This paper aims to examine the issue of translation (from source language to target language) through Benjamin's thought of flâneur, a wandering city stroller with momentary but insightful vision, and of messianic time, a new conception of historical time. Benjamin seemingly analogizes the role of flâneur to that of translator. In what sense can we say that the task of translator is like that of flâneur? Does both of them have something in common? How is a new concept of historical time correlated with the ambiguity of language oscillating between translatability and non-translatability? These issues will be covered and explored in this paper.