Jewish Pirates of the Caribbean

To my daughter, Eliza


puzzling entry in a pirate’s journal jumped out at me. Invading Jamaica in 1643, William Jackson found the island’s capital deserted except for “divers Portuguese of the Hebrew nation who came unto us seeking asylum, and promised to show us where the Spaniards hid their gold.” I had always learned that early New World adventure was the province of Spanish and Portuguese conquistadors, and that they were all devout Catholics carrying the cross. So what were Portuguese Jews doing on a Spanish island, seeking asylum with an English pirate?

It was 1967. I had moved to Jamaica from New York, and came upon Jackson’s journal in the reading room of Jamaica’s national library while perusing contemporary accounts of the island’s buccaneer beginnings. I was more than intrigued. I wanted an answer.

What I next learned was startling: Before England conquered Jamaica in 1655, the island belonged to the family of Christopher Columbus, who provided a haven for Jews otherwise outlawed in the New World. The leader of the Jewish community, the late Sir Neville Ashenheim, went even further, telling me that Columbus was a Jew, and that Jamaica’s Jews traced their ancestry to the first settlers.

I was so beguiled by these findings that I would spend the next four decades following their lead and unfolding an unknown chapter in Jewish history. Forget the Merchant of Venice—his New World cousins were adventurers after my own heart: Jewish explorers, conquistadors, cowboys, and, yes, pirates.

Forbidden to settle the New World, they came disguised as Christians. They and the other settlers were similar in spirit, but while the others came to conquer, convert the heathen, search for gold, or collect a bevy of Indian women, the Jews came to escape persecution and settle a land beyond the tentacles of the Inquisition.

The story begins with Columbus and the Age of Discovery, when secret Jews sailed with the explorers, marched with the conquistadors, and were among the first settlers in every New World colony. This early history is largely unknown because few then or since realized that these pioneers were Jewish. Forbidden entry in the New World because of their religion, Iberian Jews posed as New Christians from Portugal, the one settler group that was not required to prove their Catholic ancestry. Most Portuguese operating in the Spanish Empire were New Christians, commonly called conversos, and many maintained their allegiance to their ancestral faith.

They were Esperandos, Hopeful Ones, who expected that the Messiah would soon come, and that He, like them, would appear in the guise of a Christian and so forgive their apostasy. Until then, whatever it would take to get by in the enemy world was not deceit, but strength. As Esperandos, Jews in the New World lived and prospered. Unless exposed by the Inquisition, they went to their graves with their masquerade intact, though even death offered no assurance, as dead heretics were tried in absentia. If found guilty, their bodies were exhumed and burned, and their property confiscated.

Arriving first as explorers and conquistadors, they and the Jewish pioneers who followed soon focused on a field of expertise that had sustained them and made them welcome in the Diaspora. A mercantile people, Jews in the New World went about their business as traders and shipowners, thus becoming the first merchant class in the Spanish Empire. As long as they pretended to be Christian and delivered the goods, no one questioned their religiosity too closely. They set up the first sugar factories, pioneered grain, coffee, and tea cultivation, and traded sugar, tobacco, gold, and silver with covert Jews on the Iberian Peninsula.

First profits to the homeland were the underpinning of the mercantile system. Everything to and from the New World had to go via Seville or Lisbon. For most of the sixteenth century, the parties were content with the trade-off. The king needed the Jews to ensure his cash flow, and they needed him to keep the Inquisition at bay. However, once the trade network was established, Jews became expendable.

At the close of the sixteenth century, Inquisition fires caught up with them. In Mexico and Peru, where Jewish merchants controlled the silver trade, Holy Inquisitors were called in to purify the bottom line: Jewish leaders were burned, their wealth was confiscated, and Christians took over the fabulously rich silver trade. New World Jews got the message. More than profit, their survival in the coming century would require a haven outside the reach of the Grand Inquisitor. Unable to secure a homeland on their own, covert Jews conspired with Holland and England to seize a New World colony.

It was then that a handful of Dutch Jews, inspired by a warrior rabbi, took it upon themselves to change things. Their generation came of age in the early 1600s, when Jews were forbidden in England, France, and most of Europe, and in the Spanish Empire anyone caught “Judaizing” was liable to be burned. Only in Amsterdam could Jews safely call themselves such, and they grew up strong and free in a city that became known in the Diaspora as New Jerusalem. Their mentors were their refugee parents who settled there on the run from the Inquisition, and their rabbi, the pirate Samuel Palache.

