The fate of democratization in Asia in the post-Cold War era has been closely identified with four cases: Mongolia, the exemplar in inner Asia of establishing—in the shadow of Russia and China—a bona fide democratic system; Indonesia, the principal test case of a major, Moslem-majority country switching to the path of democratization; Malaysia, proof that democracy can weather the excesses of vast corruption; and Myanmar, the poster-boy of intense international pressure causing a military regime to agree to democratization. Of these cases, however, not one offers unqualified optimism that democratization is on a trajectory of inevitability or even sustainability in our trying times. Mongolia could be squeezed by its two strong neighbors, casting doubt on its “third neighbor” strategy of balancing great power relations. For Indonesia’s vaunted tolerance of diversity, fundamentalism is rapidly posing a grave risk to human rights. Myanmar has seen one of the most flagrant cases of ethnic cleansing, which has been enabled by democratic leadership unable to buck the power of the military. Finally, while Malaysia escaped from a close call in 2018, problems related to manipulation of its ethnic sensitivities, which have been used to distort the democratization process, are not being addressed or resolved. In 2019, as democratization hangs perilously on the cliff’s edge, these cases warrant particular attention.