Battle of Osawatomie
Kansas

The Battle of Osawatomie happened in August 30, 1856 when 250-300 Border Ruffians led by John W. Reid and Rev. Marvin White attacked the city of Osawatomie.

 


John W. Reid was intent on destroying free state settlements and then moving on to Topeka and Lawrence to do more of the same. John Brown first got word that the group was coming when they shot his son Frederick. Brown with forty or so men tried to defend the town against the pro-slavery agitators, but failed and the town of Osawatomie was looted and burned. This is one event in series of skirmishes between abolitionists and pro-slavery Missourians in what has been known as Bleeding Kansas.

his was the most memorable battle of the Border War. It was fought August 30, 1856. Capt. John Brown, Dr. W. W. Updegraff and Capt. Cline commanded the defense, and Gen. John W. Reid the attacking party of 400 Missourians. Gen. Reid's command, after crossing the Marias des Cygnes, at Bundy's Ford, four miles northwest of Osawatomie, approached the town about daylight, Rev. Martin White acting as guide. Frederick Brown was making preparations to return to Lawrence that day, and on his way to Rev. S. L. Adair's, met Gen. Reid and Rev. White with a small body of men in advance of the main force. He saluted them with "Good morning, boys; are you going to Lawrence to-day?" Rev. White replied:"Why, I know you!" and taking deliberate aim with his rifle, fired at Brown, shooting him dead in the road, about a mile west of town. This was twenty minutes before sunrise. Messengers were immediately dispatched to notify the people in town, and Capt. Brown, who was a half-mile east of town.

He, Dr. Updegraff and Capt. Cline collected their men together as rapidly as possible. At first it was designed to make use of the block-house as a defense, but learning that Reid had a cannon with him, this plan was abandoned and Brown and his men, forty-one in number, all told, took up their positions in the timber along the south side of the Marais des Cygnes, facing south; Capt. Brown, with seventeen men, on the right, Dr. W. W. Updegraff with ten men, in the center, and Capt. Cline, with fourteen men, on the left. There was also an independent command still further to the left, in the Emigrant Aid Company's mill, consisting of "Pap" Austin, an ex-regular soldier, and his large rifle, to which he had applied the fancy name of "Kill Devil", carrying an ounce ball.

When the forces were arranged in the woods the enemy was passing within about 600 yards of them, Mr. Holmes, a volunteer, advanced towards the top of the hill, on the southwest of the town to reconnoiter, and finding the enemy close at hand, fired at them, striking one of them in the mouth or chin and causing him "to bleed like a pig" as one of his companions afterwards expressed it. He then retreated to the woods, the enemy following him closely and forming a line from O. C. Brown's house to William Chestnut's premises-the high ground west of where the "John Brown monument"now stands. They then fired three guns, as they afterwards stated to Robert Reynolds, one of the prisoners whom they took, as a signal to the State force to surrender.

Capt. Brown had given orders to his men not to fire a shot until he gave the orders, but when these alleged signal guns were heard, the men became so impatient, believing the enemy had opened fire upon them, that they could not be restrained. Jason Brown raised his gun to fire, and the rest under Capt. Brown's immediate command did the same, although as one of the number states,"they knew it was contrary to orders." This first attack, which was made on the right wing of the Free-state line, was partially repulse, when the enemy brought up their cannon and placed it in position within about 400 yards of the timber where Capt. Brown's men were stationed, at each successive shot moving it farther east to scour the timber.

The cannon was loaded with grape shot but did no damage, the missiles passing over the heads of the men. During this time the Free-state forces kept moving east and returning the fire of the enemy, who finally ceased firing the cannon, dismounted and made a charge in to the timber when the main body of the Free-state men, having gallantly held their ground for an hour against ten times their number, were compelled to surrender or retreat. Most of them escaped across the Marais des Cygnes, some swimming and others in a skiff. Robert Reynolds, H. K. Thomas and Charley Keiser were taken prisoners by Capt. Warren Harris, of Platte county, MO and taken under guard to the town.

