Chapter Eight

CROMWELL’S SECRET AGENTS

Allow Jews back in England and the Messiah will come.” This, essentially, was the visionary promise that an Amsterdam rabbi shared with England’s new, Bible-quoting ruler. The date was September 1654, the same month that New Holland’s twenty-three Jewish refugees finally arrived in New Amsterdam, only to be told they were not welcome. The previous December, Oliver Cromwell had become Lord Protector of the Commonwealth, ending England’s twelve-year civil war.

Soon after the Puritans’ victory, Cromwell concluded his nation’s two-year war with the Netherlands. Although the outcome of what is known as the First Anglo-Dutch War was inconclusive (the maritime rivals would fight twice again in the next two decades), the Dutch had lost 1,500 ships.1 This blow to the republic’s sea power, coupled with the loss of their Brazilian colony, left Holland in no position to war with Spain, let alone invade Jamaica. So while Cohen and the Parnassim persuaded the States General to formally protest Jamaica’s detention of her Jewish citizens, the Dutch were not about to go to war over the incident.

Israel and Cohen, aware of this realpolitik, and knowing of the rabbi’s discourse with Cromwell, looked to England. They were privy to Cromwell’s plan to invade the New World and believed the two goals—the return of Jews to England and the liberation of Jamaica’s Jews—could augment each other. Despite their allegiance to Holland, national loyalty took a backseat to the possibility of securing two new homelands for their people, in England and Jamaica.

With the Dutch war settled, Cromwell spent the summer of 1654 formulating what he called his Grand Western Design, an ambitious plan to carve out a Protestant empire in the Spanish New World. The stage was thus set for his positive reception of Israel and Cohen’s proposal to invade Jamaica. There was only one hitch: they were too late. In late November 1654, as they were about to embark for England, one of Cromwell’s secret intelligencers and a possible relation, Daniel Cohen Henriques, told them not to bother; Jamaica was already targeted.2

Israel and Cohen therefore turned their attention to the more immediate goal of securing Jewish settlement elsewhere in the New World. Over the next fifteen months, while they were thus successfully engaged, Cromwell’s effort to allow Jews back into England would be spurred by the role of Jews in Jamaica’s conquest, and the promise of their valued assistance to develop his New World empire. As strangers in a strange land, the wandering tribe of Abraham had acquired particular skills that Cromwell needed. To understand this development, we leave Israel and Cohen in Amsterdam, holding tight the secret site of Columbus’s mine until Cromwell’s demise, when the sons of the royals who first sought it—George Villiers and Charles I—were restored to power.


In August 1654, Cromwell summoned the Spanish ambassador and bluntly told him that friendship with Spain could continue only if Englishmen were granted freedom of trade and religion in the New World. The ambassador was shocked: “Impossible,” he said. “To ask for these rights is to demand of my Master his two eyes.”3 To allow England trading rights in the New World was tantamount to recognizing England’s right to settle there. Monopoly of trade and propagation of the True Faith were cornerstones upon which Spain developed its colonial empire, and His Most Catholic Majesty was not about to share it with anyone, least of all a Puritan devil.

Cromwell, reportedly taken aback by the ambassador’s response, abruptly dismissed him. This was pure theatrics. Months earlier he had begun secret preparations to send an armed fleet to the Caribbean.4 Freedom of religion and trade were the stated reasons, but securing a major chunk of the New World was his compelling desire. Thirty years before, England had colonized a few small, empty islands in the eastern Caribbean, outside the sea lanes. Barbados, Nevis, and St. Kitts were prospering, but a more strategic base was needed if Cromwell was to break Spain’s hold on the wealth of the New World.

To Cromwell, a ruler who framed every decision as being in accordance with Scripture, the invasion’s success was preordained: “The ships would sail in accordance with God’s dictates…Its triumph would signify God’s favor…more God’s favor assured its success.”5 Cromwell was too confident, however—his vaunted plan would have failed if not for the advice of his Jewish intelligencers. With other advisers pushing Hispaniola, Cuba, Puerto Rico, or Trinidad, the leader of London’s covert Jews, Antonio Carvajal, whose knowledge of Caribbean affairs was unmatched, counseled Cromwell to follow up on Captain Jackson’s raid.

An English prisoner captured in Jamaica would confess: “The Grand Western Design was designed and financed by Jews who planned to resettle England and buy St. Paul’s Cathedral and turn it into a synagogue.” While there is no hard evidence this was true, the Spanish defenders believed it, “since the example of Brazil exhibits similar treasons & inequities committed by this blind people out of their aversion for us.”6 The prisoner, Nicolas Paine, was the interpreter for General Robert Venables, the co-leader of the invading force. He made this disclosure, recorded by the Spanish notary, after having “begged for his life in Spanish.” Where did Paine hear it? Was it scuttlebutt among the crew or something he overheard the general say? If so, where did the general hear it?

