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When democratic conditions change, professional voices are politicized in the public sphere. This article examines how professional associations in Hong Kong navigated three major legal reform controversies and subsequent mass mobilization during the city’s two-decade democratic decline following the 1997 handover of sovereignty. Reports and statements from the Hong Kong Bar Association, the Law Society of Hong Kong, the Hong Kong Medical Association, and the Hong Kong Journalists Association are analyzed, along with their media coverage. Despite operating under similar political conditions, associations responded in divergent ways: some maintained consistent visibility, while others fell silent or fractured internally. To explain this variation, the article develops a theoretical framework that analyzes how different combinations of technical and normative authority shaped associations’ strategies and reception across two sectors of the public sphere: the legislative sphere and the civic sphere. The findings demonstrate how professional legitimacy deteriorates through the erosion of boundaries between expert and political voices.