Freedoms Lost in Translation
Standing before Spanish officials in Havana in 1668, a woman of African descent from Brazil named Madalena explained how she and her daughter arrived on the island of Cuba in a stolen fishing vessel along with eleven other people. As she explained, the group had escaped captivity in Port Royal, Jamaica, with the aid of a Cuban fisherman whom they had liberated from the island’s prison. Among the captives, Madalena had spent the most time in unfreedom. In 1658, she had been taken captive off of a boat in the Bay of All Saints in Brazil by French traffickers who transported her to the island of Tortuga where they sold her into slavery. She spent two years enslaved on Tortuga, during which time she gave birth to her daughter, before she was sold again to a French merchant residing in Port Royal. Madalena lived and labored in the bustling English port city for the next seven years before her escape. Now, a decade later, Madalena defended her free status before Spanish officials, declaring that she “was born free and, as such, still is.” Crucially, this meant that her daughter inherited her mother’s free status, regardless of the circumstances surrounding her birth. Captivity by French traffickers and the experience of being commodified twice in less than ten years, as she argued, had not made slaves of Madalena or her daughter.
At least one man in the room had reason to disagree with Madalena’s articulation of her status. Listening to her testimony was Nicolás Castellón y Sánchez Pereira, the resident judge who represented Domingo Grillo and Ambrosio Lomelín in issues surrounding the newly created monopoly on the slave trade to Spanish America. Officials in Spain had responded to the increasingly chaotic nature of the transatlantic and intra-Caribbean slave trades in 1662 by issuing a new monopoly slave-trading contract, called an asiento, to a pair of merchants from Genoa: Grillo and Lomelín. The new asiento for the slave trade to Spanish America differed in important ways from previous contracts. Rather than conduct the transatlantic slave trade themselves, Grillo and Lomelín negotiated for permission to purchase enslaved Africans at English, French, or Dutch islands in the Caribbean and transport those enslaved peoples to specific Spanish American port cities.
Castellón claimed legal ownership over the Afro-descended captives who arrived from neighboring Jamaica on behalf of the new asiento holders. To Castellón, the Cuban fisherman who piloted the stolen boat was undoubtedly attempting to smuggle the Afro-descended passengers into slavery rather than free them from captivity. And, he argued, by virtue of the asiento contract, Grillo and Lomelín had the right to “all of the Blacks that are introduced [in Cuba] and the value of them,” including captives trafficked by smugglers.
Madalena’s claims to freedom also fell on deaf ears among the other men in the room, some of whom argued that she, her daughter, and her ten companions should be granted their freedom — an argument that assumed they had become slaves in the course of being taken captive in the Americas and trafficked by northern Europeans. Rather than acknowledge her free status prior to captivity, Governor Francisco Oregón y Gascón argued that Madalena should be granted her freedom because she escaped from enemy heretics and sought to live among Catholics in Spanish territory. In making this argument, Oregón articulated a new Spanish Caribbean policy intended to weaken northern European colonies in the region by encouraging individuals enslaved by Protestants to escape. In the face of those officials, Madalena continued to articulate her free status, rejecting outright the logic that captivity and trafficking had ever made her a slave.
Madalena’s testimony in 1668, and the competing interpretations of her status, lay bare the racialized vulnerability experienced by captives of African descent who were trafficked across imperial jurisdictions. Madalena’s removal from the community of her birth — where family, neighbors, and community members would have attested to her free status — led officials in Havana to treat her like a slave. Nor was Madalena’s case unique.
Territorial contestation in the form of the 1655 English invasion of Jamaica exposed different notions of race and status between the Spanish and English, while changes to the nature of the transatlantic slave trade to Spanish America meant that people who escaped captivity, like Madalena, became vulnerable to racialized interpretations of their legal status. The confluence of warfare and new slave-trading methods, in other words, had important consequences for free people of African descent trafficked away from the communities where their free status was recognized.
