This paper aims at contributing to the debate about Japan’s leadership capabilities. Lately, scholars from all around the world have referred to Japan as the “new leader of free trade”. This comes as a surprise, as the country has always been the archetype of a passive and mercantilist state. Therefore, what role is Japan playing in contemporary free trade agreements? What leadership style, if any, is the country exercising? What changes has Japanese leadership experienced in the last decades? Testing theories of this kind is challenging because there is limited information on the topic and most of it is only available in the language of the country in matter. Drawing on a case study based on the role of Japan in the Comprehensive and Progressive Agreement for Trans-Pacific Partnership and analyzing it from Young’s framework on political leadership, this article concludes that Japan is exercising a leadership role in contemporary FTAs.