The chapter explores the evolution of President Obama’s policy in the Middle East and examines his administration’s attempts to establish a lasting peace and stability in the region. It argues that in dealing with the key events in the Middle East, including the Arab Spring, Libya’s civil war, and Syria’s conflict, Obama’s leadership style exposed its innate weaknesses more than its strengths. In the case of Libya, the chapter demonstrates how Obama’s policy unveiled a deficit of long-term strategic vision as the US intervention in Libya led to chaos and the rise of jihadist groups. The study shows how this debacle prompted Washington to reduce US military involvement while promoting regional self-balancing through arms sales and diplomacy. Subsequently, in the case of Syria, Obama’s policy became excessively risk-averse. The chapter explains why, despite President Obama’s goal to rebalance America’s strategic focus from the Middle East to Asia, the region remained at the heart of US foreign policy by the end of his second term.