THE NIÑA, the Pinta, and the Santa Mariá, the most famous flotilla in the history of seafaring, departed Palos within sight of the monastery of La Rábida on Fri day, August 3, 1492, clearing the bar of Saltés at eight in the morning. Columbus planned to ride the trade winds some six hundred miles southwest to the Canary Islands. One hundred miles was a good day’s run, and they made brisk progress, approaching the nearest of the seven main islands in the archipelago, Lanzarote, which is about fifty miles off the coast of Africa, on August 7.

Surrounded by the Ocean Sea, Columbus was awash in personal debt. The crown had arranged for the Niña and the Pinta, but Columbus had turned to a Florentine merchant and slaver in Seville, Gianotto di Lorenzo Berardi, to fund his charter of the Santa María.Berardi and Columbus may have known each other in Portugal. Las Casas would assert that when Columbus wrote to Paolo Toscanelli, he entrusted the letter to the care of a Florentine merchant in Lisbon named Lorenzo Berardo (the Fernando Columbus biography changed the name to “Girardi”), who was traveling back to Tuscany. Berardi began appearing in notarial records in Seville in 1486 and served as a local factor for the Medici bank.

Columbus’s fellow Genoese formed the largest self-governing community of extranjero (foreign) merchants in the city. The Ligurians had been active in Andalusia since the twelfth century and were already established in its capital, Seville, when it was under Muslim rule, prior to the 1248 reconquista. In 1492, the Genoese Francisco de Riberol (Sir Francesco de Rivaroli), who would become one of Columbus’s chief financiers, formed in Seville a compañia or partnership with two other men. One was the Florentine Berardi; the other was an Andalusian noble, Alonso Fernández de Lugo, a veteran of the subjugation a decade earlier of Gran Canaria in the Canary Islands. The trio was embarking on a conquest of lush La Palma, the most northwesterly island in the Canary archipelago, at the very moment Columbus was sailing in the same direction.

The Canary Islands had been assigned to Spain under the Treaty of Alcáçovas in 1479, but the islands of La Palma and Tenerife were still in the hands of the indigenous Guanches. Drained financially by the decade-long struggle to conquer Granada, for which they had borrowed from Genoese financiers like the Spinolas, the Spanish monarchs were content to privatize the acquisition of the remaining Canary Islands. Riberol and Berardi put up the cash, Lugo the military know-how. Each man had an equal share of the spoils, including a 700,000-maravedis prize promised by Fernando and Isabel if the conquest was completed within a year.

Riberol may have met Columbus in Granada in early 1492, as the terms of Lugo’s La Palma conquest were being negotiated at the same time as Columbus was securing his capitulation for the first Indies voyage and arranging to borrow from Berardi the money for theSanta María charter. The relationship between the two enterprises may not have ended there. Columbus would be bound to the Canaries by the same circle of Italian financiers, by personal experience, and by one notorious lover.

THE CANARIES WERE FORMED by volcanism and are strewn across 250 miles of longitude. In the center of the archipelago is its largest island, Tenerife; the sparsely vegetated cone of El Pico del Tiede rises more than twelve thousand feet above the sea, and on clear days it wears a necklace of cumulous clouds well below its squat peak. Tiede was active in 1492, erupting from the northwest rift, Boca Cangrejo. Columbus “saw a great fire issuing from the peak of the island of Tenerife, which is extremely high.”

Columbus’s little fleet spent almost an entire month in the Canaries, from August 9 to around September 6, in a most curious layover. As the three ships approached the archipelago, the Pinta twice unshipped her rudder, which Columbus blamed on sabotage by her co-owner, Cristóbal Quintero, and another sailor, who allegedly didn’t want to make the voyage. (Whatever Columbus’s misgivings on the first voyage, Quintero would serve as the master of the flagship of the second voyage.) The Pinta was directed to the main island of Gran Canaria, where Columbus initially hoped to leave her behind and replace her with another vessel. Instead, he had her rudder repaired and her rig converted from triangular lateen sails to square sails, which were more efficient when running before the prevailing trades.

