Twenty miles northeast of San Antonio, between the small cities of Live Oak, Shertz, Selma, and Universal City a true architectural and city planning masterpiece sits, protected from outsiders, and at first glance it seems, from time. Randolph Air Force Base, built in 1931, has endured the decades, providing a beautiful, yet functional setting for the training of a many of the Air Force pilots of the twentieth century. Randolph enjoys a prominent history, rich with accomplished architects, powerful Generals, and an incredibly talented Lieutenant. As a Historic Preservation case study, Randolph provides a unique example of continual and loving preservation, as well as innovative and effective adaptive reuse. A National Historic Landmark, as well as National Register listed Historic District, Randolph has successfully ridden the waves of change, gracefully adapting, yet keeping a traditional and elegant air. Today, it faces budgetary constraints that could impact its preservation in the future. Privatization of its large historic housing inventory, the pressures of an active Air Force Base, as well as a staff of one preservation officer combine to create a complicated situation for this “Showplace of the Air Force.”