Looking back on it twenty years later, this paper argues that the US decision to engage in a war for regime change in Iraq in 2003 was less a mistake by a US president that was shortsighted and ideologically committed than a product of the US failing to ever consider a post-Cold War approach to the Middle East in terms other than imposing a US-led regional hegemonic order. As a result, the US invasion that violated international norms helped unleash new dynamics of regional intervention, lethal technologies and forms of warfare. Drawing on James C. Scott’s critique of high modernist planning in the 20th century, this paper explores how the US effort to use the 2003 war as a mean to reorder the Middle East can be understood like other misguided imperial or hegemonic projects that seek to establish new material structures and social orders. We can use Scott’s analysis of high modernist efforts to impose order to offer similar lessons about the failure of US efforts to order the Middle East as US policymakers relied on representational simplifications, were overconfidence in US technical capabilities, deployed coercive power, and failed to accommodate resistance to their plans. US policy was blind to the political dynamics at the regional and domestic levels and consistently rejected alternative options for building regional order. The paper then maps the consequences using Scott’s observation that the populations that planners seek to order often develop in reaction forms of practical knowledge, informal processes and improvisions that they use to navigate the unstable and unpredictable environment they inhabit. In this context, the states and organizations best able to develop and manage networks of self-organized actors -- such as Iran’s Revolutionary Guards and its allied militias, US special forces, and armed jihadist groups including the ISIS – have been the ones best able expand their power and influence producing a complex of rival, overlapping networks of influence. As a result, efforts to promote security, let alone regional order, have become difficult and precarious.