Seventeenth-century Port Royal sat on a thin spit of sand, a city balanced on pilings and appetite. Ships came in hard and low, their hulls scraped from reefs and running lights extinguished early—men who didn’t want questions met a town that didn’t ask them. The place lived off movement: sugar out, bullion in, and everything in between carried by hands that knew how to turn risk into profit.
Among the people who made Port Royal function were Spanish-Portuguese Jews, many of them refugees—or the children of refugees—who had crossed the Atlantic with two kinds of knowledge: how to survive hostile empires, and how to trade inside them. Jamaica under the English offered something rare for the age: room to live more openly as Jews, and room to work. In Port Royal, they were far more likely to be merchants, brokers, moneychangers, shipowners, and retailers than plantation magnates.
Port Royal’s advantage lay not in what it produced, but in where it sat within the Atlantic system—a port positioned to intercept the movement of wealth rather than generate it. The success of this economy was not found in the chaos of a raid, but in the precision of the aftermath. When a vessel under a letter of marque―a government license to raid enemy shippinge―returned to the harbor, the crew held raw cargo—indigo, cocoa, silver, or bulk cloth—that had no immediate value on a ship’s deck. The merchant class provided the bridge to utility. In a colony where the English crown often struggled to provide consistent administration, Jewish merchants operated a private infrastructure of credit and language.
Multilingualism was a logistical necessity. Many Sephardic families in Port Royal maintained ties with relatives in Curaçao, Amsterdam, and the Spanish Main. This allowed them to act as intermediaries who could decode Spanish shipping manifests or negotiate with captive crews. Because they existed within a diaspora that spanned the Atlantic, a merchant in Port Royal could issue a bill of exchange that was honored in London or New York, effectively allowing "pirate" loot to be laundered into legitimate international capital.
This laundering—or "fencing"—was a sophisticated administrative act. When a Spanish prize was brought into port, its origins had to be obscured to enter the English colonial stream. Merchants utilized a process of re-documentation: cargo was broken down from its original Spanish crates, re-marked with English weights and measures, and assigned new bills of lading. By the time a shipment of "Spanish" cocoa reached a buyer in London, it appeared on paper as a legitimate product of Jamaican trade.
Risk was managed through diversification. A single merchant might own a small retail shop on Thames Street while simultaneously holding a "fractional interest" in a privateering frigate. They advanced the necessary salt beef, ship biscuit, and gunpowder to the crews "on account." This credit system meant that the merchant took on the financial risk of the voyage; if the ship returned empty, the debt remained, but if it returned full, the merchant claimed a significant percentage of the prize before it ever hit the open market.
Then came 1692. The sea rose and took Port Royal’s streets into itself. Approximately two-thirds of the city—including the high-rent merchant districts on Thames Street and North Street—slid into the sea almost immediately. The physical "machinery" of the port (the warehouses, wharves, and ledgers) was literally erased from the surface.
Across the harbor, the Hunt’s Bay Jewish Cemetery remained—stones with dates and Hebrew letters, serving as a physical record, proving that a settled merchant class was foundational to Port Royal’s rapid economic growth. The earthquake dismantled the physical docks, but it could not sink the network. Hunt's Bay remains the physical evidence of this era—a site that marks the shift from a temporary raiding outpost to a permanent commercial center that would define Jamaican commerce for the next century.
Following the disaster, survivors and the merchant class realized that the sand spit was no longer a viable or safe foundation for the massive infrastructure required for Atlantic trade. This led to the rapid establishment of Kingston on the more stable mainland. The international credit lines and diaspora networks didn't vanish, but they migrated across the harbor, making Kingston the new commercial heart of Jamaica.
Historically, 1692 marked a shift in colonial policy. The English Crown was already moving away from state-sanctioned privateering toward more "legitimate," regulated naval power. The destruction of the primary privateering hub provided a natural (and literal) clean slate for the British to pivot the economy toward the more structured plantation and merchant systems of the 18th century.
The Silver Gauntlet: How Panama Made Port Royal Rich
Port Royal’s wealth was not a matter of luck. It was built on a simple reality of geography: a narrow strip of land in Panama that acted as a bottleneck for the world’s silver. To understand why Port Royal became the richest city in the West, you have to look at how Spain was forced to move its treasure.
