This doctoral thesis situates the Mediterranean island of Sicily as a magnet of competing political desires in the thirteenth and fourteenth centuries: for the Kingdom of Aragón, the island provides a stepping stone towards recovering the Holy Lands and recuperating a Norman legacy; for the Angevins at Naples, a strategically-placed military asset; and, according to the Papacy, a treasure stolen and tumbling to perdition. Locally, Sicilian nobility negotiated each of these claims in a variety of ways. My focus on the Chiaramonte family and their patronage of art and architecture, especially at the Palazzo Chiaramonte-Steri, demonstrates how commissions operated as a key tactic of gaining visibility and legitimacy in the face of continual upheaval. The dissertation unfolds in two sections proceeded by a comprehensive introduction to the monument and the Chiaramonte family: in the first section, composed of three chapters, I focus on the tradition of painted ceilings in Sicily and treat at length the painted beamed ceiling of the Palazzo Chiaramonte-Steri’s reception room, the so-called Sala Magna. The second part of the project, divided into two chapters, investigates the Chiaramonte family's involvement in rehabilitating Sicily’s reputation in light of its challenged religious status.