This paper analyzes modern day Cuba and draws conclusions about the most likely future political and economic events that will take place. Because of Cuba's troubled economy, leadership change and the world's continued shift towards democratization, Cuba is in a position where drastic changes in its government and economic structure may occur. This paper investigates Cuba's history, politics, economy, and the general quality of life of its citizens, which are used to help predict what may happen to the Cuban government in the near future. The paper also analyzes options for foreign nations' policy towards Cuba and summarizes what actions they may take to increase the likelihood of an economic and political transition. Cuba's economic structure needs drastic reform, the reluctant privatization only increases wealth disparity, trust in the government continues to get weaker as more information and its human rights violations are causes of huge concern. There are four possible outcomes for Cuba's future: stagnation, adopting the mixed economic model, a peaceful transition to a democratic model, and rebellion. There is evidence that Cuba will not make drastic policy changes in favor of liberalization in the immediate future, however, if the economic conditions are not improved and an economic crisis ensues, this paper asserts that another revolution or coup will likely occur. The resulting government may be a new autocratic leader that fills the vacuum of leadership, or a democratic regime depending on the nature of the rebellion. The exact future of Cuba is uncertain, but one thing is clear, change is on the horizon.