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The puzzle that this article attempts to solve is why did President Juan Manuel Santos (2010–18) succeed in negotiating a historic peace deal with the oldest insurgent movement in Latin America, the Fuerzas Armadas Revolucionarias de Colombia (Revolutionary Armed Forces of Colombia—FARC) while his predecessors failed to do so. This article contends that three critical factors led to these failures: (1) the role of the military as spoilers and beneficiaries of the low intensity war and its political economy; (2) the absence of a critical mass within a fractured dominant class favoring peace compounded by a general perception amid the powerful landowner faction that the costs of reforms exceed the costs of the continuation of war; and finally, (3) the absence of a regional–international configuration favoring a political solution. Finally, the article examines the core changes in these factors that helped Santos strike a deal in 2016.