Bloody Bill Anderson: The Civil War Guerrilla Who Created Jesse James

0:00 In September 1864, a Confederate guerrilla named Bloody Bill Anderson stopped a train in Centralia, Missouri, lined up 22 unarmed Union soldiers and had them executed one by one. Then he scouped them. An hour later, he ambushed a Union company and killed 123 more men in less than 20 minutes. The next to him, through it all, was a 16 year old kid named Jesse James, learning every lesson. This is the story of the man who created the American Outlaw. So here's what you need to understand about William T. Anderson.

1:02 He didn't start out as a monster. He started out as a horse thief, which honestly feels almost quaint compared to what he became. Born around 1840 in Kentucky, his family moved to Kansas in 1857, right into the middle of what people were already calling "bleeding Kansas". Pro slavery and anti-slavery settlers were literally murdering each other over whether Kansas would be a free state. The Anderson family was pro-southern in a free state territory, which immediately made them targets. William and his brother Jim started stealing horses, running them across state lines, making decent money at it. They were a small time frontier criminals.

1:43 Then everything changed on May 12, 1862. A former judge named AI Baker shot and killed Anderson's father over political disputes. William and Jim had to run to Missouri because they were already wanted for horse theft. Their sisters followed. Once in Missouri, the brothers joined the Confederate Bushwackers. These weren't regular soldiers. These were guerrillas who raided anti-slavery settlements, killed civilians, and disappeared before anyone could catch them. But Anderson had unfinished business with Judge Baker. On July 3, 1862, Anderson came back to Kansas with his gang. They lured Baker out of his house, shot him, kicked him down into a cellar, and then they did something that tells you everything about what Anderson was becoming.

2:29 They rolled a heavy barrel over the cellar door, trapped him inside, and they set the house on fire, and made sure Baker burned alive. They stole his horses and rode off bragging about it. That's when William Anderson stopped being a thief and became something else entirely. By 1863, the union was trying to stop the Bushwackers. These guerrillas were using their families for intelligence and supplies. So union officers started rounding up female relatives of suspected Confederate guerrillas and throwing them in makeshift prisons in Kansas City. On August 14, 1863, a three-story brick building being used as a prison collapsed.

3:10 Several women died. Several more were badly injured. Among them were William Anderson's sisters. Josephine Anderson was killed. Mary Anderson was seriously injured. The official cause has never been definitively established, but there were immediate rumors that drunken union guards had been bragging in a tavern that they deliberately removed support columns in the cellar. Whether that's true or not, Anderson believed it, and that belief transformed him completely. People who knew him said he became unhinged. Whatever restraint he'd been operating under disappeared. His grief and rage fused into a single purpose. The union had killed his sister.

3:51 The union would pay in blood. Eight days after the building collapsed, William Quantrell led about 400 Confederate raiders into Lawrence, Kansas, and killed between 160 and 190 men and boys. They burned 185 buildings. Anderson was right there in the middle of it. The Lawrence massacre was retaliation for the prison collapse. The raiders spared the women and children, which tells you this was a calculated, gendered act of revenge. The union response was General Order No. 11, which forced thousands of civilians to evacuate four Missouri counties. The idea was to deprive the gril of their support base.

4:32 Instead, it created a logistical paradise. All those abandoned farms meant unlimited access to livestock, feed, and food. The union accidentally made it easier for Anderson to survive and grow stronger. By spring 1864, Anderson had split from Quantrell and formed his own guerilla company, about 80 men who operated like a death squad. They wore union uniforms to get close to the targets. They showed no mercy. Anderson personally adopted a policy of giving no quarter, torturing prisoners and cutting off ears. His violence wasn't random. In one raid, he targeted a wealthy union sympathizer who had freed his slaves.

5:13 Anderson beat the man, raped his 12 or 13 year old black servant, and then trampled the man with a horse. The victim died from his injuries two years later. This was terrorism, racial hatred, and personal cruelty all wrapped into one package. Bill Anderson was tall, bearded, dressed with style, but people who met him talked about his eyes. They said it looked like burning coals. He earned the nickname "Bloody Bill" through sheer relentless savagery. His men decorated their saddles with scouts taken from the dead union soldiers. And right there in the middle was this 16 year old named Jesse James, who joined Anderson's band in 1864, along with his older brother Frank.

