In the early twentieth century, many American educators pinned their hopes for a revitalized nation on the character education of "youth," especially adolescent boys. Although the emphasis on student morality was far from novel--nineteenth-century common and secondary schools operated as bastions of Protestant republican virtue--new perceptions of moral decay, institutional failure, and general cultural anomie prompted a marked increase in urgency. Among the many agencies confronting this impending moral crisis, the Young Men's Christian Association (YMCA) had perhaps the most comprehensive program of regeneration for American youth, encompassing a carefully articulated system extending from boyhood to collegiate and employed young men. Through a collection of "Hi-Y" clubs, the YMCA sought to fill a perceived moral/religious gap by "creating, maintaining, and extending" masculine Christian character among high school boys. This article accounts the transformation of the Hi-Y between 1910 and 1940 that serves as a lens to view themes critical to the historiography of secondary education in these years. First, the changes in the Hi-Y give the historian an interesting perspective on the transition of one high school organization from conservatism to liberal progressivism. Second, the story of the Hi-Y demonstrates the intriguing relationship between religion and secondary education at a time when both were undergoing fundamental transformation. In many ways, the Hi-Y was an attempt to provide high school boys with a moral education rooted in Christian values and the example of Jesus. The appeal to the "Jesus way of life," however, revealed how closely Christian character values could be linked to larger cultural trends. While the released-time program of weekday religious education played an increasingly significant role in the 1930s and 1940s in exposing students to church-based teaching, the Hi-Y provided students an alternative interdenominational (and to some extent interfaith) experience in practical Christian living in American public high schools. (Contains 159 footnotes.)