In the summer of 1539, an elaborate, ephemeral programme of decoration was constructed in Florence to celebrate the wedding of Cosimo I de' Medici and Eleonora Álvarez de Toledo. Through an interplay of painting, sculpture, heraldry, and classical allusions, the programme constructed a narrative of the marriage as the culmination of a history of mutual support between the Medici family and the Spanish monarchy. In so doing, this article argues, it revealed the dynamic by which the network of political alliances and exchanges that made Spanish hegemony on the Italian peninsula possible operated. The narrative re-presented the distant and recent history of Medici–Spanish relations and re-created Florence as a middle ground between Spanish imperialism and Italian resistance and autonomy. It revealed the way in which Spanish Habsburg hegemony in Italy relied on dialogue, accommodation, mutual reciprocity, and a creative interpretation of the past and present.