For much of its recent history, North Korea has wallowed in economic ruin due to its particular brand of autarky and internal economic repression. With the loss of traditional Cold War allies due to regime change and ideological shift, North Korea has turned to using threats against its neighbors to elicit material aid. This aid is necessary to stave off starvation and complete industrial breakdown, as North Korea lacks basic amenities such as an adequate food supply and power generation. The paper analyses the cycle of aggression, negotiation and compromise which leads to the provision of such material aid by the West. Kim Jong-Il, supreme leader until his recent death, used calculated aggression to great effect – enough to bring exasperated countries to the negotiating table, but not enough to warrant a forceful regime change. Allies such as China also use their special relationship to mediate between parties and enhance their own status. This model is prone to a tumbling effect, whereby no functional equilibrium is ever reached due to Korean forcefulness and Western appeasement. The fact that such an economically ruinous regime is sustained by this material aid adds irony to the Western stance of encouraging positive change within North Korea. It is found that the “Theory of Moves” is adequate in a Cold War scenario, with functionally equal participants, such as the Cuban Missile Crisis. The destabilization of normal incentive systems, under power and information asymmetry, is what prevents an equilibrium from being reached, as one side (North Korea) overleverages its position, while the other side makes unproductive compromises due to its unwillingness to provoke a confrontation.