The Gifted Psychopath: Civil War’s “Bloody Bill” Anderson By: Will Dabbs, MD


William T. “Bloody Bill” Anderson was quite the gifted psychopath. The deadliest Confederate guerilla leader of the American Civil War, Anderson led his ruthless mob of cutthroats on a reign of terror along the rugged Kansas–Missouri border and killed hundreds along the way. The path Bloody Bill took from a well-behaved, respectful child to an inveterate butcher and rapist is a study in human depravity.

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The Tale of “Bloody Bill” Anderson

Anderson was indeed, by all accounts, a decent kid. He had two brothers and three sisters. His father supported slavery but did not own slaves. In 1860 Anderson’s mother was struck by lightning and killed.

In his late teens, Anderson killed his first man, a Native American he claimed was trying to rob him. As he came of age, William and his brother Ellis supported themselves by stealing horses. His moral compass already a bit askew, all the young William Anderson needed was some kind of catalyst to push him over the edge. In May of 1862, a Union-sympathizing judge named Baker became that catalyst.

Bloody Bill Anderson died hard and young. He was 23 years old when felled by Yankee gunfire.

William’s father heard of Judge Baker’s allegation that his family harbored Confederate fugitives, armed himself, and traveled to Baker’s courthouse in Council Grove. Baker shot and killed the elder Mr. Anderson in the ensuing confrontation, claiming self-defense. When Judge Baker was not charged for the killing, young William hatched a plan.

Bill and his brother Jim returned to Council Grove three months later and, by means of subterfuge, lured Judge Baker and his brother-in-law into a local store. When the judge realized what was afoot, the two men retreated into the basement of the store. Bill and Jim burned the structure to the ground, killing them both.

The Big Time

Bill Anderson then just went feral. He rode with William Quantrill and attracted a robust following of disaffected Southern sympathizers called Bushwhackers. Together they robbed and killed with wanton abandon, fastidiously protecting women—at least at first—but ruthlessly gunning down Union troops and sympathizers at every opportunity. They were remarkably successful. Along the way, Frank and Jesse James fell in with his crew.

Frank and Jesse James rode with Bloody Bill Anderson during the Civil War.

Union Brigadier General Thomas Ewing was directed to bring Anderson to task, something easier said than done. Bill’s sisters Josephine and Mary frequently traveled to Kansas City to purchase ammunition for Bill and his troops.

During one outing, Ewing had the women arrested and placed in a flimsy makeshift stockade. The building collapsed, killing Josephine and four of her companions. This event transformed Bill Anderson from a soldier into a psychopath.

Anderson began carrying a silken cord with him everywhere he went. Each time he personally killed a Union soldier, he tied a fresh knot in the cord. At the time of his death, the cord had 53 knots. Anderson decorated his saddle with the scalps of his Union victims.

Gifted Tactican

In addition to a certain familiarity with killing, Bill Anderson was a legitimately gifted tactician. His forte was luring Union forces into a canalized area using a small contingent of his troops as bait.

He would post his mounted forces in the tree lines or behind terrain features until enemy units entered his kill zone. Anderson then used his superior tactics and high-volume weapons to overwhelm the Union forces. He seldom left more than a token number alive.

Anderson’s “Bloody Bill” moniker was well deserved. In September of 1864, Anderson and his men moved on Centralia, Missouri, looting, robbing and killing as they went. While in the town, they seized a passing passenger train carrying 23 unarmed off-duty Union soldiers.

Anderson ordered one Yankee non-commissioned officer (NCO) held for a potential prisoner swap and had the rest shot on the spot. Anderson’s men killed one German civilian on the train for wearing a blue shirt.

Such stuff happened not infrequently. Bloody Bill once personally killed 14 Union soldiers in a single day. In the face of such brutality, his Union adversaries responded in kind, frequently riding under a black banner that told all comers to expect no mercy. Blood flowed freely on all sides.

Things came to a head in October of 1864. Anderson and his men burned Rocheport, Missouri to the ground and moved on Glasgow. Though nominally under Confederate command, Anderson opted instead to ignore his orders and pursue opportunities to loot.

While in Glasgow, Anderson sought an audience with a well-heeled Unionist. The notorious Bushwhacker raped his 13-year-old servant girl and trampled the man under his horse. The Yankee sympathizer ultimately succumbed to his injuries in 1866.

Loaded for Bear

Anderson’s troops were reported to carry four revolvers, each between their mounts and their persons. When he was killed, Anderson was packing six. Realizing that his foes were armed with accurate but slow-firing muzzleloading muskets, Anderson would typically charge enemy formations and absorb the first ragged volley. He and his men would then tear through the blue ranks, cutting down the Union troops with large volumes of close-range pistol fire.

