December 20, 1862 – Major General Earl Van Dorn led a Confederate cavalry raid that temporarily stopped Major General Ulysses S. Grant’s Federal drive on Vicksburg.
The Confederates could not match Grant’s numerical superiority in Mississippi, so they had to rely on attacking his lines of communication and supply. As such, Van Dorn led 3,500 Confederate cavalry troopers out of Grenada on a mission to destroy Holly Springs, Grant’s principal supply base and the largest Federal depot west of the Alleghenies.
Van Dorn headed northeast through Pontotoc, where Federal cavalry spotted his troopers but did not relay the news to Grant for a 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.
Grant had been busy trying to suppress Brigadier General Nathan Bedford Forrest’s raids in western Tennessee, but now he had Van Dorn to deal with as well. He notified Colonel Robert C. Murphy, commanding the 1,500-man Federal garrison at Holly Springs, to be on alert for approaching Confederates. Other Federal commands along the Mississippi Central Railroad line received the same warning.
On the night of the 19th, Van Dorn arrived 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 preoccupied with planning a ball for the following night. Van Dorn split his forces so they would advance on Holly Springs along two different roads.
The Confederates attacked the unsuspecting Federals the next day, sending most of them fleeing in panic. Major John J. Mudd’s 2nd Illinois Cavalry tried making 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.
Van Dorn captured nearly the entire garrison, including Colonel Murphy, and destroyed supplies worth $1.5 million according to Van Dorn, or $400,000 according to Grant. These included enormous amounts of commissary, medical, and ordnance supplies for the Federals. Grant’s wife Julia, who had been staying at Holly Springs, narrowly escaped capture when she received a message from her husband to come see him at Oxford; she left just before the raid started.
Murphy reported after being paroled, “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.” 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 reported that Murphy, who had almost been court-martialed for abandoning supplies during the Battle of Iuka, “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, along with Forrest’s raids to the north, forced Grant to halt 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 expecting Grant to reinforce him. The northern press soon began revisiting charges of Grant’s incompetence for failing to adequately defend his supply base.
The next day, Grant began pulling his troops out of Oxford and returning to Memphis. The Federals lived off the land as they withdrew, prompting Grant to note that he was “amazed at the quantity of supplies the country afforded. It showed that we could have subsisted off the country for two months… This taught me a lesson.”
Meanwhile, Van Dorn’s troopers headed north and attacked a Federal garrison at Davis’ Mill, near the Tennessee border. The Federals repelled the assault and then refused Van Dorn’s demand to surrender. Van Dorn abandoned efforts to take the place, instead continuing on to wreck rails on the Mississippi Central. He sustained 52 casualties (22 killed and 30 wounded), while the Federals lost just three.
The Confederates continued riding and wrecking rails on both the Mississippi Central and the Memphis & Charleston railroads. They entered Tennessee, circling Middleburg and approaching Bolivar before moving through Saulsbury on their way back to their starting point at Grenada.
Van Dorn’s troopers covered 500 miles in two weeks and successfully destroyed Grant’s reserve of food and supplies, which thwarted his 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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