This article seeks to establish a better scholarly understanding of former Russian President Boris Yeltsin’s decision to launch an ill-planned, risky, and ultimately disastrous invasion of the breakaway republic of Chechnya in 1994. Examining the decision-making environment that led up to the invasion, I conclude that while neorealism provides an adequate explanation for Yeltsin’s motives in this case, the decisions that he made in pursuit of these goals do not reflect the logic of rational utility maximization commonly associated with neorealist theory. Instead, I suggest that prospect theory – based on the idea that decision-makers tend to be risk averse when confronted with choices between gains while risk acceptant when confronted with losses – offers significantly more explanatory insight in this case. Thus, the article offers further support for an alternative theoretical approach to international relations that some scholars have termed ‘cognitive realism’, incorporating neorealist motives with a more empirically accurate perspective on the decision-making processes undertaken in pursuit of these motives.