Centralia Massacre ( Missouri ) The Centralia Massacre was an incident during the American Civil War in which twenty - four unarmed Union soldiers were captured and executed at Centralia , Missouri on September 27 , 1864 by the pro - Confederate guerrilla leader William T . Anderson . Future outlaw Jesse James was among the guerrillas . In the ensuing Battle of Centralia , a large detachment of Union mounted infantry attempted to intercept Anderson , but nearly all of them were killed in combat . Background . In the fall of 1864 , the Confederates , faced with a rapidly deteriorating position , launched an invasion of northern Missouri . It was led by General Sterling Price and his Missouri State Guard . The object was to influence the 1864 presidential election by capturing St . Louis and the state capital at Jefferson City . As part of his strategy , Price encouraged guerrilla warfare , especially the disruption of the railroads . " Bloody Bill " Anderson and his guerrilla company were among those who took part . On September 23 , 1864 , Anderson engaged in a skirmish in Boone County , Missouri , seven miles east of Rocheport . His men managed to kill eleven Federal soldiers and three black civilian teamsters . The Federals responded the next day by shooting six of Anderson ' s men who were captured at a home in Rocheport . That same day , September 24 , Anderson attacked the pro - Union town of Fayette , losing thirteen killed and more than thirty wounded . Only one Union soldier had been killed and two wounded . The Centralia Massacre . At 9 : 00 a . m . on September 27 , Anderson with about 80 guerrillas , some dressed in stolen Union Army uniforms , moved into Centralia to cut the North Missouri Railroad . The guerrillas looted the town and reportedly drank whiskey from stolen boots . Anderson blocked the rail line , and the engineer of an approaching train failed to realize it until too late , since the men he saw were wearing blue uniforms . The guerrillas swarmed over the train . The 125 passengers were divided between civilians and soldiers . A total of 23 Union soldiers were aboard , all on leave after the Battle of Atlanta and heading to their homes in northwest Missouri or southwest Iowa . The Union soldiers were ordered at gunpoint to strip off their uniforms . Anderson called for an officer . Sergeant Thomas Goodman bravely stepped forward , expecting to be shot and the rest spared . Instead , Anderson ' s men ignored Goodman and began shooting the others . The bodies were then maimed and scalped . The guerrillas then set fire to the train and sent it running down the tracks toward Sturgeon , Missouri . They torched the depot and rode away from the town . Sergeant Goodman was taken prisoner on Anderson ' s orders , with the plan that he would be exchanged later for one of Anderson ' s own men held prisoner by Federal forces . Goodman spent ten days in the captivity of the guerrillas before escaping as they prepared to cross the Missouri River near Rocheport . Battle of Centralia . At about 3 : 00 p . m . , Union Major A . V . E . Johnston , with 155 men of the newly formed 39th Missouri Infantry Regiment ( Mounted ) , rode into Centralia . The townspeople warned him that Anderson had at least 80 well - armed men , but Johnston nevertheless led his men in pursuit . The Union soldiers soon encountered the guerrillas , and Johnston decided to fight them on foot . He ordered his men to dismount and form a line of battle ( location : ) . He then reportedly called out a challenge . Anderson ' s men replied by making a mounted charge . Armed with muzzle loading Enfield rifles , the Federal recruits were no match for the guerrillas with their revolvers . Johnston ' s first volley killed several guerrillas , but then his men were overrun . Most were shot down as they attempted to flee . According to Frank James , his younger brother Jesse fired the shot that killed Major Johnston . Of the 155 Union soldiers , 123 were killed during the battle .