Union Captain Judson Kilpatrick

 | Civil War Times  | 0 comments  |  Print This Post  |  Email This Post

On July 5, following the Union victory, Kilpatrick was ordered to harass Lee’s retreat. He attacked the Rebels’ wagon trains that night, but Stuart soon appeared and drove Kilpatrick back to Boonsboro, Maryland, where he stayed for more than a week. On July 13, as the last of the Confederates forded the Potomac into Virginia, Kilpatrick rode to the river. Confederate Major General Henry Heth’s 4,000 men were waiting their turn to cross when Kilpatrick sent two squadrons–just 40 troopers–to charge them. ‘As any competent cavalry officer would foretell,’ one of Buford’s officers later remarked, ‘they were instantly scattered and destroyed.’

Kilpatrick claimed in his report that he had captured a brigade of infantry, two cannon, two caissons, and a large number of small arms. He sent the New York Times a copy of this twisted account, and the editors published his lies. When Lee saw the article, he was so incensed that he wrote a letter of protest to Meade. The Union commander looked to Kilpatrick for an explanation, but he was gone. His wife, who had visited him nine months ago in the Old Capitol Prison, had given birth, and Kilpatrick had gone to see his new son.

Returning to duty on August 5, Kilpatrick found Annie Jones, a teenage harlot, visiting his headquarters at Falmouth, Virginia. The new father immediately talked her into sharing his tent. This was not his first indiscretion. His entourage included several other women, and the word around camp was that their duties went far beyond cooking his meals. Two weeks later, Jones moved in with Custer. Outraged, Kilpatrick had her arrested as a spy and shipped off to the Old Capitol Prison.

In October 1863, Lee advanced north toward Meade. The two armies met at Bristoe Station, Virginia, on the 14th, and after a sharp clash, the Federals emerged victorious. The Rebels retreated and Kilpatrick was sent after them. On the 18th he found Stuart protecting the tail of the Confederate column near Buckland.

Stuart laid a trap for his overeager foe. When the Union horsemen charged, he fell back, luring Kilpatrick after him. Meanwhile Confederate Major General Fitzhugh Lee brought his troopers up from the south to attack the Yankee rear. When Lee arrived, Stuart whirled around and attacked Kilpatrick. Caught in a pincer, the trapped Federals scattered. ‘The rout of the enemy at Buckland,’ Stuart gloated, ‘was the most signal and complete…any cavalry…suffered during the war.’

Kilpatrick was humiliated. His career again seemed ruined, and should have been. At this low point, word came that his wife had died. He rushed east that November for her funeral, came back to his bivouac, and then returned to New York in January for another funeral; his baby son, too, had died.

Such crushing personal losses compounded Kilpatrick’s concerns for his future, and made him ready to try something desperate. He quickly devised a scheme to ride into the Rebel capital and free Yankees confined at the Libby and Belle Island Prisons. Anxious for approval of his plan, he went over the heads of his superiors and appealed directly to Lincoln. Pleasonton and Meade were irritated that Kilpatrick had bypassed them, but Lincoln’s approval forced them to support the raid. Kilpatrick would lead 3,500 riders to Richmond from the north, while Colonel Ulric Dahlgren would take 500 troopers over the James River and approach the Confederate capital from below.

The columns crossed the Rapidan River at dusk on February 28, 1864. On March 1, the raiders reached the outskirts of Richmond. ‘We were so close that we could…count the spires on the churches,’ one recalled.

Up ahead, a handful of old men and young boys manned a bulwark, the only obstacle to Kilpatrick’s riding into Richmond and carrying out his mission. He stopped and listened for the rattle of rifles that would signal Dahlgren’s charge from the south, but heard nothing. He waited for two hours in the icy rain; meanwhile, fear built up in his mind. He thought he saw reinforcements filing into the fort in front of him. When a locomotive whistle blew to his rear, he suspected that an enemy force was arriving to attack him from the north. Kilpatrick suddenly realized he had made no provisions for transporting the prisoners he hoped to liberate. The captives would have to walk about 50 miles to the Union lines.

Kilpatrick lost his nerve. He ordered his men to retire east toward the Chickahominy River. At about 5:00 p.m., Kilpatrick’s riders crossed the river and set up camp near Mechanicsville. ‘Snow was falling,’ a trooper wrote, ‘and it was very dark.’

