An important figure in the literary movement of modern Taiwan, Yang Kui (1905-85) also produced several novels in Japanese during the colonial period. In 1934, "A Newsboy," one of his most noted short stories, earned him a literary prize from an important Japanese journal. This piece was later translated in to Chinese by Hu Feng (1904-85) and was included both in Mountain Spirit: Short Stories from Korea and Taiwan and Anthology of Stories from Weak and Small Nations in the World. Yang Kui played an important role in the development of Taiwanese literature; one of his contributions was the founding of the literary journal Taiwan New Literature in 1935. Yang was born and educated in the Japanese colonial period, and his early exposure to world literature was through Japanese translations. In a talk late in his life he mentioned Numakawa Sadao (1898-1994) as one of his teachers from Japan who had a formative influence on him. Numakawa was a young teacher in a gong xuexiao, an elementary school for Taiwanese children during the Japanese colonial period. He was kind to Yang, taught him many subjects free of charge, and granted Yang access to his book collection. Numakawa was a literary person himself and published some works in Japanese newspapers based in Taiwan. This intriguing friendship between an anticolonialist Taiwanese novelist and a Japanese school teacher, who was in a certain sense a symbol of Japanese colonialism, deserves critical attention. This article investigates the life of Numakawa in order to understand the significance of this friendship in the development of Yang's literary career.