By Corey R. Orr

The War of the Rebellion in Missouri was full of colorful characters, but among the most infamous is certainly William T. Anderson. Anderson, who would become known throughout the course of his career as “Bloody Bill,” earned a nearly legendary reputation in spite of his monstrous deeds. His character is described in the 1885 History of Montgomery County, Missouri: “He is known by his deeds, and all of his deeds were evil. Of all the foul, black and bloody monsters the Civil War produced, Bill Anderson stands out pre-eminently the foulest,

the blackest, and the bloodiest. The only redeeming or palliating feature in his character was his suspected insanity by those who knew him best.”1  This man, made infamous for his guerrilla actions along the western border, participation in the sacking of Lawrence, Kansas, and his brutal executions at Centralia, Missouri, was a widely feared guerrilla leader in Missouri

and Kansas. Bill Anderson and his band of Confederate partisans, while mostly operating in the western region of the state, would venture into central Missouri on a mission to sabotage the North Missouri Railroad at New Florence and High Hill after an extended attack on Danville, Montgomery County. In many works on Anderson, the actions in Montgomery County are usually only recognized in a sentence or two. Some historians have offered slightly more substantial accounts in their larger biographies and histories, but there have been problems

and missing elements to the story. This work seeks to offer a detailed account of the raids in

Montgomery county, but first, a brief look at some of Anderson’s notable deeds is necessary.

            Bill Anderson, while he attracted some unsavory characters, did seem to possess a certain degree of natural charisma. He was a young man when the war erupted, born in 1839, and primarily grew up in Huntsville, Missouri. Hamp Watts, a young man who served with Anderson, describes his physical appearance as having “coal-black hair and eyes, sallow complexion, high cheek bone, mouth broad with thin lips, Grecian nose, thin mustache and shaggy chin whiskers.”2  He was apparently popular enough to form a small band of guerrillas early in the war, and would eventually form a sizable independent command by 1864. Anderson’s early career was not greatly distinguished from other rebel partisans along the western border. He began with horse theft, bushwhacking, and robbery of predominantly Unionist targets, although not exclusively. Anderson was motivated to support the Southern cause, but also targeted southerners if he saw benefit.  

            A persistent theme in Bill Anderson’s brutal story is revenge. The first instance of Anderson’s brand of vengeance occurred on the evening of July 3, 1862. Arthur I. Baker, a judge in Rock Creek, Kansas, had previously shot the Andersons’ father, William C. Anderson, in an armed dispute over allegations of horse theft involving the Anderson boys and their friends. The senior Anderson later arrived at the Baker’s home armed with a shotgun, but the judge was able to get the drop on him as the situation became dangerous. Then, a few weeks later, the boys had returned for revenge. Bill Anderson, his brother Jim, their friend Lee Griffin, and a couple of other men lured Judge Baker and his sixteen year old brother-in-law, George Segur, from his home and toward his store in Rock Creek. They ambushed the judge as he neared his store, wounding him twice, but not before Baker had drawn his own revolver and wounded Jim Anderson with a shot grazing his thigh. Baker and his young companion, both wounded, fled into the cellar of their store. The gang of bushwhackers then piled barrels on top

1 History of Montgomery County, Missouri 1885 (hereafter referred to as HMC 1885), (St. Louis: National Historical Company 1885; reprint undated) p. 646

2 Hamp Watts, The Babe of the Company, (unknown publisher) p. 7

of the cellar door and burned the store down, killing the poor men trapped inside.3 That was the brand of cruelty that Anderson would bring with him to Missouri as he fled Kansas. That summer, Anderson would operate his own band of brigands, mostly taking advantage of the chaos of the war. Eventually, he gained the attention of William Clarke Quantrill, another guerrilla leader building notoriety, and was integrated into his command.

Anderson, like many other southern guerrillas, sought out a variety of targets aside from

Union men and sympathizers. Black soldiers and workers, along with German immigrants,

were killed whenever possible. Bill Anderson’s first appearance in The Ocial Record of the War of the Rebellion was after the murder of 5 German immigrants during a brief raid in LaFayette county in July of 1863.4 He also hung a known southern sympathizer because he was German. The victim, Solomon Baum, had initially mistaken Anderson’s group for federal militia because they wore looted uniforms. As they revealed their true allegiance, he attempted to walk back his initial claim that he was a Union man. “Oh, string him up; God damn his little soul, he’s a Dutchman anyway.” was Anderson’s response to his pleas.5

The next tragic event in Bill Anderson’s life was formative of the remainder of his career. As the Union authorities began to crack down on the rampant problem of southern partisan bands terrorizing western Missouri and eastern Kansas, Brigadier General Thomas Ewing Jr. implemented a plan to sever the supply lines from sympathetic citizens to rebel partisans. Much like modern insurgents, guerrilla bands relied heavily on sympathetic citizens and family members for supplies and temporary camps when such things couldn’t be readily stolen or acquired. These dark networks sometimes included recruiters, secret camp locations, and

even passwords.6  Ewing’s orders caused several women related to guerrillas to be arrested and imprisoned in Kansas City. Among the captives were Bill Anderson’s sisters Mary Ellen, Josephine, and Janie, sixteen, fourteen, and ten years old. One of Quantrill’s scouts, John McCorkle, also had a sister named Charity Kerr held there.

