Hawai'i has often been the beneficiary of the insights of extraordinary men and women who visited the islands and made important observations. Among these was perhaps America's most famous philosopher, John Dewey (1859-1952). First visiting Honolulu in 1899 as the guest of Mary Tenney Castle and her family, Dewey would help establish Hawai'i's first progressive kindergartens while also assisting in the establishment of the new progressive Castle Kindergarten on King Street. Dewey was a close friend of his University of Chicago colleague and symbolic interactionist George Herbert Mead and his wife Helen Castle. He had met the late Henry Castle, a young philosopher whose life had been cut short in a shipping accident on the North Sea, in 1895. Dewey's visit coincided with the incipient efforts of educators to formulate a radical re-engineering of early education, which would forever change the way the public looked at young children and eventually lead to a comprehensive K-12 public education for the territory, and then the state, of Hawai'i. From Dewey's perspective the school was best understood as a miniature society; as such, it should be representative of the essential institutions of this society. As an ideal society, the school is the chief means of social reform. In the controlled social environment of the school, trained teachers could develop creative individuals who could work effectively to eliminate existing social evils and build a better society. For Dewey, the school was the medium for developing habits for systematic inquiry and for tolerance of the new and untried. This article describes Dewey's relationship and shared values with Mary Castle and their efforts to establish the progressive Castle Kindergarten on King Street. It goes on to highlight key aspects of Hawaiian learning which were broadly consistent with the constructivist pedagogical theory of Dewey and may explain why Hawaiian enrollment in many progressive kindergartens was relatively high.