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On October 7, 2001, 3 weeks after 9/11, U.S. forces attacked Afghanistan; bombers struck Taliban headquarters and Al Qaeda training sites. By early December, the Taliban and Al Qaeda have been defeated and had fled. However, a war that began so successfully in 2001, eventually ended ignominiously on August 30, 2021, almost exactly 20 years later, with a U.S. withdrawal and a total Taliban victory. The speed of the Taliban's triumph shocked everyone. The entire campaign, costing US$2.3 trillion and 2,488 U.S. lives, had failed—utterly. The United States had lost its longest-ever war. How is it possible to explain a defeat of that magnitude? This article seeks to address this question. Although numerous factors played a role, this article identifies three principal factors: the environment, the local politics, and the Taliban. Afghanistan is a very difficult place to conduct large-scale military operations. The West never came to terms with the local politics and consequently undermined their own efforts. Finally, although they were not militarily sophisticated, the Taliban were politically astute and very resilient. [ABSTRACT FROM AUTHOR]