Virginia Woolf`s "The Duchess and the Jeweller" has been criticized for being either trite or anti-Semitic in the representation of a Jewish jeweler. Woolf`s portrait of Oliver Bacon in the story indeed hinges on the stereotypes of Jews that were pervasive in British culture in the late nineteenth and the early twentieth centuries. Woolf`s production of the portrayal of a Jew is problematic for she does not attenuate the repellent stereotypes of a Jew with explicit sympathies with him or with heroic actions. This paper aims to contextualize Woolf`s problematic portrayal of a Jew in the formation of British anti-Semitism, its ethnographic discourses in particular that emphasize racial difference of Jews and projects them to be the racial other of the English. A close reading of the story reveals that Woolf`s caricature of a Jew raises questions about issues related to anti-Semitic stereotyping practices such as differentiation and assimilation, desire for assimilation and fear of miscegenation, and the fetishization of Englishness. Woolf`s caricature of a Jew remains purposively evasive and thereby challenging because she proposes to examine the boundaries and structures of conflicting, contesting desires and fears shaped by social and psychological customs and conventions in stereotyping Jews and producing Englishness.