As he shivered in the cold, Kilpatrick suddenly decided to mount his raid after all. While he waited safely in camp, two small groups would dash into the Confederate capital. One would free the prisoners; the other would kidnap President Jefferson Davis. But just as the men were saddling their horses, a fuss erupted in the Union rear. Wade Hampton, who had been pursuing Kilpatrick for 48 hours, had finally caught up and was attacking. Hampton had just 300 Confederate horsemen with him, but Kilpatrick was not counting noses. He called his 3,500 troopers to mount, and fled east toward Benjamin Butler’s camp at New Kent Court House.

Kilpatrick reached Butler’s lines on March 4, but Dahlgren was not so lucky. His attempt to ride into Richmond had been thwarted, and as he galloped east to rejoin the rest of the Yankee force, he had encountered some home guards, who shot and killed him. Confederate authorities claimed that orders to kill President Davis were found in his pockets. The Union officially claimed that Rebels must have forged the orders.

Meade took the bungled raid as an opportunity to demote Kilpatrick to brigade command and assigned him to serve under his replacement, Brigadier General James H. Wilson. Kilpatrick wanted no part of this purgatory. He requested a transfer to the West, where Major General William T. Sherman was just replacing Lieutenant General Ulysses S. Grant as chief of the Military Division of Mississippi. Sherman welcomed him. ‘I know that he is a hell of a damned fool,’ Sherman remarked, ‘but that is just the sort of man I want for my cavalry.’ Kilpatrick’s luck continued to hold. On April 16, 1864, he set out for Tennessee.

Sherman was moving southeast out of Chattanooga to confront General Joseph E. Johnston’s Confederates near Dalton, Georgia. Kilpatrick was given a division of cavalry in the Army of the Tennessee, which was maneuvering through the mountains below Dalton to flank the Rebel stronghold. As the army neared the town, Kilpatrick’s force advanced to scout the field. A Southern sharpshooter saw Kilpatrick coming and shot him in the thigh.

While Kilpatrick recuperated at West Point, Sherman and Johnston fought each other steadily toward the outskirts of Atlanta. They were facing each other outside the city on July 23 when Kilpatrick rejoined his command. Sherman wanted the city’s southern supply lines cut off and asked whether Kilpatrick could do it. ‘It’s not only possible,’ Kilpatrick boasted, ‘but comparatively easy.’

Kilpatrick’s division set out on August 18. After a spectacular four-day ride, Kilpatrick reported back to Sherman that his men had ripped up the tracks at Jonesboro and Lovejoy’s Station. He was still talking when a locomotive blew its whistle as it pulled into the city. The Rebels had undone Kilpatrick’s work in just 24 hours.

On August 25, Sherman marched south. His infantry cut the enemy’s supply line once and for all, and on the night of September 2, Confederate General John Bell Hood abandoned the city.

Sherman’s forces soon started on a march from Atlanta toward the Atlantic coast. Along the way, Federal infantry destroyed railroads and burned buildings that had military value, but generally left the civilian populace alone. Kilpatrick’s troopers, however, pillaged one plantation after another. ‘They drove off cows, sheep, and hogs,’ one owner said, ‘took every bushel of corn and fodder, oats and wheat, and burned the house.’ At another farm, Kilpatrick rounded up horses to replace his own worn-out mounts. His men gathered about 500 more animals than they needed, so Kilpatrick ordered the surplus killed. One by one the poor beasts were bashed on the head. The farm owner watched in horror as a mountain of dead horses arose in his yard. ‘My God,’ he gasped, knowing that he could never bury so many animals. ‘I’ll have to move.’

On November 28, Kilpatrick was attacked at Waynesboro by Confederate cavalry under Major General Joseph Wheeler. Rather than stand and fight, Kilpatrick fled west, bringing with him a black prostitute.

Kilpatrick assumed he had outrun Wheeler, so he stopped for the night outside Rock Springs. Just before dawn, Wheeler attacked his camp. Kilpatrick raced outside in his underwear, jumped onto a stray mount, and fled for his life. He left behind his uniform, a gold-hilted sword, two ivory handled pistols, his best horse, and, of course, his mistress.

For the rest of the campaign, Kilpatrick stayed close to the infantry. Sherman’s columns arrived at Savannah, on the coast; by December 21 the port city was in Sherman’s hands. For the six weeks that the Federals stayed in Savannah, they respected private property. Not so Kilpatrick. Encamped to the south near Midway Church in Liberty County, he sent his men to ravage the countryside, foraging daily and visiting the same plantations again and again. ‘There was no use to put things in order,’ one owner stated. ‘Every separate gang ransacked the house afresh.’