However skewed Paine’s admission, Cromwell would not have reached a decision about where to attack without first consulting Carvajal, who recommended Jamaica. One of the city’s prominent merchants, Carvajal owned ships that plied the seven seas. He had agents in most major ports, and the political intelligence he gathered made him one of Cromwell’s most valued advisers. But since exposure of his role might have led to the arrest of associates and relatives in the lands of the Inquisition, his consultations with Cromwell, via the ruler’s trusted secretary John Thurloe, were kept secret.

Though King John had formally expelled the Jews from England in 1290, by the mid-1600s a handful of wealthy Jewish families had managed to resettle there and became major players in international commerce. They called themselves Portuguese, attended Mass in the home of the ambassador (also a secret Jew), and were not circumcised.

Carvajal was forty-six in 1635 when he rode up to London’s city gates astride a white Arabian stallion, dressed in “fine armor” and leading a string of pack mules carrying gold bullion. Halted by the king’s guard, he announced that he was a merchant from the Canary Islands and had come to London to join his sister, whose husband was Portugal’s ambassador. Given his impressive appearance, he was allowed to proceed. Later it was revealed that he had departed the islands’ capital Tenerife a step ahead of Holy Inquisitors sent to investigate him.

Like Pasha Sinan and Rabbi Palache, Carvajal was a man of “superb and florid” personality who soon established himself as the leader of London’s covert Jewish community of thirty or so families. Though Carvajal dealt in many commodities, silver was his specialty. At a time when New World silver powered global currency, transporting it was a Jewish enterprise. Carvajal imported silver bars from converso merchants in Seville, who received them in turn from converso merchants in Peru and New Spain. From the time the ore left the mines and was melted into bars, his own were embossed with a particular stamp. He also imported annually about $1 million (in today’s money) in silver pieces of eight.7

Jamaica marked the first conquest of the British Empire, and Carvajal, who hoped to persuade England’s new ruler to allow Jews legally back into England, played a major role. While invasion plans were going forward, his associate, Simon de Caceres, who traded extensively in the Indies, confided to him that a secret Jew in Jamaica, Francisco Carvajal, headed the army there and could be relied upon to assist an attack. While there is no evidence that the two Carvajals were related, Jamaica’s Carvajal helped cement the English conquest, and when news of victory reached London, Cromwell’s intelligencer was amply rewarded.

In December 1654, the fleet departed Portsmouth under the joint command of Admiral William Penn—father of the future founder of Pennsylvania—and General Venables with an army of 2,500 men. Unlike the disciplined soldiers Cromwell led in the civil war, these recruits had been hastily rounded up, and in the judgment of one observer, were mostly “common cheats, thieves, cutpurses (pick-pockets), and such lewd persons who long lived by sleight of hand and dexterity of wit.”8 Their leaders were likewise described as “lazy dullards that have a large portion of Pride but not of wit, valor or authority.”9

First stop was Barbados, where Venables tripled the size of his army by the beat of a drum in the public square and the promise “Any bond-servant who volunteers shall have his freedom.” With little to lose and much to gain, four thousand indentured servants, comprising fully a fifth of the population, signed on. Twelve hundred more were recruited from St. Kitts, Nevis, and Montserrat. By the time the fleet embarked, Venables’s army had swelled to nearly eight thousand men but carried supplies for only half that number.10 The invasion plan called for the army to first attack Santo Domingo. Significantly, the fleet halted at the small island of Nevis, where Admiral Penn enlisted Campoe Sabada, the Jewish pilot who had previously sailed with Jackson.

This slovenly army was primarily made up of servants who had signed on for freedom and plunder; accordingly, when the general announced that there would be no taking of booty, they threatened mutiny. Confronted by “an unruly and ignorant mass,” he canceled the order. Meanwhile, it was obvious that the admiral had no respect for the general, who, to the annoyance of all, had brought along his new young wife and rarely left his cabin. Always contending for command, it was said, Penn snickered whenever Venables made an error, which Venables tended to do whenever he gave an order.

