Objective To understand what kind of individuals lead particular regimes, this study examines the most influential people in politics, the executives, to uncover the relationship between their characteristics and the type of regime they govern. Methods This article employs data mining with characteristics of executives worldwide against the state's Freedom House ranking. Results Through data mining, the results indicate that while there are still many important factors that coincide with democracy, the length of time in office and to a lesser extent the religious beliefs of executives and the likelihood of being classified as a democracy are heavily related. Conclusion This article concludes with a recommendation for supporting specific types of executives to increase the likelihood for successful democratization to minimize authoritarian rule.