Biblical interpretation within Conservative Judaism faces a fundamental tension between traditional midrashic reading and modern critical scholarship - a divide that deconstruction theory uniquely bridges. By examining Genesis 49:8-12, Jacob's testament to Judah, through both traditional and deconstructive lenses, this research reveals how definitive interpretations can paradoxically limit rather than expand textual understanding. Analysis of the Hertz Humash commentary demonstrates how predetermined theological positions often suppress linguistic ambiguities in key Hebrew phrases like "miteref b'ni alita" and "ad kiyavo shiloh," which contain multiple valid interpretations. Deconstructive methodology reveals alternative negative readings of what is traditionally viewed as a blessing, uncovering critical perspectives on Judah's character and actions, particularly regarding Joseph's sale and Judah's relationships with Canaanites and Edomites. Through careful examination of linguistic ambiguities, historical context, and intertextual connections within Genesis and broader biblical literature, the research establishes that meaning in biblical texts is fundamentally undecidable. This inherent openness to multiple interpretations, rather than being problematic, provides Conservative Judaism with a theoretical framework that honors both traditional midrashic approaches and modern critical scholarship while maintaining dynamic textual engagement.