Rather than a direct assault on Santo Domingo, Penn favored a surprise attack, and landed the army thirty miles up the coast. Unfortunately, the site was a desert, and as Cromwell’s brother-in-law, responsible for equipping the army, had forgotten to pack canteens, the soldiers had to march without water through hot, barren land without shade. They never reached the capital. Many collapsed from thirst; others were cut down by a cavalry charge of three hundred mounted Spaniards, who ran them through like knights of old with twelve-foot lances. Afterward, their leader boasted that had he had more “cow-killers” (as his men were known) he would have killed every invader. This singular breed of toughened Spaniard was a cowboy in reverse, expert not at herding cows, but at slaying them. It was later reported that during the attack, Venables hid behind a tree, “so much possessed with terror he could hardlie spake.” With no water, no discipline, and pursued by the lance-wielding cow-killers, the invading army retreated to the coast. As Cromwell’s relation also hadn’t packed any tents, the demoralized troops had to huddle in the open when days of torrential rain followed. In one week, Venables lost a thousand men, while Spanish losses numbered forty.11

The two commanders were now so distrustful of each other that the general refused to allow the admiral and his crew to board the ships ahead of his soldiers, suspecting they might sail away without them. At a council aboard ship, the officers rejected a further assault on the city, contending that any attack would have to be fought by them alone as “they could not trust their men to follow.”12

What now? An attack on fortified places like Cartagena or Havana was out of the question, and if they simply retreated to London they could lose their heads. Historical accounts state that following the humiliating defeat at Hispaniola, the decision to invade Jamaica was first mentioned. However, this is disputed by a number of English prisoners. The first, an advance scout captured a day after the English landed, confessed, “Our purpose is to take this land…then pass on to Jamaica.” Prisoners, taken later, confirmed this sequence. According to the Spanish account:


[After the cow-killers]…killed more than 800 men and compelled the enemy to retreat…two captured Englishmen [said] they intended to go to another island they had been before. In view of the prisoners’ dispositions…his Lordship immediately arranged to send a warning to Jamaica since this was the island the prisoners designated [italics added]. He sent it with all diligence to the governor, advising him of the form of fighting we employed [and] to use the same…He told him the enemy was badly used up, lost many men, and was short of victuals, in order that Jamaica might know the facts and be prepared.13


Since no account of the invasion plan mentions Jamaica, historians have followed in lockstep the contention that Jamaica was “an afterthought.” Is this simply a case of historical confusion, or is something more convoluted involved? The island’s location in the middle of the Caribbean made it a natural target. After Jackson’s raid twelve years before, the local priest spelled this out in a letter to King Philip, wherein he called upon the Crown to reclaim Jamaica:


The defense of the island is very poor…If the enemy takes possession there can be no doubt from it he will quickly infest all ports making himself master of their trade and commerce. As it lies in the way of the fleets voyaging from these kingdoms to New Spain and the plate galleons to Habana…it can be gathered how harmful it would be for ships in that trade if the enemy should take possession of this island.14


Captain Jackson’s report to Cromwell’s Committee on Colonial Affairs the previous decade had exposed a divided, lightly defended colony with a Jewish fifth column that would welcome an invasion.15 With Carvajal’s intelligence endorsing this analysis, Cromwell was fully cognizant of Jamaica’s strategic site, poor defense, and the promised support of local Jews. These facts, along with the prisoners’ confessions and the recruitment of Jackson’s Jewish pilot who had previously led his ships into Jamaica’s harbor, all point to Jamaica being a prima facie target. Why then was it kept secret?

The probable answer is revealing: When the fleet left Portsmouth, the commanders were kept in the dark as to their target. “We shall not tie you up to a method of any particular instructions,” Cromwell told them, but ordered the attack plan kept sealed, only to be opened when the army reached Barbados. Cromwell, already accused of selling out to Jews, apparently felt he would have been further tainted if even his advisers knew of their role in his Christ-ordained Grand Western Design. His far-reaching plan was to allow Jews back into England, both for economic reasons and because of his conviction that their return and mass conversion would hasten the Second Coming of Christ. But for now it was better to keep secret their role in his imperialist plans.16

On May 10, 1655, four days after leaving Hispaniola, the Martin, piloted by Sabada with the two rival commanders on board, led the fleet’s thirty-eight ships into Jamaica’s harbor. The invaders had lost a thousand men, but the army was still an overwhelming force, more than four times Jamaica’s population of 1,500 Spaniards, 750 slaves, and a hundred or so Jews. (Following Jackson’s raid, many Jews were expelled from the island.) If they could land without incident, conquest was assured. Defending the port was a small garrison with three mounted guns. After an initial salvo while the ships were still at sea, the defenders fled. Their report smacks of terror: thirty-eight ships had become fifty-six ships, and the seven-thousand-man army was reported as twice that number.

