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This article explores an oft-neglected episode of the Singapore-Republic of China diplomatic relationship between 1965 and 1971 – centred on the issue of Chinese representation in the United Nations. Relying on declassified archival materials from the Australian, British, and Taiwanese foreign ministries, this article illustrates the existence of repeated self-serving and opportunistic behaviour on Singapore’s part that sought to maintain the island-state’s national interests at the expense of the ROC’s interests on the Chinese representation issue. It challenges prevailing laudatory accounts of Singapore’s foreign policy of  pragmatism  by providing three observations. First, that the island-state’s presumption that it could separate economic and political matters at will in executing its diplomacy did not always engender optimal outcomes for itself. Second, that Singapore’s assertion of non-alignment in international issues did not prevent it from orientating its diplomacy towards facilitating outcomes to those issues that it perceived would best serve its core interests. Third, that the island-state’s professed desire to maximise its allies and minimise its adversaries did not necessarily mean that Singapore did not seek opportunities to exploit its partners’ vulnerabilities to serve its national interests.

Resolving Away a China Problem: The Issue of Chinese Representation in the Singapore-Republic of China Relationship, 1965–1971