During the 20th century, several major but importantly distinct art historians incorporated Pragmatist philosophy into their scholarship: Bernard Berenson (1865-1959), Edgar Wind (1900-1971), and Meyer Schapiro (1904-1996). The Pragmatist bases of their interpretations are documented and described-especially in relation to the pragmatic maxim-and their arguments are analyzed and evaluated against the modes of art historical research in which they each worked: formalism, iconology, social history, and semiotics. Chapter one focuses on how Berenson appropriated and transformed ideas found in the Pragmatist psychology of William James (1842-1910) to create and justify his influential yet much maligned formalist art history. I focus on Berenson's interpretation of Giotto's naturalism-a key example for his theory of "tactile values"-and I contrast Berenson's interpretation to that of his formalist peer, Alois Riegl (1858-1905), in order further to differentiate Berenson's Pragmatist commitments. Chapter two focuses on Edgar Wind's often-overlooked approach to iconology, framing Wind's project in relation to his confessed indebtedness to the philosophy of science of Charles Sanders Peirce (1839-1914). Wind's Habilitation itself is a Pragmatist contribution to the philosophy of science, and to help clarify how that early work informed his later art history I contrast Wind's interpretation of Titian's Venus Blinding Cupid to that of Erwin Panofsky (1892-1968), thereby using Panofsky's classic iconological platform as a baseline against which to throw Wind's Pragmatist commitments into relief. Chapter three focuses on what I call Meyer Schapiro's postwar psycho-social arguments. Here I analyze Schapiro's claims about Vincent van Gogh and Paul Cézanne, and how these claims differ from more orthodox Marxist and psychoanalytic interpretations, especially those of Arnold Hauser (1892-1978). Even though Schapiro was deeply informed by the writings of both Karl Marx (1818-1883) and Sigmund Freud (1856-1939), he was also indebted to the Pragmatist aesthetics and psychology of John Dewey (1859-1952) and George Herbert Mead (1863-1931), whose Pragmatist arguments help unpack the distinctive quality of Schapiro's claims. Chapter four again focuses on Schapiro-this time on his later semiotic writing and how those arguments are both indebted to the tripartite semiotics of Peirce and different from the structuralist claims of Claude Lévi-Strauss (1908-2009). In this chapter I draw on some of Schapiro's unpublished lectures on semiotics and show that his claims in his book Words and Pictures are made largely in a Pragmatist mode. I conclude by noting some analytic parallels between the neo-Pragmatist thinking of Richard Rorty (1931-2007) and one of the most ambitious contributions to art historical scholarship in recent years: David Summers's Real Spaces: World Art History and the Rise of Western Modernism. Summers himself (born 1941) has described Real Spaces in openly Rortyean terms, and in my epilogue I analyze both the potential and the challenges that such an adaptation of Pragmatism poses for art history today.