This jail house was apparently in rather poor condition and sadly collapsed on August

13, 1863. Josephine Anderson was killed, along with Charity Kerr and some of the other inmates. Mary Ellen survived, but was permanently crippled. Little Janie survived with both legs broken and many other minor injuries. Whether or not the incident was intentional on the part

of the Union authorities, the guerrillas considered it to be so.7

Bill Anderson was overcome with murderous revenge after the collapse of the jail. Historian John N. Edwards aptly described his rage: “wherever danger was blackest, from the

3 Emporia News, July 12. 1862

Also: Larry Wood, Other Noted Guerrillas of the Civil War in Missouri, (Joplin, Missouri: Hickory

Press 2015) p. 141

4 The War of the Rebellion: A Compilation of the Ocial Records of the Union and Confederate Armies (hereafter referred to as simply OR), Series I, Vol. 22, Part II (Washington: Government Printing Office 1888) p. 377-378

5 History of Carroll County, Missouri, (St. Louis: Missouri Historical Company 1881) p. 344

Also: Donald R. Hale, They Called Him Bloody Bill, (Clinton, Missouri: The Printery 1975) p. 17

6 Joseph A. Mudd, With Porter in North Missouri, (Washington D.C.: The National Publishing

Company 1909) p. 28

7 Albert Castel and Tom Goodrich, Bloody Bill Anderson, (Mechanicsburg, Pennsylvania: Stackpole Books 1998) p. 27

midst of it Anderson’s cheering voice was heard... leading the press and raging as a wild beast, Anderson fought as a man possessed of a devil.”8

The tragedy that befell his sisters was a major factor that caused Bill Anderson to agree upon exacting revenge upon Kansas Unionists with William Clarke Quantrill. Quantrill had organized one of the most daring and impressive raids of the Civil War. Their target would be Lawrence, Kansas, home of the jayhawker leader Jim Lane and a general Union hub. Lane was a hated enemy of rebel partisans, often utilizing similar guerrilla tactics and almost as

merciless. Lawrence was a long distance for these guerrillas to venture across the border. They would have to raid the town and flee back to Missouri before a sizable force of soldiers could intercept them. Good judgement, quick action, and lust for blood and loot carried the rebel raiders across the prairie and into unsuspecting Lawrence on August 21, 1863.

Much has been written about the raid on Lawrence. In brief, over 400 partisans rode into town around 5 o’ clock AM. When they left at about 9 o’ clock AM, well over 150 boys and men lay dead in a town that was devastated and burning. Anderson himself was said to have been responsible for 14 deaths, personally. He was reported to have said to one Lawrence woman: “I’m here for revenge, and I have got it.”9  Unfortunately for Missouri, Anderson’s thirst was far from quenched.

Anderson, after a brief journey to Texas with Quantrill and other guerrilla groups in the winter of 1863-1864, had returned to Missouri in the spring of 1864. Anderson had distanced himself from Quantrill and took again to mostly acting independently with his own command, just as he had done before. Anderson had a few guerrilla leaders that were cooperative with him and they often took part in raids together. This time, he commanded many more men than he had earlier in his career. Before, he was simply the head man in a small gang of bushwhackers. The expansion of his command gave Anderson many more options. He raided and killed recklessly and often throughout the summer of 1864. Bill Anderson and his men attacked various towns and homesteads in several counties, ranging farther and attacking more frequently than any other guerrilla leader of the war. He became a known terror, killing

and looting soldiers and civilians alike. As the summer came to an end, Anderson and 80 of his men fell upon the town of Centralia, Missouri on September 27, 1864. That day would bring out the worst in Anderson, his hatred for the Union and it’s soldiers reaching a climax. He wanted them to pay for what happened to his sisters and men in his command since the war began.

He would earn the name “Bloody Bill.”

Anderson and his men rode into town early in the morning and began to rob people indiscriminately. As they began to loot the stores in town, a guerrilla brought into the street a large barrel of whiskey. The rebels began to use stolen tin cups and started drinking heavily. As the morning was nearing its end, a passenger train came into town. The train had around 150 souls aboard. 23 of them were Union soldiers, some of which were on furlough from General Sherman’s army in the deeper south. One of these soldiers, Sergeant Thomas M. Goodman, recalled that the guerrillas, after robbing the civilians on board, burst into the car where the soldiers were waiting.

“Surrender quietly, and you shall be treated as prisoners of war.” One guerrilla commanded.

