One of Lee Kuan Yew’s greatest concern when Singapore first gained independence in 1965 was the issue of what language/languages were to be used by the multi-ethnic communities living in Singapore and the newly formed government. The original goals of English-knowing bilingualism were to find a common language that is ethnically neutral (i.e. English) and to allow Singaporeans to learn their ascribed ethnic mother tongue so that they can remain culturally rooted. English was deemed to be able to provide the young nation state with both global economic benefits (to allow easy negotiation in international trade) and educational access (to the wealth of research, resources and curriculum materials written in English). There was also the urgent need to maintain peace and harmony amidst a newly independent multi-ethnic and multi-lingual society. This chapter will provide a meta-analysis of Lee’s bilingual education policy in Singapore, tracing the historical roots and original goals for introducing the Bilingual Education policy, implementation journey, challenges faced, lessons learnt and make suggestions for the way forward. In his later years, Lee dubbed Singapore’s bilingual journey to be “his lifelong challenge”, but amidst the difficulties and challenges faced, the link between English-knowing bilingualism and Singapore’s educational success will also be drawn.

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