Unchallenged, Venables’s army marched eight abreast on a wide road linking the port with the capital of Villa de la Vega, and set up camp outside the city. The next morning, two Jamaican officers rode up under a flag of truce. They had come, they said, in place of the governor (a syphilitic old man with festering sores all over his body) to find out what the English wanted. They introduced themselves as the current and former Sargento Mayor (army commander). But something else the two men shared turned out to be more significant. The officers, Francisco Carvajal and Duarte Acosta, were secret Jews.17

“We have come not to pillage but to plant,” Venables told them. After some dickering, Carvajal asked Venables: “By what right do you claim the island? Spaniards have had possession of it for 140 years and it was given to them by Pope Alexander.” Before the general could reply, his adjutant interjected:


“It is ours by the right of might. Just as the Spaniards had taken Jamaica from the Indians, so we English have come to take it from them. As for the Pope, he could neither grant lands to others nor delegate the right to conquer them.” Besides, he added, only the weak get conquered: “Henry VIII offered England to any who chose to take possession, but none deigned to accept that gift.” At that, the English officers “laughed long and heartily.”18


The next day, Governor Ramariez, carried in a hammock by African slaves and escorted by Acosta and Carvajal, entered the English camp to negotiate terms. He was there for show. His Portuguese officers signed the surrender treaty, and reportedly drafted it as well. They got what they wanted: Portuguese were encouraged to remain while Spaniards were to be transported to New Spain. Venables later reported to Cromwell that the “Portugals [accepted] our invitation to stay.”19

No account of the conquest mentions the advance warning from Hispaniola that “his Lordship…sent with all diligence to the governor…in order that Jamaica might know the facts and be prepared.” Yet it was this warning that had spurred the Portuguese officers to be the first to meet with the invaders. With the ocean current favoring ships sailing west from Santo Domingo to Jamaica, the 480-mile distance would have been covered in four to five days. As such, Governor Ramariez should have received the warning more than a week before the English invasion. That he didn’t is evidence the message was intercepted. Given what transpired, it would appear that when the ship arrived, Portuguese merchants in control of the port got hold of the letter, and rather than deliver it to Ramariez, revealed its contents to the two officers who then positioned themselves to negotiate Jamaica’s surrender.

Cromwell’s army had taken Jamaica, but the Cabildo, led by Francisco de Leiba, the self-styled king of Jamaica, along with his cousin Sanchez Ysassi and the latter’s son, Arnoldo, marshaled their supporters and retreated to a sugar estate west of the capital. They hanged the two servants whom Carvajal and Acosta sent with the treaty and, loudly rejecting the surrender terms, cursed the two officers as traitors.20 Arnoldo led a rebel group into the hills, where they formed a guerrilla force and ambushed soldiers who ventured outside the capital to hunt cattle.

Jamaica was English, but in July, when Cromwell also received the news of the disaster at Hispaniola, he was not pleased. Later that month, when first Penn and then Venables returned to England, each blaming the other for Santo Domingo, Cromwell called them quarrelsome incompetents, and confined them in the Tower for deserting their forces.

An opposite reception greeted Antonio Carvajal’s “great friend,” Simon de Caceres, who returned on the ship bearing Venables.21 An international trader from Amsterdam with offices in Europe and Barbados, he had been visiting his two brothers in Barbados when the English fleet arrived. When the greatly enlarged army set sail, he volunteered to secure the extra provisions that would be needed, and was with the supply ships that caught up with the fleet in Jamaica two weeks after the conquest. Meeting with Carvajal, who had taken charge of the army’s commissary, the two took stock of what was needed. Back in England he submitted a memorandum to Cromwell “on things wanting in Jamaica.”

His “Proposal for Revictualing and Fortifying Jamaica” stressed the need to complete a harbor fort to defend against an expected counterattack from Cartagena. The report reads like a grand shopping list: 1,500 shovels, 1,000 pickaxes, 100 wheelbarrows, 2,000 hatchets, and so on. Further, “as an encouragement” for the fort workers, he recommended sending “plenty of brandy and wine…and fine linen stockings and handsome shoes [for the officers].” Self-interest likely played a part in these extra requests, as among the items he traded in were “shoes, linen, wine and brandy.”22

De Caceres told Cromwell that before he left Jamaica, one Captain Hughes had begun fortifying the tip of the peninsula at the harbor entrance. (This was the beginning of the town of Port Royal that, in the next decade, would be known as the “wickedest city in the world.”) After receiving his report, Cromwell shipped the necessary supplies and ordered Jamaica’s commander to “study your security by fortifying.”23

On August 17, 1655, with Penn and Venables in the Tower, Cromwell honored the one man who had correctly advised him on the invasion plan. Summoning Antonio Carvajal and his two sons to his office, Cromwell awarded them English citizenship, making them the nation’s first legal Jews in 365 years.24 Later Carvajal would warn Cromwell that the exiled Prince Charles had signed a secret treaty with the Spanish king, promising to return Jamaica for help in overthrowing the Commonwealth, and that Spain was outfitting a fleet to retake the island. So alerted, Cromwell’s naval forces were able to smash the fleet in Cádiz harbor before it sailed.25

