Ironically for the two sides of the Taiwan Strait that have one of the most hostile relations in the world, Singapore's ties with China were foreshadowed by its relations with Taiwan soon after the city-state became independent. Three sets of factors underscored the similarity: economics, politics and culture. Taiwan and Singapore were two Newly-Industrializing Economies that had taken off as part of the Japan-led Flying Geese formation. Politically, Taiwan and Singapore were authoritarian, although the Republic of China began life as a military dictatorship imposed on the island by a party that, having lost the civil war, was determined to recapture the mainland; and Singapore was an authoritarian democracy led by civilians determined not to return humbled to a Malaysia from which the island had been ejected. Taiwan and Singapore were united in their hostility towards communism.

“Apart from my good personal chemistry with (Generalissimo Chiang Kai-shek's son and Taiwanese leader) Chiang Ching-kuo, the foundation of our relationship was that we were both against communism. The Chinese Communist Party was his mortal enemy and the Malayan Communist Party, which was linked to the Chinese Communist Party, was mine. We had a common cause,” Lee Kuan Yew writes in his memoirs. Culturally, Taiwan and Singapore (like Hong Kong) were inhabited by maritime Chinese communities. Referring to Taiwan and Hong Kong, Lee writes: “The rapid progress of these two maritime Chinese communities gave me great encouragement. I picked up useful pointers. If they could make it, so could Singapore.” These aspects of Singapore's relations with Taiwan presaged its engagement of China as Beijing moved away from communism in its economic planning, settled for hard authoritarian politics, and unearthed a Chinese cultural self that had been subsumed by the demands of proletarian internationalism. Singapore's relations with Taiwan bore an uncanny resemblance to its relations with post-communist China.

This is true but for a crucial proviso: Singapore's ties with Taiwan are strategic, and its ties with China are not. Just two years into independence, land-scarce Singapore began discussions with Taipei on building up its military forces. The Israelis could not offer the facilities that the Taiwanese could to train pilots and naval officers.