Jewish Pirates of the Caribbean: How a Generation of Swashbuckling Jews Carved Out an Empire in the New World in Their Quest for Treasure, Religious Freedom--and Revenge

May 1504, Santa Gloria, Jamaica: For nearly a year, Columbus had been stranded in Jamaica with a hoard of gold, a mutinous crew, and a few dozen teenage loyalists, some of whom were secret Jews. Alone, melancholy, and confined to his cabin by gout, the great explorer wrote his patron Queen Isabella a despairing letter. He feared that even if he defeated the mutineers, the governor of Santo Domingo, who had promised to send a rescue ship, wanted him dead.

So much had happened since he had been making the rounds of Europe, a would-be explorer going from king to king seeking royal backing for a promised quick passage west across the Ocean Sea to India and the wealth of the East. In 1486, at his first meeting with Spain's royal couple, King Ferdinand, although intrigued by the plan, told Columbus the time was not opportune. They were in the midst of a war and could not seriously consider such an important matter until peace was restored. In parting, Queen Isabella counseled patience and awarded Columbus a retainer, promising they would meet again when the war was over.

On January 12, 1492, Columbus entered the royal quarters. He had been summoned a few days after Spain's final victory over the Moors at Granada, and the queen had sent him money to buy new clothes and a mule to ride. Encouraged by her gift, Columbus was confident. He had honed his proposal into a detailed presentation, with maps and charts from the Jewish astronomer Abraham Zacuto, and quotes from the Bible and Greek sages supporting his view that the world was round, the oceans not large, and Japan lay three thousand miles to the west, across the Ocean Sea. Prepared for questions, he received none.

After an unsettling silence, Ferdinand spoke. Victory over the Moors had emptied the treasury, he said. Moreover, he could not abide Columbus's demand for hereditary rule over lands he might discover. The queen, his admirer, said nothing. The meeting broke up and Columbus left, angry and disgusted. All this time he had waited for the war to end. Now that it had, Ferdinand was pleading poverty. Pausing briefly in the corridor, he informed the king's treasurer that he was leaving for France where Bartholomew, his younger brother, was arranging an audience with the king. If that monarch wasn't interested, he would cross the channel to meet with the English king. He would not be denied his dream, one that, as Cervantes wrote of Don Quixote, "He hugged and would not part with even if barefoot friars had begged him."

Before Columbus rode past the gates of Santa Fe, the royal treasurer, Luis de Santangel, sought and was granted an audience with Queen Isabella. The royal chronicler noted, "[Santangel] appeared distressed as if a great misfortune had befallen him personally." He had good reason: Santangel was a secret Jew, and as a member of the royal court, he was aware his people were about to be expelled from Spain. There were upward of a half million Jews in the country they had called home since the time of Christ. Where would they go? India? China? Perhaps the explorer Columbus would discover a new land somewhere. Santangel and other secret Jews in the royal service hoped Columbus's voyage would provide an answer.

The Inquisition mandated that Jews, under penalty of death, must either leave or convert to Catholicism. Santangel, like many others, had converted and became a New Christian. If discovered Judaizing, the converts were liable to be burned at the stake. The Santangel family, long established in Spain, was among the first targets of the Inquisition. Luis's cousins had gone up in flames in Saragossa, and only the intervention of Ferdinand had prevented Luis from suffering the same fate.

Santangel addressed the queen. He was astonished, he told her, "to see Her Highness who has always shown such resolute spirit in matters of great consequence, should lack it now for an enterprise of so little risk for so vast a gain." He spoke to the queen of the wealth to be acquired, and the great service she would render to God, "all for the price of a few caravels [ships]." Alluding to Columbus's plan to seek royal backing elsewhere, he cautioned Isabella, "It would be a great damage to Her Crown and a grave reproach to Her Highness if any other prince should undertake what Columbus offered Her Highness." If money was a consideration, Santangel said, he would be glad to finance the fleet himself.

A mounted messenger caught up with Columbus as he was crossing the Bridge of the Pines, seven miles from Santa Fe, and bade him return. Later that day, with all parties again gathered in the royal quarters, the king informed Columbus that the Crown would sponsor his Enterprise of the Indies, and meet his demands. No mention was made of hereditary title. Two months later, it was still a stumbling block in his negotiations when an event occurred that made its inclusion mandatory.

