Latin America has been characterized as a region where democracies struggle and countries are rife with internal power struggles. The 20th century has seen a decrease in dictatorships and brutal regimes in a majority of Latin American countries, with most shifting towards democracies. Venezuela, on the other hand, has done the opposite, now having one of the most brutal regimes in the region. Once thought of as a model democratic country with adequate civilian control and a strong economy, Venezuela now has one of the worst economies and military dictatorships in the world today. While the history of Venezuela’s democratic government has been anything but stable, late 20th century Venezuela showed promise for a newly reformed democratic government. It is impossible to pinpoint a single moment which caused the Venezuelan democracy to shift towards a dictatorship, but the leadership under Hugo Chávez is a good starting point. Venezuela’s stance (or lack thereof) towards the military, its economic reliance on oil, rampant political corruption, and its foreign relations have all contributed heavily to the creation and resilience of the Maduro regime. This paper will seek to analyze the role past Venezuelan presidents and Chávez played in creating a repressive regime through the control of Venezuela’s military, reliance on profits from oil, and international relations. With this information, the paper will help one to understand how Nicolás Maduro’s dictatorship has been able to continue even with catastrophic inflation levels, a withering civilian population, and international threats. Additionally, this paper will identify the different aspects of the government, economy, and political systems that must change in order for Venezuela to start the transition back to a democratic government. Through the analysis of these different factors, this paper will provide a better understanding for readers as to how Maduro has been able to retain power and what must change in order for the current Venezuelan dictatorship to shift to a democratic government.