It is shocking to realize that an enormous percentage of American high school students end up as only marginally literate, especially in large cities. The future well-being of the nation is in jeopardy. Public policy is in trouble. City, state and federal policies have legislated mandatory testing, dominated by the federal No Child Left Behind Act. Additionally, a small school policy, implemented nationally in many localities, requires that large comprehensive high schools be replaced by small schools in which teachers would, family like, work intimately with students and their parents to ensure that every graduate will qualify for college entrance. To evaluate these well-intended public policies I offer an in-depth ethnographic case study enriched by historical documentation and cultural analysis. Fremont High School is located in Oakland, California, just 10 minutes by car from the Mills College campus where I teach, but its inner-city realities are as distant as the barren surface of the moon. Immersed in the school for five years as a volunteer, and with the collaboration of Mills students every semester, I describe a deeply flawed and intensely frustrating process of policy design and implementation that repeatedly exhausted and demoralized Fremont teachers trapped in unintended Catch-22 scenarios.