“We can only surrender, as we are totally unarmed.” Replied one of the poor soldiers.10

8 John N Edwards, Noted Guerrillas, Or, the Warfare of the Border, (St. Louis: Bryan, Brand, & Company 1877) p. 166

9 Albert Castel and Tom Goodrich, Bloody Bill Anderson, (Mechanicsburg, Pennsylvania: Stackpole Books 1998) p. 27-29

The worst was yet to come. The captured soldiers were separated from the civilians as they all unloaded from the train. Anderson was reported to have monologued about his motive for what came next. He mentions the recent scalping of some of his men, which was a disturbing practice that he and his own band performed:

“You Federals have just killed six of my men, scalped them, and left them on the prairie... I will show you that I can kill men with as much skill and rapidity as anybody. From this time on I ask no quarter and give none. Every Federal soldier on whom I put my finger shall die like a dog. If I get into your clutches I expect death. You are all to be killed and sent to hell. That is the way every damned soldier who falls into my hands shall be served.” After some protests from the soldiers, Anderson yelled over them: “I treat you all as one. You are Federals, and Federals scalped my men, and carry their scalps at their saddle bows.”11

The soldiers were ordered to remove their uniforms, leaving them standing in their undergarments or in the nude. As the guerrillas were prepared to gun down these men, Anderson asked: “Boys, have you a sergeant in your ranks?” After a couple moments, Sergeant Goodman stepped forward, fully expecting to be shot on the spot. Rather, he was

whisked away to be put under guard by another bushwhacker. At this time, the guerrillas began pouring fire into the line of unfortunate souls. 22 unarmed men were shot dead. Goodman, appalled at seeing his dear friends and comrades slain, sought to honor their courage in his account of the grim event: “No emotion, no faltering, no entreaty—only the fixed determination to meet cruelty by sublimity, and in the presence of devils, to die like gods!”12

After the massacre, which was among the most heinous atrocities of the entire war in any theater, Anderson and his men finished ravaging the town and returned to camp to tell their fellow rebels in George Todd’s band about their gruesome show at Centralia. The carnage was to be met with force, however.

Major A. V. E. Johnston, leading about 150 men of the 39th Missouri State Militia, reached Centralia shortly after the departure of Anderson and his band. Completely enraged at what he found, Johnston left a small group of his men to protect the town while he and the balance of the force went on to hunt the guerrillas. Johnston marched into a trap as the rebel pickets had noticed his arrival and the guerrillas were able to prepare an ambush. Anderson gave the order to charge as Johnston’s force took the bait. Johnston’s men were able to fire one volley, killing three rebels and wounding ten. That was the end of their resistance as the guerrillas bore down on them. Firing at close range with revolvers and riding down the men attempting to flee, the guerrillas easily won the field. The fleeing Federals led their pursuers back into Centralia, causing the garrison left there to flee as well, fifteen of which did not survive. At this time, a few of the rebels then began diabolically mutilating corpses left on the field. Scalping, beheading, and grotesque jokes were performed with body parts. The first officer to report on the incident after the battle was Lt. Col. Daniel M. Draper of the 9th Cavalry, Missouri State Militia.

This type of activity is sickening to describe, but it is necessary to highlight the descent into madness of some of these men. These actions were some of the most disturbing scenes

of the whole war and are difficult to explain. Simple revenge for the mutilation of their own men is not sufficient considering that previously the main atrocity was scalping. The perversions that occurred at Centralia were far beyond even that reprehensible act. Drunkenness may have contributed, or even the sense that they felt they needed to “one-up” their enemy in postmortem humiliations, but it is possible that for a few of these men, insanity was a growing factor. The life of these guerrillas was hard. They had to endure a lot of pain, misery, and rage over the course of the war. Many of these rebels had suffered personal losses at the hands of

11 St. Joseph Morning Herald, September 30, 1864.

Union soldiers, leading them to deeply hate their enemies and seek vengeance. Despite any rationale they may have used to make sense of their own actions, Centralia was too much for many of the rebels. Perhaps those that indulged in the mutilation had snapped. Whatever their reasons were, these horrible things were an effective terror tactic. Bloody Bill Anderson became one of the most infamous men of the entire war. All told, 123 men of the 39th Missouri State Militia had been killed, including Major Johnston. 22 soldiers from the train of various units were executed, along with three civilians.13

After Centralia, the guerrilla bands split up and tried to lay low. They had made a lot of noise at Centralia and Bloody Bill Anderson was now the most feared and notorious rebel in Missouri. His prisoner, Sergeant Goodman, managed to escape some days later.

After Centralia, there were members of Anderson’s band that were disenchanted with the events that had unfolded, as well as the repulsive activities after their battle with Johnston. It is difficult to determine the full extent of this drop in morale, but Anderson’s effective strength was nearly halved in a short period of time. Two individuals, a father and son by the name of John and James Fridley, were two such men that had abandoned their bushwhacking careers after taking part in the bloodshed at Centralia. On September 30, 1864, they were traveling through Danville, Missouri on their way to St. Charles to stay with family. The two men stayed

at Mrs. Nunnelly’s hotel in Danville, where they gained the attention of Captain George J. Smith of Company D, 49th Missouri Infantry. He arrested the two men and they confessed to having been guerrillas from Howard county and that they were present at Centralia. The captain told the men that he would have to take them into St. Louis. Along the way, at Dryden’s old horse mill just a couple miles west of New Florence, the two men were led into a peach orchard and shot to death.14 Centralia was too recent for these men to be shown a shred of mercy.

