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The 1989 Tiananmen Square Massacre marked China out as an exception in the chapter of world history that saw the fall of international communism. The massacre crystalized the mistrust between China and Hong Kong into an open ideological conflict—Leninist authoritarianism versus liberal democracy—that has colored relations between the two since then. This article tracks the hold that authoritarianism has gained over liberal values in Hong Kong in the past thirty years and reflects on what needs to be done in the next thirty years for the balance to be re-tilted and sustained beyond 2047, when China’s fifty-year commitment to preserving Hong Kong’s autonomy expires. Still surviving (just) as a largely liberal (though by no means fully democratic) jurisdiction after two decades of Chinese rule, Hong Kong is a testing ground for whether China can respect liberal values, how resilient such values are to the …