This iteration of the American Encounters series addresses artists’ conceptions of political and military authority through portraiture during and after North American and European revolutionary upheavals in the late eighteenth and early nineteenth centuries. The works discussed demonstrate shifting ideals of leadership through examination of artistic style, from restrained Neoclassicism to dynamic Romanticism, as well as the iconography of martial and civilian power. The publication also explores the proliferation and replication of images of leaders, particularly George Washington, as well as the demand for the revolutionary hero and first president’s likeness in France. Catalogue essays elucidate the reasons for the transmission of portraits of Washington across the Atlantic in the context of artistic, political, and military exchange between the two countries. Contributions also delve into issues of colonial, post-colonial, and post-revolutionary identity, investigating the ability of artists to navigate oscillating national, social, and cultural boundaries.