This article challenges the narrative of ubiquitous late medieval Christian anti-Judaism by presenting Pablo de Santa Maria’s remarkably nuanced portrayal of Judaism (c. 1400–1430). Pablo, the rabbi of Burgos who had become its bishop, lived and wrote at the intersection of Judaism and Christianity. While longstanding historiographical misconceptions about the nature of Pablo’s intellectual and pastoral project have stifled interest in Pablo’s prolific Latin writings, recently scholars like Yosi Yisraeli have argued that these Latin writings actually contain intellectual innovations of profound importance to the development of Christian Hebraism. This article reads Pablo’s Latin writings not primarily within the Christian intellectual tradition but rather as a response to the contemporary phenomenon of large-scale Jewish baptism. Pablo was seeking to negotiate the integration of these baptized Jews into Christianity, which required him to construct positive narratives about Judaism to dispute (or at least complicate) the prevalent negative narratives. More broadly, while recent scholarship has treated Christian narratives of Judaism as emanating from intra-Christian disputes, this article suggests Christian views of Judaism were in fact formed and contested through the persons and identities of baptized Jews.