Like many battles in the American Civil War, the Battle of Monroe’s Crossing has several names. It is alternately known as the Battle of Fayetteville Road. The most interesting name given to this engagement is Kilpatrick’s Shirttail Skedaddle. It is also known as the Battle of Kilpatrick’s Pants.
The Union cavalry commander on the scene was Brig. Gen. H. Judson Kilpatrick. He was a dashing cavalry officers in the mold of his West Point classmate, George Armstrong Custer. The 28-year old Kilpatrick had the distinction of being the first United States Army officer to be wounded in the Civil War, struck in the thigh by canister fire while leading a company at the Battle of Big Bethel, June 10, 1861.
Kilpatrick was a lieutenant colonel of the 2nd New York Cavalry by the end of September 1861. That fall he began to earn some fame as a daring cavalry leader when he led his men on a raid on the Virginia Central Railroad. By early December he was a full colonel, equaling the rank of his father, Simon Kilpatrick.
Kilpatrick soon acquired the derisive nickname of “Kill Cavalry” for his reckless use of his men and their horses. He was known for ordering suicidal mounted cavalry charges. His camps were poorly maintained and frequented by prostitutes, often visiting Kilpatrick himself. He was jailed in 1862 on charges of corruption, accused of selling captured Confederate goods for personal gain. He was jailed again for a drunken spree in Washington, D.C., and for allegedly accepting bribes in the procurement of horses for his command.
Despite all of his bad attributes, Kilpatrick was appointed to command of the 1st Brigade, 2nd Division. In the Chancellorsville Campaign in May 1863. Stoneman’s cavalry was ordered to swing deeply behind Gen. Robert E. Lee’s army and destroy railroads and supplies. Kilpatrick did just that, with gusto. Although the corps failed to distract Lee as intended, Kilpatrick achieved fame by aggressively capturing wagons, burning bridges, and riding around Lee, almost to the outskirts of Richmond, Virginia.
After the Battle of Brandy Station in June 1863, Kilpatrick was promoted to brigadier general. He was engaged on a number of occasions during the Gettysburg Campaign. He took part in the pursuit of Lee’s army after its defeat at Gettysburg.
Just before the start of Lt. Gen. Ulysses S. Grant’s Overland Campaign in the spring of 1864, Kilpatrick conducted a raid toward Richmond and through the Virginia Peninsula, hoping to rescue Union prisoners of war held at Belle Isle and in Libby Prison. It was a disaster, resulting in 324 cavalrymen killed and wounded, and 1000 more taken prisoner.
No longer welcome in the Eastern Theater. He transferred west to command the 3rd Division of the Cavalry Corps of the Army of the Cumberland, under Maj. Gen. William Tecumseh Sherman. Summing up Judson Kilpatrick in 1864, Sherman said “I know that Kilpatrick is a hell of a damned fool, but I want just that sort of man to command my cavalry on this expedition.”
Kilpatrick took part in the Atlanta Campaign. and was severely wounded in the thigh at Battle of Resaca. After his recovery in July, He had considerable success raiding behind Confederate lines, tearing up railroads, and at one point rode his division completely around the enemy positions in Atlanta. Kilpatrick continued with Sherman through his March to the Sea to Savannah and north in the Carolinas Campaign. He delighted in destroying Southern property.
Kilpatrick had camped his division at Monroe’s Crossing, in Cumberland County, North Carolina. His force of 1,850 men had set up a poorly guarded camp with many of the troopers sleeping. Kilpatrick himself was was in bed with a young Southern woman he had met while going through Columbia.
The Confederate force of 3,000 cavalrymen consisted of Lt. Gen. Wade Hampton‘s and Maj. Gen. Joseph Wheeler‘s Divisions, who were joined together for the first time. One of there objectives was the capture of Kilpatrick himself. They had selected a squad of troopers for this task. Kilpatrick managed to flee the chaotic scene in his nightshirt, hiding for a period in a nearby swamp before regaining his composure and reorganizing his troops.
The Union cavalry was initially routed but quickly recovered and counterattacked. They eventually forced the Confederate cavalrymen to withdraw from their camp, recovering all of their captured equipment and supplies. THe Union force sustained 183 total casualties, while the Confederate had 80 casualties.
The Battle of Monroe’s Crossroads gained the additional time needed for the Confederate infantry to conduct an organized crossing of the Cape Fear River at Fayetteville unmolested by the advancing Federals. With their troops and equipment east of the Cape Fear, the Confederates burned the bridges as Union forces entered the city.