When Lithuanian Jewish poet I.J. Schwartz arrived in Lexington, Kentucky in 1918, he encountered a South grappling with profound social transformation—a landscape that would inspire his groundbreaking Yiddish poetry collection *Kentucky* (1925). Through detailed examination of Schwartz's nine-poem cycle written between 1918-1922, this research reveals how a Jewish immigrant masterfully captured the region's dualities: its lush sensuality against its moral corruption, its fading aristocratic traditions against rising middle-class materialism, and its systematic racial oppression beneath surface gentility. The analysis traces structural parallels between Schwartz's work and Whitman's *Leaves of Grass*, while drawing thematic comparisons to Faulkner's Southern literature. As part of the "Di Yunge" movement, Schwartz created what amounts to an American epic for Yiddish-speaking Americans, successfully translating the Southern experience through an immigrant lens while confronting universal themes of assimilation, identity, and social justice. His sophisticated portrayal of Southern society's complexities demonstrates how outsider perspectives can illuminate regional American experiences with remarkable clarity and depth.