Kingston, Jamaica, is not customarily associated with a colorful Jewish past. But the hundred or so delegates attending the annual conference of the Union of Jewish Congregations of Latin America and the Caribbean, held last winter in the Pegasus Hotel, were intrigued. There had been talk of pirates—Jewish pirates no less—as part of new initiatives by local leaders to explore the history of Jews in Jamai­ca, including the restoration of an old Jewish cemetery and the creation of a small museum.

Each table at the conference’s fare­well banquet was assigned a Jew­­ish pi­rate, his name and story written on a card. There was Jean Laf­fite, known for flamboyant outfits—and terrifying raids into the Gulf of Mexico; Subotol Deul, commander of the Brotherhood of the Black Flag, dubbed “the Hebrew Pirate” because his journal contained He­­brew cha­rac­­ters; Bar­tholo­mew the Portu­guese, whose mis­­haps give his escapades a Woody Allen flair; John Es­que­­mel­ing, the Dutch sur­geon of famed pirate Henry Morgan, who told his tale in the 17th-centu­ry book, The Buccaneers of America; and Moses Cohen Henriques, reputedly re­spon­sible for the big­gest haul in pirate history—the capture of the Span­ish Silver Fleet in 1628.

The delegates played their parts; the men donned black eye patches, tricornered hats and swords tucked into thick belts. They took photos against a painted backdrop of a burning pirate ship flying the Jolly Roger. And when conversation turned to whether Jewish pirates are fantasy or actual history, there was much to discuss.

This was especially so because a day earlier, the delegates boarded buses to the Hunt’s Bay cemetery. The grave­yard, partially hidden beyond a dusty lane in a refuse-strewn part of town, had served Jews of the pirate capital of Port Royal, across the bay, at the height of this trade in the 17th century.

Wandering the weed-covered rows of cracked head­stones, delegates were confounded to see the skull and crossbones symbol carved onto a handful of them, right next to the expected biblical verses in Hebrew and epi­graphs identifying the deceased in English or Portuguese.

The same day, at lunch, they listened to a talk by Ed­ward Kritzler, a journalist and historian on the island who has spent over 30 years browsing local archives for Jewish pi­rate tales. His book on the subject, 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(Double­day), is due out this month.

Even Amos Radian, the new Israeli ambassador to the Dominican Re­public and several other Caribbean nations, was swept up. Radian had ar­ranged to present a commemorative plate to conference or­ganizer Ainsley Cohen Henriques. As a past president of the Jamaican Jewish community, Henriques was being recognized for his eight years of service as honorary Israeli consul on the island—despite the fact, quipped Ra­dian, that one of Henriques’s ancestors had been the infamous Moses Cohen Henriques.

Fact or fiction? Truth or wishful thinking? The topic elicits strong reactions. Scholars of Jewish history tend to be dubious. “In all my research of Caribbean Jewry, conducted in five different Caribbean locations as well as in libraries and archives in the United States and Holland, I never came across the existence of people who could even remotely be called Jewish pirates,” insisted Josette Ca­priles Goldish, a research assistant at the Hadassah-Bran­deis Institute in Waltham, Massachusetts. Goldish was born in Curaçao and is working on a book about Car­ibbean Jews.

“Jewish pirates? Not in my 30 years of research,” scoffed Rabbi Isidoro Aizenberg from New York, who has also researched and written about Caribbean Jewry.

Leaving piracy aside, mention the words buccaneer, smuggler, privateer or, as Goldish puts it in Spanish, “contrabandistas,” and there is far more consensus among ex­perts that the Jews on the islands were heavily engaged in illegal trade. According to historians, restrictions and taxes imposed by the colonial powers were so tight there was no other way to conduct business.

Part of the discrepancy may therefore lie in terminology. There is a fine line between a privateer, with a government license to use his private army to attack and plunder enemy ships (and profit from the plunder), and a pirate. What does the privateer do with his assembled men when his contract is up? Is there a difference between a pirate and a buccaneer?

At least one historian does not mince words. “It is true that the Jews were involved in piracy,” conceded Stephen Alexander Fortune in his scholarly book Merchants and Jews: The Struggle for British West Indian Commerce, 1650-1750 (University of Florida Press). As an example, he said that in 1731, “Jacob Nunes of Jamaica outfitted the Judith and the Sarah, a vessel with 16 guns and 12 men, to prey on merchant shipping.”

These Jews certainly had the motivation and opportunity. They were de­scended from the Jews of Spain and Portugal who, under force, had been con­verted to Catholicism in the 15th century. Many remained Conversos, secret Jews. If they lived in the Spanish-held colonies of the New World, they still faced the threat of the Inquisition.

When it became safe to be openly Jew­ish, as in Curaçao under the Dutch and Ja­maica under the British, Jews naturally harbored an eagerness to undermine Spain. Helping to take the islands from the Spanish and put them in the hands of more tolerant powers meant greater safety and a chance to return to Judaism, if desired. Not to mention, “the loot of the buccaneers, taken from Spanish galleons—gold, silver, silk embroidery, porcelain—was very profitable,” noted Mordechai Arbell, former Israeli ambassador to Panama and Haiti. Arbell is one of the leading scholars on Jewish history of the region and discussed the buccaneers’ ex­ploits in The Jewish Nation of the Caribbean (Gefen).

