The Mesopotamia Campaign of World War I and Operation Iraqi Freedom of the Global War on Terrorism took place on the same geographic and human terrain. Though separated by nearly a century, a significant number of points of comparison are evident, particularly with regard to strategic and operational missteps. In both cases Western armies successfully invaded and occupied the present-day region of Iraq, and both armies suffered the effects of difficult insurgencies in the wake of their conventional campaigns. This thesis explores parallel mistakes committed by the political and military leadership of each operation in order to determine what aspects of the Mesopotamia Campaign might have provided useful precedents to the planners of Operation Iraqi Freedom. These comparable operations suggest an argument for studying history during the formulation of strategy and the design of supporting campaigns. If the American leadership had closely examined the earlier British encounter in Iraq, then it may have been able to avoid repeating some of that operation’s costly and deadly aspects.