As a Native Hawaiian educator whose kuleana (responsibility, obligation, privilege) is to facilitate increased college enrollment, persistence, graduation, and transfer/career entry for Native Hawaiian students at Leeward Community College, Aulii Silva has honored her personal and professional vocations by investigating how Hawaiian students' cultural well-being intersects with her college's teaching and learning structures. She has eagerly sought out accounts of the development of teaching and learning in Hawai'i that have been told via the voice, worldview, and most importantly, the lived experience, of Hawai'i's aboriginal people. It is because of this same kuleana that this article focuses on what led to John Dewey's six-week visit to Hawai'i in 1899, and what effect, if any, it had on Hawai'i's school system. Through letters, newspaper accounts, and secondary sources, there is a great deal of evidence to suggest that through the relationships he had with the American missionary descendant Castle family, and their affinity for and application of his philosophies, Dewey could be credited with indirectly affecting Hawai'i's schools. This article outlines the personal and historic contexts that motivated the Castle family to invite Dr. and Mrs. Dewey to Hawai'i, while appropriately recognizing the Native Hawaiian ali'i who established government sponsored public education within the kingdom.