Federico and Ferrante Gonzaga came of age during a time of intense change in sixteenth-century Italy: The Italian Wars (1494–1559). The first and third-born sons of Isabella d’Este and Francesco Gonzaga spent their formative years at the courts of Francis I of France and Charles V of Spain, where, as effectively diplomatic hostages, they learned valuable lessons about the transnational social codes and rituals central to sixteenth-century political life. As adults, they applied these lessons in their political and martial collaborations with Charles V: supporting his dominions in Italy, facilitating his attempted colonisation of northern Africa, and praising his attacks on Muslim pirates in the Italian Mediterranean. This book uses epistolary, literary, and material sources to argue that the boyhood and adult experiences of Federico and Ferrante Gonzaga are illustrative of wider strategies adopted by elite Italians to respond to conflict and crisis in a global age.