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Civil War generals are among the most celebrated figures of their time. In the post-Civil war era, many of these officers retreated to farms, and businesses and disappeared into obscurity. This was not the case with Colonel John Singleton Mosby, who quickly transformed into a figure whose legacy from the Civil war gave him a unique place in the American imagination as the legendary Gray Ghost of the Shenandoah Valley of Virginia. He lived until 1916, a remarkable fifty years filling those decades with a host of accomplishments in public service both at home and abroad. His legacy is complex, and his life is a fascinating story of myth, contradictions, and romanticism that has provoked continual reexamination of his accomplishments and failures.