Guided by the twentieth century hermeneutic idea that application co-determines understanding, this paper explores the conversations between theory and application that evolved during the implementation of three Olympic-related curriculum projects. Each of these projects was informed by specific fields of then-current educational theory, and offered understandings and insights that were applied in the next project. These understandings guided the development of the toolkit for the Olympic Values Education Program (OVEP) of the International Olympic Committee. The author suggests that the collective insights from this ongoing curriculum development process have the potential to provide a theoretical foundation for a pedagogy of Olympic values education. Roland Naul, another Olympic scholar, describes the approach to Olympic education that evolved from this process as a "lifeworld" orientation, in which the Olympic ideals act as a motivation for learning activities in all aspects of life, integrated with active participation in sport and physical activity. Questions that are addressed during the discussions of the various projects include: What current educational theory will best support the flexible delivery of Olympic-related activities in support of school-based learning outcomes? How do children and youth learn positive behaviours and values, and what teaching methodologies support this learning? Do the Olympic values have relevance in cultural contexts other than the ones based on Euro-American traditions? Are they, as the Olympic Movement professes, universal? Are the methodologies proposed for teaching values in Euro-American contexts appropriate in other cultural contexts? How can international Olympic education and fair play initiatives represent global cultural perspectives? (Contains 10 notes, 1 table, and 1 figure.)