This paper discusses the nexus between North Korea’s power configuration, economic conditions, and its WMD development. The isolated Stalinist country could dodge the economic difficulties it experienced since the 1990s with its consolidated one-man dictatorship. However, the regime’s inflexibility has retarded its economic transformation despite the severe economic plight during the mid-1900s. Transition to a market economy could put the hierarchical ruling system in danger of experiencing a serious regime crisis. The dilemma of having to choose between maintaining internal stability and guaranteeing the regime security has driven the North Korean leadership to design a risky strategy of missile and nuclear development. That was the only choice it could take for getting international attentions. International sanctions have proven to be insufficient to penalize the maverick country that dared the missiles and nuclear tests in 2006 and in 2009. The success of a tit-for-tat game is highly dependent upon the astute consistency of rewarding and punishing, and the policy coordination among the stakeholder countries. This is hardly possible in the case of the North Korea nuclear issue because of the limits in monitoring ability and of the lack of effective leverage to enforce it. Six-Party talks, therefore, cannot bear any fruits. In the future, nothing would guarantee the viability of North Korea so overridden with structural contradictions.