A debate between liberal and realist international relations theories centres on the influence of trade interdependence on state action. While liberal theorists tend to see interdependence as only a mechanism for peace, realists view trade dependency as a potential for state vulnerability. Dale Copeland’s trade expectations theory offers a bridge to this divide by arguing perception of future trade accounts for whether states perceive trade as a vulnerability or mechanism for cooperation. Copeland’s novel theory argues when states possess a positive expectation of future trade, they will continue to pursue trading relationships, as argued in liberal theory. However, once these expectations turn negative, states may face a trade-security crisis stemming from the trade vulnerabilities. This thesis applies Copeland’s theory the Russian experience leading up to the 2013 – 2014 Ukraine Crisis. The application of the theory addresses two key criticisms of trade expectations theory: first, the question of what constitutes “reasonableness” within the expectations of trade, and second, grounding the theory within the broader international relations literature. Copeland’s reliance on a “reasonable man” test of trade expectations lacks a nuanced understanding of what a reasonable perception of a state is. Through the addition of militarism as a state bias and belief, this thesis shows the theory’s logic developing within a defensive realist framework. The thesis applies the case study to a two-level security dilemma, grounding the theory’s core contribution, the trade-security dilemma, within defensive realism. Placing Copeland’s theory within this framework reveals trade expectations to be an intervening variable within a balance of power competition. Finally, the application of trade expectations theory to Russia and the Ukraine Crisis gives greater depth in understanding Moscow’s dilemma. Framing a trade-security dilemma within the broader balance of power dynamic exposes the Russian trade crisis which occurred as Kyiv shifted towards the West.