The Imperial Bottleneck
In the seventeenth century, silver extracted from the great mines on the Pacific side of the Andes could not be shipped directly to the Atlantic world. Instead, it was moved north along the Pacific coast to Panama City. There, the Spanish Empire confronted a brutal but unavoidable task: hauling tons of bullion across fifty miles of dense jungle and broken interior terrain to reach the Caribbean. It was a daunting choice, yet far easier than the alternatives.
This crossing is referred to by Historians as the Silver Train—vast convoys of mules and men that moved the treasure through the rainforest. It was a slow, grueling process with only two main paths:
- The Camino Real: A rugged overland trail through the heart of the jungle.
- The Camino de Cruces: A route that used mules for the first half, then small boats to float the silver down the Chagres River to the coast.
These journeys were never risk-free. The jungle itself was a predator, but the greater danger lay in the knowledge that the route was vulnerable. Ever since Francis Drake’s legendary ambush of the mule trains a century earlier, the Spanish understood that this crossing could be targeted, forcing them to move their wealth under constant, high-stakes anxiety—even when no enemy was immediately present.
This narrow corridor became a “Silver Gauntlet”—a place where the rigid Spanish system was forced to slow down and expose its greatest treasures to the elements and the enemy. On the Atlantic side, the silver eventually arrived at fortified ports like Portobelo. Because the Spanish only moved their treasure in large, organized fleets for protection, the silver often sat in these ports for months, waiting for the ships to arrive from Europe.
The Rhythm of the Trade
This waiting period created a predictable pattern that the merchants in Port Royal learned to read. They didn’t need secret maps; they simply watched the timing of the Spanish fleets.
When the great galleons arrived from Spain, it was a signal that the silver would soon be moving across the jungle to meet them. If the ships were delayed in port, it usually meant the mountain trails were washed out or the mule trains were running late. For the merchants and privateers in Port Royal, this wasn’t just news—it was the data they used to plan their next move.
They knew exactly when the silver was most vulnerable: not when it was on a heavily armed ship, but when it was being lugged through the mud of the Panama jungle, far from the protection of the fleet.
Those who could read this rhythm best were not the captains, but the merchants who turned timing into profit.
The Merchants: The Minds Behind the Money
While the privateers provided the force, a specific group of people provided the intelligence: the Spanish-Portuguese Sephardic Jewish merchants of Port Royal. Because they were part of a diaspora—a “nation” of families spread across Amsterdam, London, and the Spanish colonies—they had access to information that no English official could find.
- Trusted Intelligence: Through letters from relatives living inside Spanish territories, these merchants knew the volume of silver leaving the mines and the exact day the mule trains were scheduled to depart. They turned “maybe” into “exactly.”
- The Business of Ransoms: They also acted as the essential middlemen for more delicate business. If a Spanish official or a high-ranking priest was captured, the Jewish merchants used their language skills and family ties to negotiate the ransom. They were the only ones both sides trusted to handle the exchange.
- Turning Spoils into Capital: Most importantly, they knew how to make the loot “disappear.” When stolen Spanish cocoa or silver arrived in Port Royal, these merchants would quickly repackage it, mark it with English labels, and issue paperwork that made the goods look like a legal product of Jamaica.
The Architecture of the Prize
Ultimately, the "Silver Gauntlet" of Panama functioned as the primary trigger for Port Royal’s economy. The movement of the mule trains didn't just signal a physical journey; it set the timing for a global network of trade. While the privateers provided the force to intercept the empire's wealth, the Sephardic merchants provided the system that made that wealth usable.
By using their intelligence to track the convoys, providing the credit to fund the voyages, and managing the "cleansing" of whatever booty—silver, cocoa, or cloth—arrived in the harbor, they acted as a private clearinghouse for the Atlantic. They were the ones who turned the irregular spoils of the sea into the stable, documented currency of empires, ensuring that even when the "Gauntlet" was miles away, its riches always found a home in the ledgers of Port Royal.
By the time the cargo reached a buyer in London, the “blood” had been washed off the ledgers. The Silver Gauntlet provided the opportunity, but it was this network of merchants who turned a rough pirate outpost into a sophisticated global financial center.