While the Pinta was being refitted, Columbus sailed (perhaps with both the Santa María and the Niña) one hundred miles to the west to Gomera, the small island between La Palma and Tenerife, the two landfalls still under the control of the Guanches that Lugo and his partners Berardi and Riberol were aiming to subjugate. Columbus reprovisioned at Gomera, taking on wood, water, and meat, but first had to sail back to Gran Canaria to collect the Pinta on September 2 before bringing aboard the supplies at Gomera. The flotilla at last departed Gomera on September 6.

The Las Casas abstract of Columbus’s journal never explained why he chose to bide time at Gomera while the Pinta was being refitted so far to the east, as the distance needlessly complicated his communications and preparations for the coming ocean passage. The least seamanlike but most romantic explanation is that he was remaking his acquaintance with a lover.

Columbus would also call at Gomera in 1493 and 1498. His childhood friend Michele da Cuneo, who was along on the second voyage, would write in 1495 that they paused at Gomera in October 1493 “because of the lady of the place with whom our lord admiral had once been in love.” At some point in the past, Columbus had conducted a passionate affair with the island’s governor, Beatriz de Bobadilla.

Doña Bobadilla was a notorious beauty. Born at Medina del Campo in 1462, she joined the court as a lady of honor to Isabel at age seventeen and is said to have become a mistress of Fernando. Isabel got rid of her by arranging to marry her off to Hernán de Peraza, governor of Gomera, in 1482. Peraza had been summoned to answer charges that he was complicit in the death of Juan Réjon, commander of a Castilian flotilla that had been sent to conquer La Palma and Tenerife in 1481. The Duke of Medina-Sidonia brokered a deal: Peraza would not be held responsible for Réjon’s death if he agreed to mount the conquest himself and to marry Bobadilla and take her with him, far from Fernando. The conquest failed to come off, and Peraza was killed in a slave rebellion in 1488, which he is said to have ignited by his advances on a Guanche woman. Bobadilla then governed Gomera in the name of their son, Guillén, who would become the first Count of Gomera. She would be remembered foremost for her tempestuous love affairs and her cruel treatment of the Guanche slaves who toiled in her sugarcane fields.

Columbus and Bobadilla could have first met at Santa Fé in early 1492, when Peraza’s widow is believed to have been at court and both Lugo’s invasion plans and Columbus’s voyage scheme were being negotiated with the crown. If so, it was an encounter crowded with portent: Not only would Bobadilla become Columbus’s lover, she would also marry Lugo in 1498, and her brother would bring Columbus home from the Caribbean in chains in 1500.

One can imagine the explorer all but consumed by the volcanic passions of Doña Beatriz at the Castillo in San Sabastián de la Gomera while Tiede spewed fire and ash to their east. But it is also an absurd explanation for how an expedition Columbus had sought to mount for years could be waylaid for an entire month only days after getting under way. Feeding some ninety men and maintaining discipline for that long was a serious burden on the little expedition. Columbus would have been fortunate even to have a fleet to command after such a lengthy delay. Rerigging and repairing the Pinta on Gran Canaria could account for some of the layover, but whatever he might have been up to with Beatriz de Bobadilla, Columbus was at Gomera at precisely the time the Lugo invasion of neighboring La Palma was being mounted.

Alonso de Lugo raised a force of nine hundred, much of it in Seville, but he also found men in the Canaries. Lugo received his royal commission on July 12 and would have established himself first in the conquered islands of the Canaries before mounting the La Palma invasion, while Columbus was in the archipelago. On August 20, a number of men on Gran Canaria and Gomera—the two islands Columbus was moving between—were contracted as foot soldiers for Lugo’s invasion force. Lugo is thought to have landed on the beach at Tazacorte on La Palma’s west coast no later than the end of September—no more than a few weeks after Columbus resumed his voyage westward.

Columbus’s venture shared many key figures with the simultaneous Canaries conquest. Isabel’s accountant, Alonso de Quintanella, played a lead role in advancing both enterprises; so did Castile’s treasurer, the Genoese Francisco Pinelo, who also administered with Luis de Santángel the Sancta Hermandad, the source of royal funding for Columbus in 1492. Given Columbus’s close relationship with the financier Berardi (and the close partnership that would emerge with Riberol), the explorer likely was serving the invasion in an advance role when he paused at Gomera. Columbus could have gathered intelligence, even scouted the landing beach at Tazacorte, and attended to logistical matters at Bobadilla’s Gomera, which became a base of operations for Lugo and a holding pen for captive Guanches. Columbus assuredly did not depart Gomera until the Lugo invasion force was prepared for the Tazacorte landing.

