English education has played a vital role in facilitating Singapore's global city ambitions since the country's independence. While the state has prioritized English education's cognitive objective emphasizing information processing and effective communication skills, it has given insufficient attention to the role of English in equipping students with the necessary cosmopolitan capacities. The first part of this paper discusses the roots of a communicative cosmopolitan impulse in language through the works of key philosophers, namely Jürgen Habermas and Emmanuel Levinas. The second part analyzes English Language and Literature in English national syllabuses from the 1980s to the present to show how English education has been directed by strategic cosmopolitanism operating through selective governmental strategies of differentiation and prioritization. Given the realities of an increasingly networked world, I argue, in the third part, for a more holistic perspective of English education grounded on a communicative cosmopolitan intent.