Any translation can be a new opportunity to revisit a given text. Via close reading, translators transfer texts in their source languages to target languages; and, to avoid the loss of historical and cultural meanings of the texts, adding annotations to the translated texts can be a useful strategy for them. “My Gali Grandma,” Chung Li-ho’s short story, was translated into English in 2014 and 2015, by T. M. McClellan and Terrence Russell, respectively. After we compare how the culturally loaded terms, such as “Gali,” “Guba,” “savage frontier,” and “headhunting,” in the story have been translated and interpreted in the annotations, enquiries can be made about many issues. How can “Gali,” a term related to a certain Indigenous ethnicity, be properly translated? What exactly is “Guba”? How can we define correctly “savage frontier,” a historically existent border between the areas resided by the Han Chinese and Indigenous peoples in Taiwan? How should we put “headhunting,” a traditional practice of Taiwan’s Indigenous peoples, into context in translation annotations? In order to discuss the cross-cultural understanding function of translation annotations, this paper will analyze comparatively how the terms mentioned above have been translated by the two translators.