A Miscellany of five secular Yiddish chapbooks was created in late sixteenth-century East Swabia. Two of the chapbooks, “Keyser Oktavian” and a collection of “mayses”, were illustrated by their scribe Yitzhak bar Yuda Reutlingen. A Jewish owner also drew on a blank folio. This essay seeks to address two issues. First, although in the past these drawings have often been dismissed as derivative or crude, this article will dispute this assertion. Then this essay will question the ways in which some scholars have masked the manuscript’s Jewish identity, and will explore how the scribe and owner express the distinctly Jewish nature of the Miscellany through their drawings.