Hugh Judson Kilpatrick was born in Deckertown, New Jersey in 1836. Even though he only attended school through the primary grades, he was still accepted to the United States Military Academy in 1856. Kilpatrick graduated from the academy in 1861, as the Civil War began. Kilpatrick volunteered for the United States infantry as a captain, and at Big Bethel, Virginia, he was the first regular Union officer wounded in the war.
After recovering from his injury, Kilpatrick joined the 2nd New York Cavalry in September 1861. In late June 1863, Kilpatrick engaged Confederate General J.E.B. Stuart’s cavalry in many small skirmishes before the Battle of Gettysburg. At the time, Stuart’s force was scouting for General Robert E. Lee’s army.
During the second day of the Battle of Gettysburg (July 2, 1863), Kilpatrick’s Cavalry clashed with General Wade Hampton’s Cavalry. Kilpatrick, known for being an over-dramatic glory seeker, claimed he had battled both Hampton and Stuart and that he whipped the Confederates. On the final day of the battle (July 3), Kilpatrick led an assault on the rear of Lee’s infantry. Kilpatrick continuously charged the heavily fortified Confederate position and suffered heavy losses. After the Battle of Gettysburg, Kilpatrick earned the nickname “Kill-cavalry” for his reckless command actions and for needlessly endangering the lives of men in his command.
In the fall of 1863, Kilpatrick’s cavalry skirmished with the Confederate cavalry. On multiple occasions the Confederates seemed to have surrounded Kilpatrick, but each time the general was able to escape. At Brandy Station, Kilpatrick was surrounded but escaped after a lengthy battle. Near Buckland Mills, Kilpatrick followed Stuart’s force into a trap. After a firefight covering five miles, known as the Buckland Races, he escaped. However, several hundred Union cavalry were captured.
In February 1864, Kilpatrick led about 4000 cavalry in a raid into Virginia. Kilpatrick attempted to liberate Union soldiers from a Confederate prison and rode within five miles of Richmond. However, Hampton surprise attacked Kilpatrick, and the Richmond raid failed. Union officials questioned Kilpatrick’s intelligence and judgment and one Union officer called him “a frothy braggart without brains.”
In spring of 1864, Kilpatrick was reassigned to Major General William Tecumseh Sherman’s army in Georgia. Kilpatrick led a cavalry charge outside Resaca, Georgia and was shot in the thigh, but he succeeded in forcing the Confederates to retreat. Before the Battle of Atlanta, Kilpatrick was tasked with destroying Confederate rail and supply lines. He had limited success due to heavy rains, but when he reported back to Sherman, he claimed the operation was an overwhelming success. Sherman recognized Kilpatrick’s foolishness and tendency to exaggerate yet said: “I know Kilpatrick is a hell of a damned fool, but I want just that sort of man to command my cavalry on this expedition.” On November 15, 1864 when Sherman took Atlanta, Kilpatrick rode at the front of the line.
On the March to the Sea and the Carolinas Campaign, Kilpatrick was notorious for the path of destruction left in his wake. Kilpatrick confiscated any supplies found and burned everything else. Kilpatrick’s cavalry led the march into North Carolina toward Fayetteville and skirmished with Hampton on numerous small occasions. On March 9, 1865, Kilpatrick narrowly avoided capture after Matthew C. Butler’s division of Hampton’s Cavalry surprised and captured Union riders. On March 10, 1865, after forgetting to post lookouts, Hampton, Butler, and Joseph Wheeler attacked Kilpatrick’s camp. The following battle was known as the Battle of Monroe’s Crossroads or Kilpatrick’s Shirttail Skedaddle. Kilpatrick narrowly escaped. Still wearing his nightclothes, he misdirected a group of Confederates by claiming General Kilpatrick was escaping on a horse. The general then regrouped, rallied his forces, and counterattacked. Kilpatrick was able to turn the battle around preventing total defeat. The battle delayed the Union advance to Fayetteville and provided the Confederates enough time to retreat. After the Battle of Monroe’s Crossroads, Kilpatrick was cautious and stayed close to Sherman’s infantry.
Kilpatrick’s Cavalry engaged General Hardee and Wheeler at the Battle of Averasboro on March 15 and March 16, 1865. Kilpatrick was successful at forcing a Confederate retreat but suffered numerous casualties. At the Battle of Bentonville, Kilpatrick’s poor reconnaissance provided Sherman with false information regarding the location and concentration of the Confederates. On the morning of March 19, the beginning of the Battle of Bentonville, Kilpatrick told Sherman that General Joseph Johnston was concentrating his forces at Raleigh. Not realizing the entirety of the Confederate army was at Bentonville, only the left wing of Sherman’s army, commanded by General Henry W. Slocum, engaged the Confederates on the first day. The Union army survived because of an exemplary performance by General James D. Morgan’s division and poor command decisions by Confederate General Braxton Bragg. Kilpatrick was involved in the battle on the following days and eventually the Confederates retreated. With the road open, Sherman took Goldsboro. The misinformation at the Battle of Bentonville and the near disaster at Monroe’s Crossroads made Sherman request the transfer of Major General Philip H. Sheridan to head the cavalry in North Carolina, but Grant felt Sheridan was too valuable in Virginia. Therefore, Kilpatrick remained in command.
After Bentonville, Kilpatrick engaged the Confederate cavalry on multiple occasions on the march to Raleigh, North Carolina. Kilpatrick was the Union officer responsible for the Union’s delay of the dispatch sent by Governor Zebulon Baird Vance to Sherman regarding the surrender of Raleigh. As a result, Vance and most of the Confederate legislature in Raleigh evacuated before Sherman’s response reached the city. When Sherman entered Raleigh on April 13, 1865, Kilpatrick was at the head of the division. Later on April 13, Kilpatrick engaged General Wheeler’s Cavalry at Morrisville and captured three train cars full of Confederate supplies. Sherman then gave Kilpatrick the order to hold advancing and fighting unless Johnston refused to surrender.
Serving as Sherman’s escort, Kilpatrick was present at the Confederate Surrender at Bennett’s Place on April 17, 18, and 26. Kilpatrick did not trust Johnston and believed that the Confederate General would attempt to escape. In dispatches sent to Sherman before the surrender meeting, Kilpatrick wrote, “I have no confidence in the word of a rebel, no matter what his position. He is but a traitor at best.” Sherman, however, believed in Johnston’s sincerity and dismissed Kilpatrick’s concerns. On April 18, 1865, Sherman and Johnston agreed to a ceasefire thus ending hostilities. The politicians in Washington rejected the agreement, and Sherman and Johnston met once again on April 26 and reached an agreement officially surrendering the Confederate Army.
After the war, Kilpatrick was involved in politics. He was appointed twice as the United States Minister to Chile (1865-1868, 1881), and he unsuccessfully ran for the United States House of Representatives in New Jersey in 1880. In Chile he married a wealthy Chilean woman. He died in Santiago in 1881 shortly after arriving for his second appointment as the minister to Chile.