In the mid to late 1960s, art critic Leo Steinberg (1920–2011) carried out research on Titian that was never published and has remained so far unknown to scholars. By examining research material now held in the special collections of the Getty Research Institute, this study reconstructs Steinberg’s inquiry on the topic and discusses more broadly its methodological significance in relation to both his critical thinking and key issues concerning the study of Renaissance art. In particular, it deals with Steinberg’s interest in the relationships between the picture plane and the real space, site-specificity, and the spectator’s engagement. Steinberg’s critical attitude is analyzed by comparison with that of art historians Erwin Panofsky (1892–1968) and David Rosand (1938–2014), with whom he was principally concerned throughout the investigation of Titian’s Presentation of the Virgin (1519–26). The article evaluates how Steinberg’s approach can today effectively serve the analysis of premodern artworks from an alternative perspective to mainstream art history.