Donald Rumsfeld’s desire to transform the Department of Defense into a lean, flexible, and expeditionary organization in 2001 was not a bad initiative. However, in applying the transformation based on three strategic influencers to the plan for Operation Iraqi Freedom, the result was a failed strategy. The first was a wrongheaded application of the lessons learned in Operation Desert Storm. Second, an emerging Revolution in Military Affairs predicated on network centric and rapid decisive operations underestimated the amount of military power required on the ground in Iraq. Finally, a “New American Way of War” focused on small numbers of special operations forces supported by airpower that initially saw success in Afghanistan reinforced Rumsfeld’s concept for regime change in Iraq. The combination of these factors in the decade between Operation Desert Storm and the 9/11 attacks resulted in flawed assumptions and a failed strategy for Operation Iraqi Freedom.