Did ancient rabbis read religious texts literally, or did they understand deeper symbolic meanings? Rabbi Shimon ben Lakish (Reish Lakish), a towering third-century Palestinian sage, offers surprising evidence for sophisticated religious interpretation that parallels modern approaches. Through analysis of key midrashic and talmudic passages, Reish Lakish emerges as a figure who embodied what James Fowler called "Fifth Stage" faith—maintaining deep religious conviction while openly engaging with texts as repositories of symbolic and mythological truth. His bold declarations that Job "never existed, never was created," his philosophical fusion of Satan, the Evil Inclination, and Angel of Death into unified symbolic concepts, and his poetic descriptions of Sinai through metaphors of divine fire and celestial writing reveal a conscious distinction between literal history and religious meaning. This evidence, drawn from close textual examination, suggests that contemporary Conservative Judaism's non-literalist biblical interpretation may represent continuity with classical rabbinic thought rather than departure from tradition. The findings illuminate rabbinic epistemology and validate sophisticated approaches to meaning-making within Jewish interpretive tradition.