Jews Expelled by Spain Became Pirates for the Dutch and the Ottomans
The 1492 expulsion decree pushed Jews who knew navigation and trade into the arms of Spain's enemies; they used privateering licenses to claw back wealth, and they also took part in slavery and colonial atrocities.
The argument · tap a timestamp to hear it
Skull and crossbones on the gravestones
Some of the earliest European settlers' gravestones outside Kingston are carved with Hebrew script, and above them a skull and crossbones. These were Jews who fled secretly from Spain and Portugal, scattered after the 1492 expulsion across the Netherlands, the Ottoman Empire and Jamaica. Many were experts in navigation and cartography who sold their skills to new masters, with revenge on Spain as one goal. The show notes that Jewish piracy is a relatively new field of research, that plenty of errors circulate online and in books, and that details may be updated as research progresses.
In 1492 the two events were one
In 1492 Spain did two things at once: it issued the Alhambra Decree, ordering Jews to sell their property and leave by July 31, and it funded Columbus's voyage. Columbus's journal opens by noting that his orders and the edict expelling the Jews were issued in the same month. When his fleet set sail, only days remained before the expulsion deadline, and he very likely saw displaced families boarding ships in the harbor. Later, Columbus family rule over Jamaica gave Jewish refugees a haven the Inquisition could not reach.
Converting didn't get you past the Inquisition
The Spanish Inquisition was founded in 1478 and later became a standing bureaucracy that ran for more than three centuries, something like a secret police. Inquisitors collected secret denunciations, arrested people and confiscated their property to feed the prisoners, could use torture in trials, and a conviction could mean galley slavery or an auto-da-fé public execution. The show points out that Jews were trapped: practicing openly could get you killed by a mob, while converting let the Inquisition arrest, torture and execute you on the flimsiest evidence. In 1492 the Grand Inquisitor persuaded Ferdinand that an open Jewish community was too great a temptation for converts, and so all were expelled.
Jewish pirates are not a hero story
Sinan Reis was probably born in Anatolia to an expelled Jewish family; Sinan was the Islamic name he took after joining Barbarossa, and reis was a captain-level rank. In 1534 he sailed with Barbarossa's 70 galleys against Tunis, and later at Preveza he faced the Holy League's 300 ships with 122, attacking in the morning calm and capturing or sinking 128 ships that day without losing a single one of his own. But the show states plainly that this is not a hero story: Barbarossa was known for terror tactics, both sides rowed with slaves, and this conflict was literally powered by slavery.
Samuel Palache sold intelligence to everyone at once
Palache was born around 1550 in the Jewish quarter of Fez, his parents expelled from southern Spain in 1492. He was a rabbi, a merchant, a diplomat for the Moroccan sultan and a Dutch privateer. He brokered the first treaty between Morocco and the Dutch Republic, trading spices, diamonds and sugar for Dutch cannon, muskets and gunpowder. He raided Spanish ships with a ship from the Dutch prince and a privateering license from the Moroccan sultan, while selling Dutch intelligence to Morocco, Moroccan intelligence to the Dutch, and both sides' intelligence to Spain. In 1614 he was arrested in England; the Spanish ambassador demanded he be hanged, but the Dutch prince Maurice wrote to protest, and English lawyers ultimately conceded that executing him would violate international law.
One raid fed the Dutch army for eight months
On September 8, 1628, in Matanzas Bay, Cuba, Moses Cohen Henriquez was the first to leap aboard a Spanish galleon. The Dutch fleet had chased for a full day; the day before it had taken three ships and forced nine to surrender, and the last four were the largest in the Mexican treasure fleet, loaded with gold, silver, indigo and cochineal dye. It was the first time an entire Spanish treasure fleet was captured, and the Dutch suffered zero casualties. The booty totaled 11.5 million Dutch guilders, more than a billion dollars today; unloading took five days and filled hundreds of carts, and it was enough to supply the Dutch army for eight months.
The oppressed also oppress
The show stops specifically to note: riding with the conquerors, taking part in piracy and building Caribbean industry meant being entangled in atrocities from slavery to the genocide of indigenous peoples. A group being oppressed does not mean it will not oppress others. In 1528, Hernando Alonso became the first person in New Spain to be denounced by the Inquisition and executed; he had served as a conquistador during the Spanish invasion and built ships for Cortés, later owned the most profitable cattle and pork farm in Mexico, and was secretly accused of retaining Jewish traditions and pouring wine on a baby's head to wash away baptism; he confessed under torture and was burned in the central square of Mexico City.
The Jews of Dutch Brazil went to New York
Henriquez used his share of the booty to work as a privateer in Dutch Brazil, and bought a private island, fortified it as a pirate base, and sold it to the governor ten years later. Dutch Brazil lasted only 24 years, but the Dutch West India Company shipped 26,000 African slaves to Brazil, leaving another terrible legacy. In 1654 Portugal retook Brazil; most Dutch Jews stayed, but 23 boarded a ship heading north, hoping to find a place in New Amsterdam — later New York. Henriquez went to Jamaica, which England turned into a pirate port, with a Jewish community large enough to have a Jewish shopping street and two synagogues, whose floors were covered in sand to commemorate the need to muffle footsteps during secret worship.
In their own words · checked verbatim
Because above the Hebrew lettering, these tombstones carry another mark, the skull and crossbones.
In other words, Jews couldn't win. If they were openly Jewish, they risked being murdered by a mob. And if they did convert, the Inquisition could arrest, torture, and execute them on the flimsiest of evidence.
It was reported at Rome a few days ago. It says that Andrea Dorya was informed that the famous Jewish pirate had prepared a strong fleet to meet the Spanish galleys which are to join Doria's 19 ships.
And let's not forget that both sides of this war utilized vessels driven by or slaves, meaning this conflict was literally propelled by slavery.
I think he's a Spanish Jew sailing a Dutch ship with a crew of Barbary Corsa, Jews, and Dutch sailors who are plundering Spanish shipping while under the Moroccan flag while he's also selling everyone's secrets to everyone else.
And that bears mentioning just because a group is oppressed doesn't mean they can't also oppress others.
Their floors covered with sand in Sephardic style to remind the worshippers of when they practiced in secret and had to muffle their footsteps.
Figures
| Alhambra Decree expulsion deadline | July 31, 1492 | 1:09 |
| Size of Barbarossa's fleet against Tunis | 70 ships | 9:13 |
| Holy League ships at the Battle of Preveza | 300 ships | 16:23 |
| Barbarossa's galleys at the Battle of Preveza | 122 ships | 16:23 |
| Ottoman ships captured or sunk at the Battle of Preveza | 128 ships | 17:25 |
| Booty from the Matanzas Bay raid | 11.5 million Dutch guilders | 33:40 |
| African slaves shipped to Brazil by the Dutch West India Company | 26,000 people | 35:41 |
| Jews who sailed from Brazil to New Amsterdam in 1654 | 23 people | 35:41 |
Glossary
- conversos
- Spanish Jews and their descendants who were forced or chose to convert to Christianity.
- auto-da-fé
- A public ceremony staged by the Inquisition in which the condemned were paraded and then executed.
- Sephardic
- From the Hebrew name for Spain; refers to Iberian-descended Jews.
- privateer
- An armed private vessel holding a government license to legally plunder enemy ships.
- Barbary Corsairs
- Muslim privateers based on the North African coast at Tunis and Algiers.
How to listen
Founders and investors interested in early globalization, Jewish diaspora history, privateering and the law of religious tolerance — especially anyone who wants to understand how expelled technical talent turns against its home country.
After 37:43 it's calendar, playing-card and other merch ads; skippable.