In the United States, agricultural production using row-crop farming has reduced crop diversity. Repeated growing of the same crop in a field reduces soil productivity and increases pests, disease infestations, and weed growth. These negative effects can be mitigated by rotating cash crops with cover crops. Cover crops can improve soil’s physical, chemical, and biological properties, provide ground cover, and sequester soil carbon. This study examines the economic profitability for a four-year wheat–corn–soybean study with cover crops by conducting a field experiment involving a control (without cover crops) at the Soil Health Farm in Chariton County, MO, USA. Our findings suggested that economic profitability of the cash crop is negatively affected by the cover crop during the first two years but were positive in the fourth year. The rotation with cover crops obtained the same profit as in the control group if revenue from the cash crop increased by 35% or the cost of the cover crop decreased by 26% in the first year, depending on the cost of seeding the cover crop and terminating it. This study provides insights for policymakers on ways to improve the economic efficiency of cost-share conservation programs.