American and Arab Gulf relations with the Maghreb have suffered from a variety of deficiencies ranging from tunnel vision to lack of vision and from transactional proxy battles to transactionless withdrawals. None of the traditional approaches to international relations theory offer satisfactory explanations nor remedies for increasing dysfuntionalities in these relationships, in large part because these theories privilege one set of relationships over another, while insufficiently theorizing and addressing the main motors of regional instability, those which are not primarily state-driven, institutionally driven, socially-constructed nor grounded in poverty and economic marginalization. This paper analyzes the ongoing failure of American and Gulf engagements in the Maghreb adequately to address major challenges afflicting the region due to errors of analysis, strategy and implementation, the latter failures often having to do with optics, process, and scaling. The paper will examine failures to find a path towards peace and stability in Libya, failures to help Tunisia produce tangible revolutionary dividends, failures in reform assistance in every Maghreb country, and, when policies do adequately address the most pressing problems, failure to effect desired change or scale to challenges, whether, for example, in reducing corruption, assisting with the establishment of the rule of law, or empowering youth. The paper then looks at what theoretical building blocks will be necessary to analyze the causes of current systemic failures, in both theory and practice, and what elements of these new approaches can influence policy reorientation and improve project design. The paper is based in large part on the author's experience in a variety of government, non-government, and analytical organizations and roles over three decades, which made thousands of conversations and interactions all of the donor countries and recipient countries of international assistance to the Maghreb possible. This empirical data is supplemented by the author's previous experience interviewing over 5000 young people in all five Maghreb country while working in a variety of research and professional capacities, much of that during 13 years of residence in the region. This data is organized around episodes in American-Maghreb and GCC-Maghreb engagements--including a number of MEPI programs--framed as cautionary tales/learning moments. These will be compared with GCC funding in a variety of sectors, with none of the donors analyzed applying much conditionality. The conclusion of the paper will lay out analytical frames and tools to assist in re-imagining these relationships.