The Holly Springs Raid

Lieutenant General John C. Pemberton’s Confederate Army of Mississippi held a defensive line at Grenada, Mississippi. Pemberton faced Major General Ulysses S. Grant’s Federal Army of the Tennessee moving overland from Oxford toward the key port city of Vicksburg, on the Mississippi River. A detachment of Grant’s army under Major General William T. Sherman was moving down the river to threaten Vicksburg from the water.

Pemberton could not match the Federals’ numerical superiority, so he had to rely on attacking Grant’s fragile lines of communication and supply. As such, he detached 2,500 Confederate cavalry troopers under Major General Earl Van Dorn to attack the stores at Holly Springs, Grant’s principal supply base and the largest Federal depot west of the Alleghenies.

Van Dorn’s troopers rode out of Grenada on the early morning of December 16, moving northeast through Pontotoc. The Confederates were not told where they were going. They were spotted by Federal cavalry, but news of their movement did not reach Grant until the next day. During that time, Van Dorn rode through New Albany toward Ripley, around Grant’s eastern flank. He drove off Federal scouts along the way before turning west toward Holly Springs.

December 19 was cold and clear as Van Dorn’s Confederates rode to Ripley, far behind enemy lines. Grant had been preoccupied with Confederate raids on his lines in western Tennessee when he received word of Van Dorn’s movement. Unaware of Van Dorn’s exact whereabouts, Grant ordered a cavalry pursuit. He also notified Colonel Robert C. Murphy, commanding the 1,500-man garrison at Holly Springs, to be on high alert. Other Federal commands along the Mississippi Central Railroad line received the same warning.

Gen Earl Van Dorn | Image Credit:

By the night of the 19th, Van Dorn was within five miles of Holly Springs. He sent disguised troopers into the Federal base with forged passes to scout the area; they reported that the base was lightly defended and therefore vulnerable. In fact, the Federals were busy planning a ball for the following night. Van Dorn split his forces to advance on Holly Springs along two different roads.

The Confederates attacked the unsuspecting Federals the next day and sent most of them fleeing in panic. Major John J. Mudd’s 2nd Illinois Cavalry tried to make a stand but was forced to withdraw after losing 100 of 350 men. Van Dorn had Holly Springs by 8 a.m. He posted troopers south of town to prevent the arrival of Federal reinforcements, and the Confederates spent the next 10 hours destroying supplies, cutting telegraph wire, and wrecking railroad tracks. This included burning a new 2,000-bed Federal hospital to the ground.

A southern correspondent described a scene of “tents burning, torches flaming, Confederates shouting, guns popping, sabres clanking, abolitionists begging for mercy, ‘rebels’ shouting exultingly, women en dishabile clapping their hands frantic with joy, crying ‘Kill them! Kill them!’” The Confederates caught Colonel Murphy in his nightclothes, and he quickly surrendered his entire command.

Van Dorn captured nearly the entire Federal garrison and destroyed supplies worth $1.5 million by his account, or $400,000 according to Grant. These included enormous amounts of commissary, medical, and ordnance supplies for the Federals. Grant’s wife Julia had been staying at the Walter House in Holly Springs, but she had gone to see her husband at Oxford just before the raid started. Van Dorn ordered that she be protected at the Walter House, unaware that she had narrowly escaped. Her carriage was burned but all her other possessions were left untouched.

Many men of the 109th Illinois were Confederate sympathizers and eagerly surrendered so they could be paroled and sent home. Van Dorn refused to accept their surrender, asserting that “a disloyal regiment in the Union Army was a much greater asset to the Confederacy than even a larger number of prisoners who would be shortly paroled.”

Murphy reported, “My fate is most mortifying. I have wished a hundred times to-day that I had been killed. I have done all in my power–in truth, my force was inadequate.” Major Mudd countered, “I cannot doubt but that the place could have been successfully defended by even half the force here had suitable precautions been taken and the infantry been concentrated, their officers in camp with them and prepared to fight.”

Grant later wrote, “Colonel Murphy was the officer who, two months before, had evacuated Iuka on the approach of the enemy…” but Grant had considered it “an oversight and excused it on the ground of inexperience in military matters.” Now Grant thought otherwise: “The surrender of Holly Springs was most reprehensible and showed either the disloyalty of Colonel Murphy to the cause which he professed to serve, or gross cowardice.”

Grant reported that Murphy “took no steps to protect the place, not having notified a single officer of his command of the approaching danger, although he himself had received warning, as hereinbefore stated.” He later dismissed Murphy from the army, retroactive to “the date of his cowardly and disgraceful conduct.”

This disaster, coupled with Confederate raids to the north, forced Grant to end his overland advance toward Vicksburg. It also left him unable to communicate with Major General William T. Sherman, who proceeded as planned to the Yazoo River in expectation that Grant would reinforce him. The northern press soon began revisiting charges of Grant’s incompetence for failing to adequately defend his supply base.

Grant later wrote of Holly Springs: “This demonstrated the impossibility of maintaining so long a line of road over which to draw supplies for an army moving in an enemy’s country. I determined, therefore, to abandon my campaign into the interior… and returned to La Grange and Grand Junction destroying the road to my front and repairing the road to Memphis, making the Mississippi River the line over which to draw supplies.”

The next day, Grant began pulling his troops out of Oxford, burning bridges and railroad track along the way. He then ordered his troops to commandeer supplies from civilians within a 15-mile radius of the rail line to make up for the loss of goods at Holly Springs. Grant was “amazed at the quantity of supplies the country afforded. It showed that we could have subsisted off the country for two months instead of two weeks without going beyond the limits designated. This taught me a lesson… Our loss of supplies was great at Holly Springs, but it was more than compensated for by those taken from the country and by the lesson taught.” Nevertheless, the troops were forced to go on half-rations and then even third-rations, with nearly every man going hungry for a time.

Black refugees from nearby plantations flocked to the troops as they boarded the trains bound for Memphis. A witness recalled, “Their terror of being left behind made them swarm over their passenger and freight cars, clinging to every available space and even crouching on the roofs. The trains were moved very slowly and with the utmost caution, but even so the exposure of these people–men, women, and children–was indescribable.”

As the Federals marched back through Holly Springs, they moved through the smoldering fires left by Van Dorn’s Confederates and noted the many houses and “fine, large public and business buildings” that had been destroyed.

Meanwhile, Van Dorn’s troopers headed north and attacked a Federal garrison at Davis’ Mill, near the Tennessee border. Unlike Murphy, this Federal commander repelled the assault and then refused Van Dorn’s demand to surrender.

Van Dorn abandoned efforts to take the place and instead continued on to wreck track on the Mississippi Central and the Memphis & Charleston railroads. He sustained 52 casualties (22 killed and 30 wounded), while the Federals lost just three. The Confederates entered Tennessee, circled Middleburg, and approached Bolivar before they rode through Saulsbury on their way back to their starting point at Grenada. They returned to Pemberton’s main lines on the 28th.

Van Dorn’s troopers had covered 500 miles in two weeks and successfully destroyed Grant’s reserve of food and supplies, which thwarted Federal plans to advance on Vicksburg. Moreover, Van Dorn regained a portion of his reputation that had been damaged by his defeat at Corinth in October. Federal cavalry led by Colonel Benjamin Grierson rode hard but failed to stop the Confederates after they destroyed Holly Springs.


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