Baseball is not only a popular sport, but also a central cultural and social symbol in Japanese, Korean and Taiwanese societies. These nations have produced some tremendous performances internationally, from the World Little League Competition to the Olympic Games. Most significantly, in the recently instituted World Baseball Classic, Japan won all previous tournaments – 2006 and 2009 – with South Korea winning Silver in 2009 and Bronze in 2006. Baseball in the region has, however, always been embroiled in the maelstrom of domestic politics, international relations and economic difficulties. Exchanges at all levels between these three nations have rarely been congenial, proactive or stable. As the world and baseball enter into a new era of globalisation and internationalisation, this triangular sporting relationship appears to be awkward and clumsy, even though player mobility, media exposure and international competitions continue to grow. This paper overviews the historical development of baseball in these powerhouses of Asian baseball, with an emphasis on the inevitable and fragile relationships between them, discussing the social and political factors underpinning these relationships.