Envoys and Missed Opportunities for Conflict Resolution: Richard Goodwin, Che Guevara, and U.S.-Cuban Relations, 1961

Can individual diplomats clear the path to détente between adversaries? The litany of failed overtures between the United States and Cuba, and the sheer duration of official hostility from the Dwight Eisenhower administration to Barack Obama’s second term, present compelling puzzles about peacemaking. Were structural obstacles insurmountable, or did failures stem from personnel and process? I analyse a negative case through archival research, presenting a revisionist account of Che Guevara’s August 1961 meeting with Kennedy staffer Richard Goodwin. During a crucial opportunity for conflict resolution between the Bay of Pigs and the Missile Crisis, the personal characteristics of diplomatic envoys (not domestic opposition, mistrust, or incompatible preferences) chiefly explain the failure to negotiate a modus vivendi. Further, although the Kennedy administration, the press, and scholars have downplayed this encounter while emphasising continued U.S. covert operations against Fidel Castro, I argue that the Goodwin-Guevara meeting held significant promise, that its failure affected regional security and the Cold War in Latin America, and that it offers lessons for analysts and practitioners of international conflict resolution.