The Meditteranean was plundered by both the Pirate Rabbi of Holland Samuel Palache, and Sinan the Jew, Barbarossa’s 2nd in command; Chile was Suboltol Deul base, and Moses Cohen Henriques’ pirate island was off the coast of Brazil.
“But o.k. if we have to go with that title, there were a couple of Jewish pirates in the Caribbean.” I told him about Jamaica’s Bartholomew the Portuguese, a successful failure, famous not for his successes but for his escapes, and the pirate Jean Lafitte known to Americans as the hero of the battle of New Orleans who wrote “my Jewish-Spanish grandmother, a witness at the time of the Inquisition, inspired in me a hatred of the Spanish crown” And it was off Cuba that in 1628 Moses Cohen Henriques captured the Spanish Silver fleet, a billion dollar haul in today’s currency.

So, I told him I’m fine with Jewish Pirates of the Caribbean. But can he give it a broader subtitle like Sephardic Pioneers or Underground in the New World? "No," he said. But for you my UJCL readers, you are mishpoche and therefore I have to tell you the full story.
The major role of Jews and pirates was we were like the brains behind their brawn, i.e. We advised and backed them.

From the Age of Discovery, 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 knew these pioneers were Jewish. Forbidden entry because of their religion, Iberian Jews posed as New Christians from Portugal, the one settler group that did not require proof of Catholic ancestry.

A mercantile people, Jews in the New World went about their business
(as merchants, traders and ship owners) of becoming the first merchant class in the Spanish Empire. As long as they pretended to be Christian and delivered the goods, no one questioned too closely their religiosity. For most of the l6th century, the parties were content with the trade-off: The king needed the Jews to insure his cash flow, and they needed him to keep the Inquisition at bay.

Each colony had an underground community of Jews known only to each other and brethren in other colonies. Together they dominated commerce.
In the 16th century, when the known world doubled in size and international trade became big business, conversos established a trade network that spanned the globe. In concert with Jews scattered world-wide by the Sephardic Diaspora, they formed a global tribe of inside traders, a world wide intelligence network bonded by heritage, language and a hatred for Spain.

Once their trade network was established, however, Jews became expendable. In the l6th and l7th centuries, thousands of New World conversos were arrested, tortured and tried. Found guilty, their wealth was confiscated, and they were first flogged, then either imprisoned, strangled, burned to ash, condemned to work in the salt mines of Venezuela, or row galley ships across the Pacific from which none returned.

Jamaica Haven
“They are good and useful spies,” said Oliver Cromwell of the Jews who when the Inquisition threatened, advised him in the conquest of Jamaica. Welcomed by the English, Jews from all over the New World shed their converso cloaks and moved to Jamaica. The community soon included ship owners from Mexico and Brazil, traders from Peru and Columbia, and ship captains and pilots from Nevis and Barbados. Together their knowledge of New World trade was unsurpassed. By 1660, Jamaica had become the Jews’ principal haven in the New World. Situated in the middle of the shipping lanes, Jamaica was an ideal base from which to strike at Spanish shipping, and engage in contraband trade with the Main. Jamaica’s Jews were major players in both activities.

Having convinced the island’s new leaders that the best way to defend the colony and have it prosper was to invite the pirates of the Caribbean to move there, Port Royal became the home base of the feared Buccaneers of the West Indies and piracy the island’s chief industry. Jewish merchants, in coded correspondence with converso merchants in the Spanish colonies, were able to ascertain what ship was sailing when, its cargo, route, destination, and what its captain may have secreted in his cabin. Thus informed, they financed and advised the buccaneers, and got first dibs on the booty.

Port Royal’s English merchants, new to the New World, could not compete with those they called “descendants of the Crucifers of our Lord,” and repeatedly petitioned for their expulsion. One complained:
“The infinite number of Jews who daily resort to this island have made Port Royal their Goshen and will do nothing but trade…This is a great and growing evil and had we not warning from other Colonies we should see our streets filled and the ships hither crowded with them. This means taking our children’s bread and giving it to the Jews. We did not want them at Port Royal, a place populous and strong without them.

Another by 72 “Christian merchants” accused the Jews of practicing what is today normal business practice:
“The great Mischief we suffer by them is that their trading is a perfect monopoly, for they are a kind of joint stock company, and not only buy the choicest and best goods, but frequently buy up whole cargoes, and undersell petitioners, which they can better bear by their penurious way of living…”

Prejudice could not stand up to economics. Jews’ contribution to Jamaica and England’s prosperity determined the Crown’s position in their favor. In two decades (1656-1676), in large part due to the role of these proven entrepreneurs of wealth in the silent trade (illegal trade with Spanish colonies) and their dealings with the buccaneers, Jamaica funneled to England an estimated four million pounds of silver. England’s Committee of Accounts noted the island had become “the base for the greatest flow of silver and gold [and] more bullion is yearly imported from thence than from
all other of the King’s dominions laid together.”

Port Royal, with its wealthy Jewish merchants, ship owners and synagogue, was known as the “Treasure House of the Indies”. In the ascendancy of the Buccaneer Admiral Henry Morgan, the Jews found their “Joshua.” His six raids on Spanish ports, financed by the merchants, and culminating in the burning of the “Golden City of Panama,” brought the Spanish Empire to its knees. In the Treaty of Madrid in l670, Spain acceded to Europe’s right to settle the New World...and Jews were finally free to be Jews.

The Great Earthquake of 1692 brought a climatic end to the pirate port when the sea swallowed two-thirds of Port Royal. From an infamous pirate capital, Jamaica, by 1698, had become a sugar island worked by 40,000 slaves, and after 1713, “the centre for slave distribution in the Caribbean and North America.” It was then that England’s Royal African Company was awarded by the asiento – the monopoly right Spain granted to conduct the slave trade with Spanish America. A few Jamaican Jews did participate in the trade, but most dealt in dry goods. This fact was noted in a London petition in 1735 that protested the on-going effort of rival merchants to exclude Jews. Their defenders (92 Jewish and non-Jewish merchants) wrote: “The Jews [in London] are almost the only persons that send any dry, fine goods to Jamaica, at their own risk, and on their own account…for the supply of the inhabitants of the island, and for making proper sortments of goods for the Spaniards…”

As Jewish involvement with piracy petered out in the Caribbean, the rovers and their Sephardi sponsors disbanded, only to reunite when in the following century a budding new nation would enlist them in its fight for liberty. In the American Revolution, a dozen prominent Jews sided with the rebels as privateers. Celebrated as founders of early Jewish congregations, it is not commonly known that these men owned and operated more than a few of the pirate ships that captured or destroyed over 600 British ships and took cargoes and prizes with an estimated value of $18 million.