On the morning of March 31, 1492, Columbus was in his room in Santa Fe overlooking the main square when the sound of trumpets brought him to his balcony. Below, the town crier, flanked by mounted guards, read the expulsion order of the Inquisition: Jews had four months to leave. After that, any "caught in Our domains will be punished without trial by death, and seizure of property."

The Jews of Spain had been threatened with expulsion before. Rulers since the Visigoths had used this threat to extract more money from them. A period joke compared the Jews to a "money box" that you break open when you need money. But this time it was different: The Church was involved.
To the Jews of the royal court who supported Columbus, the expulsion order made it essential that Columbus hold out for hereditary rule. If no Asian kingdom welcomed Jewish refugees, Columbus, as the ruler of a new land, would be able to provide a haven for Spanish Jews.

It is thought that Columbus himself was a descendant of Spanish Jews, the Colon family, who had converted and moved to Genoa a century before on the heels of the Massacre of 1391. Some even contend he was a Cabalist. Whatever his genealogy, he was in sympathy with the People of the Book, and they with him. In his early years, in Portugal and Spain, he lived in a largely Jewish and New Christian world of navigators, cartographers, astronomers, and mathematicians. While others looked askance at this wandering sailor and laughed at his dream, Iberian Jews and conversos assisted Columbus in developing his Enterprise of the Indies. In their learned circles, they dealt with a round world. Church geography did not apply to them.

On April 17, Columbus agreed to the Capitulations of Santa Fe, which limited his rights to lifetime rule. Two weeks later, this ruling was reversed, and Columbus was granted hereditary rule. No account exists of the final negotiations, but it is likely that court Jews, facing the forced exile of their people, counseled Columbus to hold firm to his demand. One imagines a scene in the royal chambers with Santangel persuading the royals that the explorer's demand should not trouble them. If his voyage were successful, Columbus and his crew of ninety men could not possibly subdue one of the powerful Asian nations. On the other hand, if he took possession of a few islands along the way, the Crown would benefit by having way stations for Spain's trading ships plying the shortcut passage to the wealth of the East.

Whether or not such a scene took place, Ferdinand finally relented: Columbus would sail with his right to rule any new lands he discovered, to be "enjoyed forever by his heirs and successors."

After Columbus returned from his successful first voyage, he made three more trips across the Western Sea. He never reached Asia, and didn't live long enough to fulfill his pledge to Santangel and the court Jews to provide a homeland for converted Jews. But it would be kept by his family in the "new land" the Crown did bequeath to Columbus's descendants, the island of Jamaica. How this came about goes back to a promise he made to the teenage conversos who stood by him when he was marooned there.

Returning from his fourth voyage to the New World, Columbus had been forced to beach his ships in Jamaica after sailing from Panama with a cache of gold objects bartered from the Indians. His two ships were leaking badly. Columbus hoped to reach Santo Domingo to obtain others to return to Spain. But his worm-eaten caravels, described by his son as "more full of holes than a bees' honeycomb," barely made Jamaica. With water rising in their holds, he ran them aground and lashed them together in a shallow, becalmed bay on the island's north coast, "a cross bow's shot from land." Atop his foredeck he fashioned a palm thatch hut to serve as his cabin.

In his first letter to the queen, written soon after he arrived, he bragged that he had discovered the source of Solomon's gold in the mines of Panama, and claimed to have seen more gold in a few days there than in all his previous trips. His fourteen-year-old son Fernando, brought along as cabin boy, later recorded that his father had traded small bells and mirrors for sixty-three gold pendants and other gold objects with the Veragua Indians of Panama.

This was his second trip to Jamaica. When he had discovered the island in 1494, he had named the half-moon bay where he was now stranded Santa Gloria for "the beauty of its glorious landscape." After a year, he thought he might never leave. Was this where his life was to end? Uncertain of his future, he wrote his queen:

We have been confined 10 months, lodged on the decks of our ships. My men have mutinied. My brother, my son, and those that are faithful are sick, starving and dying. Governor Ovando of Santo Domingo has sent to see if I am dead rather than to carry me back alive. I conclude Your officers intend my life should terminate here.

