In this study we examine how the agribusiness industry works to manipulate conventional farming masculinities in the United States to facilitate agricultural deskilling, a process that has serious implications for the future of sustainable agriculture uptake among American farmers. Through analyzing one year's worth of advertisements in three conventional farming magazines and through conducting participant observation and interviews at the second largest indoor farming show in the United States, we examine the ways in which agribusiness companies, such as chemical, seed, and farm machinery manufacturers, represent farmers and farming masculinities in their advertisements and marketing materials. We observe a shift occurring among certain agribusiness sectors away from representations of a rugged, strong, solitary farmer, who dominates nature through his manual labor, to depictions of a “businessman” farmer, who farms in collaboration with certain qualified partners (i.e., company representatives). We ultimately argue that these new representations of farming masculinity aim to more deeply entrench conventional farmers' dependence on chemical inputs and agribusiness products by promoting a process of deskilling, effectively alienating the farmer from the land.