Especially after World War II, the British visibly improved, in Hong Kong, on what was already a successful authoritarian–legality-based governance structure dating back to 1842. As one looks more closely at this extended, political–legal experience, it becomes clear these prominent governance achievements were built on particular British constitutional foundations forged over many centuries. Due to the largely unwritten nature of the British Constitution, the way was left open for a scholar possessed of remarkable understanding to analyze and describe – indeed, reveal – the essence of this historically tempered set of resilient governance principles. That scholar was Professor A. V. Dicey. Our analysis draws pointedly on the work of John Rawls as we analyze how “Diceyan constitutionalism” fundamentally shaped the development of governance institutions within the new British colony – working in conjunction with what has come to be known as “Chinese familialism.” Our aim in this chapter is to examine: how Hong Kong’s authoritarian–legality governance system has come to pass; the essence of that system; how thoroughly it has been stress-tested; and how well it may be placed to cope with tests yet to come.