The object of his cynicism was the arrival the previous week of a ship from Ovando. It had anchored outside the reef in the late afternoon, and left before dawn. Before sailing away, its captain ferried over a side of ham, a barrel of wine, and a message from the governor that a rescue ship would soon be sent.

The governor's message did confirm the safe arrival of Columbus's first mate, Diego Mendez, who ten months before had set forth in a dugout canoe to carry news of their plight to Santo Domingo. But, as he wrote the queen, he really believed the ship had been sent "to spy on how I might be totally destroyed."

Made furious by his suspicions, Columbus concluded his letter with an angry vow. Should he die in Jamaica, and his proprietary rights be withdrawn, "ingratitude will bring down the wrath of Heaven, so that the wealth that I have discovered shall be the means of stirring up all mankind to revenge, and the Spanish nation shall suffer hereafter."

Fortunately for Columbus, Isabella never received his threat. Having no way to send this letter, Columbus could only call on "the good angels that succor the oppressed and innocent to bring this paper to my great mistress." Apparently no Heavenly couriers were listening as this little known letter never left the island. His earlier letter, carried by Mendez, had been forwarded to her from Santo Domingo.

The mutiny referred to in his despairing missive had broken out five months earlier, when Francisco Poras, captain of one of the ships, burst in on the admiral in his straw cabin and demanded they leave at once. He and his brother Diego, the fleet's notary, accused Columbus of having deliberately marooned them in Jamaica knowing he was unwelcome in Santo Domingo. The Poras brothers' insurrection was joined by most of the older seamen, who after six months in Santa Gloria wanted out. Columbus declared he would not leave, but rather than battle the mutineers, agreed to let them go.

Crying, "I am for Castile--follow me," the rebel leader seized the dozen canoes Columbus had bartered from the Indians. Forcing the natives to row, the rebels made three attempts to overcome the fierce currents of the 108-mile-wide channel to Hispaniola. On their final try, they gave up, though only after throwing eighteen Indian paddlers overboard, and chopping off the hands of those who clung to the side. Five months later, after a two-week march across the island, marked by rape and pillage, they were encamped in an Indian village a half mile from Santa Gloria, intending to seize the admiral's ships.

Columbus had just finished his troubled letter to the queen when the two men he had sent to parlay with the rebels returned. They had taken an offer of pardon and a promise that they would soon be rescued. But Poras rebuffed them.

When his emissaries reported that Poras's men were preparing for battle, Columbus withdrew to his cabin in despair. But Bartholomew, his fierce younger brother, convinced him to take the fight to the enemy. He armed the fifty young loyalists and set forth to attack the rebel camp. When the mutineers saw Columbus's teenage army approach they laughed. There was no way mere youths, "brought up in a softer mode of life," could defeat such "hardy sailors, rendered robust and vigorous by the roving life." But the rebels' confidence was premature: In a superhuman effort, Bartholomew slew the six mutineers sent to attack him, and had the point of his sword at Poras's breast when the rest surrendered. The Poras brothers were put in irons aboard ship, and the forty-eight rebels were disarmed and kept on shore. With peace restored, a reunited, mistrustful crew nervously awaited their promised rescue.

Even if Ovando did send a ship, Columbus had little faith his gold medallions would be safe in Hispaniola, whose previous governor, he wrote the queen, "robbed me and my brother of our dearly purchased gold." He expected no less from Ovando. During the tense five weeks before two rescue ships arrived (one sent by Mendez, the other by Ovando), he rarely left his cabin. Never again did he set foot on Jamaica.

What happened to the gold of Veragua? The Crown had instructed Columbus that if treasure was found, "you must draw up an account of all this in the presence of Our Notary_._._._so that We may know everything that the said Islands and Mainland may contain." Yet the sixty-three medallions from Panama are not mentioned in the notary's account, nor are they listed in the inventory of the ship that brought him home to Spain. Unsure his gold would survive Ovando's rescue, Columbus would not have left the gold in Hispaniola. Columbus also had reason to fear a renewed mutiny on the way back to Spain. It is therefore unlikely that he kept the gold with him.

That leaves Jamaica. Since he never left the ship, and trusted no one but his son and brother and a core group of loyalists, he presumably asked members of this latter group to transfer his gold to safety.