This paper examines drivers of land-cover change in the U.S. Great Plains in the last half of the twentieth century. Its central aim is to evaluate the dynamics of grassland preservation and conversion, across the region, and to identify areas of grassland that were never plowed during the period. The research compares land-cover data from 400 sample areas, selected from and nested within 50 counties, to aggregate data from the agricultural and population censuses. The spatially explicit land-cover data were interpreted from aerial photographs taken at three time points (1950s, 1970s and 2000s). Sample areas were chosen using a stratified random design based on the Public Land Survey grid with in the target counties, in several clusters across the region. We modeled the sequences and magnitudes of changes in the interpreted air photo data in a multi-level panel model that included soil quality and slope of sample areas and agricultural activities and employment reported in the U.S. Censuses of Agriculture and Population. We conclude that land retirement programs and production subsidies have worked at cross purposes, destabilizing micro-level patterns of land use in recent decades, increasing levels of switching between cropland and grassland and reducing the size of remaining areas of native grassland in the U.S. Great Plains.