Enslaved people sought freedom by any means possible. Most often they achieved free status through hard work, financial accumulation, negotiation, and legal confrontation. Building on slaves’ initiatives, Chapter Two looks at two legal areas in which Cuba diverged from Virginia and Louisiana: manumission and interracial marriage. Although seventeenth-century Virginians set no restrictions on the ability of a person of color to become free, or to marry a white person, that began to change toward the end of the century. By the early eighteenth century, manumission and interracial sex and marriage were restricted in both Virginia and Louisiana, unlike Cuba, where manumission never faced a serious legal challenge. Slaveholders and local authorities in Cuba resented the existence and social assertiveness of free blacks but were constrained by a deep-rooted legal order in which manumission was firmly entrenched and not tied to racial concerns. In Virginia and Louisiana, however, manumission became tied to the development of legal racial regimes that linked freedom to whiteness. In Cuba, black freedom became a contested but integral part of colonial society.

Chapter One traces the development of local legal regimes in Cuba, Virginia, and Louisiana in which blackness was identified with enslavement and social degradation. We demonstrate that legal and social precedents such as those invoked by Frank Tannenbaum and Alan Watson mattered deeply to the development of these new slave societies, yet not in the way traditional comparisons argued. By the time the Iberians arrived in the New World, they were familiar with the enslavement of sub-Saharan Africans, and set about immediately to establish a racially based society in Cuba. In Virginia, by contrast, distinctions of race were not systematized in law until slave status was set in stone decades after the colony’s settlement. The French arrived in Louisiana at a much later point in the development of their empire, and had already written a code for slaves and “noirs.” Across the regions, colonial legislators established a degraded status for people of African descent, but they did so much more quickly in Cuba and Louisiana.

The Introduction discusses some of the main questions that the book seeks to answer and relates the book to previous scholarship on race, slavery, and the law in the Americas. We approach the early comparativists’ broad questions about the development of regimes of race and slavery with the tools and approaches of cultural-legal history close to the ground. Rather than start with static legal traditions to trace their effects in law, we look at the way legal practices, emerging not only from doctrines and traditions but also from participants’ strategies, including slaves’ actions, shaped institutional change. It also explains the choice of three plantation societies for the study: Cuba, Virginia, and Louisiana. Historians have often paired Cuba and Virginia as exemplars of the Spanish and British systems; this book adds a third point of comparison, the hybrid legal system of Louisiana, where it is possible to examine how slaves took advantage of shifting legal regimes during the eighteenth and nineteenth centuries to obtain freedom.

Chapter Four shows how slaveholding elites across jurisdictions responded to the growth of the free population of color during the Age of Revolution with fear and repression. They feared large-scale slave revolts, the rise of abolitionism, and the assertiveness of free people of color. Beginning in the 1830s, and with increasing fervor in the 1840s and 1850s, white slaveholding elites across the Americas sought to crack down on free people of color and manumission. They also looked for ways to remove free people of color from their midst through various “colonization” schemes, to realize the old dream of a perfect, and perfectly dichotomous, social order of blacks and whites, enslaved and free. This chapter explores the growing restrictions on manumission and free people of color in Louisiana and Virginia during the antebellum era, which stand in contrast to the significant but less successful efforts of Cuban slaveholders to limit the rights of free people of color. By 1860, these jurisdictions were on truly divergent paths concerning race and freedom. Black freedom was described as an anomaly or a legal absurdity in Virginia and Louisiana, but not in Cuba.

The Conclusion revisits some of the book’s main arguments and notes that although, by the mid-nineteenth century, Cuba, Virginia, and Louisiana were mature slave societies, their racial orders differed in consequential ways. In most parts of Virginia and Louisiana blackness was almost coterminous with enslavement: an enslaved person could live his entire life without ever meeting a free person of color. This was virtually impossible in Cuba, where free people of color represented a significant proportion of the total population. The link between whiteness and citizenship did not crystallize in the same way in Cuba. A free person of color in Cuba could be a rights-bearing subject, participate in public life, and marry across racial lines; on the eve of the Civil War, a person of color in Virginia or Louisiana could do none of those things. Laws regulating free people of color also served as a template for post-emancipation societies seeking ways to degrade black people. Slavery laws did not translate forward in the same way that regulations based on race did.

Chapter Three studies the impact of the Age of Revolution on the formation of communities of free people of color. Across the Americas, the chaos of war, ideologies of equality and liberty, and the specter of slave rebellion in Haiti, inspired legal forms of claims-making and created new opportunities for emancipation. The period from 1763 through the 1820s could be said to be the era of greatest commonality across these jurisdictions. During this period, both Louisiana and Virginia developed significant communities of free people of color, especially in urban areas. Yet freedom was often the unintended consequence of retrenchment and reform rather than revolution. The growth of these communities had radically different political connotations. In Virginia, manumissions became linked to wider debates about slave emancipation and were opposed as a dangerous step toward black citizenship. In Cuba–and by extension in Louisiana under Spanish control–manumission was linked to the regulation of customary practices that had nothing to do with abolition or with republican notions of equality but instead concerned traditional understandings of vassalage, status, and royal justice.

Chapter Five continues the discussion of slaveholders' efforts to limit the rights and standing of free blacks. It looks closely at the 1850s, when Louisianan and Virginian slaveholders built a white man’s democracy in which whiteness was the sole basis for political power and free people of color could never be citizens. The legislatures of Virginia and Louisiana sought to isolate and degrade people of color in every realm of the public sphere, shutting down their institutions, such as churches and schools. In Cuba, where the colonial state could not afford to alienate the free black population and where black freedom was not linked to white man’s democracy, free people of color managed to withstand the slaveholders’ assault on their traditional rights and institutions. Regulations based on race rather than status predictably led to litigation over racial identity, and the chapter compares trials of racial identity and cases of interracial marriage. Whereas courts in the U.S. drew tight connections between whiteness and the possibility of citizenship, the Cuban courts held out the possibility that a person of color could be honorable and marry across the color line.