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Thanks mainly to the confidence of Gen. Braxton Bragg and the timidity of Maj. Gen. Ambrose E. Burnside, the Confederate seige of Union-held Chattanooga was succeeding. Pushed back into the city after the disasterous Battle of Chickamauga, Maj. Gen. William S. Rosecrans and his hungry troopers were in desperate need of supplies and ammunition. Sending no relief, Burnside was content to stay onguard at Cumberland Gap, sidestepping any confrontations with cavalrymen Maj. Gen. Nathan B. Forrest. Only one alternative remained to Rosecrans: the Sequatchie Valley road, a winding, narrow swath through the south Tennessee woods and the only supply route open to the Federals.
On September 27th, Bragg decided to deliver a final blow to the starving Federals by cutting off Chattanooga's lifeline. To lead this raid he chose a reluctant Maj. Gen. Joseph Wheeler, who questioned the ability of his already depleted force to carry uot the order. However, he assured his subordinates; "I have my orders, gentlemen, and I will attempt the work." That "attempt" turned out to be one of the most audacious cavalry raids of the war. Highlighted by a series of quick, sharp strikes, Wheeler's Raid left the Union army in the West a shambles.
As Maj. Gen. George Crook peered across the Tennessee River at Wheeler's cavalrymen on October 1st, the 27-year-old Wheeler suddenly ordered his troops to cross. Under heavy fire, the men forded the river, leaving their dead and wounded in the water, intent on storming the Union position. On the western bank, they charged with abandon into Crook's 4th Ohio. It was the 1st in a series of Confederate successes and typical of Wheeler's actions in the future.
Joined by some of Forrest's brigades, Wheeler organized 3 divisions, ordering them to move out at dusk toward Walden's Ridge. In the night rain and mud, the Confederates trudged up the slopes. Suddenly, the advance guards ran into a Union patrol. Again, Wheeler immediately ordered a charge, scattering the Federals through the woods. The Confederates spent the next day plodding toward the ridge. That night, Wheeler laid out his strategy, ordering Brig. Gen. John A. Wharton to proceed to McMinnville while he and Brig. Gen. William T. Martin converged on the Sequatchie Valley and captured the Union supply trains.
During the next week, Wheeler galloped through the valley, destroying nearly everything in sight, with Crook's men in close pursuit. This raid inflicted 2,000 Union casaulties; 3,000 Confederates were either killed or wounded. Wheeler destroyed or captured more than 1,000 supply wagons, hundreds of draft animals, 2 towns in Tennesse, 5 critical bridges, miles of railroads, and millions of dollars of supplies. The Confederates suffered only 212 casaulties and caused an upheaval in the entire Union command structure.