In an attempt to determine whether or not Miguel de Cervantes Saavedra challenges or perpetuates colonialism in his famous work Don Quixote of La Mancha, this essay applies a post-colonialist lens to two separate episodes from Don Quixote: the galley slave episode and the captive’s tale. This essay argues that in the galley slave episode, it appears that Cervantes criticizes the Spanish empire’s colonialism because he gives a voice to the galley slaves, who one can consider people colonized by the Spanish empire, in order to reveal the injustice of the galley slaves’ oppression. However, the episode’s pessimistic end suggests that Cervantes does not believe that decolonization is possible. In a similar way, the captive’s tale tries to reveal the oppression of the Moors as a colonized people, but the representation of the Moorish woman and the focus on the experience of the Spanish instead of the Moor in reality perpetuates the racial hierarchy because it takes away the voice of the oppressed. Ultimately, although Cervantes tries to criticize colonialism, he had internalized the racism of his time, was limited by the fact that his readers were Spanish, and therefore did not successfully write an anti-colonialist work.