• michellebennington

Remembering the Simpsonville Massacre

Updated: Dec 28, 2021

In April, on one of our many trips to Louisville for my husband’s medical concerns, the headstones and American flag on the side of the road caught my eye because it seemed like such an odd spot for a cemetery. We pulled over to find a small cemetery dating back to the Civil War.


When I read the placards, I was astounded by the story of the fallen Civil War era soldiers who didn’t die in a famous battle. Rather, they died in a conflict with Confederate guerillas. Further, their story remained largely unknown until 2006. I took a few pictures of the headstones to show and honor the names of the fallen.


With Memorial Day coming up, I feel like this is a good time to remember the fallen Civil War soldiers from Company E of the 5th United States Colored Cavalry whose remains are tucked away in a small cemetery on the side of a road in rural Shelby County.

The 5th United States Colored Cavalry was a regiment of the United States Army during the American Civil War; it was one of the more notable black fighting units and was organized in Kentucky in October 1864, after its first two battles. It was commanded by Colonel James Brisbin until February 1865, when he took over the 6th US Colored Cavalry. His executive officer, Louis Henry Carpenter, commanded the regiment until March 20, 1866.


The regiment was composed of ex-slaves, freedmen and slaves who had escaped to Union lines. They fought in the following battles and engagements in 1864:

2 October - Saltville, Virginia - Battle of Saltville I

21 October - Harrodsburg, Kentucky (engagement)

12 December - Hopkinsville, Kentucky – (engagement)

13 December - Kingsport, Tennessee (flanking movement & skirmishing)

17–18 December 1864, Marion, Virginia - Battle of Marion

20–21 December - Saltville, Virginia - Battle of Saltville II


Then on January 25, 1865, a unit of the 5th USCC was ambushed in Simpsonville, Kentucky in what is now known as the “Simpsonville Massacre.” It’s a harrowing story of the brutality and horrors of war.


About 80 members of Company E under the leadership of 2nd Lieutenant Augustus Flint were transporting about 900 head of Federal cattle from Camp Nelson to a stock market in Louisville. Naturally, that many cattle would draw attention.


On January 24th the detachment camped near Shelbyville close to Bullskin Creek. The owner of the land allowed the troops to put the cattle in a fenced lot and the soldiers pitched tents to shelter for the night.


Confederate guerillas were quick to spot the cattle and set about planning an ambush. They sent a scout (name unknown, perhaps this is Henry Magruder mentioned later?) to pull down some of the fence rails and release some of the cattle. This gave him an opportunity to pose as a farmhand to get close to the troops and gather information about how poorly organized they were, the weapons at their disposal, and to get a feel for the leadership. The scout asked to speak to the leader and he informed 2LT Flint of the loose cattle. Flint asked the spy what could be done about it. The spy, sensing his opportunity, asked how many men Flint had at his disposal to help round up the cattle. Flint divulged that he had almost 100 men and nearly 1,000 cattle. The spy recommended a solution and said he’d be happy to help, but he didn’t have proper shoes for working in the snow. Flint loaned the spy his own boots. The spy then moved through the camp to rouse the troops.This resulted in tiring out the men who had to corral cattle in the dark. The spy rushed back to his camp to relate the information he’d gathered.

The next morning, January 25, 1865, was freezing, near zero, and the ground was blanketed with snow. 2LT Flint borrowed boots from the farmer where they’d stayed the night then woke the troops early to cover as much distance as possible before dark. The men were assigned mostly to the front and rear of the spread-out herd of cattle. About 41 men were bringing up the rear. Since it was cold, and no danger was expected, the Flint didn't enforce much discipline and allowed the troops to straggle along. Worse, Flint himself often dropped out of the march to warm his nearly frozen feet since the boots he'd borrowed weren't equipped for marching in the snow.


As the soldiers and cattle moved through Simpsonville, Flint stopped in a store to warm his feet and shop for new boots. The rear guard of the detachment was just out of sight when 15 guerrillas rode into town. Some say they were led by ruthless Confederate Henry C. Magruder; some say Captain Dick Taylor led the ambush.


One of the placards on the site of the massacre claims Taylor led the charge. The placard claims that when the guerillas approached a citizen ran into the store shouting, “Here comes Taylor and his guerillas!” It’s possible the citizen was mistaken because other sources claim Magruder led the ambush. It could be that Taylor was the head of a unit in which Magruder served. But that’s speculation. Since I’ve seen more evidence pointing to Magruder, I’ll go with him as the gang leader because he was a well-known guerilla from Bullitt County, Kentucky who regularly located other escaped Confederates and led them in raids against Union military targets south of Louisville.


Either way, Flint lost all interest in boots, ran out the back of the store, and hid under the storeroom until the guerillas passed. The guerillas terrorized the store’s customers and robbed them and the store of about $1200 in money and goods before turning to ambush the cattle herd.


The guerillas soon caught up to the herd’s rear guard since they were only about half a mile out of town. The guerillas had superior fire power, firing 6-shot revolvers, and some of them had more than one revolver.


Panic ensued. The cattle stampeded, startled horses turned over the supply wagon full of tents and rations. Some men died before they could unsling their muskets; others were shot down as they tried to surrender. Some died while they tried to fire muskets that failed due to fouled powder. Only two of the 41 men escaped unharmed: One fell face down in the snow and played dead; the other hid under the overturned wagon bed. The guerillas made short work of the rear guard, seized all the weapons and ammunition from the dead and wounded troops, and returned to Simpsonville within half an hour.

At this point Flint, who had cowered while his men died, left his hiding spot, jumped on his horse and fled to Louisville.


A group of citizens led by Captain Richard George waited until they were certain the guerillas were gone then set out for the scene of the massacre.


The frozen ground and glaring white snow were stained red with blood. 35 dead and wounded bodies were stretched out on and near the road. Four more were later found, dead of wounds or exposure. The men of Simpsonville took twenty wounded men back to town, eight of the men so severely wounded they were not expected to live. Four of those men later died of their wounds. The citizens cared for the soldiers until ambulances arrived a few days later to carry them to Louisville. A total of six men died on the way to Louisville.


The Confederate perpetrators were never charged or convicted for their part in the massacre. However, Henry Magruder was brought to trial for other murders. He was convicted as a spy and terrorist, and then hanged in Louisville on October 20, 1865, at the age of 21.


In 2006, Jerry Miller, a member of the Shelby County Historical Society, learned about the event when he was conducting genealogy research. He found a diary kept by one of ancestors that described the event. Miller said, “I’ve lived in this area 50 years, and I’d never heard of this, I’m a Civil War buff, I couldn’t believe it.”


A memorial marker commemorating the ambush and murder of US Colored Troops was unveiled in 2009.



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