The current political crisis in Hong Kong is characterized by a level of social unrest that the city has not seen since the riots of 1966–67. After that earlier round of turmoil, the British colonial regime secured legitimacy through socioeconomic improvement in Hong Kong. “Prosperity and Stability” became the hallmark of Hong Kong's success, which extended into the period of political uncertainty in the 1980s. Transcending the handover of Hong Kong to China in 1997, this catchphrase was adopted as the slogan of the Hong Kong Special Administrative Region government in its bid for legitimacy through socioeconomic appeals. Against this perennial state rhetoric, grassroots protesters began to demand “Democracy and Freedom” around June Fourth. These public demands have escalated since the Umbrella Movement in an environment of socioeconomic regression. Examining these two pairs of keywords—prosperity/stability and democracy/freedom—this article underscores the contention in the legitimacy of governance in Hong Kong since the closing decades of British rule. This analysis indicates that it would be unproductive for the governing authorities or the protesters to deny the earnestness of either the political or socioeconomic assertions in the ongoing contention of legitimacy to govern Hong Kong.