Compared to the direct style of communication prevalent in Western cultures, people in Asian countries prefer a less explicit, more contextual information exchange. According to Hall (1967), the Japanese style of communication is characterized by a strong contextual framework, where the context (e.g., situation, nonverbal expression) is more critical than the words, and verbal statements tend to be formulated implicitly and indirectly. In many Western countries, the opposite is true, in that words are given a more decisive role than context, and verbal expression is usually explicit and direct. Referring to this culturally determined typological difference, this chapter addresses the question of how rhetorical usage (strategic communication aimed at persuading the audience) influences Japan’s political landscape. In particular, the question of how politicians find consent and support from the electorate, given the fact that their primary method of communication is language (words) and political speeches to voters. Specifically, this chapter is about the questions: what kind of rhetorical usage is adopted and how has it evolved over time in the highly contextual culture of Japan? The chapter provides an overview of rhetorical usage from a diachronic as well as a synchronous point of view.