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===Civil War era=== Although Sikeston was a small village during the [[American Civil War|Civil War]], its position at the railroad and highway intersection gave it strategic significance. Around July 1861, Confederate forces of [[Brigadier General]] [[Gideon Johnson Pillow]] planned to link up with units commanded by [[Sterling Price]] and [[Benjamin McCulloch]] for an advance on St. Louis, using the Sikeston-area road of Kingshighway. In preparation for this advance, Confederate General [[M. Jeff Thompson|Jeff Thompson]] gathered Missouri state troops and irregulars near Sikeston; he robbed a bank in nearby [[Charleston, Missouri|Charleston]] to pay men and buy arms and supplies. Legend has it that he hid part of his money in Sikeston under one of the oak trees at the corner of New Madrid Street and Kingshighway. In the fall of 1861, General Pillow pushed a column of troops from [[New Madrid, Missouri|New Madrid]] towards Sikeston and [[Cape Girardeau, Missouri|Cape Girardeau]]. On October 4, Confederate General Jeff Thompson reached Sikeston, planning to strike Cape Girardeau; however, his manpower was limited, and he decided to retreat into the swamps off to the west. On November 3, from [[Cairo, Illinois]], US [[Brigadier General]] [[Ulysses S. Grant]] wrote a letter to Colonel [[Richard J. Oglesby]], commander of the Union Headquarters District Southeast Missouri at [[Bird's Point, Missouri|Bird's Point]], ordering his troops to "strike for Sikeston" from the [[Mississippi River]] town of [[Commerce, Missouri|Commerce]]. [[Brigadier General]] [[Benjamin Prentiss]] and [[Colonel (United States)|Colonel]] [[W. H. L. Wallace]] also converged in the Sikeston area in preparation of Grant's attack at the [[Battle of Belmont]]. In 1862, Sikeston was used as a transportation connection as Union Brigadier General [[John Pope (general)|Pope]] sent his artillery across the river to Commerce, Missouri, to be sent by rail to Sikeston for cart transportation to New Madrid, in preparation for the [[Battle of Island Number Ten]]. On February 28, 1862, Pope left Commerce with his army of 12,000, arriving in Sikeston on March 2. US Colonel [[William Pitt Kellogg]], future [[List of Governors of Louisiana|governor of Louisiana]], commanding the 7th Illinois cavalry, was the first to encounter the rebel sabotage of recently burned bridges and other obstructions. The federals were attacked just south of Sikeston by a small group of rebels led by General Thompson (he was called the Swamp Fox, a nickname after the [[American Revolutionary War|Revolutionary War]] Brigadier General [[Francis Marion]]). Thompson commanded a detachment of 85 horsemen and four to six experimental cannons that had been manufactured in [[Memphis, Tennessee|Memphis]]. Seeing that Colonel James Morgan's Illinois troops were reinforced by Brigadier General Schuyler Hamilton's 2nd Division, Thompson fled. Entering the area from [[Bird's Point, Missouri|Bird's Point]], Brigadier General Eleazor Arthur Paine, commander of the 4th Division of [[Army of the Mississippi]], repaired the railroad and telegraph lines and used troops from [[Illinois]] to form a garrison for Sikeston, [[Bertrand, Missouri|Bertrand]], and [[Charleston, Missouri|Charleston]]. War records indicate that on March 31, 1862, there were six Union officers and 143 Union soldiers present in Sikeston. On September 22, 1864, during [[Price's Raid]], a Confederate force of 1,500 men near Sikeston, under the command of Colonel William Lafayette Jeffers, attacked Captain Lewis Sells' company of Union soldiers who were moving from Cape Girardeau to reinforce two companies of soldiers in [[Bloomfield, Missouri|Bloomfield]].<ref>{{cite book | author = Larry J. Daniel and Lynn N. Bock | year = 1996 | title = Island Number Ten: Struggle for the Mississippi Valley | publisher = The University of Alabama Press | location = Tuscaloosa, Alabama | id = 0-8173-0816-4 }}</ref>
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