Most of the community’s fifty or so families were elite merchants from Spain and Portugal whose commercial skills and connections had made them welcome in what was fast becoming Europe’s trading capital. Rabbi Palache, a Barbary pirate who was still capturing Spanish ships in his late sixties, held the first religious services in his home. While the aim of their parents was to live freely, grow wealthy on New World trade, and have their portraits painted by Rembrandt, their ultimate goal was nothing less than to bring down the Spanish Empire. Their proxy armies in this struggle were the Dutch, the English, and in the final, successful assault, the buccaneers of the West Indies.

Jewish Pirates of the Caribbean
is the history of Sephardic Jews in the early New World, involving intrigue, horror, defeat, survival, and final victory over the hooded Inquisitors of the Holy Terror. It concludes with their last hurrah—their search for the legendary lost gold mine of Columbus. After achieving Jewish rights in Europe and the New World, three Dutch Jews, accompanied by their sons, went into the mountains of Jamaica to find Columbus’s mine. They reported that their search was not successful. But I found their map and have reason to believe it was.


n August 1, 1492, when Christopher Columbus set sail for the New World, ethnic cleansing was the order of the day: 100,000 Jews left Spain, expelled as mandated by the Royal Edict of Expulsion of the Jews. Those who remained behind, or crossed the border to Portugal, converted to Catholicism. The more adventurous went on to the New World. It is about this group that our story is told.

Long before Spain was Spain, Jews were living there. King Solomon’s trading post (1000
.) developed over the millennium to become Sephard, a strategic outpost of the Roman Empire. It was there, in the first century
., that Emperor Titus, after conquering Israel and burning the Temple, exiled thousands of Jews. Although the Jews of Sephard flourished, they were always tenants. The Visigoths who replaced the Romans made it illegal for them to own land, and Spain’s subsequent rulers, the Vandals, Moors, and Catholics, found it expedient to continue the ban. Despite this and other restrictions, the tribe of Moses grew and prospered.

In Spain’s feudal society, Jews were an educated elite, a merchant class also respected as physicians and financiers. At the end of the fourteenth century, after some 1500 years of residence, the 500,000 Jews of Sephard (half the Jews of Europe) represented the oldest and largest Jewish community outside Palestine. Their leaders boasted lineage to King David and considered themselves the aristocracy of Jewry. These were halcyon days for a people who were unwelcome in most of Europe. But their very prosperity and superior lifestyle were resented by an uneducated mass whose all-consuming religious beliefs could be inflamed by virulent anti-Semitism.

Ferrant Martínez, a friar in Seville, provided the spark. Following a frenzied sermon in which he accused Jews of everything from causing the Black Plague to killing Christian children and drinking their blood, he incited the crowd to rise up and destroy this accursed race. Descending on Seville’s Jewish quarter, the rabble slaughtered four thousand men, women, and children. What is known in Jewish history as the Massacre of 1391 had commenced. Pogroms spread from city to city. The mob’s admonition “Convert or die” resulted in 100,000 dead Jews, and 100,000 converts for Jesus.

After a bloody year, peace was gradually restored. Spain’s 300,000 remaining Jews came forth from hiding places and reconstructed their lives. Those who remained faithful continued to live as Jews but under a host of restrictions. But the 100,000 converted Jews, freed from religious bondage, rose over the next century to positions of power that had been denied them as Jews. Called conversos, or New Christians, to distinguish them from the dominant “Old” Christians, they achieved major positions in government, the army, and universities, and married into the highest nobility. They were prominent at court and in the hierarchy of the Church. However, conversion by coercion rather than conviction had an unforeseen consequence. Forced baptism had brought infidels into the Church, but in doing so, created heretics within.

In the last decades of the fifteenth century, there began what came to be called the Holy Terror. Queen Isabella vowed she would root out all heretics from her kingdom once the Catholic reconquest of Spain from the Moors was complete. Meanwhile, she would begin by ferreting out heretics in Seville, a city known for Jews pretending to be Christians. Her means was the auto-da-fé (act of faith), the church’s idea of Judgment Day on earth, with a Grand Inquisitor playing God. In 1482, Isabella gave that role to her confessor, Tomás de Torquemada. In the course of his eighteen-year reign, the former Dominican friar personally condemned nine thousand Jews to the stake at the
(burning ground) outside the city walls. He also exhumed the bodies of seven thousand dead heretics and burned their remains. (Whenever Torquemada appeared in public, he was accompanied by fifty agents on horseback and two hundred armed guards.)

