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The dissertation explores the relationship between padronism and the practice and ideology of free wage labor during the peak years of immigration to North America. The padrone, an immigrant labor contractor who allegedly kept his compatriots enslaved through debt and physical coercion, sparked debates about the ambiguous and culturally contested boundaries between unfree and free labor during the Progressive Era. The dissertation is organized around the social histories of three padrones: Italian Antonio Cordasco of Montreal, Canada, known as the "King of the Laborers," Greek Leonidas Skliris of Utah, nicknamed the "Czar of the Greeks," and the powerful Mexican labor contractor, Roman Gonzalez of El Paso, Texas. Using immigrant newspapers, autobiographies, oral histories, court cases, union and company records, and the writings of dime novelists, reformers, and government investigators, the dissertation integrates western, labor, immigration, and cultural history by considering how immigrant padrones, contract workers, and native-born residents of North America each adapted free labor ideology to their own separate and often conflicting ends. The comparative scope of the dissertation highlights cross-ethnic comparisons and the importance of space--geographic, corporate, and legal--in the development and persistence of unfree labor relations in North America after emancipation. In so doing, the dissertation brings western and labor history into productive collaboration by examining how padrones extended the long reach of the international labor market, not by annihilating space, as predicted by Karl Marx, but by commodifying its varied geographic, corporate, and legal aspects in North America. The first half of the dissertation explores the creation of padronism, focusing upon the spaces that padrones commodified, while the second half explores the role of gender, race, and class relations in redefining those spaces and subverting padronism. While padrones initially exploited transient immigrants by controlling the geographic and cultural boundaries separating them from North Americans, immigrant workers were remarkably successful over time in taking control of those same spaces and eliminating the padrone system in North America.