The Columbus expedition was a small-change venture compared to the invasion being mounted by Berardi and his partners in the Canaries. To Berardi especially, who was providing Columbus with private financing for the Santa Maríacharter, the Columbus voyage might well have seemed a side trip for the sizable Canaries venture: the Santa María at least could pitch in with advance planning for Lugo’s assault and then, having already sailed as far as the westernmost islands in the Canaries archipelago, strike out toward the setting sun with the Niña and Pinta. As the voyage journal would reveal, Columbus expected to make his first landfall within about a week, which was about as arduous as sailing from Spain to the Canaries. Even if Columbus found nothing, at least he would have been of help in launching the subjugation of La Palma. The Guanches would be enslaved, the sugarcane would be planted, the investment capital would multiply rapidly, and the profits would be able to seek new opportunities—perhaps, if Columbus proved successful, farther to the west.

Columbus departed Gomera on Thursday, September 6, and learned from a caravel arriving from Hierro (Ferro) “that three caravels from Portugal were cruising in the area with the intention of detaining him; it must have been due to the envy the King felt at his having gone to Castile,” according to Las Casas.

Columbus was becalmed that day, between Gomera and Tenerife. The stillness lasted all night and into Friday. It was not until three in the morning on Saturday that the breeze returned and allowed the flotilla to clear the archipelago. The wind blew hard from the northeast, and heavy seas broke over the ships’ bows as they struggled westward. No harassing Portuguese warships were spotted. Six months would pass before Columbus was heard from again, and by then, the fighting for La Palma was almost over.

CABOT COULD RUN, but he could not hide. The Venetian creditors he had been avoiding included merchants who conducted business in ports as far away as England; their sources were everywhere, among sailors, fellow merchants, diplomats, and bankers in their networks of European commerce. Valencia was a major trading center in the western Mediterranean, where the Venetian galleys sometimes called. Perhaps his face was recognized on the waterfront, directing reconstruction of a wave-racked wooden pier, or his name had raised eyebrows as locals chattered about this ambitious Venetian prowling the beach of Grao, making measurements and sketching a vision in cut stone.

However the word returned to the Rialto, the news spread that Cabot was no longer in Milan, Genoa, or Savoy—if he had ever been there at all. A fresh Cabot creditor appeared before the senate, securing a “letter of recommendation to justice” for Valencia on July 5, 1492. Cabot (Ionnes Gaboto) was identified along with a man named Giorgio Dominici as owing 130 ducats to Giorgio Dragan, another figure from Venice’s maritime economy. Dragan was a merchant active in the Mediterranean who had a carrack delivering wine from Crete to Flanders and Sandwich in the late 1470s. In September 1493, he would turn up in records shipping artillery and munitions on the order of the Count of Veglia, a city on the Dalmatia coast of the Adriatic.

This debt was far less onerous than the two previous ones that engendered letters designed to bring Cabot to justice. And by the time Dragan had the letter in the hands of Valencia’s ruling jurors, Cabot probably wasn’t even around, doubtless having decamped to Barcelona with Gaspar Rull to patiently wait, for months if necessary, an audience with Fernando for his harbor scheme.

Two years later—and only weeks before his travels caused him to truly converge with Cabot’s life and career—Jerome Münzer made his own September visit to Barcelona, the largest city in Aragon’s principality of Catalonia. He was impressed by the walled city and its formidable battlements, laid out in a circle on the shore of the Balearic. But ever since the Catalonian civil war of the 1460s, Münzer observed, commerce had been leaving Barcelona for Valencia, which had become “the market of Spain. And now Barcelona is almost dead, compared to its previous state.”

