Recent studies on the Buddhist threefold wisdom model and its suggested potentialities have warranted a rediscovery of the model in different historical and cultural contexts. Saichō (最澄, 766/7–822), founder of Japanese Tendai Buddhism, references the three wisdoms in his documents outlining the Tendai monastic education curriculum. Through modification of translation and analysis of related original texts by Saichō, and an interview with the current dean of the Tendai monastic education institution, this paper aims to (1) uncover Sino-Japanese history of expressions of threefold wisdom and Buddhist education, (2) clarify the content of Saichō’s curriculum, and (3) examine the role of compassion in said curriculum. This paper argues that the threefold wisdom served as a foundational framework of Saichō’s education; he envisioned that his graduates would develop into religious leaders of the nation who would benefit all sentient beings through their own training, preaching the Dharma, and contributing to social work. At the same time, it became clear that compassionate attitudes were considered to be fundamental to all practices of the three wisdoms at Mount Hiei, which makes Saichō’s curriculum a captivating case of a theological application of the threefold wisdom.