The optimism about democratization that rose sharply in the second half of the 1980s and stood strong in the 1990s has fallen to its nadir in 2018. There have been many post mortems at each stage of the descent: some have focused on the reversal of development in Russia and the lack of transition to democracy in many former Soviet republics; others have dwelt on the Middle East from the shattered illusions raised in the Iraq War to the disastrous results of the “Arab Spring.”1 In Southeast Asia the record has been mixed, but supporters of the benefits of democratization have found ample reason for disappointment there, too.2 During the 1990s, expectations were high for how Northeast Asia, Southeast Asia, and South Asia would benefit from ongoing democratization. It would open borders to Japan and South Korea, each of which was prepared to offer generous terms for integrating with parts of Northeast Asia. And it would demonstrate the advantages of both Taiwan and Hong Kong as they set an attractive example for Greater China. ASEAN would find it easier to solidify as a regional organization because of the strengthening democratization among its members. Australia and New Zealand would become less marginalized as they pursued closer ties in Asia. Finally, by the early 2000s, there was talk of India’s new linkages to the east as it rose as the anchor of a democratic network connecting the Indo-Pacific. What lessons should we draw from the setbacks to these high hopes and from what has been revealed about conceptualizing democratization with clear awareness of national identities as well as the advancing realities of great power rivalries?