In this chapter, an explanation will be offered on how the factors of state and society outlined in Chapter 2, together with a few others, constrained the top-down and bottom-up democratization in Hong Kong between 1946 and 1985, before the Sino-British negotiations on Hong Kong’s future ended and the indirect elections unprecedentedly introduced to Hong Kong’s legislature. Since the democratic transition in Hong Kong during the 1980s was a “planned” and relatively “stable” one, there was no dramatic collapse of institutions as found elsewhere. The causal impacts of those structural factors are therefore particularly important. Not only could they partially explain the lack of both regime-led and bottom-up democratization in Hong Kong during that period, more importantly, they have restricted the democracy movement and democratization (1986-90). These factors could then first answer why Hong Kong was an anomaly to modernization theory before 1984. Among these factors, the positions of the Chinese and British Governments with respect to the status of Hong Kong were the most crucial constraints shaping Hong Kong’s democratization. It will be shown that, as Communist China insisted on its claim to Hong Kong’s sovereignty, and rejected Western democracy, the British Government perceived a serious threat from China to the continued viability of Hong Kong if democracy were to be implemented. Consequently, no top-down democratization took place between 1946 and late 1985. Britain’s perception of the Chinese Government’s objection also frustrated bottom-up democratization by encouraging internal constraints to democratization, i.e., the quasi-bureaucratic authoritarian institutions, a politically weak civil society, and the apolitical culture of the people. Attention is also given to the domestic environmental factors because, as shown in Chapter 2, they were important in shaping democratization elsewhere. They all created internal hurdles to bottom-up democratization one way or another during the period. Given the status of Hong Kong as a British colony and partly leased from China, we shall look first at how China placed constraints on Britain’s democratization of Hong Kong before 1984.