This project looks at two members of Florence’s Medici family, Cosimo il Vecchio (1389-1464) and Duke Cosimo I (1519-1574), in an attempt to assess how they used the patronage of art to facilitate their rule. By looking at their individual political representations through art, the specifics of their propagandist works and what form these pieces of art came, it is possible to analyze their respective rules. This analysis allows for a clearer understanding of how these two men, each in very different positions, found art as an ally for their political endeavors. While they were in power only one hundred years apart, they present uniquely different strategies for the purpose of creating and maintaining their power through the patronage of art.