The Chinese education issues in Malaysia appear frequently in political discourse, often featuring contentious discussions of language learning and national education policies. Applying an historical approach to contextualize a political discourse, this thesis examines the politics and transformation of Malaysian Chinese education, in microcosm, at the level of a renowned Chinese school, Chung Ling High School in Penang. It explores and maps the question of "Chineseness" through the examination of the history and development of Chung Ling since its establishment in 1917. This thesis also aims to elucidate the complex negotiation between multiple stakeholders of the Chinese community which took place at different historical junctures in a postcolonial and multi-ethnic nation. I discuss memorial activities for two deceased educationists, David Chen and Lim Lian Geok, which have been readapted into contemporary discourse by different factions of educationists to express their dissatisfactions toward state hegemony on education policies. Lastly, I argue that the persistent pursuit of "Chineseness" is counterproductive to the aim of safeguarding interests of Chinese schools within and outside the national education system today.