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Singapore’s exit from the Malaysian Federation in 1965 is one of the few cases in the world during the Cold War era where separatism occurred. This rare event makes it an important case. How and why did Singapore extricate itself from a political arrangement in which it appeared so deeply committed to at the onset? In this paper, I explore the contentious politics of Malaysian nationalism and Singapore’s separatism in the aftermath of World War Two. Specifically, I examine the more proximate roles of competing elite visions of inter-ethnic accommodation, alongside divergent post-War trajectories of single-ethnic and multi-ethnic political party formation in Peninsular Malaysia and Singapore respectively. Additionally, I investigate the critical antecedent of one specific post-War colonial legacy – the British introduction of the Malayan Union project that artificially separated the bureaucratic administration of Peninsular Malaysia and Singapore. I argue that this one act was the seed through which the separate imagined geopolitical communities of Malaysia and Singapore would germinate and grow.