The world continues to become more and more connected place, especially in the field of trade and international investment. Cuba remains as one the last strongholds of Communist ideology in the 21st century, but the government has started to allow for more Foreign Direct Investment which brings the question as to what economic model Cuba will use in the future. The introduction of free market activities like FDI and also the growth of private markets has created a drastic shift in the identity of the Cuban economy. This shift has led me to the question and what does this change represent the ideological stance of the Cuban government? At the moment there is no one economic model that is similar to the current Cuban economic status, some scholars try to compare the Cuban model to the Chinese model but the Cuban economy does not have the market prowess and consumer power that the Chinese market hold. I will attempt to conduct a historical analysis using a case comparison using Mill’s method of difference, focusing on three distinct periods of the Cuban economy to try to provide an understanding as to what factors can lead to socialist actors partaking in free-market activities. These findings can be used to examine how economic actions by socialist states might show signs of lack of belief in communist economic ideas or show actions towards the economic survival of a state.