In 1658, Carvajal’s imports accounted for 8.3 percent of London’s customs revenue.26 A description of him that year shows that (like Pasha Sinan and Rabbi Palache) age had not mellowed him. The occasion was his arrest. Custom officers had seized one of his shipments. Feeling his goods unjustly impounded, he broke into their warehouse, and holding the guard at sword point, threatened to run him through while his servant emptied the place. The police report described him as “of grizzled beard and fiery temper…and no ’prentice hand with the rapier,” while his servant Manuel Fonseca “could double his fist with any Englishman.” Charges were dropped when the man known as the Great Jew died later that year.27

In the fall of 1655, England’s leader announced a settlement policy for Jamaica that is significant in what it omits: His proclamation opened Jamaica to every “planter or adventurer” without regard to religion or national origin.28 He also granted citizenship in Barbados to a prominent Jewish refugee from Recife, Dr. Abraham de Mercado.29 Like the Cohen Henriques brothers, de Mercado was one of Rabbi Palache’s old boys. Considered the first Jewish physician in the New World, he proudly wore the title of doctor, but in spy circles went by the code name Plus Ultra, as when he tipped off Dutch authorities in Brazil that the Portuguese banquet they were to attend was to be an assassination party.

Cromwell’s actions sent a message to Jews, albeit a circuitous one, that they might henceforth look to him as their defender. Cromwell evidently felt that for his Grand Western Design to succeed, he needed Jews in place. He is said to have looked on with envy at the boost they gave the Dutch economy. Jews had helped make Amsterdam Europe’s richest port, and as they helped Holland, he believed, so they could make London “the common warehouse of Europe.”

Granting special favors was Cromwell’s way of demonstrating his intentions. England’s colonies were open to Jews. But not the mother country, at least not yet. However, in honoring Carvajal, Cromwell revealed his inclination to revoke the ban on Jewish settlement. Besides their business skills and trade, there was the matter of securing intelligence. As he confided to Bishop Burnett: “They are good and useful spies…skilled purveyors of foreign intelligence.”30 With England’s exiled prince ready to strike, and Spain’s declaration of war over Jamaica, Cromwell needed to work closely with London’s Jews and their agents. They, in turn, were grateful for the opportunity to demonstrate their loyalty and economic clout.

The midseventeenth century was a time when True Believers ruled and every action was righteous and backed by Scripture. It was the politics of Holy Inevitability, and Cromwell liked to frame his policies in those terms. Along with commerce, and intelligence, Cromwell’s religious convictions presented him with an irresistible motive for Jewish resettlement: Only when Jews were allowed back in England, he believed, would the Messiah return. His public expression of this religious rationale garnered him the fervid support of England’s philo-Semites, who saw this as necessary for the redemption of the whole human race.

From 1607, when King James published an English translation of the Bible, the Old Testament had become required study among Puritans. Its influence was seen by their adoption of biblical references during the recent civil war: The Lion of Judah was inscribed on the Puritan banner; King Charles was referred to as Pharaoh, and his rule as the Egyptian Bondage. After Cromwell’s victory, a messianic group called the Fifth Monarchists proclaimed the Puritan Commonwealth to be the so-called Fifth Empire prophesied in the book of Daniel, which was destined to usher in the thousand-year reign of Jesus Christ. (The other four were Babylon, Persia, Greece, and Rome.) They also quoted Deuteronomy (18:64) to argue that God would not reappear until his Chosen People were readmitted to England. The passage actually predicts that the Jews will be scattered to the “end of the earth,” but Puritan clerics preached that since the French called England Angleterre, a phrase which Jewish medieval literature used to signify the “angle” or “end” of the earth, it was clearly God’s will that they admit the Israelites, “so they might be brought to see the truth.” Whatever the merits of this twisted reading of Scripture, for Cromwell the message was clear: Allow Jews back into England, and the Messiah would return…and so would trade.31

Meanwhile, in the Diaspora, homeless Jews favored any argument that would work. Their horizons were rapidly narrowing: New Holland was no more; in Spain and Portugal, Inquisition burnings were on the increase and the great autos-da-fé in Mexico and Peru had left the remnant of Jews in Spanish lands looking to move on. In New Amsterdam, they were engaged in a struggle to stay. In Eastern Europe, galloping hordes of saber-wielding Cossacks were killing Polish Jews by the tens of thousands.

