Abstract: The Russian city Kaliningrad’s unique geographic position has placed it in the position of an exclave (defined as the territory of a country that is completely surrounded by foreign states) embedded amongst EU member states. Kaliningrad’s geopolitical existence is detrimental to EU-Russian relations, as its security and crime-based issues, as well as economic underdevelopment negatively impact their relationship. Economically, Kaliningrad operates as a Special Economic Zone (SEZ), which had created many benefits for Kaliningrad. But Russia’s entry into the World Trade Organization (WTO) harmed the city’s economy, as Kaliningrad’s benefits are no longer exclusive. Given Kaliningrad’s lack of resources and dependence on foreign investment, this is problematic. Kaliningrad’s security issues encompass social, border, and transit security. Kaliningrad is an epicenter of criminal activity. Its geopolitical location has given organized criminal activity a base from which it can enter the EU. Kaliningrad’s military position also threatens EU-Russian relations. As Russia’s relationship with the West has deteriorated and tensions have risen, Kaliningrad has become home to missiles as well as an increased military presence. Continued economic woes within Kaliningrad will lead to further crime, which will result in the heightening of tensions between Russia and the EU, negatively impacting their relations.