Note here the statement of hundred or more wagons often being in town. Note also the story of whiskey barrels being destroyed and whiskey running in rivulets down the hill. Also note that it was the central business section of town that was burned. Given what I've learned about Osceola I now understand why Sterling Price picked the confluence of the Sac and Osage rivers for his rendezvous point for the MSG. It had the infrastructure to support an army of 12,000. It was also politically important for Democrats being the home of US Senator Waldo P Johnson. I think John T Coffee came from St. Clair county as well.

"History of Henry and St. Clair Counties, Missouri, 1883

The Burning Of Osceola By The Jayhawker Jim Lane

Osceola, the pride of all Southwest Missouri and portions of Arkansas, was razed to the ground, not a house being left to mark the spot where a few hours previously had teemed and toiled nearly 2,000 souls.
From a correspondent of the Osceola Sun we extract the following, giving a vivid description of the destruction of this important town and trading post:

The "Border War" was known all over the United States long before the first cannon boomed at Sumpter, and grew out of the questions that had long been agitated, whether Kansas should be a free or slave state, and it culminated in the election, the freesoilers carrying the day by a small majority. Jim Lane and others of less notoriety began a warfare all along the frontier counties in Missouri, bordering on Kansas. This grew more bitter when Missouri began retaliation, crossing the border into Kansas and committing many depradations in revenge for deeds that had been committed in their state.
It was these bands that afterwards became noted as the Missouri and Kansas guerillas. Jim Lane, long before 1861, had threatened to make a raid on Osceola, for the purpose of robbing the bank at this point. Osceola, at that time was the great metropolis of southwest Missouri, and in fact, it was the greatest commercial city west of Jefferson City or southwest of Boonville. The people of St. Clair County had nothing to do with casting illegal votes in the Kansas election, nor had they taken any part in the border war. About the first of December, 1860, Jim Lane collected together about one hundred and fifty of his followers and started for Osceola. After moving his band as far east as Papinville, he retraced his steps back across the border line, and his band disbanded, subject to the call of their leader. The cause of his sudden change of mind was that the citizens of St. Clair County had been informed of the object of his visit, and had collected in force for the defense of their beautiful county seat. Fully five hundred well armed men were ready to meet him and they remained on guard till all danger was over. Lane kept up his agitation of a raid on Osceola, and pictured to his followers in glowing colors the vast amount of wealth that would be secured from the town and bank, but they well knew that the old pioneers would never give their consent, and that the streams would be dyed with blood as long as the old Virginians and Kentuckians, by whom the county was populated, had strength enough to level the ever ready and never failing rifle. Soon after this futile attempt of Lane's the thunder of battle sounded along Columbia's southern shore.
Fort Sumpter fell, star after star shot from the cluster of states, and southern blood and valor were at fever heat and rallying to arms. 1861 was here, and war was inaugurated. The blaze of battle began to scorch the fair fields of the sunny south, and the great commonwealth of Missouri was suffering terribly from invading armies on three sides of her, she being almost a desolate daughter of the Southern Confederacy. Illinois joined with Kansas and sent untold numbers of plunderers into the richest districts of Missouri. Banks were robbed, the wealthiest citizens plundered, stock driven off, and wagons and teams stolen and loaded with the goods taken from the people, and wearing apparel and jewelry of every description was taken from the ladies. There never was a richer field for plunder than Missouri in 1861. The people flew to arms. Old men and boys alike, regardless of age, formed themselves into home guards for protection against the numerous bands of outlaws that overran the state. Guerilla bands were organized all along the bloody border, and a jayhawker and guerilla war began in earnest. Old men and boys were murdered by the jayhawker bands for opinions' sake, and "blood for blood" became the rallying cry; and, to give a more bitter aspect to the feeling, black flags were unfurled by both parties, and the glare of the burning houses served to show where the human monsters had left their prey.
As men were now hurrying off to join the regular army the Missouri border was left pretty much unprotected, and the Jayhawkers widened their field of operations. In September 1861, while General Price's army was at Lexington, and no Confederate soldiers in St. Clair County, except a few stragglers and recruiting officers, Lane considered his chance for carrying out his long neglected threat of burning and sacking Osceola. It stands on the right or south bank of the Osage River, and is one of the healthiest towns in the West, being situated upon a beautiful elevation of 200 feet above the river bed and surrounded by beautiful, rolling ridges, at the foot of which gush forth springs of sparkling water of the finest quality and taste. St. Clair County was settled up by a thrifty and enterprising people, who turned their attention largely to stock raising, and a majority of them had grown wealthy before hostilities began. Men of wealth and enterprise bought property in Osceola and went into business. The town is considered at the head of navigation, although the boats have ascended as far up the beautiful stream as Taberville, at or near the western boundary of the county. Boats ascended the river as far as Osceola regularly before the breaking out of the war, and the town became the great shipping point for eleven counties in the Southwest, and goods were also hauled from this point to Benton County, Arkansas.
