For the past few centuries, democracy has become increasingly dominant as a political system, especially in the West, and has projected itself to the rest of the world, with many believing that it is the best available model that provides economic development and stability. However, democracies have collapsed in the past and given way to autocracy, raising the question of why such failures occur and how sometimes people, through the electoral process, voluntarily enable the rise of dictators. This paper will thus examine historical cases of democratic collapse, particularly the Weimar Republic, and suggest that these failures were not solely due to factors like economic crises or political extremism, but due to the inherent contradictions within its basis of ideologies that make democracies hard to defend during times of crisis as opposed to autocracies. Exploring the reasons behind the failure, this discussion will, at last, apply itself to the current political climate and suggest that although today’s democratic institutions are more resilient and trusted, the potential risks of collapse remain deeply rooted.