The majority of cropland in the rain-fed region of the North Central District of Oklahoma in the US is seeded with winter wheat (Triticum aestivum) and most of it is in continuous wheat production. When annual crops are grown in monocultures, weed species and disease agents may become established and expensive to control. For many years prior to 1996, federal policy provided incentives for District producers to grow wheat and disincentives to diversify. In 1996, the Federal Agriculture Improvement and Reform (FAIR) Act (Freedom to Farm Act) was instituted, followed by the Farm Security and Rural Investment Act (FSRIA) in 2002. The objective of this study was to determine the impact of FAIR and FSRIA programs on crop diversity in the North Central District of Oklahoma. The economics of three systems, monoculture continuous winter wheat, continuous soybean (Glycine max) and a soybean–winter wheat–soybean rotation, were compared using cash market prices (CASH), CASH plus the effective loan deficiency payments (a yield-dependent subsidy) of the FAIR Act of 1996, and CASH plus the effective loan deficiency payments of the FSRIA of 2002. We found that the loan deficiency payment structure associated with FAIR provided a non-market incentive that favored soybean. However, under provisions of the 2002 FSRIA, the incentive for soybean was adjusted, resulting in greater expected returns for continuous wheat. Due to erratic weather, soybean may not be a good alternative for the region. Research is needed to identify crops that will fit in a rotation with wheat.