Barcelona nevertheless possessed what Valencia did not: a superb harbor. Since 1474, a mole, or breakwall, sheltering vessels from the open sea in a deeper anchoring area had been under construction; it would proceed fitfully until the mid-eighteenth century in defiance of the city’s economic decline. Valencia may have been capturing Barcelona’s wealth, but what Valencia needed was Barcelona’s port facilities. Cabot proposed to deliver the latter. With Gaspar Rull likely along to finesse the courtly introduction, Cabot had set out for Barcelona. In the process, he had given yet another creditor the slip, for the time being. Perhaps Cabot adopted the additional name Montecalunya in hope of shaking his pursuers.

Despite the change in the cities’ fortunes, Fernando and Isabel still chose Barcelona rather than Valencia as a home for their roving court, which moved between major centers in Castile and Aragon throughout the year. The palace where the monarchs stayed, Münzer related, was so beautiful, so admirable, as to be without equal. “All the rooms of the palace have floors covered with clay tiles baked with drawings in various colors. The ceilings are all covered with very pure gold, adorned with diverse golden flowers. What a superb palace!”

John Cabot would have made his presentation to Fernando amid this royal splendor. The monarch was then forty years old. After meeting him at Madrid a few years later, in January 1495, Münzer described Fernando as a man of medium height, in whose face cheerfulness and congeniality were mixed with a certain gravity. Portraits depicted him with a long nose, a full if pursed mouth, cheeks ample to the point of jowly, and a weak double chin. “He acts only with great things in his heart,” wrote Münzer. “He enjoys an excellent constitution.” Münzer expected Fernando to continue to be fit for a long time because of his hunting pursuits. “Now that the kingdoms are peaceful and everything has been returned to good order, he is concerned especially with religion, restoring ruined churches and founding new ones.”

Fernando’s life wasn’t half as idle in early 1495 as Münzer suggested, but it would have been far more contemplative when Cabot met him in September 1492, nine months after the end of the lengthy and costly Granada campaign. Still, Fernando’s recent decisions to evict all Jews who did not convert to Christianity from his kingdom and to sell Moors captured at Málaga into slavery spoke of a ruthlessness that would account for the gravity Münzer later detected mingling with cheerfulness and congeniality in his face.

Cabot laid out the drawings before Fernando and explained the concept. Unfortunately neither the drawings nor a record of the presentation’s details have survived, although we can surmise what he had in mind. Valencia’s shipping facilities were feeble for such a major economic center. The river Turia on which it fronted was too shallow for major ocean traffic, but earlier proposals to dredge it had been rejected. On May 28, 1483, the year after construction began on Valencia’s new trading facility, La Lonja, a man named Antoni Joan secured a privilege from Fernando to develop the city’s first coastal port infrastructure: a wooden pier on the beach of Grao (la playa del Grao) on the north side of the mouth of the Turia. The city further granted him the exclusive right to operate the pier, which became known as the Pont de Fusta (meaning in Catalan simply “wooden bridge” or “wooden deck”). The pier cost ten thousand florins to build and another six hundred florins a year to maintain. Exposed to the Balearic, it was soon in such disrepair that Joan wanted to fashion a replacement, and on March 17, 1491, he renewed his privilege with Fernando.

Antoni Joan’s pier refurbishing seemed more than coincidental with John Cabot’s arrival in Valencia about two years before September 1492 and his subsequent interest in creating an artificial harbor at the same beach. The foundations of Pont de Fusta have survived beneath the modern streetscape of Valencia and its extensive harbor works. The cribs of loose rocks corralled in wooden frames are the type of construction employed in building foundations in Venice. Cabot could have been involved with the construction of the new Pont de Fusta from the earliest days of his appearance in Valencia; if so, he would have recognized that this pier was doomed to repeated replacement unless it was adequately protected. Valencia needed what Barcelona was receiving: breakwalls. A surviving letter mentions “arms” as part of the Cabot plan, which indicates at least two breakwalls creating a sheltered harbor area. But another letter also mentions a jetty, which suggests a project in direct competition with Joan’s modest Pont de Fusta. And Joan was noticeably absent from Cabot’s proposal.

