In 1995, Yu-fei translated Jan Morris' "Conundrum", a memoir that depicts Morris' transsexual treatments, surgeries, physical rehabilitation, mental, emotional struggle and adaptation. Unlike Jan Morris, Yu-fei lived in a different socio-cultural context that was conditioned by China's cultural evolution, and therefore his writing style, reflected in his translation, is quite direct, bold, critical through adaptation of the original message. Yu-fei's Chinese translation, based on the 1974 version of Conundrum, carries a different outlook from the source text, meeting Lefevere's concept of "translation as rewriting" and supporting the claim that the ideology of the translator prevails when it comes into conflict with language considerations. In factuality, Yu-fei's translation, that reveals a particular position, view and ideology, is differentiated from the source text as the result of the distinctive differences between author/transsexual/insider and translator/heterosexual/ outsider.Yu-fei's rewriting strategy pushes us to reconsider the problem of translation fidelity. Furthermore, the well-established, taken-for-granted master/slave relationship between the original work and the translated works is subject to deconstruction. It is noted that the translated work represents (not to copy) not only the original work but also the translator him/herself. Using some basic concepts extracted from Lefevere's Translation, Rewriting, and the Manipulation of Literary Fame and Benjamin's "The Task of the Translator" as the theoretical framework, this research investigates how Yu-fei rewrites/adapts the source text, and simultaneously discusses the relevant, twin issues of translation fidelity and the status of the translator.