Eleven days later, Anderson made his way to Boonville on October 11th to meet with Major General Sterling Price, who was attempting to reconquer Missouri for the Confederacy. Price was disgusted with Anderson and his men, some who had hung scalps from their bridles. These men, repulsive as they could be, were also useful irregular troops. Anderson was recognized as a Captain and was given orders by Price to cause permanent damage to the North Missouri Railroad:

Headquarters Army of Missouri

Boonville, October 11, 1864.

Captain Anderson, with his command, will at once proceed to the north side of the Missouri River and permanently destroy the North Missouri Railroad, going as far east as practicable. He will report his operations at least every two days.

By order of Major-General Price:

Maclean,

Assistant Adjutant-General15

Bill Anderson reported to Price at Boonville with around 100 men, but some left his company left there to join the regular Confederate Army under Brigadier-General Joseph O.

13 OR, Series I, Vol. 41, Part III, (Washington: Government Printing Office 1888) p. 420, 423

Also: OR, Series I, Vol. 41, Part I, (Washington: Government Printing Office 1888) p. 440-441

Also: Centralia Battlefield Memorial; Montgomery County Historical Society, “Search For

Identity of Nine Civil War Soldiers, The Centralia Dead” (unpublished article and discussion)

14 HMC 1885, p. 642-643

15 OR, Series I, Vol. 41, Part IV, (Washington: Government Printing Office 1888) p. 354

Shelby. One of these men, teenager Hamp Watts, seemed eager to leave behind the guerrilla lifestyle.16

Anderson and his band, numbering perhaps half of their original number when they left Boonville, worked their way through Callaway County. They picked up a few recruits along the way, the Berry brothers, at Williamsburg. The Berry’s had previously fought alongside Quantrill earlier in the war. After a brief stay there and gathering information from locals, they made their way along the Boone’s Lick Road toward Danville on the evening of October 14, 1864

Danville, the county seat of Montgomery County at the time, was a target for Anderson for a variety of reasons. The rebels certainly wanted to loot the stores in the village, but it is also possible that Anderson had heard of the execution of the Fridley’s and sought revenge as the men may have departed his company on friendly terms. It is possible the Fridley’s simply never rejoined the command after dispersing after Centralia. Danville was also home to many Union families and had been occupied by Union soldiers of the 81st Ohio infantry regiment earlier in the war.17 One individual, Dr. Samuel J. Moore, who was the President of the Danville

Council of the Union League of America, led a few Danville citizens to face off against Callaway county bushwhackers on the Boone’s Lick Road, managing to retrieve a horse and some of their other possessions on September 12th.18 Jim, Dick, and Ike Berry may have also been seeking revenge for the alleged rape of their sisters by Union men in Danville, contributing another reason for Anderson’s band to stop to raid the village on their way to the railroad.19

Danville was not garrisoned with active Union militia when Anderson arrived. Many militia units had been called up to help repel General Price’s invasion, so only a few civilians were left to protect the village, though several of these men had served time as Union militiamen and had been mustered out of service.20 A few of them were discussing who would take on guard duty near the Watkins & Drury store in town when the band of guerrillas appeared quite suddenly before them in the twilight, between 8 and 9 o’ clock at night. Anderson gave the order to “Fire on them.” The attack had begun. Within moments there were guerrillas all over town. M. A Gilbert and Henry L. Diggs were the first men to be killed in the initial moments.

Anderson’s men began to burn houses and stores. The Watkins & Drury store, which had been temporarily storing the county records until a new courthouse could be built, was destroyed along with the Montgomery county records from 1818 onward. Homes were robbed and torched. Orin A. Gardener’s printing office was destroyed. Sheriff Ira H. Ellis’ home was spared only by his wife’s efforts to put out the fires each of three times it was attempted to be burned. The first Masonic Lodge in Montgomery County, formed at Danville in 1843, lost its records, jewels, and original charter to the raid.21 The Nunnelly hotel was among the few places

16 Hamp Watts, The Babe of the Company, (unknown publisher) p. 26

17 Frederick H. Dyer, A Compendium of the War of the Rebellion, Vol. III (New York: Thomas

Yoseloff, 1959) p. 1534

18 OR, Series I, Vol. 41, Part III, (Washington: Government Printing Office 1888) p. 233-234

19 Ovid Bell, from Missouri Historical Review, January 1930 (Columbia, Missouri: Missouri

Historical Society 1930) p. 290-291

Also: Paul R. Petersen, Quantrill of Missouri: The Making of a Guerrilla Warrior, (Nashville: Cumberland House, 2003) p. 348

20 Missouri Digital Heritage: Soldiers’ Records (s1.sos.mo.gov) The records have service cards for M.A. Gilbert, Benjamin Palmer, Henry L. Diggs, and William C. Ellis.

