This paper is aimed at expounding the evolution of the United States Defense acquisition system from a pragmatism perspective. The arguments indicate that, influenced by the distinct positions to view this dynamic society, people usually hold disparate norms and values to interpret the phenomena of this corporeal world. The diversified interpretations give rise to a complex problem. Given the difficulty to tackle a complex issue, this paper reflects a successful case of redesigning the acquisition system by employing Interactive Management. The redesigning used Interactive Management as a mechanism, which is grounded in pragmatism principles, to embrace multiple perspectives. The case study is succeeded by synthesizing the characteristics of the complex problem and to outline the weakness and strength of conventional ideas of dealing with complex issues. In light of the weakness of conventional approaches, some vital concepts of dealing with complex problems are advanced in the hope of assisting a decision maker in making sound decisions on dealing with national policies. The postulations are grounded in pragmatism philosophy and systemic thinking.