In October, a Cabalist rabbi from Amsterdam arrived at Cromwell’s invitation to discuss the divine argument proffered in his book The Hope of Israel. The religious sage was the former child prodigy Menasseh ben Israel, who it will be recalled stayed late at synagogue immersed in the mysticism of Cabala while the Henriques boys and their rebel pals frequented the docks, absorbing sailors’ tales of exotic lands. Menasseh held that the Torah contained divine revelations which prophesied the coming of the Messiah, and in The Hope of Israel he identified England as the Promised Land to which the Jews must return before the Messiah appears. (He and Cromwell agreed on that, disagreeing only on whether or not He had been here before.) Menasseh, a pragmatic scholar, peppered his prophecies with a discourse on what Jews could do for England’s economy.32

In December 1655, Cromwell called a conference of leading personages to debate the issue. The conference ended without making any recommendations, except to agree that there was no legal bar to Jewish resettlement. All that was required for readmission was for Parliament to approve it. Cromwell tried, but was unable to get Parliament to act. He was not deterred. As a royalist spy told Prince Charles, “Though the generality oppose, the Jews will be admitted by way of connivancy.”33 An opportunity presented itself when, shortly after Spain declared war, Parliament ruled that Spanish property would be confiscated. London’s Jews, though calling themselves Portuguese, were considered Spanish subjects, and their goods were therefore subject to seizure. The situation came to a head in what is known as the Robles trial.

In February 1656, customs officials seized two ships in the Thames carrying wine from the Canary Islands and a safe with forty thousand ducats in gold. London’s Jews were alarmed. The ships and strongbox belonged to Antonio Robles, a member of their community. If his property could be legally confiscated, their holdings could likewise be taken. What to do? With Carvajal and de Caceres leading the way, a decision was reached for the converso community to come out of the closet and declare that they were Jews, and loyal to England. On March 12, 1656, they confronted Cromwell with an either/ or demand, saying in effect: “Your conference accepted that there is no legal bar to our admission. The issue is therefore between you and us: as you well know, we are not Portuguese Catholics; we are Jews and we want the right to worship and bury the dead in our manner.” Not stated, but implied, was a threat—“otherwise we will look to Holland.”34

Robles followed suit. He petitioned the court for the recovery of his ships and goods on the grounds that he was “of the Hebrew nation.” He recounted how he had been on the run from the Inquisition that killed his father, tortured his mother, and burned at the stake many close relatives. He had come to England, he said, hoping to find a home among a people also considered heretics. In the course of the trial, ten London Jews sent in affidavits supporting his submission; others testified they knew Robles to be “of the Hebrew nation and religion.”35 When the six-week trial ended, the court declared Robles “a Jew borne in Portugal” and restored his ships, wine, and box of gold.36

On April 3, 1656, London’s thirty-five Jewish families gathered in the Great Jew’s home for Passover Seder to celebrate the Israelites’ freedom from Egyptian bondage and their current liberation. After 366 years, England’s Jews were no longer illegal aliens. Henceforth, as followers of the Law of Moses, they would seek their rights openly rather than hide behind a foreign identity and a Christian cloak. To consecrate this new day, Cromwell’s chief intelligencer proudly changed his name to Abraham Israel Carvajal.

Although Cromwell, still facing opposition in Parliament, never formally reversed the ban on Jewish admission, his religious convictions were sincere and only added to his desire for the mercantile skills and connections Jewish settlers would bring. As Bishop Burnett commented in his diary, “it was more on that account than in compliance with the principle of toleration that he gave them leave to build a synagogue.”37 Later that summer, their two leaders, Carvajal and de Caceres, rented a cemetery plot and a building for a synagogue, and sent to Amsterdam for a Torah.

In Jamaica, meanwhile, things were not going so well. With England’s occupying army having tripled the island’s population, there was not enough food to feed everyone. Weakened by hunger and “the bloody flux,” the ranks suffered from malaria. Many soldiers rebelled when ordered to plant food crops. They had been promised freedom and booty, not bondage. As for the officers, the only thing they wanted was to return to England. In October 1655, six months after the conquest, nearly half the army was dead. Cromwell’s newly arrived commissioner Robert Sedgwick wrote home:


For the Army, I find them in as sad, and deplorable, and distracted a condition as can be thought of; their commanders, some having left, some dead, some sick…the soldiery many dead, their carcasses lying unburied in the highways and among the bushes…As I walked through town many that were alive lay groaning and crying out, bread for the Lord’s sake…It is strange to see young lusty men, in appearance well, and in three or four days in the grave, snatched away in a moment with a confluence of many diseases. The truth is God is angry and the plague is begun, and we have none to stand in the gap.38


By January 1656, the mortality figure had risen to more than five thousand, and a month later included Sedgwick as well. Only the sailors aboard ship under Vice Admiral William Goodson, who had their own provisions, remained healthy. In these harsh circumstances, the Jewish pilot, now addressed as Captain Campoe Sabada, and known to be familiar with the island from his time with Jackson, was sent to reconnoiter the western end. In February 1656, he landed a hundred soldiers at Great Pedro Bay and captured the two rebel scouts who had been trailing them. The governor of Cartagena, they said, had got word to Ysassi that two galleons with a thousand men were being readied to join “an armada from Spain to come to Jamaica harbor to beat the English from the land.”39

