At the onset of the Cuban Missile Crisis, Fidel Castro sought strategic weapons to deter US ambitions to depose his regime, secure his legacy, and solidify a key strategic partnership. Kim Jong-un continues to develop North Korean nuclear weapons capabilities for arguably similar purposes. This paper explores the context and background surrounding the Cuban Missile Crisis and the current tensions between the United States and North Korea, then compares them in order to make recommendations for either avoiding or resolving a future crisis between the US and North Korea. Graham Allison and Scott Sagan provide frameworks regarding leader behavior as well as motivations for pursuing nuclear weapons to compare and contrast the Cuban Missile Crisis and the current situation on the Korean peninsula regarding nuclear weapons. Comparing and contrasting the events leading up to the 1962 Cuban Missile Crisis and the current conditions between the US and North Korea leads to recommendations for creating a series of diplomatic pressure valves similar to the security and economic solutions between the US and USSR during the Cuban Missile Crisis. These recommendations allow for a relief of tensions while preserving North Korean pride and self-reliance versus compelling changes to the North Korean government and society. By preserving the aforementioned aspects of North Korean national identity, the potential exists for the creation of an internally driven change to the current dynastic regime structure.