21 Olive Baker, Life and Influence of Danville and Danville Township, from Missouri Historical

Review, July 1913 (Columbia, Missouri: Missouri Historical Society 1913) p. 219

spared, likely due to their family being known southern sympathizers, Mr. Granville Nunnelly having been murdered by Union soldiers earlier in the war.22

Mr. Benjamin Palmer was shot while standing in his kitchen doorway, but was able to crawl into his yard and cover himself with lumber to hide until two women, Mrs. Hughes and Mrs. Ford, were able to assist him. He was fortunate.

Resistance was light against these guerrillas. Despite several of the men present in town being armed, the village was taken by surprise. Historian John N. Edwards, who is rather sympathetic to the rebel partisans, describes a heated and close battle at Danville, with around

60 militiamen defending the town, but that narrative of organized and effective militia resistance in Danville is pure fantasy.23 While Anderson and his band aimed to “kill all men they get hold of who have been in the U.S. Army,”24  some of the citizens and ex-militiamen did bravely stand

up to the raiders.

Dr. Samuel J. Moore attempted to fight back. He was alerted of the attack by Mr. Johnson, taking his revolver and shotgun outside to confront the raiders. He managed to shoot one rebel, known as Gooley Robinson, off of his horse, mortally wounding him. Moore

heroically exchanged fire with the other nearby guerrillas, fighting courageously to the last. His remains were found near a stable, beaten badly and shot three times.25

The Baker plantation home, still present on the eastern edge of town, was also targeted by Anderson’s men. Sylvester Marion Baker erected the building in 1854. He and his family were a prominent business family and owned slaves. Some legends exist around the home,

one of which includes the cannon ball lodged into the upper portion of the west-facing wall. Legend tells that during a guerrilla raid, a cannon was fired at the house, which has quite thick walls. Another explanation for the cannon ball was that Union forces skirmished with rebels there and fired a cannon into the house. Neither story is likely or supported by substantial evidence. The cannon ball was most likely placed there when old decaying brick was patched and repaired. Guerrilla forces almost never had artillery and it is highly improbable that a skirmish involving any artillery occurred there. Where the ball came from is unknown. It is possible that various troops such as the 81st Ohio Infantry, who had camped there from the winter of 1861 through March 1862, accidentally left a ball lying around while moving to a different post. It is also possible that the ball was acquired or found elsewhere and brought into Danville after the war. According to the application for the structure to be added to the National Register of Historic Places, the house was burned in two rooms, once in the entry hall, the

other in Mrs. Baker’s bedroom. The bedroom was reportedly set afire when a guerrilla burned her bed and clothes. Both rooms were extinguished and the home was saved.26

Interesting scenes unfolded at the Danville Female Academy. The academy was opened in 1853 by Rev. James H. Robinson. If it was not the first institution of its kind west of the Mississippi River, it was certainly among the earliest. While only the chapel remains today, it used to consist of “5 buildings in a semi-circle; first the school building with the recitation rooms, next the Chapel, then the three dormitories with parlors, music rooms and dining halls.

22 HMC 1885 p.618-619

23 John N Edwards, Noted Guerrillas, Or, the Warfare of the Border, (St. Louis: Bryan, Brand, & Company 1877) p. 323-324

24 OR, Series I, Vol. 41, Part I, (Washington: Government Printing Office 1888) p. 888

25 HMC 1885 p. 646-650

26 National Register of Historic Places Application for Baker Plantation Home

The cabins for the negro servants were standing some distance off from the other houses.”27

This description comes from Mrs. Mary Lee Kemper, who published reminiscences from her

mother’s notes, who was present at the academy, though only 9 years old. Her mother was

Mary Robinson, later to marry a Kemper in 1873.

A small group of guerrillas entered the academy grounds during the chaos, with Bill Stuart leading the way. Stuart was another partisan who had at times led his own small command, but had thrown in his lot with Anderson. Stuart and his men pounded on the chapel and dormitory doors, ordering the girls outside. They believed that there were Union soldiers hiding inside and were determined to find them. The girls, many panicking and still in their night gowns, were dragging their trunks with their possessions outside as they realized the men intended to set the school buildings afire. Some of the guerrillas attempted to strike up conversations with the girls who had taken refuge in a nearby wood line, bringing them food and drink they had stolen in the store. A few guerrillas were heard boasting about their actions at Centralia. It is said that some of the girls welcomed the raiders, as they considered themselves to be southern women. One of these girls, Ella Brizandine, was thought to have been too familiar with these rebels and was later arrested on the charge of being a spy. The results of her trial, if any, are not known and it is likely she was released.28