Kilpatrick himself was busy with a new mistress, an Oriental laundress named Molly. When Sherman headed north into South Carolina, Molly moved with Kilpatrick. She was pregnant. ‘He has done me so,’ she insisted, ‘and I will stick to him and make him take care of the baby for it is his.’

The cavalry entered Barnwell, South Carolina, on February 6, and burned most of its public buildings. Kilpatrick established his headquarters in a home called ‘Banksia Hall.’ That evening, Kilpatrick held a ‘Nero’ ball for the ladies of the nearby plantations. As they danced to music played by Kilpatrick’s band, his troopers set fire to their homes. ‘It was the bitterest satire I ever witnessed,’ one of Kilpatrick’s officers professed, ‘and justly stained the reputation of Kilpatrick.’

On February 10, Kilpatrick started toward Aiken. He had learned Wheeler’s cavalry was there, and he planned to attack him. As he approached the village, Kilpatrick spotted enemy riders. He immediately ordered a charge that sent his cavalry into yet another carefully planned ambush. The surprised Federals turned and fled for Barnwell and the protection of the Union infantry. Kilpatrick could not make up his mind how to report the incident. ‘[We were] furiously attacked by Wheeler’s entire command,’ he said in one account, ‘and fell back to fight gallantly.’ In a letter to Sherman, however, he claimed the action was’simply a reconnaissance.’

Sherman’s troops entered Columbia on February 17. Before the day ended, the city was ablaze, though it remains unclear who started the fire. As the army paused for a rest, Kilpatrick found himself yet another female companion, a beautiful young woman named Marie Boozer who had been forced to flee her home. ‘She was,’ one admirer remembered, ‘the most beautiful piece of flesh and blood I ever beheld.’ Kilpatrick played the role of savior, abandoning his military responsibilities to ride with Boozer in her elegant carriage. It was in that carriage, with his head nestled in Boozer’s lap, that Kilpatrick entered North Carolina on March 3, 1865.

As Sherman headed for Goldsboro, Kilpatrick rode north of the Union columns, protecting them from enemy assaults. On the evening of March 9, after failing to intercept a Rebel cavalry command led by Wade Hampton, Kilpatrick took refuge in a cabin that lay hidden in a pine forest. He was in bed with Boozer when Hampton paid him a ‘morning call.’

Hearing gunfire outside, Kilpatrick jumped up and opened the door. Rebels were everywhere. In a shocking repeat of his embarrassing flight at Rock Springs, the scantily clad general leaped onto the nearest horse and raced from the scene. His men later recaptured the camp and rescued Boozer.

Kilpatrick rode into Fayetteville on March 11, where he was soon joined by the rest of Sherman’s army. The Yankees rested there for four days, during which time Boozer left Kilpatrick. She sailed down the Cape Fear River to the coast and married a Union officer in Wilmington, using him as her ticket to the North and safety.

On March 19, Major General Henry Slocum’s wing of Sherman’s army, including Kilpatrick’s cavalry, was attacked as it passed Bentonville, North Carolina. As the fight began, Kilpatrick raced up to Slocum. ‘My cavalry is on the field,’ he proclaimed, ‘ready and willing to participate in the battle.’ Slocum scoffed at Kilpatrick’s offer, and sent him to the rear.

Soon, however, there was an outlet for Kilpatrick’s brand of fighting. Johnston, who had been restored to command of the Confederate Army of Tennessee, was retreating to the west, trying to link up with Lee, who had evacuated Richmond on April 1. Sherman’s army took off after Johnston on April 10. ‘You may act boldly and even rashly now,’ Sherman instructed Kilpatrick, who led the Federal advance. ‘This is the time to strike quick and hard.’

Kilpatrick hurried through Raleigh and on to Morrisville, where he was greeted by a Southern cavalryman waving a white flag. Lee had surrendered, the messenger reported, and Johnston felt it was time to lay down his arms too. Kilpatrick sent a courier off to notify Sherman, but when the reply came, Kilpatrick was no longer around to pass it on to Johnston. He had ridden to Durham Station to be with yet another mistress.

