In A Troubled Marriage, Sean F. McEnroe highlights a consequential yet often overlooked undercurrent of early modern American history: the profoundly transcultural lives of some Indigenous leaders, mestizos, and Europeans who, by chance or design, found it necessary to straddle colonial cultural divisions, form alliances, and learn from one another. This included Native intermediaries who pursued the interests of their home communities within the diplomatic and commercial structures of European empires, Indigenous Christians who transformed the aesthetics and theological emphases of the colonizers' religion, and individual Europeans who found themselves beyond the reach of colonial hegemony and compelled to engage Indigenous peoples on equal, or even disadvantageous, terms. In a vivid and well-curated series of minibiographies, McEnroe highlights and juxtaposes dozens of individuals whose lives exemplified such cross-cultural “marriages.” In doing so, he illuminates a dimension of the fraught, centuries-long Columbian encounter that contemporary disciplinary tools sometimes struggle to recognize and comprehend, as it was defined less by overt violence and coercion than by mundane dealmaking and pragmatic adaptation.The Native elites, educated mestizos, and marginal Europeans highlighted in A Troubled Marriage are unrepresentative of the colonial population writ large. Nonetheless, their stories help explain the long-term evolution of American regional and national cultures as novel developments rather than mere satellites of Europeanism. They demonstrate that transculturation, syncretism, mutual cultural appropriation, negotiation, and reciprocity were, alongside violence and hegemony, fundamental and perennial factors within American cultural development. Many of the intercultural individuals addressed in the book won renown in their own time, including Álvar Núñez Cabeza de Vaca, Antonio Valeriano, Pocahontas / Rebecca Rolfe, Catherine Tekakwitha, Tupac Amaru II, and Louis Riel, to name only a few. McEnroe offers synthetic treatments of these well-documented lives supplemented with a handful of complementary examples drawn from archival research. As transculturation often lies in the small details, the author foregrounds the lived complexities and contradictions of those who existed along the seams of colonialism. This tactic is very effective when biographical data are plentiful, but it also highlights the unfortunate lack of such detail in the cases drawn from archives, which were certainly no less rich.A Troubled Marriage builds on recent scholarship emphasizing Native agency. Its most ambitious and definitive historiographical aim, however, is to achieve a fully continental perspective on early modern American history. In linking and analogizing the experiences of Native leaders from North, Central, and South America, McEnroe intentionally disregards artificial and misleading distinctions imposed retroactively by linguistic and national borders—including the hoary specter of US exceptionalism—that have long obscured the broader unity of American history from Canada to Chile. And he largely succeeds, drawing information in multiple languages from almost two dozen archives on both sides of the Atlantic as well as from digital and published sources from the English, French, and Spanish empires. The Iroquois, Aymara, Nahua, Cherokee, and Guaraní all share in a large-scale story, even if archives and historical subfields often obscure it.Interestingly, in overcoming such obstacles, the book runs against yet another challenge: the very diversity of Native America itself. As a story of European empires, a hemispheric view is perhaps easier to achieve; but a holistic account centered on Native perspectives is inherently more difficult by an order of magnitude. The author handles this challenge well, however, because while the book's scope is sweeping, its interpretive goals remain quite modest. Rather than precisely theorize or define the shared experiences of Native elites across the continent—which would be methodologically and empirically unwarranted—McEnroe simply details illustrative cases, clarifies their defining idiosyncrasies, and provides relevant regional and cultural context. The book's overall interpretation of Indigenous elites, then, lies primarily in the conceptual organization of the volume itself—not by region or period but by the particular mode of transcultural “marriage” that each individual embodied or participated in: religious, artistic, intellectual, political, or literal (i.e., intermarriage).Lively and highly readable, the book will refine and elevate undergraduate perspectives of early modern America and mestizaje beyond simplistic or teleological story lines inherited from nationalistic or essentializing histories. Yet its continental perspective is an important historiographical intervention as well, one that will benefit advanced scholars examining analogous experiences within Portuguese America and the Caribbean as well as African-descended populations throughout the hemisphere. McEnroe's vivid and even loving prose reveals a deep appreciation for America's subtle transcultural heritages and empathy toward the individuals who embodied them. The book's emphasis on marginal case studies is not celebratory and largely complements today's reigning narratives of colonialism but also reminds us that individual lives are inclined to transcend and resist the caricatures and classifications assigned to them, whether by haughty contemporaries or later scholars brandishing theories. A Troubled Marriage effectively encourages scholars to account for and integrate such underlying complexity in their own work.