This paper traces the trajectories of successful commercial smallholders operating under differing sets of market institutions. Analysis focuses on maize, cotton and horticulture, three widely marketed crops with strikingly different market institutions. Maize receives intensive government input and marketing support. In contrast, cotton relies primarily on private contract farming schemes, while horticulture enjoys no large-scale institutional support from either the public or private sectors. Using a mix of quantitative and qualitative methods, the analysis aims to identify personal characteristics and institutional factors that enable smallholder transitions to high-productivity commercial agriculture. The study concludes that only a small minority of Zambian smallholder farmers succeed in transitioning to high-productivity, high-volume commercial agriculture. Only about 20% of cotton farmers and less than 5% of maize and horticulture farmers succeed as top-tier commercial growers. By tracing the long-term agricultural trajectories of successful commercial smallholders, the paper identifies two broad agricultural pathways out of poverty. The low road, exemplified by cotton production, involves a two-generation transition via low-value but with well-structured markets. The more restrictive high road, epitomized by horticulture production, offers a steeper ascent, enabling prosperity within a single generation, but requires commensurately higher levels of financing, management and risk.