This paper examines the possibility of the assassination of Kim Jong-un and assesses what type of assassination has the highest probability of occurring in North Korea. Although one cannot predict when and how Kim Jong-un might be assassinated or by whom, we can still compare various types of assassinations for probabilistic analysis. I propose four types of assassination, named in reference to the historical cases that typify each: “Valkyrie,” “Brutus,” “Oswald,” and “Kim Jae-gyu.” Based upon this general typology and its application to the context of North Korea, I argue that the assassination of Kim Jong-un is more likely to be carried out by a lone assassin from the upper echelons of leadership at a private gathering than by a group of plotters during a public event. This analysis has several policy implications for] strategists in Washington and Seoul. It is recommended that they incorporate assassination scenarios more specifically in their contingency planning for the future of North Korea and prepare for timely and direct intervention in the North Korean affairs as Washington did so effectively during the process of German unification.