Ten years later, on the very day Columbus set sail, Spain’s monarchs banished her Jews to purify and thereby unite their nation. Jews settled everywhere they were permitted and, disguised as Portuguese New Christians, where they weren’t. Along with other pioneers in the far-off New World, they carved out a niche for themselves, living possibly the most original experience the world has ever known. They thought themselves safe, but the white-hooded Inquisitors soon followed. In the sixteenth and seventeenth centuries, thousands of New World conversos were arrested, tortured, and tried. Found guilty, they saw their wealth confiscated, and they were first flogged, then imprisoned, strangled, burned, or condemned either to work in the salt mines of Venezuela or to row galley ships across the Pacific, a sentence from which none returned.

Inquisitors were thorough in their questioning of heretics, and the trial transcripts offer an intimate look into the condemned Judaizers’ secret lives. During the day, they went about as exemplary Catholics, attended Mass, went to confession, and had their children baptized. But on certain nights they met secretly in one another’s homes, reverted to Hebrew names, and read from the Torah. History would come to call these secret Jews Marranos, meaning pigs. Though this term has generally lost its pejorative meaning, I prefer to call them what they called themselves in the sanctity of their homes: Jews.

Each New World colony had an underground community of Jews known only to one another and their brethren in other colonies. Together, conversos in the New World dominated commerce. In the sixteenth century, when the known world doubled in size and international trade became big business, they established a trade network that spanned the globe.

• In Lima, Peru, the Inquisition reported: “The city is thick with [Jews]. Everything goes through their hands…from brocade to sackcloth, diamonds to cumin seeds…to the most precious pearl and the vilest Guinea black.”

• In Potosí, Bolivia, with its silver mountain, the Inquisitor reported the silver trade “is almost exclusively in the hands of crypto Jews.”

• In Port Royal, Jamaica, English merchants protested, “Descendants of the Crucifiers of Blessed Jesus eat us and our children out of all trade. [They] purchase the entire cargo of a trading ship, divide it according to paid shares, and distribute the goods through agents in each of the colonies.”

In concert with their fellow Jews, scattered worldwide by the Sephardic Diaspora, they formed a global tribe of inside traders, bonded by heritage, language, and a hatred for Spain. New World Jews traded with covert brethren on the Iberian Peninsula, and later sold directly to Jews in Amsterdam and London, often in ships leased from Jewish shipowners in Amsterdam and Antwerp.

Dealing with the People of the Book was very attractive. Their innovative letters of exchange and credit made capital portable. For instance, a shipping merchant trading in pirate waters doubled his risks if he returned with gold. On the other hand, if he could leave the gold and return instead with a draft on a Jewish banking house, he was safe. As a link in a world trade network at the onset of international trade, Jewish merchants were the world’s most coveted capitalists. The historian of capitalism Fernand Braudel writes: “It has too quickly been assumed Jews did not invent capitalism; certainly they participated wholeheartedly in its beginnings…It is not unrealistic to refer to…the 17th century as the ‘age’ of great Jewish merchants.”

Piracy was another lucrative area of commerce in which these Jewish merchants specialized. Questions of morality did not apply. It was the normal business of every nation to license mercenaries to seize and rob enemy ships and share the proceeds. The only difference with the Jews was they did not have to license their freebooters. In coded correspondence with fellow merchants in other colonies, they were able to ascertain what ship was sailing when; its cargo, route, and destination; and what its captain may have secreted in his cabin. Thus informed, Jewish merchants were the brains behind the brawn—financing, advising, and sometimes leading the Caribbean’s emerging fighting force: a ragtag crew of misfits of every nation that coalesced as the dreaded pirates of the Spanish Main.

A precedent for this unholy alliance was set by fellow Sephardim in North Africa who had assured their welcome among the Moors by profitably backing and sometimes leading the Barbary pirates. Sinan, Barbarossa’s second in command, was referred to in Crown correspondence with England’s Henry VII as “the Great Jewish pirate,” and the brothers Samuel and Joseph Palache would go from commanding pirates to founding Amsterdam’s Jewish community.


In the first decades of the seventeenth century, rival Christian merchants wanting a share of the fabulous wealth being generated by trade in the New World sought to expose the conversos as heretics before the Holy Office of the Inquisition. Thus threatened, covert Jews, beginning in the 1620s, conspired with Holland and England to seize a New World colony. Writing in code to agents in Europe, they proposed to serve as a fifth column in the body of the enemy. “They are good and useful spies,” said a confidant of Oliver Cromwell, regarding the Jews who advised Cromwell in the conquest of Jamaica.

