This essay examines the influence of Aby Warburg and the Warburg Institute, as mediated by Edgar Wind, on R.B. Kitaj from the late 1950s until his death in 2007. It is based on research in the National Portrait Gallery, the Warburg Institute Archive, the Wind archives in Oxford, Kitaj’s unpublished autobiography and correspondence between the author and the artist dating back to 1972. It explores Kitaj’s creative response to Warburg’s brand of cultural history which encouraged his early eschewal of the prevailing focus upon formal values in favour of ‘symbolic images’ and suggestive content. This tendency was enhanced by his increasing celebration of his Jewishness and aspirations towards the creation of ‘a Jewish art like the Egyptian figurative style’. Kitaj’s portrait of Ernst Gombrich (1986) was commissioned by the National Portrait Gallery at a time when he was becoming obsessed with his Jewish project while Gombrich was confirming his rejection of the category Jewish, in other than a religious context, altogether. Discussion of Jewishness and the arts in the twentieth century is supplemented by the identification of David Allan’s Origin of Painting (done in Italy in 1775) as the inspiration for Kitaj’s Los Angeles series of pictures in which his late, lamented wife is depicted as the Hebrew deity, Shekinah.