Éamon de Valera was unquestionably one of the most significant political actors in twentieth-century Ireland. His political career, spanning almost six decades from the Easter Rising in 1916 to his death in 1975, makes him a fascinating subject for study. Indeed, de Valera's time in high office was arguably one of the longest of any democratically elected leader in history. Perhaps his most significant political achievement was the 1937 Irish Constitution. Controversially, this document proclaimed that "mothers shall not be obliged by economic necessity to engage in labour to the neglect of their duties in the home,"1 inviting the following question: What connects gender and political power in de Valera's career? How, for instance, was the representation of de Valera's masculinity used to confer political legitimacy? Conversely, how were representations of his perceived lack of masculinity used to denigrate his legitimacy? This essay analyzes the representation of de Valera in the period 1922–39 through the medium of political cartoons. It argues that cartoons demonstrate how discourses of masculinity were central to the construction of political power in the Irish Free State, using de Valera as a case study.