Bloody Bill Anderson

Frothing at the mouth, growl-screaming a fearsome Rebel Yell, his long, wild, unruly dark hair falling out from under his flamboyant wide-brimmed hat, this psychotic madman raced for the center of the Union line, unleashing a storm of bullets from a pair of .44-caliber revolvers.  Bearing down on the inexperienced Union militiamen as they fumbled to reload their rifles with shaky hands, Anderson discharged twelve rounds, dropped his pistols, drew two more revolvers, and continued firing, his macabre collection of human scalps and a silk cord with 57 knots tied in it – one for each man he's killed – serving as frightening proof of his skill and deadliness in combat.

Cox's militiamen finished reloading just as Bloody Bill and his small cohort reached their lines.  Their second volley of fire, unleashed at point-blank range, riddled the charging men with hundreds of bullets.  Anderson was dead before he hit the ground.

There are a lot of characters in the Civil War that can be looked at objectively, as men taken out of their time of history, fighting for what they believed in even though they may have had their own personal faults.

Bloody Bill was none of these things.  He was a bad, bad man, any way you wanna look at it.

The most feared outlaw of the Civil War, Bloody Bill Anderson was born in Missouri, sometime around 1838-ish.  His dad was a haberdasher who moved the family north across the border to Kansas during a magical time known as "Bleeding Kansas", which sounds about as fun as it actually was.  Basically, Kansas was going to become a state, so since the U.S. government couldn't decide if it should be a slave state or a free state they decided to let the state's residents vote on it.  Naturally, this meant that everybody in the state who had an opinion on the subject went around killing everyone who disagreed with them.  Destruction, disorder, arson, and street fights were a daily occurrence.  Crime was out of control.  Death was a daily event.

Bloody Bill fit right in.

Getting his start robbing liquor stores and stealing horses owned by anti-slavery activists, things got personal for Bill in 1862, when Bill's father was killed with a shotgun.  Apparently, Bill's dad got pissed off when a neighbor boy refused to marry his daughter, so pops broke into the guys house with a shotgun.  The neighbor boy got the drop on Bill's dad and shot him point-blank in the chest, killing him instantly.  Bill, whose mother had already died from being struck by lightning a few years earlier, responded by going to the neighbor's house, killing him and his brother-in-law, burning down their family liquor store, fleeing to Missouri, and forming a band of 30 outlaws intent on killing every pro-Union person they could catch.

Anderson eventually hooked up with the most infamous of the Missouri guerillas – Captain William Clarke Quantrill.  Quantrill, an Ohio schoolteacher turned murderous raider, was fighting a private, unauthorized war for the Confederacy in Missouri, attacking Union troops, trains, and supply depots across Missouri to disrupt their war operations.  Anderson was made a Lieutenant, going on several raids against Federal forts and positions, but, by his own account, he wasn't even all that interested in the Southern cause or any of that stuff – he just enjoyed robbing, killing, and looting.  A 19th-century rebel without a cause riding the high plains in search of booty and mayhem.

He changed his tune in August 1863, when Union General Thomas Ewing, Jr., eager to smash Quantrill's group of outlaws, issued arrest warrants for every woman in Missouri that he believed had provided aid to Quantrill's Raiders.  Anderson's three sisters – aged 10, 14, and 16 – were thrown into an old prison in Kansas City.  On August 14, 1863, the prison building collapsed, killing Anderson's sister Josephine and crippling his sister Mary.

Now it was personal.

A week later, Bloody Bill Anderson and Quantrill's Raiders rode into the pro-Union town of Lawrence, Kansas, looted the stores, pillaged, set fire to every building, and killed 150 unarmed men and boys (in Quantrill's words, "every man big enough to hold a gun") in cold blood, with Anderson personally accounting for 14 murders.  A few months after that the Raiders, who included infamous future outlaws Frank James, Jesse James, and Cole Younger, took Fort Blair from the Union – and Anderson saw to it that every man in the fort was killed, right down to the Army band.

Pursued by thousands of Union troops seeking retribution for these heinous crimes, Quantrill's men headed to Sherman, Texas, where they could chill until things cooled down.  Even though Sherman was a pro-Confederate town, this didn't stop Bloody Bill from killing a couple guys and robbing some of the stores, pausing his mayhem only long enough to get married to a local saloon girl.  While they were in Texas, Quantrill of all people accused Bloody Bill of being too out-of-control psychotic, so Bill told him to get lost and broke off from Quantrill's unit.  Frank and Jesse James went with him.

On June 11, 1864, local residents in Northern Missouri found the bodies of 12 Union soldiers who had been killed and scalped, their bodies left to rot.  Bloody Bill was back.

For the next four months, Bloody Bill Anderson's gang of guerillas, never more than about 50 men wearing stolen Union uniforms, went on a rampage across Kansas and Missouri, killing and raiding Union forces, cutting telegraph wires, burning rail bridges, and leaving behind a wake of mutilated corpses. 

The most brutal of these raids took place in Centralia, Missouri, on September 27, 1864.  Anderson's crew, in town hoping to get word from Confederate General Sterling Price about an upcoming Rebel expedition to Missouri (Price turned Anderson's offer for help down, saying that he didn't want to work with psychos), ended up getting drunk, setting fire to the city, and robbing half the stores.  When the noon passenger train arrived, Anderson's men boarded it, robbed everyone, and forced 24 uniformed Union soldiers to get off the train.  Bloody Bill stripped off their jackets, lined them up, and shot them in the head one by one.  A few hours after this, a militia unit under Major A.V.E. Johnson arrived on the scene, responding to the disturbance with a force of 120 men from the 39th Missouri Infantry, but they rode straight into a trap – Anderson and his men ambushed the inexperienced troops, rode them down, killed anyone who tried to surrender, then executed all the wounded and decapitated their corpses. 

It was at this point that Samuel P. Cox was called in to deal with Anderson.  He ambushed Bloody Bill outside Albany, Missouri, catching him in his own trap and gunning Anderson down as he fearlessly charged straight into a vastly-superior force, surrender never being an option for such a violent man.  His body was displayed publicly in Richmond, Missouri for two days.  On the third day, pro-Unionists pulled his body down, decapitate it, put his head on a pike outside the city, and dragged his body through the streets behind a horse.  It was eventually recovered and buried just outside town.  Much to the mayor's chagrin, the local townspeople came out and put flowers on it every night.

"If I cared for my life, I'd have lost it long ago. Wanting to lose it, I can't throw it away."
- Bloody Bill Anderson