The painter Paolo Rodocanachi, a descendant of a wealthy Greek merchant family from Chios, was born and died in the Genoa region of Italy, but enlisted twice in the Greek Army. In 1916 he was in eastern Greek Macedonia, who was at the time engaged in a conflict with Bulgaria, in the context of a political crisis that led to the National Schism, the final break between the supporters of King Constantine I and those of Prime Minister Venizelos. Rodocanachi got enlisted in the IV Army Corps, which got involved in a political and military imbroglio that ended in a paradox: the “deportation” of some 7,000 men to Germany, in a camp sheltered by the small town of Görlitz. There, the Town Hall building hosted the painter’s first solo exhibition in 1918. When this unprecedented captivity ended in 1919, Paolo Rodocanachi returned to Italy, but in 1922 he was mobilised again for a mission as a painter of the Greek Army, this time in Asia Minor. His drawings were lost in the “Great Disaster” that followed. After these two unheroic but highly exceptional adventures, Rodocanachi retired to Italy for the rest of his life, devoting himself essentially to landscape painting, with a naturalist and lyrical attitude thus turning his back on the modernist avant-garde. By tracing the exceptional destiny of this original character, we aim to consider his aesthetic in the light of his patriotic commitments and the political and ideological issues of his time.