This book looks at Costa Rica’s careful equilibrium it had to maintain as it was ubicated at the heart of the battle between Communism versus Capitalism during the Cold War. It does so by building up to the Contra war on its doorstep in the mid-1980s and examining how Communist forces took ahold of the Central American region, Nicaragua specifically. As the only democracy in the region, Costa Rica was centered between Communist forces on one end and Right-wing Military regimes on the other. Its decision making had to be precise as it did not want to lose regional autonomy but yet confronted dire economic circumstances. The book then examines failed US efforts at thwarting Communism in the Central American region and Costa Rica’s role. Next, it scrutinizes the trilemma between the US, Nicaragua, and Costa Rica and the careful balance of power Costa Rica had to maintain between all parties. A closer look at the 1980s occurs next describing the debilitating impacts of exogenous events outside of Costa Rica’s control that hindered the Contra War from ending while paving the way for drug trafficking to penetrate into the nation. The book follows by examining conflicting interests amongst transnational parties with Costa Rica at the heart of these interests. The attempted Peace Processes with hopes of bringing an end to the blood shed in the Central American region is then scrutinized. The Capitalistic-military regime-CIA-proxy-drug trafficking nexus is later looked at using the case of the Contras and the Santa Elena airstrip among others in Costa Rica. Following is an examination of US complicity in this affair and the deceitfulness of the Reagan Administration. The book then takes a look at Costa Rican history from the 1990s-2010s and the lingering impacts of the Contra-War/drug trafficking and Costa Rica’s emerging role in the political economy of the global drug trade. Immediately following is a section revolving around the ongoing militarization of the war on drugs and Costa Rica’s police forces. The book concludes with some somber thoughts as Costa Rica enters into a more dangerous era.