Consider the paradox of Prime Minister Abe Shinzo, who presented himself as the Japanese leader most committed to pursuing value-laden issues, becoming touted by 2019 as the one world leader in the caldron of Northeast Asia eschewing such issues for pragmatic pursuit of the national interest. Whether dealing with the leader of the United States, China, or Russia, Abe has established himself as the grown-up in the room without renouncing the symbols of his long-time values orientation. He has prioritized diplomacy, catered to the emotional whims of other leaders, and offered deals conducive to forward-leaning relations. Even in his handling of South Korea since the end of 2015, Abe has gained the upper hand as the pragmatist, showing less concern for identity issues. Yet, the recent, rapid deterioration of Japan-ROK relations and the perilous nature of Japan-US ties in light of Trump’s obsession about their unfairness raise questions about how Abe will continue to manage the nexus between interests and values in the difficult environment Japan now faces. Abe is bound to be tested anew in these conditions.