In North Korea, Latin American leftist intellectuals and political leaders were forced to come to grips with an extravagant personality cult centred around Kim Il Sung. Part of what made the North Korean model of socialism palatable to some in the 1960s, is that the Cuban Revolution had given new credence to the concept of the “maximum leader.” The New Left often romanticized charismatic leaders from the global South like Fidel, Kim, Mao, and Ho Chi Minh, even while being critical of the autocracy they perceived in the Soviet Union. Admirers of North Korea’s political system argued it reflected the needs of a society in rapid transition from colonial-feudal backwardness to socialist modernity, and that ideas such as “freedom” were subjective and culturally determined. Such narratives of historical and cultural relativism were, ironically, also common among those critical of the North Korean model. This chapter looks at the different ways the North Korean political system could be interpreted within the Latin American Left, with examples from the Dominican Republic, Costa Rica, Venezuela, and Chile.