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Within the physiognomic discourse of the Zohar’s parshat Yitro, the thirteenth century kabbalists describe the figure of Messiah, or “seed of David,” in surprising and disruptive ways. Rather than idealized features, the Zohar enumerates messianic facial characteristics more normally associated with sin, immorality, and evil. Internal Jewish thinking prompts some of this description, as evidenced by concern with David’s “ruddy” appearance– a characteristic potentially associating him with the Sitra Ahra’s evil forces. Yet the kabbalists have other reasons to construct a figure who, like Aragorn in Tolkien’s Fellowship of the Ring, may “look foul and feel fair” (Tolkien, 1954). Participants in the medieval fascination with physiognomic discourse, Jews in the Castilian kabbalists’ social milieu were inundated with Christian verbal and pictorial images of a physiognomically idealized Christ. As Thomas Aquinas suggested, “Christ had the best complexion…owing to the fact that he had the most noble soul” (Resnick, 2012). These perfect images of Christ were juxtaposed with depictions of Jews comprising “the vilest examples of physiognomic intolerance” (Sauerlander, 2006). Medieval Jews, including the kabbalists, responded to these Christian claims in various ways. One strategy was to embrace the harsh images while redefining their meaning. This strategy is famously encapsulated in the early 14th century polemic Nizzahon Vetus section 238, which reflects on “heretics” asking Jews, “Why are most of the world’s nations white and beautiful, but most Jews are black and ugly?” (Berger, 1979). Rather than offering a counterargument for Jewish external beauty, the polemic redefines whiteness and beauty to signify negative spiritual qualities, and blackness and ugliness to signify good ones. This paper suggests that the Zohar’s presentation of the seed of David employs a similar strategy, while also commenting subversively on Christian ideas about the appearance of Christ and Antichrist.