British imperialism profoundly influenced the development of the modern world order. This same imperialism created modern Singapore, shaping its colonial development, influencing its post-colonial reorientation. Winston Churchill was British imperialism's most significant 20th-century statesman. Churchill never visited Singapore, yet their two stories heavily influenced each other. Singapore became a symbol of British imperial power in Asia to Churchill, while Singaporeans later came to see him as symbolising that power. The fall of Singapore to Japanese conquest in 1942 was a low point in Churchill's war leadership, one he forever labelled by calling it "the worst disaster in British military history". It was also a tragedy for Singapore, ushering in three cruel years of occupation. But the interplay between these three historical forces -- Churchill, empire, and Singapore -- extended well beyond this most dramatic conjuncture. No single volume critically examines that longer interplay. This collection of essays does so by analysing Churchill's understanding of empire, his perceptions of Singapore and its imperial role, his direction of affairs regarding Singapore and the Empire, and his influence on the subsequent relationship between them.