This article examines why the “history issue” continues to hinder Japanese-Korean relations after nominally successful negotiations such as the 1965 Treaty on Basic Relations between Japan and the Republic of Korea and the 2015 comfort women agreement. It contends that leaders put off and quite possibly sacrificed reconciliation in order to achieve treaties and agreements that addressed more immediate security, economic, and political needs. However, because agreements were not transparently negotiated, partly due to the lack of a neutral third-party mediator, Koreans believe the treaties were not fair nor final settlements. Additionally, the reconciliation process has been flawed because it haphazardly tackles disagreements and does not consider time. A third-party such as the United States should mediate a settlement between Japan and South Korea to ensure adequate confidence building measures. Such measures will lower the costs of giving and accepting an apology, increasing the chances of an enduring and legitimate treaty.