The paper discusses the implications for critical lexicographic studies and for research into the interplay between power and resistance between dominating and dominated cultures. The body of the study is devoted to the analysis of those shifts taking place in the entries, definition, illustrative examples and pragmatic labels in a bilingualized English-Chinese dictionary, which, when viewed cumulatively, significantly reshape the ideological positioning of the dictionary. The paper then argues that a synergy of critical discourse analysis and postcolonial studies can reveal the inter-cultural ideological struggle implicit in the bilingualizing lexicographic practice. The monolingual dictionary (American English) is the core component of the Oxford Picture Dictionary Third Edition program, building students vocabulary, reading, and critical thinking skills for success in their daily lives. It first proposes viewing the (bilingualized) dictionary as discourse and emphasizes bilingual lexicography as a site of an asymmetrical linguistic and cultural power dynamics. This paper conceptualizes dictionary bilingualization as a recontextualizing practice and explores how ideology and power play out in the recontextualization of lexicographic discourse across languages and cultures to result in the transformation of meaning.