We develop a theory of trading middlemen or entrepreneurs who perform financing, quality supervision and marketing roles for goods produced by suppliers or workers. Brand-name reputations are necessary to overcome product quality moral hazard problems; middlemen margins represent reputational incentive rents. We develop a two sector North-South model of competitive equilibrium, with endogenous sorting of agents with heterogenous entrepreneurial abilities into sectors and occupations. The South has a comparative advantage in the more labor intensive good which is subject to a greater moral hazard problem. Trade liberalization raises inequality between Southern export sector suppliers and middlemen. Northern middlemen have incentives to offshore production to the South. The distributive effects of such offshoring tend to be the opposite of trade liberalization.