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James Calhoun was the Mayor of Atlanta. He surrendered the city to Major General William Tecumseh Sherman on Sept.2,1864
The difference was more generational than leadership-oriented, plus the slavery-anti-slavery issue was involved. Henry Clay, Daniel Webster, and John C. Calhoun were the leading figures of the generation preceding the Civil War, with Clay and Calhoun pro-slavery and Webster against. William Seward and Stephan Douglas (who both lost the presidential primary to Abraham Lincoln), were instrumental in Lincoln's cabinet in winning the Civil War.
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Henry Clay and John C. Calhoun.