One of the most complex challenges facing the U.S. military today is the problem of imposing stability over the chaos that follows major combat operations. Despite the U.S. military's predilection to distill warfare into the linear, Newtonian paradigm, recent experience in Operation Iraqi Freedom (OIF) suggests that the cause and effect correlation between high-velocity major combat operations and achieving a complex political endstate such as regime change is becoming less certain in the contemporary strategic environment. The transition to stability operations in a non-linear, dynamic environment is proving more difficult, and perhaps more decisive, than the major combat phase of a campaign. At some point in every war, the focus must shift from rupturing the existing system to stabilizing and legitimizing a new one; the center of gravity from the enemy's military forces to ending the chaos and violence that follow major combat operations. The aim of this study is to examine the difficulty in planning and executing these transitions from a historical perspective.