China resumed the exercise of sovereignty over Hong Kong and Macao in 1997 and 1999 respectively under the “One Country, Two Systems” principle (OCTS) whereby the Chinese socialist state allows the two territories to remain capitalist as special administrative regions with a “high degree of autonomy”. More than two decades later, these two regions have practised diverging versions of OCTS: Whilst Macao prospers as a leisure, tourism, and trading hub in relatively peaceful circumstances, Hong Kong struggles to maintain its rankings as an international financial centre, civil aviation and shipping hub, separate custom territory, and regional dispute resolution centre amid political imbroglio and civil unrest. This paper suggests the centrality of trust in producing this divergence. Trust reposed by the Macanese on the Central and local governments enables coordination and cooperation. Distrust by Hongkongers of the Central and local governments builds up checking, refrain and disregard.