Before the guerrillas could burn any of the school buildings, Mrs. Robinson approached the guerrillas. Initially, she had been hiding her husband’s important papers. Professor Robinson was away in Washington, apparently for his safety considering that he and his family were staunch Unionists. They had even lost a son in the Union army at Vicksburg. One of the guerrillas pointed a revolver at Mrs. Robinson’s chest, demanding keys to the chapel. Then, rebel John T. Hubbard ordered the man to stand down from harming Mrs. Robinson: “Take that pistol from that woman’s breast. Leave these grounds, every one of you!” Mrs. Robinson then approached him and asked for his protection. She revealed who she was and acknowledged that many of her girls were southern and had family in the CSA. Hubbard had apparently attended school under her husband for a brief time before the war. As the girls began to plead with him not to harm her, he silenced them: “Be quiet. Not one of you shall be harmed.” As he turned to leave, some of the girls detained him by holding his reins and not letting him go. It is unclear what they did to truly hold him, so they must have been showing gratitude and appealing to him to stay for their safety. Another woman, who was apparently a secessionist

with a child in Confederate service, came forth to support Mrs. Robinson with an undergarment tied to the end of a pole to act as a flag of truce. The girls also appealed to Hubbard for the safety of Professor Watts, who lived nearby. One of the rebels went to his house, dragged him out and led him to the school. The poor man probably assumed he was to be shot, but was instead protected with the students and Mrs. Robinson.29 After the war, several of the girls would appear at Hubbard’s trial for the events at Danville and were able to assist in his acquittal.30

Another source for events at Danville and around the Female Academy comes from Laura Draper, a young girl of fifteen years who studied music at Danville. Laura’s older sister Eliza had taught at the Danville Female Academy until recently before the raid when she moved to Clarksville. They were both sisters of Lt. Col. Daniel M. Draper, who was the first officer on

27 Mary Lee Kemper, Civil War Reminiscences at Danville Female Academy, from Missouri

Historical Review, Spring 1968 (Columbia, Missouri: Missouri Historical Society 1968) p.

314-315

28 HMC 1885 p. 646-651

29 Mary Lee Kemper, Civil War Reminiscences at Danville Female Academy, from Missouri

Historical Review, Spring 1968 (Columbia, Missouri: Missouri Historical Society 1968) p.

317-320

30 HMC 1885 p. 662

scene after Centralia. Local historian Arthur G. Draper was the great grand nephew of the Draper sisters, and had served as curriculum director for Hermann schools. After the war, Lt. Col. Draper would operate the Star, a “Radical Republican” newspaper in Danville for a couple of short years.31

Laura Draper commented in a letter to her sister about some other details of the raid. She mentioned that while the southern girls were entertaining a few of the rebels on the seminary grounds, Anderson himself paid them a visit. Some of the girls asked him for souvenirs, and he dispensed with his coat buttons from a frock coat taken at Centralia, as well as a lock of his hair. He also traded a knife to one girl in exchange for a kiss. Another, more horrific, detail mentioned was the post-mortem scalping and hanging of Mr. M. A. Gilbert, one of the first men to be shot by the raiders.

The young Draper also reported about one bushwhacker that did not get away. Mr. Johnson, who had warned Dr. Moore about the raid previously, returned to his home to find it in the process of being burned by a guerrilla. He beat the man with his gun and left him in the burning house. His bones were later found in the ashes and ruins of the house.32

Among the other victims that fell to the guerrillas was a young boy of no more than twelve years, Ira Chinn. It was no accident, as the moon was reported to be bright along with the raging fires of many buildings. The monster that shot the boy knew well what he was doing.

As the raiders prepared to leave, they stole a buggy from the widowed Mrs. Powell. They had taken some prisoners, but released a few before leaving. Merrill S. Simons and William C. Ellis were both mounted on horses and rode to the edge of town with Anderson’s trusted lieutenant “Little Archie” Clements. Clements was only 18 years old, but was known to be cruel and diabolical. He asked if Simons had ever been in Union service. Simons had been

a member of Company C, 9th Missouri State Militia and confessed as much. He was shot dead immediately.

From this point, the band of rebels sent their wounded comrade west with a few companions. The rest rode east toward New Florence to make good on their mission to destroy the railroad. They left Danville around 11 o’ clock, riding just a couple miles to New

Florence. The rail depot and two cars were looted and burned. A case of uniforms intended for Captain Kendrick’s militia company at Rhineland were also stolen. After looting a few places, including a store and the post office, the band of rebels moved again eastward into High Hill.

Just a few miles down the Boone’s Lick Road, the guerrillas burned the depot at High Hill and cut the telegraph lines. They also stole weapons and easily transported loot, watches being a favorite. Around $1000 cash was also stolen. They attempted and failed to burn the water storage tank. Anderson and his men robbed the stores of Tom Klise and Frank Craig, as well as Emil Rosenberger’s saddle shop. Mr. Rosenberger was also whipped badly with whips from his own store. A southern sympathizer named Jesse Diggs was also tormented during the brief visit. The guerrillas then ordered Mr. Hance Miller’s wife to begin making them breakfast, and after taking food, loot, and extra horses, the rebel band made ready to leave. Eugene Rosenberger counted over 35 raiders at this point.33

Bloody Bill’s mission to destroy the North Missouri Railroad had failed. The guerrillas considered a couple of burned depots, cut telegraph lines, and burned rail cars to be sufficient. General Price later complained that Anderson and his men failed to go as far as the Perruque Creek bridge east of Warrenton, which was his real desired target.34

