Based on an analysis of Sherwood Anderson’s letters, this study explores the novelist’s principal inspiration during his final years (1939–1941): his exposure to Latin America. Thematically arranged correspondence traces his positive reception in South America—a place he saw as a source of fresh ideas and publishing opportunities—his desire to promote cultural relations with North America, and his legacy among Spanish-speaking readers. The author discusses the political and economic climates of mid–20th century South American nations, their emerging liberal ideologies and the concerns Latin American readers had regarding societal upheaval, urbanization and the inequities of capitalism—all vividly depicted in Anderson’s works.