Sabada hurried back to so inform Admiral Goodson, who wrote Cromwell (March 12) that he was sending ships to Cartagena to intercept the galleons, and was equipping others to patrol for the armada. Goodson’s letter went on to stress the advantages of strengthening island settlement and the need to complete fortifications:


once well peopled [Jamaica] is so advantageous, being in the midst of the Spaniards’ country, that having a considerable force here to make inroads upon the enemy, and a fleet to secure the seas, it might become the magazine of all the wealth in the Indies. To affect this we must have a considerable recruit of seamen, landmen and some commanders, to give life & vigor to the action; besides which, we must also hope for a good supply of provisions; those we have should last four months longer. In short, if your highness continues your resolutions to proceed in this great design, you must in a manner begin the work again.40


With the threat of a Spanish attack from without, and battling Ysassi’s forces within, it was essential to find a defense that did not depend on recruiting reinforcements for a disgruntled and dying army. The answer was to be found on a small island off the northwest coast of Hispaniola, where a rough breed of men once eked out a living hunting wild cattle and hogs. How this came about, and how these men evolved from hunters of cattle to hunters of men, is worth taking time out from this narrative. We begin with the man thought to have recommended their recruitment, Carvajal’s “close friend,” on whom Cromwell relied for on-the-spot intelligence of “things wanting in Jamaica.”

Though a generation removed from Rabbi Palache’s old boys, Simon (Jacob) de Caceres was cut from the same cloth. The temper of the man, who at the Robles trial proudly testified, “I am of the Jewish nation of the tribe of Judah,”41 is evident in a brazen proposal he submitted to Cromwell on the heels of his Jamaican shopping list. In it he offered to conquer Spain’s New World empire with “people of my nation” as an advance guard for English forces. If Cromwell would give him four ships of war and a thousand men, he would sail around Cape Horn and attack the Spanish Main from the Pacific side, à la Drake, and invade the continent via Chile. In the meantime, anticipating Cromwell’s favorable decision, he was off to Holland to recruit “young men of my own nation, [who] shall go as Englishmen for his Highness’ service only.” To finance the bold invasion, the would-be conquistador intended to capture Spain’s silver fleet. Although Cromwell did not respond to de Caceres’s grand scheme, there is evidence that he considered the Jew’s strategy.42

A flamboyant character, de Caceres was described by a friend at the Robles trial as a “proud Jew who made no more ado about not being a Christian than how he had fought the dogs of the Inquisition on the Sea & Land.”43 He named his ship the Prophet Samuel. Like the prophet, he believed it was his godly duty to unite all Jews and was known to frequent the docks hoping to persuade newly arrived conversos to come out as Jews.

De Caceres was a successful international merchant, and Carvajal’s friend (although twenty-five years his junior). He had offices in London, Amsterdam, and Hamburg, two brothers in Barbados, and relatives in Martinique and Suriname. Besides England’s leader, he was on friendly terms with the king of Denmark and the queen of Sweden.44 His plan to conquer the New World shows him as a man of militant vision, one that he likely followed with a further recommendation that set the course for Jamaica’s immediate future.

With England’s army dying and surrounded by enemy forces, it was not enough to build a fort. Cromwell knew that once he withdrew his army and navy, the colony would require a defensive force that could protect the colony, wage war on the Spanish, and at the same time feed itself. As a shipowner and illegal trader throughout the Indies, de Caceres knew precisely where to find such a force: the hunters of Hispaniola, a communal society of anarchists, exclusively male, who switched from hunting beef to robbing boats after the aforementioned cow-killers wiped out their prey. Crowded on a small offshore island, and now calling themselves the Brethren of the Coast, they were looking for new opportunities.

The challenge for Jamaica’s survival was to intercept Spanish shipping on the high seas, and thereby cut the umbilical cord that fed the Spanish Empire. The Brethren could do this, and knowledgeable Jews, like Jamaica’s Portugals, could both outfit and direct their attacks. From their extensive trade with fellow conversos in each colony, they knew what ship sailed, when it sailed, what it carried, and what the captain had hidden in his cabin.

De Caceres saw England’s conquest of Jamaica as the first step in the liberation of his people. Step two was assuring that the Grand Western Design stayed afloat. Bring the Brethren to Jamaica, legalize them as privateers, and their attacks on Spanish shipping and land settlements would keep the Spaniards on the defense (and make their backers rich in the process).

This sort of game was not new to exiled Jews. From the time of their expulsion, Sephardim in North Africa had profitably backed the corsairs of the Barbary Coast.45 De Caceres’s friend Carvajal, who came from Las Palmas, a pirate port in the Canary Islands where conversos also had a sponsoring role, would certainly have endorsed his proposal.