31 Ibid. p. 769

32 Draper-McClurg Papers (State Historical Society of Missouri)

Also: Arthur G. Draper, “Dear Sister” Letters from War-Torn Missouri, 1864, from Missouri

Historical Review, Spring 1993 (St. Louis: Missouri Historical Society 1993) p. 52-55

33 HMC 1885 p. 651-652, 717

34 OR, Series I, Vol. 41, Part I, (Washington: Government Printing Office 1888) p. 714

Anderson and his band of marauders decided they’d had enough as the night became morning. They rode back west, turning south to camp in a patch of timber on the farm of Joshua Morris, just off the Hermann Road, which is roughly the route of Highway 19 today. Behind them these men left a small amount of damage in New Florence and High Hill, but total devastation in Danville, where only a few buildings were left unburned. 4 adult men and one child were dead, along with two of the rebel bushwhackers, as the man wounded by Dr. Moore in Danville did not survive his wounds. Danville, a once prominent town in the county, is now but a ghost of its former self. It would never quite recover from the damages of the war.

The carnage was not over, unfortunately. As Anderson and his men made camp, they were being pursued by elements of Col. Canfield’s 67th Enrolled Missouri Militia out of Wellsville. Captain Pew, Lt. McIntyre, and over 50 men, including some Danville citizens, were on the trail of the guerrillas, having been alerted of the raids around 2 o’ clock on the morning of the 15th. As they neared the Morris Farm, they alerted a rebel picket and fired on him. He managed to escape to warn the rest of the camp.

In the camp, the guerrillas began to bring themselves to order, gathering their belongings and what loot they could carry. They had also acquired a few prisoners since capturing some civilians traveling along the Hermann Road. These captives included F. M. Ellis, John Marlow, and Ira Tatum, who were captured on their return from delivering rations to Captain Kendrick’s men in Rhineland. Other prisoners were Christopher Logan and his young son, John Anderson, a boy named William Whitesides, and Mr. Hatton.

Captain Pew and Lt. McIntyre spread their men out, armed primarily with shotguns and revolvers, in an effort to attack the guerrilla camp on a broad front and envelope their east

flank. His plan may have been effective if the guerrillas had planned to stand and fight. Instead, they left much of their loot and their prisoners in the camp, firing over them into the brush at

the approaching militia. They withdrew after firing ineffectively, making a quick escape. Sadly, the militia didn’t quite grasp the entire situation, as they approached the camp cheering and firing through the brush. Only the young Whitesides and F. M. Ellis survived. Mr. Marlow was mortally wounded and perished at home the next day. Some anecdotes from modern locals suggest that Christopher Logan was intentionally executed by the militiamen after the skirmish due to southern sympathies. His son, John Robert Logan, survived. Interestingly, Col. Canfield’s report to Brigadier-General John B. Gray regarding the incident did not mention the slain civilians and even claims that the militia had killed thirteen of the rebels, which is untrue.35

Bloody Bill and his rebels made a hasty retreat back west, eluding pursuing militia along the way. Because of the actions of he and his men, 10 innocent people perished, along with 2 rebels. Anderson and his guerrillas worked their way westward until they arrived at Glasgow, Missouri.

Anderson’s arrival at Glasgow is one of the historical problems with the raid on Danville. There has been disagreement about whether or not Bill Anderson himself was actually present for the raids on Danville, New Florence, and High Hill. There are a few different schools of thought arguing for Anderson’s absence from the Montgomery County raids, including the problem of time needed to travel, Anderson’s morale and willingness to complete the mission, and a claim that Anderson accompanied General J.O. Shelby on his attack on Glasgow.

Anderson’s arrival at Glasgow is linked to the problem due to the time required to travel there from Montgomery county. The earliest that an historian places Anderson at Glasgow would be late in the evening on October 15th,36 meaning that he and his men would have had to ride all morning and all day into the night after their camp was broken up by the Wellsville militia. This is not an impossible feat. These men had freshly stolen horses and were

accustomed to long trips in the saddle. The historian placing Anderson in Glasgow at that time,

35 HMC 1885 p. 653-655

Also: St. Louis Daily Missouri Democrat, Oct. 22, 1864

36 Donald R. Hale, They Called Him Bloody Bill, (Clinton, Missouri: The Printery 1975) p. 72-73

Donald R. Hale, cites William F. Switzler’s History of Missouri, which offers no specific arrival time. Switzler only mentions that Bloody Bill arrived in town sometime after Confederate Brigagier-General J. O. Shelby left Glasgow after capturing it on the 15th.37 It is most likely that he arrived within a couple of days after fleeing Montgomery County. He was certainly in town before October 21st, when he and one of the Berry brothers, most likely Ike,38 were said to have robbed and terrorized a local Union man of significant wealth named William B. Lewis. After Anderson’s arrival, he and his men would spend several days in Glasgow, indicating a much needed rest.

