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.For the second half of the 20th century, fighting communism was clearly the agenda for the United States and its allies, while the Soviet Union and its satellites were actively opposing the capitalist West. The end of the Cold War not only reorganized the world order with the breakup of many states and the rejection of communism as a viable option, it also brought about a dramatic change in foreign policy for most of the world. Instead of combating communist regimes, the United States and its allies (often through NATO) focused their attention toward authoritarian regimes, and now especially those regimes that support international terrorist groups. Whether through the use of military persuasion or soft power, American post-Cold War foreign policy actively targets the political stability of authoritarian regimes, i.e., former Yugoslavia and later Serbia, Afghanistan, Iraq, North Korea, Cuba, Iran, and Venezuela to name a few.Whereas Russia and China are largely left alone to their authoritarian ways, foreign policy makers remain deeply concerned with attaining knowledge on the "how to" for installing democratic regimes in the rest of the world. Recent events from the Arab Spring, especially NATO participation in *