This book gives an account of the literary representation of Jews as businessmen from the early nineteenth century to the onset of the Third Reich. The historical context provides the background for an examination of the literary representation of Jewish businessmen and presents evidence for the perpetuation, transformation, and combination of stereotypes. The double bind of assimilation – that the Jews were vilified whether they succeeded or failed – is illustrated from literary treatments by the Romantic writer Wilhelm Hauff and the early twentieth-century writers Lion Feuchtwanger and Paul Kornfeld of the historical figure of ‘Jud Süß Oppenheimer’. Gustav Freytag’s use of the Jews as ‘counter-ideals’ in his notorious bestseller Soll und Haben (1855) and the onset of racial anti-Semitism in Wihelm von Polenz’s Der Büttnerbauer (1895) are illustrative of how literary anti-Semitism hardened in the course of the nineteenth century. The book considers a number of literary texts, some well known, some less familiar, which are revealing of the way in which Jewish–Gentile relations were imagined in their time.