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Under what conditions do smaller powers solicit the influence of major powers and why do some of these efforts succeed or fail? This paper deepens international relations theory by looking at a little-known attempt in nineteenth century Latin America to create an international organization of liberal democratic republics called the Panama Congress. Despite offering lucrative incentives to entice Great Britain to participate in the organization, Simón Bolívar ultimately failed to persuade the British to join the Congress. We examine the role played by geopolitical risk and argue that a lack of either internal or external security creates contradictory demands for smaller and major powers. Insecurity both stimulates smaller powers to solicit assistance from major powers yet disincentivizes major power involvement due to the heightened probability of political conflict or foreign policy crises associated with smaller powers. This historical episode featuring the failure of the first attempt to create a liberal democratic international organization yields insights into the challenges of achieving international cooperation in contested political environments.