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This paper proposes a framework explaining the evolution of property rights in land under the assumption of two unequal groups of actors, namely, elites possessing means of violence and nonelite cultivators. It then shows that all intermediary groups—between chief violence holders, or rulers, and cultivators—are variations on the two main groups (they are, in effect, greater or lesser rulers and cultivators). The theoretical framework proposed in this paper explains how different, hierarchically arrayed claims over land and the resulting allocation of rights was a function of asymmetries in power and information between three groups: rulers, direct cultivators, and intermediaries (between the two) without their own means of coercion. It explains inter alia why absolute private property in land was not likely to emerge in this configuration, and that the (non-private) property rights of the other two groups wouldn’t attain stability as long as rulers perceived an information asymmetry vis-à-vis them. Land rights would attain neither ‘private,’ nor ‘public’ character in such a situation. An implication of the framework is that cultivators’ rights would be better protected when intermediaries intervened between them and rulers than when there was no such ‘middleman.’ The framework explains most of the developments in the evolution of land rights in nineteenth century colonial India, including the two principal variations in systems of land rights, namely the zamindari, and ryotwari systems respectively. Finally, the explanation has implications for the debate on the long-term economic effects of colonial rule in India.