On this day in 1862, Confederate General Earl Van Dorn thwarts Union General Ulysses S. Grant's first attempt to capture Vicksburg, Mississippi, when Van Dorn attacks Grant's supplies at Holly Springs, Mississippi.
Grant planned a two-pronged attack on the last Confederate stronghold on the Mississippi River. He would take a force from western Tennessee to approach Vicksburg from the interior of Mississippi. Meanwhile, Union General William T. Sherman would lead an army down the Mississippi River for an attack from the north. Grant said, "We can go as far as supplies can go."
The plan started on a good note for the Yankees when Grant's army pushed aside Confederates in northern Mississippi. In response, Confederate cavalry colonel John Griffith suggested attacking Grant's supply line at Holly Springs, and recommended Van Dorn for the mission. Up to that point, Van Dorn had done little to build his reputation. He lost the Battle of Pea Ridge in Arkansas and the Battle of Corinth, Mississippi, earlier in 1862, and was known for his drunkenness and tendency to cavort with prostitutes.
Van Dorn gathered three cavalry brigades and left Grenada, Mississippi, on December 17. On December 20, his forces fell on the Union supply depot at Holly Springs, driving the Yankee defenders away and capturing materials. What could not be carried was destroyed. Van Dorn remained in the area a few more days, cutting rail and telegraph lines, before fleeing in the face of pursuing Union cavalry. The Confederates rode 500 miles in two weeks, returning on December 28 after successfully disrupting Grant's campaign. The raid was the highlight of Van Dorn's military career. He was murdered five months later by the husband of a woman with whom he was having an affair.