In education, the adoption of textbooks establishes an authoritative means to transmit and deliver official knowledge. Guided by the tenets of sociology of school knowledge and critical theories (e.g., Althusser’s ideology and Williams’ selective tradition), this study focused on the investigation of representations of the historical figure Christopher Columbus in seven senior high school history textbooks in Taiwan. The research involved an analysis of how the explorer is introduced and whether the textual depictions can cross the border of power relations to provide another story that differs from the mainstream story presented in the United States. Critical discourse analysis was adopted as a theoretical framework as well as an analytic strategy to undertake a three-layered analysis involving linguistic analysis, intertextual analysis, and an analysis of power relations. The research concluded that the Eurocentric historical tradition of assessing Columbus is still favored. The voices of the Native people are muted, and the devastating effects initiated by the explorer and his crewmen through their voyages to the Americas are ignored. Although presenting an extensive detailed version of history is not possible in textbooks, the incorporation of a more complicated illustration with multiple points of view is feasible and essential.