An analysis of the experiences of people taken captive and trafficked away from communities of belonging intersects with a growing body of scholarship on the movement of people of African descent across imperial borders in the 17th and 18th centuries. Historians have shown, for example, that self-liberated Africans and their descendants drove the creation of a sanctuary policy in Spanish America in which enslaved people who escaped from English, French, and Dutch colonies and sought baptism in the Catholic church were granted their freedom. By the late 17th century, the Spanish sanctuary policy provided important avenues for freedom for enslaved people who could escape and travel to Spanish territory.
Some scholars have interpreted the experience of Madalena and her companions through the lens of this sanctuary policy, arguing that everyone in the group save one received their freedom. The experiences of the escapees from Jamaica, however, were more complicated and their eventual fate more ambiguous because of the profound changes enacted to the intra-Caribbean and transatlantic slave trades during the 1660s. Religion and vassalage, in other words, were not the only factors that influenced what happened to individuals of African descent who sought sanctuary in the second half of the 17th century. Rather, people of African descent encountered a Spanish Atlantic profoundly shaped by the unprecedented authority that the Spanish Crown granted to representative factors of the Grillo and Lomellín asiento. The formalization of the slave trade under the new asiento, as scholars Tatiana Seijas and Alejandro García-Montón have argued, “Africanized” slavery in Spanish America as other forms of licensed trade in bound labor were subsumed by the Grillo and Lomelín monopoly. These wider changes meant that the statuses of Madalena and her companions were contested by representatives of the asiento in Cuba who viewed the group not as potential converts or vassals but as Blacks and slaves.
Territorial contestation between the English and the Spanish and subsequent changes to the intra-Caribbean slave trade unsettled many of the recognized social and corporate statuses that undergirded the position of Africans and their descendants in Spanish Caribbean society. This was particularly true for individuals who moved between Spanish and English spheres by coercion or by choice.
In 1661, the French merchant who held Madalena and her daughter, Dominga, captive in Tortuga sold the mother and daughter to James Martine in Port Royal. Martine’s purchase of Madalena and Dominga from another man who claimed ownership over them created a documentary record of their enslavement and covered the illicit provenance of the two captives; should officials in Port Royal ask, Madalena and Dominga were already enslaved when Martine purchased them. It is likely, however, that no one asked about the provenance of the young mother and her child. The English town that Madalena and her daughter resided in for the next seven years was in the process of a rapid transition from a line of warehouses with a poorly built fort to a well-defended and thriving commercial hub. When Madalena arrived in 1661, Port Royal had just under 700 free residents and around 50 enslaved people. A decade later the population had grown to 1,669 people who held 312 individuals as slaves in the town.
Port Royal quickly emerged as a bustling economic and maritime center for English Jamaica. The brick homes and patios built by Port Royal’s mercantile community might have been disorienting for Spanish American captives and the town’s streets, which were designed around a triangular shape, beguiling for travelers accustomed to Spanish America’s gridded urban centers. Unlike Spanish Caribbean towns, which tended to be built inland to secure against foreigners attacking by sea, Port Royal’s orientation was thoroughly maritime. Even fresh water had to be rowed across the harbor from Passage Fort near the Rio Cobre and stored in cisterns in order to maintain the population of Port Royal. Captives in Port Royal labored both for English Jamaica’s maritime trades and for English administrators in building fortifications to defend against a feared Spanish or Dutch invasion. Port Royal’s growth during the 1660s relied heavily on the traffickers who brought specie, trade goods, and captives to the town.
When a Cuban fisherman named Simon Rodriguez contracted a fever while imprisoned in Port Royal, his English captors called upon Ignacio Hernández — one of the eleven people who later escaped with Madalena — to nurse him back to health. The Cuban fisherman had been taken captive when he sailed from Havana in 1666 for a tangle of sandy islands and reefs off of Florida’s southern coast. Following the seasonal migrations of sea turtles to the Bahamas, Rodriguez joined a multiethnic assortment of sea workers who hunted the marine creatures to provision regional markets. But in the shallow waters off the coast of Abaco, an English crew took him captive and forced him to labor aboard their vessel, likely in hunting the same turtles Rodriguez sought before being taken captive himself. After a month, Rodriguez’s captors left Bahamian waters to sell their catch to the rapidly growing population of Jamaica.
