This chapter explores the Portuguese Empire’s expansion in the sixteenth century through the lives of Dom Pedro Mascarenhas and Dom Francisco Mascarenhas. It traces Dom Pedro’s rise from a third-born fidalgo to a seasoned diplomat, naval commander, and ultimately Viceroy of India, highlighting his service in North Africa, Europe, and Asia. His career demonstrates the crown’s reliance on loyalty, marriage alliances, and overseas service to reward and elevate noble families. The narrative continues by following the trajectory of Dom Francisco, another Mascarenhas who would later govern India, foreshadowing the change from service before reward to reward before service.