Battle of Okolona The Battle of Okolona took place on February 22 , 1864 , in Chickasaw County , Mississippi , between Confederate and Union forces during the American Civil War . Confederate cavalry , commanded by Maj . Gen . Nathan Bedford Forrest , faced over 7 , 000 cavalry under the command of Brig . Gen . William Sooy Smith and defeated them at Okolona , causing 100 casualties for the loss of 50 . Smith ' s force had been ordered to set off from Memphis , Tennessee , and rendezvous with the main Union army of 20 , 000 that was stationed at Meridian , Mississippi , and was under the command of Maj . Gen . William Tecumseh Sherman . However , Smith disobeyed orders and delayed his march for ten days . When he eventually left , he encountered the Confederate cavalry force on February 21 , and on February 22 was engaged in a running battle across eleven miles with Forrest ' s forces . With Confederate reinforcements , Forrest routed Smith but did not pursue due to lack of ammunition , and Smith limped over the state line to Tennessee on February 26 , where he was criticized for putting Sherman ' s Meridian Expedition in danger . Background . Meridian was an important railroad center , and was the objective of a campaign launched from Vicksburg , Mississippi , on February 3 by Sherman , who brought 20 , 000 men to the outskirts of the town . Seven thousand cavalry under Smith ' s command were stationed in Memphis , and on February 1 these were ordered to leave for Meridian along the Mobile & Ohio Railroad and rendezvous with the main Union force on February 10 . While Sherman feinted his way towards Meridian to throw off Confederate forces , Smith delayed his own advance for 10 days before leaving on February 11 . His force moved unopposed through the countryside , destroying railroads and crops as well as picking up 1 , 000 slaves . On February 16 he passed through New Albany , his progress slowed due to muddy roads . On February 18 he drove a Confederate force from West Point , and he was 90 miles from Meridian , just outside West Point , on February 20 when Sherman eventually left his position in the town and returned to Vicksburg , fearing for Smith ' s whereabouts . Smith , hearing of this , turned about and headed for Okolona . Later on February 20 , Smith fought an initial battle with Confederate forces under Forrest ' s command at Prairie Station and Aberdeen . On February 21 , having decided to withdraw to West Point because of concern over the size of the Confederate forces and the fate of the slaves if they were captured , Smith was lured into the swampy area around the Tombigbee River by a Confederate cavalry brigade under Col . Jeffrey Forrest . Smith was forced again to retreat , leaving a rearguard , which followed his main force two hours later . The battle . Forrest arrived to conduct the battle as the rearguard began to retreat , and led the first attack at dawn on February 22 on the prairie south of Okolona . The Union forces had dismounted and constructed barricades around their positions . Forrest began a frontal assault and probing flank attacks , and with Confederate reinforcements , cut gaps in the Union battle lines and prompted a general retreat , with five cannons being abandoned . The Union forces reformed on a ridge , and during a flurry of attacks and counterattacks Col . Forrest , the major general ' s younger brother , was killed by a shot to the neck . He allegedly died in the arms of his brother , who muttered " Jeffrey , Jeffrey . " Faltering after the colonel ' s death , the Confederate attack was revitalized by the older Forrest , who led a charge to " exact vengeance " and break the Union positions . During the pursuit , Forrest and his group were briefly overwhelmed before Col . McCullough arrived with reinforcements . The Union forces began an eleven mile running battle as they withdrew , falling back through a series of defensive positions including plantations and roadblocks . However , these positions were quickly abandoned in the face of Confederate attacks . Towards the end of the day , the Union forces drew into three lines on a field , and charged the Confederates , who used volley fire to disrupt both charges at a range of 40 yards . Facing such defeat , Smith began a further withdrawal . Forrest quickly ordered the end of the pursuit due to lack of ammunition , but Smith was forced to contend with other Mississippi militia units for the rest of his retreat to the Tennessee border . At Collierville , Tennessee , Smith crossed the state line on February 26 with the remainder of his forces , where he was reprimanded for disobeying his initial orders to start out for Meridian on February 1 . Due to failing health Smith left the military in September 1864 and returned to civilian life .