5:57 Jesse's immediate mentor was Anderson's chief lieutenant, a small, ruthless killer named Archie Clement. People called Clement Bill Anderson's scalper and head devil. He taught young Jesse James that murdering unarmed men was not only acceptable, it was expected. Jesse James didn't become an outlaw despite his civil war experience. He became an outlaw because of it. He learned it from the best, and Bloody Bill Anderson was the best at what he did. Throughout the summer of 1864, Anderson's force rampaged across Central Missouri. They ambushed union patrols. They burned railway property. All of it was building towards September 27, 1864, in a small town called Centrelia.

6:41 Anderson and 6280 of his bushwackers rode into town, looted it, robbed a stagecoach, and drank all the liquor they could find. Then they did something that had never been done before in the Civil War. They captured a passenger train belonging to the North Missouri Railroad. First train captured by Confederate guerrillas in the entire war. When that train were 22-24 unarmed union soldiers, probably recruits or men heading home, Anderson berated them, selected one sergeant named Thomas Goodman for a potential prisoner exchange, and then had his men execute the rest in a line, one by one. Then they mutilated and scouted the bodies.

7:23 Goodman, the only survivor, later called it the most monstrous in human atrocity he'd ever witnessed. He bills men, set the train on fire, and sent the burning engine down the tracks toward the next town. But the real disaster was still coming. The smoke from the burning train drew a union major named Andrew Johnson and 147 men from the 39th Missouri Volunteer Infantry. These were raw recruits, inexperienced, riding on farming horses and mules. They were armed with slow, muzzle-loading infield rifles. When Johnson challenged Anderson outside of Centralia, Anderson's guerrillas responded with a mounted charge. It was a slaughter.

8:05 The union line collapsed immediately. Anderson's men had rapid fire revolvers. They knew how to fight on horseback. They were experienced killers facing green troops. Out of 147 union soldiers, 123 were killed. Anderson's force only lost three men. James later claimed that his younger brother Jesse fired that shot that killed Major Johnson. The Centralia massacre demonstrated that Anderson was more than a sadistic killer. He was a cunning, lethal commander who knew exactly how to exploit his enemy's weaknesses. The Centralia massacre made bloody bill the most hunted man on the border. One month later, on October 26, 1864, Union forces lured Anderson's band into an ambush near Albany and Ray County, Missouri.

8:54 Bloody Bill Anderson was killed in the fight. His men desperately tried to recover his body, losing up to 10 more men in the attempt, but the union held the corpse. Union militia took Anderson's body to Richmond, Missouri. A doctor named Richard B. Keiss photographed him. In the 10 type, Anderson is propped up wearing his guerrilla shirt with a pistol in his hand and a union soldier holding his head upright for clear identification. Then they decapitated him. Officially, they put his head on a spiked telegraph pole and dragged his body through the streets before burying it in an unmarked grave. The union wanted to prove bloody bill was dead. They wanted to terrorize his followers.

9:36 Instead, they created a martyr. That public mutilation gave Anderson surviving men a visceral reason to keep fighting. After Anderson died, Archie Clement took command of the guerrilla band. Jesse and Frank James stayed with him. They refused to recognize the end of the Civil War. They kept fighting, even after the Confederate surrender in 1865. In 1869, the James Younger gang robbed a bank in Gallatin, Missouri. During the robbery, Jesse James shot and killed the cashier, John Sheetz. But the robbery wasn't about money. Jesse believed Sheetz was Samuel P. Cox. The man he thought had killed Bloody Bill Anderson.

10:17 He was wrong about the identity, but the motive was clear. The first major crime of the James Younger gang was revenge for Anderson's death. Bloody Bill Anderson was killed at 24 years old after a two-year reign of terror. Union forces tried to erase him by mutilating his corpse and burying him without a marker. But in 1967, over a century later, a sympathizer convinced the United States government to officially mark Anderson's grave with a headstone that highlighted his service to the Confederacy. Anderson's real legacy is Jesse James. The systematic murder of unarmed men, the refusal to show mercy, the belief that violence is the only legitimate response to grievance.

11:00 That was Bloody Bill's lesson. Jesse James learned it at 16 years old, and he carried it for the rest of his life. The American outlaw tradition didn't start with bankruptries and train heists. It started with a guerrilla commander who decorated his saddle with scouts and taught a teenager that murder was business. That's the story of Bloody Bill Anderson, the butcher of Centrelia, the man who created Jesse James, the ghost that haunted the American frontier long after his head came off that telegraph pole. Thanks for listening to 10 Minute Murder, Bingeable True Crime Stories.

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