<p>Liberal and realist theories of international relations fundamentally disagree over the influence of trade on conflict. While liberals focus on the pacifying influence of interdependence on conflict, realists tend to see trade and interdependence in terms of vulnerability to state security. Dale Copeland’s (2015) trade expectations theory attempts to bridge this divide, arguing state expectations of future trade determine how states will pursue policies of cooperation or securing the source of their vulnerability through force. The cornerstone of Copeland’s theory hinges on the concept of a “reasonable” expectation, but he dismisses state factors such as bias in this calculation. By incorporating domestic pathologies into trade expectations theory, this article shows how interdependence can lead to greater conflict in what Copeland describes as a “trade-security dilemma.” Applying the theory to the 2014 Ukraine Crisis, this article reveals how integral the state’s deeply held biases and beliefs are to Russian decision-making in the post-Soviet space.</p>