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The Mesta was the association of the migratory shepherds of Castile, controlling fine wool production between the thirteenth and the nineteenth centuries. Its royally granted privileges have often been blamed for the stagnant Spanish agricultural productivity during the early modern period. I argue that the Mesta's privileges allowed Medieval Castile to develop its comparative advantage in wool, and that the Crown was able to restrict their scope and application when economic conditions favored arable farming interests. I support my argument with extensive archival data, including a new series of wool prices and a detailed analysis of lawsuits involving the Mesta.