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Historical literature on the colonial period in The Gambia tends to focus on the roles of the outsiders such as British colonial agents like the Commissioners and soldiers, in the administration of the oldest British possession in Africa. This approach marginalizes the salient role of district chiefs in the running of the colonial state. Although most recent scholarship has started to address the leadership trajectory of chiefs in Gambia’s Protectorate administration, their cardinal role as factors in the colonial economic system has not been addressed. In this study, I argue that they were the backbone of the protectorate economic set up. To do so, I shall examine the role of chiefs as tax collectors; chiefs as agents in the production of ground nuts; and chiefs as proponents of the “cottage” industries in their districts. This article shall further our understanding of the critical African agency in the success of the colonial project in West Africa.