In Eastern European Jewish culture, the figure of the Red Jews – a red-haired, red-bearded or ruddy-complected Yiddish variant of the Ten Lost Tribes – thrived well into modern times. Writers and artists engaged the image of the Red Jew in new ways during the late nineteenth- to early twentieth centuries. At the forefront were the founders of modern Yiddish fiction, Mendele and Sholem Aleichem, who penned several short stories about Red Jews living in the Pale of Settlement, and Marc Chagall, who famously immortalized the association of Jews with red hair on canvas in his Jew in Bright Red. All three of these artists harnessed the Red Jew as a vehicle for expressing their generation’s perception of exile. They creatively explored the modern Jew`s dilemma of homelessness within the evolving nations of Europe by weaving the destiny of the originally anti-Jewish Christian iconography of the Wandering Jew into their narrative of the Red Jew. The paper suggests that, despite having drawn on the old Yiddish legend of the Red Jews which itself had been reappropriated from medieval German culture, the red-bearded Jew in modern Yiddish culture should also be understood within a renewed battle of images between Jews and Christians. This modern Jewish-Christian contest over color symbolism becomes impressively visible when the use of red by Chagall is compared with this same color in anti-Semitic iconography. The red-headed Wandering Jew, attributed to Gustave Doré (Le Juif-Errant, 1852) provides an infamous exemplar of the latter category.