This comparative analysis of Chinese and Taiwanese English-language press narratives about Hong Kong’s handover on 1 July 1997, buttressed by a historical, sociological and political contextualization of the media accounts, shows the power of the pen, generating varying media realities about the same Hong Kong story. The three newspapers examined, the China Daily (China), and the Taiwanese papers, the China News and the China Post, are each rooted in their different political beliefs, cultural assumptions, and institutional practices, in short, their ideological positions. Drawing on insights from Linguistic Pragmatics and Critical Discourse Studies, the study identifies discursive processes such as legitimation strategies, group categorization, naturalization of events by presenting fluid processes as fixed truth claims, and privileging some voices over others, and provides a theoretical model for studying Chinese official discourse about the Self and the Other. The volume shows the benefit of a historical analysis serving as an antidote to recency bias, oblivious to the set conditions that accompanied Beijing’s vague promises to Hong Kongers of political autonomy for fifty years. This book is written for anyone interested in the methodology of text analysis and in the history of and political developments in Hong Kong and Taiwan.