Winter stocker grazing programs are commonly used by cattle producers in the South. A number of decisions are made in these production systems including type of forage, planting dates, fertilization rates, grazing periods, stocking rates and strategies, and feed supplementation. Of course, some important variables such as rainfall, cattle prices, weather, and rates of gain are out of producer’s control. There is a rich literature examining costs and returns to winter grazing. This research is unique in that it uses 40 years of East Texas winter pasture data to analyze the economics of alternative winter grazing production systems. The data includes planting dates and fertilization, rainfall, types of pasture, stocking rates, in and out weights, monthly weights, and supplementation. Pasture establishment costs, feed supplementation costs, and cattle prices are included in the data. Costs and returns for each strategy are estimated and the grazing strategy that leads to the maximum profits over time is identified. Simulation and econometric methods are used in the analysis of each strategy. A set of key management factors including dates for each production practice affecting profit are estimated.