The article presents a biographical reconstruction of the life of the painter Isaak Izrailevich Brodskii (1884–1939) through the lens of his painting “Vladimir Lenin in Smolnyi” (1930). Brodskii (and his work) are shown against the background of the terror of the 1930s, an ideological rupture in his artistic vision and his attainment of personal success. The diaries of Pavel N. Filonov help us to see Brodskii from an unusual angle. The impulse to write articles was an exhibition of “old art” (“Ars Nobilis”), which was held in the exhibition halls of Volkswagen in Berlin from October 18–27, 2002. Two portraits of Lenin by Brodksii were displayed there: “Vladimir Lenin in Smolnyi” and “Lenin reading Pravda” (1930) from the private collection of Otto von Mitzlaff.