In the Philippines from 1640 to 1750, Spanish authorities feared that they would lose control of the Pacific colony to its multiracial resident populations. Essential to imperial fear was a fundamental misunderstanding of racial and gender dynamics within colonial labor spaces. Imperial officials discursively constructed laboring populations as “lazy indios” and Chinese “infidels”; such men were potential enemies of empire who outnumbered Spanish residents and incited disorder. This dissertation examines imperial correspondence, labor laws, and colonial reports to highlight the processes, discursive and material, through which Spanish imperial authorities conceptualized race and masculinity in the markets, the lumberyards, the mines, and the haciendas of the colonial Philippines. I argue that in the century prior to the Bourbon Reforms, colonial authorities – confronted with the challenge of making the local Philippine economy more efficient– consistently recalibrated their assumptions on racial formations to ultimately convince themselves that some races, and some men, could be redeemed from the category of “enemies of the empire.” Moving from racial formations situated within the binaries of Spanish and non-Spanish, imperial officials progressively reimagined race and masculinity through the lenses of religion, scientific intellect, and economic practicality. As they toiled in colonial labor regimes, indigenous and Chinese men mirrored racialized and gendered assimilation for their Spanish superiors while simultaneously building their own networks of economic and sociopolitical power.