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The U.S. and Iran have been locked in a decades-long standoff, driven by missteps, misunderstandings, and conflicting ambitions. This collection of essays delves into the complex dynamics behind this ongoing conflict, shedding light on why American policies have repeatedly failed to understand the true nature of Iran’s transformations and its role in the Middle East.Drawing on two decades of political analysis, the essays explore the history of U.S. intervention in the region, focusing on the enduring sanctions imposed on Iran and the persistent perception of the Islamic Republic as a major obstacle to American power. Despite the repressive policies of the state, Iran has remained a vibrant society with active intellectual, cultural, and social justice movements. The book examines these internal changes and shifts in Iranian politics, offering crucial insights into why American policies have often been blind to these developments.By challenging the conventional image of Iran as a totalitarian regime, this collection urges readers to appreciate the country’s diverse society and complex political landscape. It calls for a re-evaluation of how the U.S. engages with Iran, advocating for a more informed, nuanced approach to Middle East diplomacy. At a critical moment when U.S. policy is being reshaped, these essays serve as a timely reminder: without acknowledging Iran’s transformations, both nations will continue to face new events—and the same old questions.