On November 4, 1863, to divert Federal forces from Chattanooga, Confederate Gen. James Longstreet led two reinforced divisions from the city to attack Union Gen. Ambrose E. Burnside’s garrison in Knoxville. Burnside confronted Longstreet outside Knoxville, then withdrew to his fortification on November 12, and Longstreet besieged the city. After Union Gen. Ulysses S. Grant’s army defeated Confederate Gen. Braxton Bragg’s forces at the end of the month in Chattanooga, Grant ordered Gen. William T. Sherman to reinforce Burnside, and as Sherman marched toward Knoxville, Longstreet withdrew on December 4. Madisonville, the seat of Monroe County, was divided during the war, with residents serving in both Confederate and Federal units and each side occupying the town at different times. On June 9, 1863, the Knoxville Daily Southern Chronicle reported that young women of Madisonville and vicinity presented tableaux and a concert to raise funds for sick and wounded Confederate soldiers, realizing one hundred and eighteen dollars, and praised the town’s unity of feeling and purpose for the Confederacy and its final triumph. On December 7, 1863, during the Knoxville Campaign, Union Gen. William T. Sherman ordered Gen. Jefferson C. Davis to occupy Madisonville, and a soldier in the 86th Illinois Infantry recalled that the regiment spent a pleasant night there, with nearly every family set to work baking cornbread, cakes, and other food, though he called it forced hospitality. The year 1864 was disastrous for Madisonville: Federal troops burned the courthouse and, together with local citizens, demolished the county jail for building materials. County seat records show that local officials first considered repairing the damaged courthouse but then decided to raze it and build a new one in 1868.