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Should the United States retrench from the Middle East, and if so how? After four turbulent years under Donald Trump and a disorienting global pandemic, the time has come to reassess American foreign policy in the Middle East. Drawing on the experience of all great power transitions since 1870, this paper compares current power shifts to past power shifts, evaluates the systemic incentives facing the United States, and weighs the costs and benefits of various policy options open to current policymakers. It finds that the United States continues to be in moderate relative decline, that conditions favor American retrenchment, and a gradual withdrawal from the region is likely to reallocate resources closer to home and redeploy greater forces to the Pacific. Structural conditions are receptive to American retrenchment because the country is falling from the highest rank, has capable allies in the region, faces little commitment interdependence problems, and the local conquest calculus favors defense. The potential threats in the region — nuclear proliferation, civil conflict, and oil disruption — are not positively influenced by forward deployments, and the opportunity costs to maintaining forward deployments are straining strategic solvency. The policy recommendations that flow from this analysis are to reduce military spending, revise force structure, reform institutions, and reallocate resources.