Another argument made against Anderson being present for the Montgomery county raids involves his motivations and morale in regards to his mission from Major-General Sterling Price. Historian Richard Brownlee39 claims that Anderson did not care enough about Price’s orders to carry them out himself, instead sending other men in his band to do the work. This argument seems weak at best, considering there is little to no documentation supporting this

statement. Brownlee cites segments of the Ocial Record of the War of the Rebellion that do not support his claim. While Anderson’s mission may not have been very significant in a military sense, he seemed motivated enough to address it with his own manpower. It is unlikely that he would have done so without being present himself, considering that his men had been abandoning him at alarming rates since his display of insanity and depravity at Centralia. Anderson would have been better served leading in person and motivating his band to stay together as a cohesive command.

The final argument against Anderson’s presence at Danville is that he stayed in Boonville after meeting with Sterling Price and eventually tagged along with Shelby, sending some of his men to perform the raids in Montgomery county. Historian Bruce Nichols, in a massive, four volume collection of material covering guerrilla activity through every year of the Civil War, makes this case for Danville.40 The trouble with this assessment is that at no point in Shelby’s reports and correspondence does he mention Anderson, who had become a very notable individual.41  Even Hamp Watts, the young guerrilla who left Anderson’s band to join the regular Confederate army under Shelby, does not mention Anderson following along.42 In

accounts of the action at Glasgow, the Daily Missouri Democrat only mentions Quantrill, Jackman, and Jeffries as the guerrilla leaders along with Shelby.43

While discussing these arguments, it helps to review Anderson’s reasons for carrying out the raid. While Anderson’s loyalty to the southern cause has been weak at some points of his career, Anderson always gained from his Confederate service. He not only collected

material gains, but was able to avenge his sisters and friends with the blood of Unionists. There is also a possibility that Anderson felt a common urge to avenge the Berry brothers’ sisters, considering that his own sisters suffered as the prisoners of Union men. The presence of Ike Berry at Glasgow during the torture of Mr. Lewis on the 21st of October contributes to the case

37 William F. Switzler, History of Missouri, (St. Louis: C. R. Barnes 1879) p. 435

38 St. Louis Daily Missouri Democrat, Nov. 12, 1864

Also: Gallatin North Missourian, Nov. 3, 1864

39 Richard S. Brownlee, Gray Ghosts of the Confederacy, (Baton Rouge: Louisiana State

University 1958) p.225

40 Bruce Nichols, Guerrilla Warfare in Civil War Missouri, Volume 4, (Jefferson, North Carolina: McFarland & Company 2013) p. 126-128

41 OR, Series I, Vol. 41, Part I, (Washington: Government Printing Office 1888) p. 649-652

42 Hamp Watts, The Babe of the Company, (unknown publisher) p. 26

43 St. Louis Daily Missouri Democrat, Oct. 21 and 24, 1864

that Anderson was present at Danville, considering that the Berry brothers were recruited into Anderson’s command prior to the raid on Danville and would likely have been traveling with that same group. Anderson also may have been motivated to avenge his men, the Fridley’s, who had been killed after Centralia in Montgomery county, or to retaliate for the harassment of other Callaway county rebels in September of 1864 by Dr. Samuel J. Moore.

The story is not perfect. One cannot be absolutely sure that Anderson was along with his men on the North Missouri Railroad mission. But there is not sufficient evidence to exclude him from that narrative either.

Anderson did not meet a peaceful end. He was caught up by Union militia in Ray county near modern Orrick on October 26, 1864. Bloodthirsty as ever, he led an impetuous charge, costing him his life. He was publicly laid out for others to see, including being set up in a chair and photographed, and was later buried in Richmond, Missouri. Anderson was a troubled soul, possessed with a desire to avenge the wrongs done to his family and his friends. A case may be made for his insanity, though he does not deserve such a defense. He managed to accomplish many terrible things in such a short life. While his raids into Montgomery County are not as infamous as his actions at Centralia or the sacking of Lawrence, their story still deserves to be told. For the village of Danville, the raid was another mortal blow. Before the

war, the North Missouri Railroad missed Danville, which was certainly an unfortunate development for the small town. Anderson’s raid left it in ruins with little hope. It would slowly dwindle away. The village, numbering around 300 individuals before the war, is left with only 34 as of the 2010 census.44 Danville remains a proud little town with a colorful history worth sharing.

As for Anderson, most remember him as the vengeful man that he was. A comment from Harrison Trow, who had ridden with Anderson and fought at Centralia, is a fitting description of the rebel partisan’s experience: “Like the war of La Vendee, the Guerrilla war was one rather of hatred than of opinion. The regular Confederates were fighting for a cause and a nationality- the Guerrilla for vengeance.”45

44 Olive Baker, Life and Influence of Danville and Danville Township, from Missouri Historical

Review, July 1913 (Columbia, Missouri: Missouri Historical Society 1913) p. 221-221

Also: Discussion of 1860 census and population with Walt McQuie of the Montgomery County

Historical Society (2020).

45 Harrison Trow, Charles W. Quantrell: A True Report of his Guerrilla Warfare on the Missouri and Kansas Border During the Civil War of 1861 to 1865, (Project Gutenberg ebook edition

2020; original printing Vega, Texas: 1923) p. 2