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Over the last 20 years, hostage diplomacy, or the detention of an individual with intent to use them for diplomatic leverage, has become an increasing problem across the international landscape. Making up roughly 50% of hostages worldwide, American citizens are at particular risk of being detained by state and non-state actors. Despite a U.S policy of not negotiating with terrorists, some Americans are ultimately freed. When detained by state actors, there is a lack of clarity and consistency behind the label “wrongful detainee” and the order in which individuals are freed via negotiations driven by the presidential administration. In looking at a comprehensive case study analysis that compares six cases of hostages and five cases of wrongful detainees across 25 factors within the framework of media attention and political landscape, this paper aims to understand why an American presidential administration would choose to publicly negotiate for certain individuals but not others. With the rising threat of arbitrary detentions, it is important to understand how American presidential administrations are persuaded to secure the release of their citizens while deterring future action from state and non-state actors.