The chapter explores how the activities of Spanish officials and men-at-arms impacted identity-making processes against the background of debates over the significance of the movement toward defining the benemérito category and the hierarchy of the meritorious. The chapter argues that, beginning in the second half of the sixteenth century, imperial agents faced the challenge of fashioning notions of a deserving self or undeserving other while balancing two opposing metrics of merit: rootedness and mobility. It first examines the unwillingness of conquistadores and first settlers, and their descendants, to serve in the Philippines and the ways such unwillingness reinforced development of negative stereotypes associated with these privileged social categories. Subsequently, it explores the efforts of Melchor López de Legazpi, Pedro de Robles, Diego García de Palacio, and Rodrigo de Vivero to use their Pacific service as a basis for fashioning themselves as meritorious subjects. Finally, it considers how debates over the hierarchy of the meritorious shaped ideas about New Spain’s transpacific connections and the region’s position between Europe and Asia.