Kawakami Otojiro, the founder of Japanese modern theater, visited Taiwan in the late November of 1902, where he made a field survey for his new production Othello, which was staged later in Tokyo, capital of the Japanese empire. Adapted from Shakespeare's namesake masterpiece, Kawakami's Othello was staged to demonstrate his arguments for "Seigeki (Drama)," which he derived from the western theater and regarded as the paradigm to be made for the modernization of Japanese theater. Therefore, Othello serves as a crucial turning point of Kawakami's theatrical career. This article explores the theatrical experiences and pursuits of Kawakami, reestablishes and examines the actual course and results of his trip to Taiwan, and reviews the way was "Taiwan" was represented on the stage of Othello in Tokyo. The author argues that both the travel notes Kawakami published after his trip to Taiwan and his Othello imply an urgent colonial discourse aiming to reinforce the legitimacy of Japanese colonial rule and manifest the imperial order centered around Japan. By examining and criticizing this production staged a hundred years ago, this article intends not only to speak for the traumatized Taiwan people from a post-colonial viewpoint, but to suggest a historical example for the contemporary cross-cultural theater workers to beware of.