalunya, the Venetian” (johan caboto montecalunya venesia) who “arrived at this city two years ago.”

The name Montecalunya, which is otherwise unexplained, suggests that he had spent time in the neighboring region of Catalunya (alternately Calunya, or Catalonia), perhaps in the mountainous region of the Catalan Pyrénees, far from the reach of the merchants seeking to exact payment. He may have cooled his heels there in Roussillon, a disputed county of Catalunya that remained in the hands of French troops until it was returned to Spain through the Treaty of Barcelona in January 1493. And although Cabot may have moved down from Catalunya’s high country to Valencia, his creditors did not lose his scent. Cabot the pelt trader and property speculator was being herded by his financial misadventures into Christopher Columbus’s world.

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