The neoliberal global food system has intensified the uncertainties associated with peasant farming and agrarian livelihoods around the world. This article examines processes of precarization among smallholder farmers in the Majes Irrigation Project in Peru. By discussing price volatility and uncertainty related to the “free market,” I argue that the conditions of small-scale entrepreneurial farmers today can best be understood in terms of gambling and precarity. After four decades of neoliberal deregulation, farmers in Majes describe agriculture as a “lottery” where one can win or lose everything. Despite prospects of growth and progress, most farmers rely on low-income dairy farming or contracted crops for agro-industrial corporations. The freedom to take risks in the open market entails uncertainty and often results in loss, and farmers must negotiate the ambiguous relation between autonomy and dependency.