Since its commencement in the late 19th century, trade between Japan and Russia has gone through numerous distinct stages. Despite there being obvious historical differences between the two countries, during each of these stages, political dynamics strongly influenced trade relations; additionally, each country’s share of bilateral trade was extremely low, and Japan mostly supplied manufactured goods in exchange for Russian raw materials. These characteristics of Japan–Russia trade restricted options vis-à-vis further economic development, and can thus be seen as illustrating path dependence. This study argues that the initial years of the 2010s have brought significant changes to the traditional model of trade. Namely, market forces have replaced politics as the primary driver, the amount of trade has surpassed previous records, and Japan’s investment in the Russian energy sector and participation in automotive manufacturing have provided Russia with the capital and technology it has needed to undertake high value-added production.