The latest object of Kilpatrick’s attention wore an army uniform, and Kilpatrick called her Charley. If the masculine name and garb were meant to be a disguise, the ruse was not working. ‘I know she were a woman,’ a witness related, ‘for I seen her making water. She always let down her pantaloons and squatted.’ Another observer related, ‘General Kilpatrick was very fond of Charley…. He used to lie pretty close to her in bed.’ Poor Molly, meanwhile, heavy with child, was still a laundress, cleaning Kilpatrick’s and Charley’s soiled clothes.

Sherman’s message for Johnston finally found Kilpatrick, who in turn arranged a meeting at the home of James Bennett, halfway between Raleigh and Hillsboro. Sherman and Johnston met on April 17. An agreement was reached, but officials in Washington rejected the pact because it included civil terms over which Sherman had no authority. A second meeting on April 27 resulted in a simple military capitulation.

As a reward for his service with Sherman, Kilpatrick was promoted to major general and given command of troops occupying North Carolina. He soon left his post, however, to go home and campaign for the Republican nomination in New Jersey’s gubernatorial race. Kilpatrick was on to the second step in his life’s plan.

Things went awry fast. Another candidate, Marcus Ward, carried the convention, so Kilpatrick settled for the next best thing: he would work to get Ward elected, in exchange for a Federal government post. In November, Ward won the governor’s seat. Secretary of State William H. Seward kept the Republican Party’s promise and named Kilpatrick ambassador to Chile.

Ever the paramour, Kilpatrick met a young married woman, a Mrs. Williams, during his long voyage to South America. He soon induced her to accompany him to Chile. He remained in Valparaiso, the country’s principal port, for a few days before presenting his credentials. During this period, he was entertained by the Americans living in the city. Williams attended these receptions, where Kilpatrick presented her as his wife.

If Kilpatrick expected to make a clean break with Williams, he was mistaken. On March 12, 1866, he went to Santiago, leaving her in Valparaiso. He expected her to sail quietly for the United States. Instead, she took to the streets as a prostitute. The scandal filtered back to the states in vague terms. One newspaper referred to ‘an American diplomat serving in a South American country.’ Seward cabled the ambassador. ‘It is supposed,’ he said, ‘the one [mentioned] may be yourself. The president deems you should deny the charges.’

Fortunately for Kilpatrick, public interest in his affair ebbed quickly and he was able to keep his job. He proved a surprisingly good ambassador–especially after he met, wooed, and married Louisa Valdivieso, cousin of a future president of Chile and niece of an archbishop of the Catholic Church.

In 1869, Kilpatrick’s affair with Williams returned to haunt him. New President Ulysses S. Grant did not care for such behavior, and he recalled Kilpatrick from his post. When Kilpatrick made another run for the New Jersey governorship that fall, the party convention rejected him for the same reason.

Kilpatrick returned home to Deckertown to begin a career as a lecturer and farmer. He toured the country in the winter, delivering speeches on the Civil War, and the rest of the year tended the fields of his family’s homestead. Nevertheless, Kilpatrick still entertained thoughts of becoming president, and as a stepping stone, in 1880 he ran for a seat in the U.S. House of Representatives. He lost, but President James Garfield restored him to his old post in Chile.

Shortly after arriving in Santiago on July 20, 1881, Kilpatrick was struck down by Bright’s disease, a deterioration of the kidneys. In December, just when his strength seemed to be returning, he suffered a relapse and died. He was just 45 years old.

During the Civil War, the egotistical, reckless, and immoral Kilpatrick had proven himself a poor commander. Yet in 1875, the Comte de Paris described him as ‘one of the most brilliant cavalry officers in the late war.’ Kilpatrick built his career on boasts, lies, and imaginary victories. ‘His memory and imagination,’ Major General Oliver Otis Howard once noted, ‘were often in conflict.’

He had been fortunate to wrangle his way into the Union cavalry early in the war. Then, Federal cavalry commanders were so desperate for fighters that they overlooked Kilpatrick’s failings. His willingness to fight put him among a new breed of more capable Yankee cavalrymen such as Farnsworth, Custer, Merritt, and Gregg. But his poor performance made him stand out in ridiculous contrast to these competent officers.

This article was written by Samuel J. Martin and originally published in the February 2000 issue of Civil War Times Magazine.

For more great articles, be sure to subscribe to Civil War Times magazine today!

Help HistoryNet by bookmarking to

Tags: Civil War Times, Historical Figures

You can follow any responses to this entry through the RSS 2.0 feed. You can leave a comment, or trackback from your own site.