Kritzler, who holds a bachelor’s degree and graduate credits in Latin American history and who has published widely on Caribbean history, argued that these Jews were ideally situated for piracy. They owned many merchant ships and had trading networks with family members back in Holland, France and England, so they could readily peddle goods. They had language skills to decipher official messages sent back and forth in Spanish. And they had regular contact with Conversos still in Spain who could tip them off to the whereabouts of Spanish treasure galleons.

Kritzler, whose rugged build and weathered face suggest he might well have been such an adventurer himself had he lived back then, noted that Jews were most often “the brains behind the brawn,” equipping and financing the voyages, rather than actually sailing on the sloops and schooners.

He explained that he was initially attracted to this chapter of Jewish history because it presented such a sharp contrast to the stories of passive Jews that filled his childhood in Roslyn Heights, New York.

“The Inquisition was confiscating the assets of their people,” he said, “so they would have felt justified.”

Henriques agreed: “They were probably acting out of revenge for what the Spanish had done to them.” Many of these “pirates” had friends or relatives among known secret Jews in the New World. Further, Henriques said, by ha­ras­sing the Spanish, they could protect those who were still being imprisoned by the Inquisition. “It was like, ‘We’ll show you we are big and bad, too,’” he said. “‘And if you’re not careful, we’ll attack you.’”

In his autobiography, The Journal of Jean Laffite, the pirate talks about “My Jewish-Spanish grandmother who was witness to the days of Inquisition.” Her teaching “inspired in me a hatred of the Spanish crown and all the persecutions…against the Jews.”

However, this slender volume, now in the Sam Houston Center–Texas State Li­brary and Archives Commission in Liberty, has never been au­then­ticated as the infamous pirate’s writings. Schol­ars still argue about the credibility of his Jewish heritage, although there are Jews today who claim to be his descendants.

A whitewash or the truth? Aizenberg argued that this is a neglected area of study, so it is difficult to know. He suggested that this oversight might also affect any interpretation of the skull and crossbones symbol on the gravestones in Hunt’s Bay.

It is generally agreed that the symbol itself is ancient, first known to have been used in a pirate context on the ships of the Knights Templar as they preyed on merchant shipping in the Me­d­­iterranean Sea during the Mid­dle Ages.

While there is no consensus re­garding why the skull and crossbones appears in Jewish cemeteries in the Caribbean from around the 17th century, theories abound.

Aviva Ben-Ur, an associate professor of Judaic and Near Eastern studies at the University of Massachusetts in Amherst, has studied and written about Caribbean Jewish cemeteries. She proposes, along with her colleague, Wim Klooster, associate professor of history at nearby Clark University, that it was a fashionable mortality symbol commonly used by Christians. Jews simply copied it.

Or it may have been a symbol of the messianic belief in resurrection described in Ezekiel, according to Rachel Frankel, a New York architect who has led a Jamaica team to document inscriptions on Jewish stones in other parts of the Caribbean.

The pirate connection gets even weaker, says Goldish, when one considers that tombstones of at least two Jewish women, who were unlikely to have been involved in piracy, carry the same symbol: one in the Netherlands and an­other in Curaçao.

However, in Jamaica, noted Kritz­ler in his book, at least one gravestone with the symbol belonged to a man named Abraham Alvarez, who died in 1693. Alvarez was a colorful “merchant” whose apparent booty included a gilded throne “covered in azure velvet [and] richly fringed” that he offered as a gift to the island’s governor, the second Duke of Albemarle.

In telling the tale in his book, Kritzler quoted from a journal written by a traveler named John Taylor. Not surprisingly, Kritzler is so concerned that readers will not believe his stories that a third of his 288-page volume is devoted to source notes.

No self-respecting pirate adventure would be complete without a treasure map, coded language and hidden booty. From the outset, Jamaicans held fast to a legend that Christopher Columbus had found gold somewhere on the island, but the site was never located and the idea was ultimately debunked.

Rummaging through a routine batch of court cases in the Jamaican national archives in Spanish Town, the old capital, in 2001, Kritzler found a map, dated 1670. Together with some auxiliary documents locating a specific site, but with the coordinates given only in code, it showed the possibility of finding gold in an interior mountainous area. Putting that information together with a bitter legal dispute occurring at the time between Moses Cohen Henriques and his brother, Abraham, regarding land holdings in the same area, Kritzler figured there might be more to the dispute than simply acreage.

In 2005, the Jamaican Ministry of Mines tested the soil and confirmed it contained “significant anomalies for gold.” Kritzler and Ainsley Cohen Henriques have since taken out a license to prospect the site.

Could they strike gold?

Stay tuned.

Andrée Aelion Brooks can be reached atandreebrooks@hotmail.com.