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This chapter analyzes how patterns of political corruption across Latin America influence regional entrepreneurial activity as well as the effectiveness of different solutions that have been proposed to promote entrepreneurial initiatives. For this purpose, the causes of this institutional failure and its influence on the regional entrepreneurial system will be explored under a literature review. This review is used to identify its main issues to propose an analytical framework, based on game theory and social network analysis, to understand the dynamics of the different players involved in the interaction between the corrupt political contexts and the regional entrepreneurial ecosystem. This framework is extended to further analyze several well-known regional corrupt business cases and the suitability of different solutions to revert this failure to foster entrepreneurial initiatives with a positive developmental impact in the region.