The author uses his father's autobiographical writings about the small-town, baseball experiences of his youth as background for discussing the significant cultural shifts that have dramatically changed the nature of the game from a free-play experience for neighborhood kids to an organized youth-league sport. In contrast to his father's day, the author claims that the playfulness of youth baseball has become nearly extinct. After a brief overview to define the essence of play, the author explains how his father's kind of free, unstructured, deliberate play has been diminished by complex cultural and social shifts such as rationalization, suburban sprawl, and changing child-development philosophies. He concludes that the continual decline these forces have created in free play will not only significantly influence the future of baseball as a sport but also the quality of children's growth, development, and health.