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Maj. Gen. Sterling Price's Missouri Expedition had changed course from St. Louis and Jefferson City to Kansas City and Fort Leavenworth. The engagement at Westport marked the end of a disappointing but ambitious Confederate raid into Missouri, and was the end of the line for Price’s Raid as an offensive mission. It had already been forced away from its prime objectives, first St. Louis, then Jefferson City, the state capitol.
As his army neared Kansas City, Maj. Gen. Samuel R. Curtis's Army of the Border blocked its way west, while Maj. Gen. Alfred Pleasonton's provisional cavalry division was closing on their rear. Now it was headed west without clear objectives except to raid and stay effective.
Price had no real objective, and should have headed southwest towards Confederate territory, but he was not a good commander and mainly let events carry him along. With Union forces on 3 sides, Price hoped to defeat them one-by-one. Price had led his 12,000 men from Arkansas. Only 1/3 of them were armed initially, but they were augmented by 14 pieces of artillery. Hoping to take St. Louis, then to invade Illinois, they were forced to adopt an alternative plan: to cut a swath westward across central Missouri. taking a number of towns, they captured Union garrisons and caches of arms and supplies.
On the 22nd, his rearguard had been smashed by Pleasanton’s cavalry division. With Pleasonton still behind him, Price focused his attention on Curtis’ troops to his west. Presumably he hoped to scatter Curtis, and thus break the ring around him while at the same time opening a route for further advance. Curtis had established strong defensive lines and during a 4-hour battle, the Confederates hurled themselves at the Union forces but to no avail.
Gen. Jo Shelby commanded 3 brigades of horsemen who tried various ways to break through the Kansans, but were repelled at each turn. Then the Confederate rearguard collapsed, and Pleasonton’s horsemen broke the Confederate army in half. Shelby’s brigades were cut off to the north, and he immediately turned them south and cut his way out through the disorganized Union pursuit.
Once through to safety, 2 of the 3 brigades kept going, joining the rest of Price’s “army” in rout, while Shelby’s original Iron Brigade held together and by force of will defeated repeated Union efforts to gobble up Price’s remnants.
Still, the Union attempts were not well organized or strong – many Union troops were fanning out across the battlefield rounding up prisoners and seeking for souvenirs and loot. Many prisoners were wearing pieces of Union uniform, and Pleasanton’s Union troopers tended to hang or shoot these “bandits” while the Kansas Militia was more lenient with its prisoners, probably because they themselves were not in uniform. retreating 61 miles in 2 days, Price halted on the 25th to fight a costly rear-guard action at mine Creek in kansas. He returned toArkansas with only 6,000 surviviors and had gained no material advantage for the Confederacy.
Westport was the decisive battle of Price’s Raid, and from this point on the Confederates were at best retreating, at worst fleeing.