This chapter examines the implementation of Obama’s grand strategy in the Middle East, with an emphasis on the consequences of the retrenchment strategy and the White House’s responses to regional developments. For a better understanding of Obama’s presidential policies, each Middle Eastern state is explored in detail here. Starting with the withdrawing from Afghanistan and Iraq, the chapter highlights the resulting turmoil and instability in the region. The chapter also discusses how the Arab popular movements in countries like Tunisia, Egypt, Libya, Syria, Bahrain, Jordan, and Yemen exemplified the implementation of Obama’s retrenchment strategy. It explores how Obama navigated between supporting democratic demands and safeguarding national interests, aligning his actions with the grand strategy. Additionally, the chapter analyzes Obama’s approach to the Iran nuclear talks, Israeli-Palestinian tensions, and the battle against terrorism in the Middle East. It examines how multilateral policies were pursued to prevent regional hegemony and how policies were crafted through the UN and allies. Despite supporting Israel, Obama sought to reduce costs by emphasizing the UN’s involvement in dealing with Israeli-Palestinian tensions. Lastly, the chapter also addresses the impact of Obama’s grand strategy on the campaign against terrorist organizations such as DAESH, PKK/PYD, Al-Qaeda in the Arabian Peninsula (AQAP), Nusra, Hamas, and Hezbollah.