From ancient Jewish texts to European Romanticism, the archetypal figure of the Shlemiel traces an unexpected literary journey, originating not in the fictional town of Chelm but in the biblical figure of Shelumiel ben Zurishaddai, a prince of the tribe of Simeon. Through rabbinic interpretation, this census-taker transformed into Zimri, the ill-fated consort of Moabite women killed by Phinehas - a transformation that would later influence Adalbert von Chamisso's 1814 character Peter Schlemihl and Heinrich Heine's poetic works in "Romancero." Drawing from textual analysis of the Book of Numbers, talmudic commentary (Sanhedrin 82b), midrashic literature (Tanhuma, Pinhas 2), medieval rabbinic responsa, and nineteenth-century German poetry, this research uncovers a continuous literary tradition spanning millennia. The evolution of Shlemiel from a specific biblical personage to a universal symbol of the hapless individual reveals the sophisticated ways Jewish literary motifs have permeated and enriched broader cultural contexts.