Drawing on the author’s experience of collaborative research with the Cañamomo-Lomaprieta people in the western Colombian Andes, this article discusses the challenges of conducting ethnohistorical research on Indigenous land claims from the double role of historian and lawyer. It argues that this dual position presents both risks and benefits for ethnohistorical research. On the one hand, wearing both hats entails the risk of digging into the past to make a case for current land claims, thus losing sight of a more complex and comprehensive understanding of the past on its own terms. On the other, the lawyer-historian gaze may provide critical insight into the workings of the law in past processes of privatization and commodification of Indigenous lands. Legal training better equips historians for understanding the technical details of land transactions, lawmaking, and judicial decision-making. It also enables the historian to raise questions about the legal validity of past judicial decisions and land transactions that still impact current land disputes.