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===Civil War=== {{further|Battle of Booneville}} The Mobile and Ohio Railroad that ran through Booneville was completed shortly before the Civil War began. It was converted to military use and became a critical military target. 184 miles of the line from [[Union City, Tennessee]] to [[Okolona, Mississippi]] would be totally destroyed by 1866, causing severe financial strain for the railroad even after it was eventually rebuilt.<ref>{{cite web|url=https://www.columbusky.com/river-railroad.php|title=The Mobile & Ohio Railroad & The Mississippi River|website=columbusky.com|access-date=13 December 2020}}</ref> On May 30, 1862, [[Colonel (United States)|Col.]] [[Washington Lafayette Elliott]] of the [[2nd Iowa Cavalry Regiment]] led a [[Union Army|Union]] brigade to Booneville, where they destroyed the local depot and a large train loaded with munitions and captured 2,000 sick and wounded [[Confederate States Army|Confederates]].<ref>{{cite web|url=http://files.usgwarchives.net/ia/state/military/civilwar/book/cwbk_2c.txt|title=Second Regiment Iowa Volunteer Cavalry|website=usgwarchives.net|access-date=13 December 2020}}</ref> On June 28, 1862, Col. [[Philip Sheridan]] of the Union fortified a position in Booneville after hearing that the Confederates intended to move from [[Tupelo, Mississippi|Tupelo]] to [[Corinth, Mississippi|Corinth]] in an attempt to recapture the rail junction there. [[Brigadier General#United States|Brig. Gen.]] [[James R. Chalmers]] of the Confederacy led 4,700 troops in an assault that pushed the Union troops to withdraw to a backup position {{convert|2|mi|km}} closer to the town. The bulk of the Union force stayed on the defensive while Sheridan sent the [[2nd Michigan Volunteer Cavalry Regiment|2nd Michigan Cavalry]] under [[Captain (United States)|Capt.]] Russell Alexander and the 2nd Iowa Cavalry under [[Lieutenant Colonel (United States)|Lt. Col.]] Edward Hatch to attack the Confederate rear and left flank. It is estimated 65 of Chalmers' men were killed; Federal casualties were one dead, 24 wounded, and 16 missing.
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