Despite being located faraway from one another, North Korean leader Kim Il Sung and Zimbabwean leader Robert Mugabe formed an unlikely friendship during the late 1970s and 1980s. As guerilla fighters-turned postcolonial leaders, these two autocrats developed close emotional bonds built around admiration, fear, and trust. Using archival sources from the United Kingdom’s National Archives, North Korean press reports, and journalistic accounts, this article emphasizes emotions as a window into examining this Afro-Asian alliance. From wanting to emulate North Korea’s land reform program to sending a group of librarians and academics to the communist state to learn from Pyongyang’s educational system, Mugabe’s government admired the Democratic People’s Republic of Korea (DPRK) as a model of socialist development during the 1980s. Fearing instability at home, Mugabe also sought North Korea military assistance to squash his political rivals. Finally, Mugabe trusted Pyongyang as a “war-time friend” that had always been there for his African state. Thus, Zimbabwe continues to align itself in the post-Cold War era with North Korea while much of the world cuts off ties with the increasingly isolated state.