Positioned to assist Spain’s enemies, they did. Jewish trade links, cultivated since 1492, when Sephardim settled the far corners of the globe, doubled as a worldwide intelligence network. From the time Jews in Portugal got word to Queen Elizabeth that the Armada was sailing, they shared secret intelligence with the enemies of Spain.

Jews had been outlawed from living in France since 1394 and from England since 1290. However, when those two nations and Holland settled a dozen small, uninhabited Caribbean islands between 1624 and 1635, Jews were welcome. Their connections and knowledge of New World trade were indispensable to the success of the new colonies. And they spoke the language. Who else but Sephardic merchants could better pursue illegal trade with the Spanish colonies? How else could these small settlements survive? The islands constituted mere footholds in what was called the New Spanish Sea. Together they totaled less than 1,500 square miles, while the Spanish New World encompassed millions.

The first openly Jewish settlement in the New World was in Brazil. In 1624, the Dutch captured Brazil’s capital, Bahia, from Portugal with an invasion force that included “several dozen declared Jews.” The invaders were assisted by local conversos who had gotten word that an Inquisition office was to be established in their province, where two hundred of them were living as counterfeit Christians. A year later, King Philip IV of Spain sent a twelve-thousand-man army and temporarily threw the Dutch out. Afterward, the Inquisitor’s report charged: “[Secret Jews] had written Holland and asked the Dutch to liberate them…had initiated plans for the invasion and agreed to share its costs. [The] Heretics had suckled at the breast of the Mother Church [and when the Dutch came]…openly professed the Jewish faith.”

In 1630, Holland’s forces again invaded. Landing north of Bahia, they conquered Recife and surrounding provinces in northeast Brazil. Under Dutch protection, a Jewish community thrived there for twenty-four years. They called their congregation Zur Israel (Rock of Israel), marketed sugar, and taxed Jewish privateers 3 percent of their booty. Sugar and piracy transformed Recife into the richest trading port in the New World outside of Havana, and Jews, integral participants in both industries, lived a high life. Their favorite pastimes may be glimpsed from what they outlawed: Synagogue leaders banned card playing on Friday afternoon (as too many members missed Sabbath service), and levied whopping fines on members caught taking Christian women into the
, the ritual bath.

The situation in Brazil was unique. Elsewhere in the New World, as the midcentury approached, the long-established secret Jewish communities in Peru and Mexico came to a flaming end, with each found guilty of a “great conspiracy.” In 1638, hundreds of Peru’s Jews were arrested. Their leaders, accused of plotting to blow up Lima’s harbor in advance of a Dutch invasion, were burned at the stake. In the 1640s, Mexico’s Jews were charged with conspiring to burn down the House of the Inquisition, and by 1650 the methods of the Inquisition—the dungeon, the rack, and the stake—marked a decade-long succession of autos-da-fé that decimated the Mexican community. In both countries, the heretics’ wealth was equally divided between the Crown and the Inquisitors, and their property was auctioned off to Old Christians.

In 1654, a similar end threatened the congregants of the Rock of Israel when Portugal reconquered Recife. After twenty-four years, the only legal Jewish community in the New World was no more. Jews were given three months to leave or be turned over to the Inquisition. The destruction of brethren communities in Mexico and Peru convinced the refugees the New World was again off-limits. They departed Recife on sixteen ships: The fifteen that sailed for Holland arrived safely; the ship that went north to New Amsterdam did not.

This ship ran into a storm that, “by the adverse,” drove it into Jamaica’s enemy waters, where it was seized. The island was home to a secret Jewish community called “Portugals” who had been living as merchants and traders since Columbus’s son had settled the island in 1510. The Columbus family owned Jamaica and, in deference to their converso settlers, had kept the island out of bounds to the Inquisition. But when the identity of the Dutch refugees became known, Jamaica’s leaders, looking to oust the Columbus family, used the arrival of these “suspect heretics” to invite Inquisitors from Colombia to Jamaica.

Fearing an investigation of the refugees might lead to their own exposure, Jamaica’s Portugals sent a note to Cromwell’s agent: Jamaica could be conquered with little resistance, and they pledged their assistance. The following year, a Jew from Nevis led thirty-six English ships into the harbor, and two local Jews negotiated and signed the peace treaty surrendering the island to England. The treaty exiled the Spanish, and Cromwell invited Jamaica’s Portugals to stay on openly as Jews.

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