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The primary objective of this paper is to gain a meaningful understanding of how security relationships develop between former colonies and their former colonizers. Identifying the conditions that prompt a former colony to reject a security partnership with its former colonizer, and, in contrast, the factors that encourage a former colony to embrace a security relationship with its former colonizer will expand one's understanding of the nature of security relations within international politics. Northeast Asia's political climate presents a fascinating case study to examine the politics of alignment. Specifically, this paper aims to first peer through the lens of Korea and Taiwan's unique colonial experiences under Japanese rule to provide historical context to understand why the ROK and Japan struggle to develop a robust military relationship despite perceiving some external threats in the region similarly, and, in contrast, why Taiwan welcomes a security partnership with Japan today. However, this does not mean that Japan and the ROK do not work together to advance each other's interests totally, nor does this study suggest that Japan and Taiwan do not face conflicts of interest. To achieve a more comprehensive understanding of Japan's relationship with Korea and Taiwan, this paper also considers how Seoul and Taipei's unique colonial experiences and contemporary security relationships with Japan affect cooperation across diplomatic channels and economic partnerships. This study also acknowledges that assessing Japan's relationships with Korea and Taiwan prior to the colonial period would be insightful, though it will focus primarily from 1895 to the present. In particular, four critical factors help to explain Japan-ROK's toxic security relationship and Japan-Taiwan's strong, albeit, de facto security partnership: 1) national identity shaped by each country's unique colonial experience under Japanese rule, 2) the United States' managerial role across both of its security triangles in Northeast Asia, 3) shared perceptions of common threats, and 4) the politics of formal military alliances versus the politics of de facto security partnerships. [ABSTRACT FROM AUTHOR]