While there were dozens of different types of handguns in common use during the American Civil War, two were the most common. Colonel Colt’s 1851 and 1860 Model revolvers armed soldiers on both sides. The Remington New Model Army was not quite so popular but also saw widespread use. Each gun has an interesting story.

Colt Revolver

Samuel Colt did not invent the revolver—he optimized it. Under Colonel Sam’s guidance and marketing, his eponymous wheelguns filled holsters across the country and throughout the world.

The 1851 Colt Navy.

Colt operated manufacturing facilities that churned out his pistols in both Connecticut and in London, England. While the Model 1851 and Model 1860 differed slightly in some details, the designs were conceptually quite similar. Both guns were evolutionary developments of the previous 1849 pocket pistol.

The 1851 Colt Navy featured a positively retained pivoting ramrod underneath the barrel to assist with reloading chores and a characteristic open architecture around the cylinder.

While this offered relatively easy cleaning and ready access to the nipples, the gun was notorious for dropping its spent percussion caps down into the action. Under the wrong circumstances, this can lock the mechanism up tight. I myself have had this happen several times in the decades I have been shooting these old pistols.

These Colt handguns typically fired either .36– or .44-caliber balls and were constructed of both steel and brass components. Colt produced 215,000 copies domestically and another 42,000 in England. The Griswold Gunnison was a copy of the 1851 Navy built in Georgia for Confederate use.

The 1851 Colt Navy was a popular sidearm on both sides of the Mason-Dixon line including with people like Bloody Bill Anderson.

Remington Revolver

These days the Remington New Model Army revolver is frequently called the Model 1858. This is a reference to the September 14, 1858, patent date engraved on the revolver. I have read, however, that this term is a modern contrivance. The guns did not see wide-scale production until 1861. Some people have claimed that the Model 1858 reference arose in the Navy Arms marketing literature during the 1960s.

Regardless, the Remington New Model Army is an altogether more rugged design than that of the Colt. The steel frame on the Remington gun features a topstrap that wraps up and over the cylinder, offering a great deal more strength.

To remove the cylinder on the Remington New Model Army, one need only drop the ramrod and pull the cylinder pin.

The design of the Remington pistol also allows the cylinder to be removed more readily than that of the Colt competitor. As loading cap-and-ball revolvers is quite laborious, it was an accepted practice to carry separate loaded cylinders that could be exchanged after partially disassembling the guns. This process is easier on the Remington weapon.

Eliphalet Remington approached the U.S. Army in late 1861 and offered to sell his guns to the government for $15 apiece—this at a time when Colt was getting $25. Regardless, the Union Army was still slow to embrace the weapon. However, by the end of its production run, the New Model Army had seen ten variants and more than 230,000 copies produced.

Solid, heavy and reliable, the Remington New Model Army was indeed a serious soldier’s pistol like Bloody Bill Anderson would carry.

The End Of The Story

On October 27, 1864, Bloody Bill Anderson fell for his own ruse. Lt. Col. Samuel Cox and a contingent of 150 Union troops located Anderson’s encampment and lured him and his men into a narrow lane bounded by thick woods.

Assuming these Yankees would break as easily as those he had previously dispatched, Anderson charged their formation without hesitation. A heavy volley of accurate Union fire dropped several of the Bushwhackers, taking the spirit out of their charge.

Anderson and two others continued on and tore through the Union lines. As he wheeled his mount around for another pass, a second volley raked the three rampaging Confederates. Bloody Bill Anderson caught two rounds to the head and died where he fell. He was 23 years old.

Force Of Nature

These Colt and Remington pistols served much the same way as the German P08 Parabellum and Walther P38 9mm handguns throughout World War II. There were never enough to go around, and production of both weapons was always inadequate. So it was with these two vintage revolvers.

I recently found myself in the market for an original 1851 Colt. I located a copy for sale online at a decent price. However, on closer inspection, it seemed that the barrel rode at a slightly upward cant relative to the frame. Such was the sensitivity of the design. I passed on the gun as a result.

While the Colt is undeniably the prettier of the two pistols, the Remington is much more rugged. In the hands of men like Bloody Bill Anderson, these six-shot wheelguns were indeed a force of nature.

Dixie Gun Works ( can get you copies of these two classic Civil War wheelguns in kit form at a good price.

This article was originally published in the Guns of the Old West Winter 2022 issue. Subscription is available in print and digital editions at Or call 1-800-284-5668, or email

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