This article argues that the strong relationship between Malaysia and Japan is also stimulated by symbiotic ties binding together both countries' respective major political parties, i.e., the United Malays National Organisation (UMNO) and the Liberal Democratic Party (LDP). UMNO, especially under the leadership of Mahathir Mohamad (1981-2003), derived political lessons from developments affecting LDP in Japan. First, emulation of Japan's success in economic development became the basis for the Look East Policy launched in 1981. Second, which is the focus of this article, lessons were drawn from the failure of LDP to retain power twice, in 1993 and in 2009. Although LDP's reversal of fortunes served as a landmark for UMNO in situating changes to its trajectory since 1993, the analogical reasoning and political lessons applied by UMNO leaders were, to a large extent, flawed. Arguably, politicians frequently do misjudge in analogizing between different situations which at a glance seem to be comparable.