Kaliningrad’s post-Soviet economic interconnection with Europe is encountering obstacles due to specific Russian governmental idiosyncrasies as well as its particular regional challenges. In essence, the Kremlin’s direct control from afar and European misgivings have influenced the territory’s economic development in relation to Europe. The distance of the region from Russia, exclave status, large size for an exclave, and conflicted history subject the area to contradictory forces. On the one hand, it links Kaliningrad to Europe because of a shared history and geography. On the other, it promotes a sense of political instability and geographical isolation that discourages economic integration with Europe. © 2019, © 2019 Association for the Advancement of Baltic Studies.