No longer useful, and possibly a source of profit, Rodriguez’s captors attempted to sell him in Jamaica “to work for the space of seven years in the countryside.” The intervention of Jamaica’s governor prevented Rodriguez from being sold as an indentured servant, but he remained a captive in the island’s jail, likely so that he could serve in the same kind of prisoner of war exchange that Breton had used to gain entrance to Portobelo. Attending to the Cuban fisherman’s bedside, Ignacio recognized the utility of an experienced mariner for escaping the English island. In Rodriguez’s testimony about their escape, he referred to the other ten individuals as “companions” of Ignacio’s, indicating that it was Ignacio who maintained social ties with the other Spanish American captives and that the idea of escape by sea might have originated with the initial encounter between Simon and Ignacio.
For the Afro-descended captives, deciding to escape Jamaica with Simon Rodriguez meant weighing the risk of being caught alongside their particular vulnerability in a Caribbean context where their racial backgrounds made them a potential source of profit. Could they trust the Cuban fisherman to pilot them to freedom and not to slavery elsewhere? At least one member of the group had reason to fear being betrayed. According to Simon Rodriguez’s testimony, Ignacio made the Cuban fisherman promise not to reveal their plans to escape and told him that the rest of his companions were “people in whom he could trust.”
On the night of their escape each member of the group made their way to the beach where they seized a boat and rowed away from Port Royal under the cover of darkness. True to his word, Simon Rodriguez piloted the stolen boat over four hundred nautical miles between Port Royal, Jamaica, and Puerto de Batabano on the southwestern coast of Cuba. Rather than freedom, the arrival of a Cuban fisherman with eleven people of African descent raised questions, especially from the island’s representative of the Grillo and Lomelín asiento, an elite Cuban named Nicolás Castellón y Sánchez Pereira. With a shadow of suspicion over them, Madalena and her companions were marched to Havana where they were confined by Castellón. Their situation was made worse by the fact that their escape to Cuba coincided with a deadly epidemic on that island during which time official business ceased. The disease environment of the port city meant that Ignacio and his companions languished for a year under Castellón’s authority before the governor of Cuba, Francisco Oregón y Gascón, received a petition from members of the group and called for their interrogations in October 1668.
The petition, penned in the same notarial hand as the subsequent testimonies and signed by three of the eleven captives, contested the claims of the island’s asiento representative. The three signers — Ignacio Hernández, Gregorio Rodriguez, and Leonisio Rodriguez — explained that they had been held captive by the English for many years but, “as loyal vassals” of the Spanish Crown, they “risked their lives to escape tyranny and servitude among English heretics.” In contrast to the claims of Castellón, they argued that they were “free as any children of Adam,” and that it was simply circumstances that brought them before the governor of Havana to plead for a recognition of their freedom. The petition forcefully rejected the claims of Castellón that the captives were enslaved Africans smuggled into Cuba by Simon Rodriguez. As “free as any children of Adam,” the petitioners demanded that the governor of Havana adjudicate their case.
Governor Oregón responded by ordering the captives to explain the situation. For Oregón, Ignacio and his companions deserved freedom because they were “negros” who arrived in Cuba seeking to live among Catholics. Castellón and Oregón presented different arguments, but the fundamental assumptions remained the same. The growth of the intra-Caribbean slave trade and the expansive jurisdiction of the Grillo and Lomelín asiento tethered the status of people of African descent to slavery in moments of maritime mobility.
Excerpted from The Predatory Sea: Human Trafficking and Captivity in the Seventeenth-Century Caribbean by Casey Schmitt. Copyright © 2025 by the University of Pennsylvania Press. Reprinted by permission of the University of Pennsylvania Press.
