Decisions made by individuals representing states do not only impact citizens living within the state’s political jurisdiction, but also those from other political jurisdictions. The U.S. Executive’s role in global and international politics is quintessential case of how behaviors of individuals representing a state can shift the balance of power in the global political system. This study aimed to gain a new understanding into how this phenomenon occurs by analyzing the influence of personal characteristics on behaviors of individuals with executive decision-making powers. The Jerusalem Embassy Act of 1995 was used as the case to understand which personal characteristics at the level of cognitive idiosyncrasies were present in Obama’s and Trump’s decision-making processes regarding the Act. The study was an interpretivist enquiry which analyzed speeches gathered using a discourse analysis method and analyzed through the lenses of the cognitive idiosyncrasy theoretical model. Results showed that there were cognitive idiosyncrasies of framing, anchoring, images, evoked set, cognitive consistency, availability of information, historical analogies and verbal styles present in both presidents’ behaviors. The study concluded that though personal characteristics influence decision-making, the extent of their influence varies depending on the individual’s experience, expertise, and interests in the foreign policy problem.