“It is with the Jews that the connection with the buccaneers began…” is how Jamaica’s foremost nineteenth-century historian, Robert Hill, links the two nomadic tribes whose alliance transformed the English colony into the pirate capital of the New World. Considering what de Caceres was up to, and the Sephardic involvement with the Barbary corsairs, Hill’s statement rings true.46 In any case, the strategy found favor with Cromwell, and by 1657, Jamaica was home to the formidable deterrent force known to history as the buccaneers of the West Indies.


In the first half of the sixteenth century, before the natives of Hispaniola died out, animal tending was Indian work. By the 1550s, with few Indians left, the animals ran free, and many settlers, lured by the attractions of the Main, quit the island. Those who remained abandoned the countryside for life in the city. Cattle, pigs, and horses, first brought by Columbus, returned to the wild, turning the island’s northwest region into a vast animal kingdom.

By the 1620s, the huge herds had attracted a weird assortment of hunters, New World outcasts who settled, one by one, the small offshore island of Tortuga. They were misfits of every stripe and color: runaway bondsmen, ex-soldiers, marooned seamen, escaped slaves, heretics, criminals, and political refugees. Here they found the anonymity they craved: last names were discarded; each considered his former life “drowned.” The hunters, mostly French and English, owed no allegiance to the Old World.

Unable or unwilling to return whence they came, they resigned themselves to a life of essentials. For a year or so, groups of six hunted with packs of dogs until they had enough hides and meat to sell. Known for the way they barbecued beef on a green wood grill called a boucan, they were called boucaniers, later Anglicized to buccaneers. Innocent enough, but to the Spanish across the island in Santo Domingo they were dangerous intruders.

By the 1640s, Tortuga had become a thriving settlement. Six hundred boucaniers moved between Hispaniola and Tortuga’s fortified port of Cayano, where they bartered beef and hides to passing ships for guns, bullets, and brandy. With a secure base, they began raiding ranches on the north coast and set up two permanent camps there. To the hidalgos on the other side of the island, the situation was intolerable. The boucaniers had effectively annexed the northwest coast. Spanish pride would not allow this. However, rather than a direct attack, they conceived a seemingly ingenious plan: they would eliminate the boucanier by eliminating his prey. They reasoned that with no game to hunt, the hunters would leave, and Tortuga’s raison d’être would cease.

In the summer of 1650, a mounted regiment of three hundred Spaniards, armed with twelve-foot lances, fanned out over the savannahs, running the cattle through on the gallop, and left the slain animals for the vultures. These were the aforementioned “cow-killers” who later routed the English on Santo Domingo. Within a year, the great herds of cattle had been wiped out, and in 1653 the Spanish delivered a coup de grâce. They invaded Tortuga in full force and deported the boucaniers. Though many returned when the Spanish withdrew to Santo Domingo to counter Cromwell’s invasion, the day of the boucanier was over; the day of the buccaneer had begun.

Spanish policy had corrected a problem with an unanticipated result. By eliminating the cattle, they created a nation of rude warriors committed to vengeance. Deprived of their livelihood, the hunters of cattle became hunters of Spaniards, and within a year, Tortuga was a thriving pirate capital.

The buccaneers formed a guild, calling themselves Brethren of the Coast, and began by seizing small coastal and inter-island trading ships. With each success they grew bolder. When Pierre Le Grand and a small crew went forth in a canoe and returned with a treasure galleon, the sea was theirs. Something like the forty-niner gold-rush fever took hold. From all over, alienated adventurers flocked to join the outlaw nation. But the situation was tenuous. Tortuga was overcrowded, and when the invitation came to move to Jamaica, they gladly accepted and soon found ready recruits among the distressed soldiers of Cromwell’s ragtag army.

Though lawless by disposition, the buccaneers adopted a stern code of discipline that welded them together into a dreaded fighting force. At first, they elected and disposed of their captains at will. Since their ship had usually been captured, the prize belonged to the whole company and the Brethren were equal partners. All plunder was divided by shares and disabilities—the loss of a right arm brought six hundred pieces of eight or six slaves; loss of a finger was compensated with a hundred pieces of eight or one slave; death in battle entitled one’s heirs to a thousand pieces of eight. The captain received five or six shares and officers from one to three. Rewards were given to the first man who spotted the prize and the first to board her.

Later, once formally licensed as privateers by the government of Jamaica, they came under the leadership of stern captains such as Henry Morgan, and their ships were owned and outfitted by merchants who received the major share of the plunder, and were first in line to buy the remainder. So began the golden age of piracy.

The involvement of Jews in the conquest of Jamaica, and the promise of their continued assistance in expanding England’s sphere of influence in the New World, convinced Cromwell to ignore the dissenters and grant London’s Jews, and a few others, residency rights. But with no formal declaration for their readmittance, his sudden death in 1658 left them vulnerable and uncertain of the future.

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