Why do voters support riskier candidates when they are facing bad economic times? This paper explores the reasons behind the electoral success that some unorthodox candidates have achieved in several presidential elections of Latin America. These are riskier candidates because there is more uncertainty about their expected performance, if elected, due to their lack of political experience. Classic decision theory would predict avoiding the possibility of bigger losses by selecting the safer option in an unfavorable environment, such as when people are voting during an economic crisis. However, a significant portion of the electorate has supported riskier candidates under these circumstances. We propose here an explanatory model of voting behavior in presidential elections that is based on Prospect Theory, which accounts for this phenomenon. This theoretical approach predicts that people will select riskier options when they are in a domain of losses, therefore it is reasonable to expect better electoral fortunes for candidates who offer more ambitious platforms during challenging times. In order to test this model, we rely on an original dataset that contains information on the main candidates that competed in several presidential races of the region during the last three decades, as well as the core indicators that constituted the economic environment when they took place.