This chapter reveals the great level of control that local elites accumulated over both local and royal institutions in Santo Domingo, to expand their influence to other parts of the Spanish Caribbean and acquire a profitable network of associates and introduce contraband goods into the city. Rodrigo Pimentel’s political life provides an illuminating example of the particularities of Santo Domingo’s institutional life, but on a larger scale, it also reveals the profound limitations that the Spanish Monarchy’s bureaucratic apparatus had to govern its own Caribbean territories and, by extension, most of its colonial dominions beyond Mexico City and Lima. Under the Habsburg, colonial centers of royal authority, Audiencias and governors often became extensions of the communities that hosted ministers and royal officials, and not anchors of royal power in remote Spanish possessions, as the crown initially intended. In theirdealings withhigh courts, these local groups of power both made and unmade the Spanish empire: they limited the influence of Madrid, but by using royal institutions for their own ends, they shaped the edges of the empire according to their own interests.