Two years ago, the relationship between Pyongyang and Washington remarkably changed from hair-triggering military tension to unprecedented rounds of summits. However, those diplomatic overtures suddenly fell away again over the course of 2019-2020. How can we understand this spectacular shift in the geopolitics of the Korean Peninsula? What kinds of solutions can we (re-)try amid a long post-Hanoi impasse in nuclear talk? With the Trump presidency coming to an end, it is high time to look back on what really happened in this turbulent international drama, in an attempt to explain the serpentine trajectory of the Korean conundrum. In this context, I ask if mapping competing historical analogies can shed light on our understanding of the potential U.S.-DPRK rapprochement. Each mainstream political force in the Republic of Korea has mobilized contrasting historical reference points as heuristics to analyze the changing relations between America and North Korea, as well as to construct policy options to respond to them. There are competing discourses related to specific historical events, such as the Munich Agreement of 1938, the Paris Peace Accords of 1973, and Gorbachev’s “New Thinking.” In the near future, we will see if the North Korean supreme leader is a Gorbachev initiating fundamental reforms or a Hitler who exploits idealistic appeasement moves. Thus, the series of summit conferences between Washington, Seoul, and Pyongyang in 2018-2019 will be remembered as a crucial watershed in the long history of the East Asian Cold War, similar to the Gorbachev-Reagan period during the Cold War in Europe.