Jessie Scout Raid Against a Confederate Cavalry Brigade

The men in gray uniforms had been up from their cots in snug tents located within a guarded area since midnight. Jim White, from Company D, First West Virginia Cavalry Regiment, watched as each new volunteer donned their clothing and prepared their equipment for their first operation together. Their new commander insisted on placing them within the closed compound that had armed infantrymen posted around its perimeter after the selected volunteers reported to Sergeant Joseph McCabe, the chief scout for Sheridan’s army in the Shenandoah Valley in November 1864. They would be departing soon on a mission to be conducted in their recently issued Confederate uniforms and all would ride together under the leadership of their new commander, Major Henry Harrison Young.

was used, but was functional, and each man placed a revolver in both of his high-topped cavalryman’s boots. Spare loaded cylinders were carefully wrapped in paper, after being loaded and caps placed on each nipple on the rear of the cylinder, to prevent the grease smudged over the open end of the cylinder that was used to prevent simultaneous discharge of all charges of powder when the revolver was first fired from leaking on their clothing. Only a second was needed to remove the paper before inserting the loaded cylinder into the revolver as a rapid reload system that saved many cavalry man in a fight. Each trooper was issued a short-barreled shotgun that contained a double load of buckshot.

The November night was cold as the gray uniformed men assembled near their horses, mounted, and rode silently out of the Federal army’s camp near Winchester, Virginia. Guides led them as they passed the final perimeter of guards as the silent column passed beyond their camp. They rode along the road in a southerly direction for about two hours before being halted by Young and Sergeant McCabe. They were advised now for the first time of their precise mission against the Confederate army and the role each was to play in the attack.

Major Young and Sergeant McCabe had scouted the area two days earlier and discovered while inside an enemy camp that a large Confederate cavalry unit, probably an under strength brigade, would be traveling northward on this road today. The newly formed scout group was to receive their baptism by fire — the sixty Union cavalrymen now dressed in Confederate clothing were going to attack the much larger Rebel brigade as their first operation.

recently captured enemy uniforms. They rode as a group posing as a returning patrol as they rode toward the center of Bradley Johnson’s camp that was adjacent to McCausland’s bivouac area and initiated the battle by attacking Confederate Major Harry Gilmor.

With this proven tactic as an example, Young and his new men, including the very scouts who were at Moorefield, rode forth to verify this concept against a mobile target. This raid was also a good opportunity for Young to test the new volunteers who volunteered for scouting duty. Sixty men involved in attacking even a chronically under strength Confederate cavalry brigade was sheer lunacy — but this would also be the last thing the Confederate commander would expect to occur along his route of march within his own territory.

At the end of their long ride, the scouts moved into a nearby tree line adjacent to the road and waited in silence for the approach of their target. The strain on each cavalryman was great as they stood by their mounts in the pre-dawn cold, but they all understood the risks they were taking and the tension was as sharp as the November wind they were facing. The volunteers were intending to attack a vastly superior force composed of veteran enemy cavalrymen and each scout knew they faced death from either bullets of a rope if they failed and were captured. The laws of warfare as practiced by both sides left no protection from an enemy “drumhead court” and death at the end of their own leather reins tied to a tree limb might await them. The thought of a “forlorn hope,” a suicide operation, must have crossed the minds of many of the participants, but all of the young soldiers remained true to the duty for which each volunteered.

The wind was their only companion as they waited and the cold must have begun to seep into ill fitting uniforms as they stood beside their mounts. No sounds came from either man or horse as they stood quietly in the trees as they fought the freezing chill and their individual fears. Shortly before dawn, they began to hear the quiet rustle of horses, riders, and the sounds of hundreds of sabers and canteens knocking about on saddles and riders. 

At a silent signal from Major Young that was passed from man to man along the line, the scouts mounted, rode slowly from the tree line, and approached the head of the slowly moving Confederate column. They passed the leading elements of the large column before falling in with the tired, cold, and dozing Confederates who obviously noticed their arrival — and to whom Young’s men seemed nothing but a returning outrider patrol. They all rode along together quietly as the Confederate soldiers who were roused by the scout’s arrival began to settle into what little comfort was available until a loud yell from Young galvanized each of the scouts into instant action.

The disguised major swerved his horse toward the rear of the Confederate column as he fired his double-barreled shotgun into the nearby torsos of the surprised Rebel soldiers as he pulled his pistol and fired repeatedly as he rode past the confused soldiers. The rest of his men were doing exactly the same thing as they rode the length of the Confederate column as they fired into the mass of cursing cavalrymen. Screams and yells of “Cease fire!” and “Stop firing, Goddammit! You’re shooting your own men!” rang out from every direction. The entire group of sixty scouts wheeled in the direction opposite to the line of march of the Confederate column and fired into it as they rode past.

As was the case in Moorefield, the sudden ferocity of the attack from their midst destroyed any opportunity for a cohesive response from the veteran Confederate cavalrymen. Each Rebel trooper who came into the view of a scout having either a shotgun or a revolver hesitated to return fire, fearing that he was about to fire on a friend in the melee. Young’s scouts had no such compulsions. They were so few and the numbers of the enemy were so great that they could fire at anyone with a high degree of assurance that they were shooting an enemy. The fatal hesitation of the Confederate cavalrymen resulted in the chaos among the victims of the attack as the scouts rode the entire length of the Rebel column, firing into it as they rode away.

The mathematics of the situation was obvious to the scout commander as his men rode to a pre-designated rally point to the east of the road where they had done the work of an executioner. Sixty Union soldiers in Confederate uniforms had severely damaged a Confederate cavalry brigade at the cost of a single man lost. These quiet professional soldiers rode slowly back toward their camp in silence without any demonstrations of emotion about their one-sided victory. They survived their first operation, but all of them knew that the short major who was now their commander would lead or send them forth to possible death again and again until the war was won.