Numerous confederate cavalry raids into Missouri occurred during the American Civil War as part of the fight for Missouri. These raids were the result of multiple failed campaigns by conventional rebel forces to seize and hold Missouri for the Confederate government. Beginning in December 1862, Confederate cavalry forces operating from central and southern Arkansas launched periodic raids into Missouri. These raids varied in size and geographic objective. Joseph Orville "Jo" Shelby was one of the more imaginative and flamboyant Confederate cavalry commanders to operate west of the Mississippi River. He rose from Captain of his homegrown "Shelby's Rangers" to Brigadier General and command of a cavalry division by war's end. Shelby earned this rank upon completion of his 1863 cavalry raid into Missouri. Shelby led this raid into central Missouri to recruit, prevent Missouri troops from reinforcing the eastern theater, and provide a short-term victory for the rebels in Arkansas, demoralized by recent Federal successes. This thesis explores Shelby's abilities as a cavalry commander and explains how Shelby's raid, although executed utilizing enduring principles of war, did little to advance the strategic and operational goals of the Confederate Army in the Trans-Mississippi Department.