The royal response to Cabot’s pitch was superlative. Fernando wrote the governor-general of Valencia, Diego de Torres, on September 27, 1492, three weeks after Columbus’s fleet had departed Gomera for the western horizon. The same king who had renewed Joan’s privileges for the Pont de Fusta eighteen months earlier was impressed by Cabot’s presentation.

Fernando explained how

we have been informed by Johan Caboto Montecalunya, the Venetian, that he arrived at this city [Valencia] two years ago, and during this time he has considered whether on the beach of this city a port could be constructed, and on finding that the aforesaid port could be constructed very easily both on land and sea, he has designed and painted plans of them, and he has brought them to us; and, having seen them and heard the aforesaid Johan Caboto, it appears to us if the said port and jetty could be constructed in the sea just as in the plan he has brought here, it would be something which would result in a great benefit for the common weal of this kingdom.

Fernando asked Torres to form a committee to examine the specifics of Cabot’s plan, which involved quarrying stone from Cap de Cullera, a coastal promontory twenty miles south, and moving it to the construction site by barge. It was a process Cabot surely knew from his Venetian experience: Stone used in construction in the Signoria was quarried in Dalmatia and ferried along the Adriatic.

The committee reported back to the king on October 25 with a list of issues it said needed to be investigated. The list included how much sand or clay was in the proposed beach construction site, the depths in the beach area where Cabot proposed to construct the arms of the harbor, the depths of water for barges, and the expense and logistics of quarrying the stone. Stone cutters would have to be sent to Cap de Cullera “to cut stone of the size which the said Johan Cabot will indicate, and to have a boat carry it over the said shore and to see more or less what it will cost to put a stone in the place where the said port must be constructed.” Once they could calculate how many stones were required for the depths of the waters in which Cabot had chosen to build, they would “have some idea of what the said port and jetty will cost.”

Torres praised Cabot’s choice of stone from Cap de Cullera: “[I]t is of such a nature and so good for carrying and cutting that nobody could ask for so good a stone as it has been found, in price and expense, for progress in the said work.” Torres was generally optimistic about the plan’s prospects and fairly persuaded of the benefits: “[M]any have argued that the building of this port will ennoble and enrich this city and even the whole kingdom.”

Compared to Columbus’s exploration scheme, Cabot’s harbor project was pragmatic in the extreme, a civil engineering works with indisputable benefits. But the poorly conceived and interminable breakwall project at Barcelona may not have encouraged broad and unquestioning enthusiasm for Cabot’s claims of easy execution. And the sticking point was the same as it always had been for Columbus’s voyage proposal: how to pay for it all.

Cabot meanwhile appeared to have given his latest creditor the slip; he was able to return to Valencia and leave again for Barcelona without apparent incident. He and Rull were en route to another meeting with the king, and as Torres explained in his letter (which Rull was carrying), they “will tell Your Highness orally some expedients for obtaining money for building the said port; when Your Majesty hears that, you will see which is most satisfactory and least burdensome for Your Majesty and least harmful for this city.”

Torres advised Fernando to consult his general treasurer and the royal financial scribe, both of whom (as Torres reminded him) were in Barcelona. The general treasurer was Luis de Santángel. Indeed, as a Valencian tax farmer who had just masterminded the financing of the Columbus expedition, surely Santángel could figure out for Fernando how to pay for a long-overdue artificial harbor for such a crucial economic center.

These men, Torres counseled, “are very knowledgeable in the affair of this city and kingdom. From them Your Highness will be able to obtain a full relation of where the money can come from.” Torres was concerned that the project would never proceed if the city’s lieutenant-general and its ruling council, the jurors, were left to decide how to fund it: If they “had to see where [the money] had to come from, they would never agree, but only Your Highness can best see what is most satisfactory for your service and order it to be put into execution.”

On the day Torres wrote the letter that Rull and Cabot were carrying to Fernando at Barcelona, Christopher Columbus was guiding his three ships through the low-slung islands of the Bahamas to deliver a letter of his own. He had been in the archipelago for almost two weeks and was steering for a group of “seven or eight islands in a line from north to south”—the Ragged Islands on the southeastern edge of the Great Bahama Bank. Columbus was carrying a greeting from Fernando and Isabel that he had every hope of presenting shortly to the Great Khan, ruler of Cathay.

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