The town had grown to large proportions, and was a mine of wealth to the citizens of the county. To show the flourishing condition of our county in 1860, it is only necessary to say we had a common school fund of $98,000. There were twelve or fifteen business houses in town, and several did wholesale as well as retail business. Prominent among the business men we may mention Johnson & Vaughn, John F. Weidemeyer & Son, dry goods: John Yeater, dry goods and groceries; Sterns & Baker, saddlery, and Sterns also had a shoe shop; Dorchester, hardware; Clark Vaughn, hardware; Dr. Dorrell, drugs; Henry Pollard and Richard Fuell, hotels and livery. Besides these we had one furniture store, several saloons and blacksmith shops, several church houses, a carding factory, tan yard and several other businesses, including a bank and newspaper office. The newspaper was owned by Richard (Dick) Devin, who died not long since. The bank was controlled and principally owned by Messrs. Johnson, Vaughn and Weidmeyer. The court house was a fine brick structure which had been built at a cost of $15,000 to the county. Johnson & Vaughn and John F. Weidmeyer & son did wholesale business, and at times as many as a hundred wagons from the southwest counties were on the streets or backyards waiting for loading at these two business houses. The place had long been the "apple in the eye" of Jim Lane as the richest strike in the southwest, and on the 22nd day of September, 1861, he collected together about two hundred of his band and from a point near Fort Scott made a bee line for the town.
The bank deposits, amounting to about $150,000, had been removed to other cities for better security, as the directors knew the exposed condition of the place, and Lane's desire to raid the town. The line of march of the Jayhawkers led down the south side of the Osage River from Fort Scott to Osceola, a distance of about sixty miles. They crossed Sac River at the Waldo Ford. Sac River is a small stream that empties into the Osage two miles above Osceola. On the 23rd day of September, 1861, about eight o'clock p.m., Lane and his band entered the town with torches in hand and two pieces of artillery. No Confederate soldiers were occupying the town at the time of their entrance, but Captain John M. Weidemeyer and forty men chanced to be in the vicinity, and as Lane entered the town they fired upon him from the brush, and then slowly retreated in the direction of Warsaw. Weidemeyer has since often been heard to say that if he could have pictured the scene which a short twenty-four hours was to bring forth, he and his men would have died in their tracks before deserting the doomed city. The pillage soon began. Instead of pursuing Weidemeyer the Jayhawkers burst open the doors of the bank and removed the safe that had contained the money, and blew it open, but only a few private papers of no value to anyone except the owners rewarded them for their trouble. Finding himself balked, Lane flew into a towering rage, and swore the whole town should suffer the consequences, and be burned and pillaged. The clan were ordered to search the town for anything of value. No citizens from the country were allowed to pass the pickets under any circumstances while the pillage was going on.
The morning of the 24th, Dr. John Trollinger and three others wished to cross the river into town, not knowing that it was infested by Lane and his band. They arrived on the opposite side of the river and hallooed for a skiff to bring them over. This was done, but no sooner were they safely landed than they were fired upon by fifty or sixty outlaws. The doctor received eleven buckshot wounds, though not of a serious character, and one of his friends, named Summers, was shot in the mouth with a minnie ball, which carried away a part of his jawbone and injured him for life. The other two managed to escape, leaving their horses in the hands of the enemy.
As Zachariah Lilley, one of the old pioneers of the county, and a man greatly beloved by all who know him, was fording the river on horseback, aiming to come to town, he was fired on by the guard, and the gentleman had to wheel his horse and dash into the timber to save his life, the bullets whistling around him in a very unpleasant manner, but fortunately he escaped unscathed.
In this manner they fired on everyone who dared to approach the town. By night the pillage was over, and a large wagon train had been loaded with the spoils. Negroes swarmed to Lane like flies around a carcass, and were permitted to load themselves down with goods of every description. What was considered of little value or too bulky for easy removal was thrown into the streets. Hundreds of barrels of whiskey had their heads knocked out, and the contents formed little rivulets and ran into the river. The court house was broken open and the county records destroyed. And now Lane ordered his men to scatter and apply the torch to every house in town. The band went to work, and soon the business portion of the town was a seething mass of flames.
The fire leaped from house to house. The flames and smoke seemed to have reached their element, but still the storm raged on. The county buildings were soon enveloped by the devouring fiend, but still the flames went up. It was not long before the entire city of magnificence and wealth - the pride of the entire people of Southwest Missouri, was a smoking mass of ruins. Even the women and children were not allowed to move anything from their burning houses, and much suffering was the result. Soon the work of destruction was finished. Lane and his men started with their plunder for Kansas, leaving old age and helpless innocence to keep vigil over the dead and wounded, and water with tears the spot which only a few short hours before had been peaceful, contented, happy homes. In Lane's official report to the government he said he had taken $1,000,000 worth of goods away with him, and it could not have fallen short of that amount, and it is safe to say he destroyed a great deal more than he carried away.
But the city of Osceola was fearfully avenged when Lawrence, Kansas, was razed to the ground, and the inhabitants scattered to the four winds of heaven."

John R