My dissertation recasts the early years of Spain’s imperial formation, which has been long framed from the perspective of monarchs, to focus on the lives of conquistadors who fought in multiple theaters of the nascent empire. At this time, Spain underwent a remarkable string of territorial acquisitions, conquering various possessions in the Atlantic, the Mediterranean, and Iberia, including Granada, the Canary Islands, Melilla, Oran, Naples, Navarre, the Caribbean, and New Spain. While scholars traditionally investigate the individual histories of the respective localities, my research posits a conceptual link between them, using the lives of several dozen conquerors whose footsteps crisscrossed these lands. Drawing on an array of archival documents housed in Spain and Mexico, such as letters, interrogatories, land grants, and royal contracts, my research tracks the movement and activities of this cohort of men across the empire, illustrating how the skills and expertise that they acquired in one setting prepared them to excel in others. My dissertation demonstrates how the success of the early Spanish empire depended greatly on networks of peripatetic conquistadors, whose services in multiple areas of the realm connected the imperial polity and ensured its proper functioning. In scrutinizing the lives of Iberian conquerors, my dissertation seeks to contribute to several important strands of scholarship, including the historiography of conquest, empire, conquistadors, and transnational studies of the early modern world.