While attempting to swim his horse across the river, George Partridge was shot. Samuel Wright sprang into the river on the same horse, swam across, and, by means of the bushes climbed the steep bank on the north side of the river and escaped. The Missourians, on entering the town, commenced to pillage and burn it, first firing on the block-house, in which were stationed several men, who escaped before the cannon was brought up. There were no women in town except those belonging to the families of Messrs. Chestnut and Sears. Every house but four was burned-Mr. Starkey's, Mr. Woodbury's and two small cabins. The invaders left town with twelve covered wagons, two filled with wounded men and a large part of the remainder of the plunder.

As General Reid's command approached the town in the morning, David R. Garrison and George Cutter, who remained in the house of Mr. Carr over night, attempted to escape to the timber along the Pottawatomie, and give the alarm to the town. A detail of Missourians was made to pursue them, Garrison was killed, and Cutter seriously wounded and left for dead. The invading force retired from the town about 10 o'clock a. m., taking with them as prisoners William Bainbridge Fuller, Robert Reynolds, Charley Keiser, H. K. Thomas, Mr. Morey, young Spencer Brown, who was taken prisoner at the burning of his father's house, and William Williams, from Miami Village.

Of these prisoners, Williams, formerly of Westport, Mo., which place he had been forced to leave on account of his free-state proclivities, was taken to the edge of the town site and there shot; Charley Kaiser was shot September 1-the second day following. Keiser was one of the party under Captain John Brown who captured F. N. Coleman, the murderer of Charles W. Dow, at the battle of Black Jack, and Coleman had then made threats against him. When therefore, Keiser found that Coleman was among his captors, he declared to his companions his belief that he would be killed.

The party encamped, Sunday night, on the east side of Cedar Creek, on the old Sante Fe road, and Keiser was taken out on Monday morning to a guard of Kickapoo rangers and shot. Besides the Free state losses mentioned, must be added Theron P. Powers, who was, at the time of the invasion, lying sick in a house near the timber. He crawled out of the house and into the woods for protection, and was lying there completely exhausted, when he was found by the ruffians and shot.

Among those who participated in the defense of Osawatomie were John Brown, Sr., Captain; Dr. W. W. Updegraff, Captain; --Cline, Captain; Harrison Updegraff, Charley Keiser, Cyrus Tator, George Ferris, August Bondi, Robert Eaton, George Grant, George Partridge, William Partridge, Samuel Wright, J. M. Anthony, William Quick, Hugh Kilbourn, William A. Sears, ____Mills, R. W. Wood, D. W. Collis, Capt. Holmes, H. K. Thomas, James Clark, J. J. Holbrook, Jacob Benjamin, Caleb Shearer, __Baker, __Woodbury, Henry Kilbourn, Freeman Austin, Luke Parsons.

As before stated, Frederick Brown and David Garrison were killed on the approach to the town, and George Cutter badly wounded; George Partridge and T. P. Powers were killed during the progress of the battle and the retreat; William Williams on the outskirts of the town and Charley Keiser at Cedar Creek. Dr. Updegraff and D. W. Collis were wounded. The Freeman Austin, or "Pap Austin," alluded to, was encountered on the return march of the Missourians. After burning and sacking the town, they started eastward, with the purpose of crossing the Marais des Cygnes, in the vicinity of the Emigrant Aid Company's mill. Here they encountered Austin and the "kill devil" Austin opened fire upon them, calling out "Come on boys, plenty of men here," loading and firing as rapidly as possible. Not anxious to encounter "plenty of men" Reid faced about and left Osawatomie by the way he came, crossing the Maria des Cygnes at Bundy's Ford, four miles above.

The Free-state men who escaped re-assembled at a log house north of the river, Brown and Updegraff among them. The next day they removed to the south side, and commenced fortifying another camp, but were prevented by sickness from carrying out their design.

The losses of the Missourians are not generally known--probably not much greater than those of the Free-state men. There are numerous surmises and guesses as to what those losses were; but according to Reid's own statement, it was two killed and a few wounded. The disparagement in number-ten to one - and with but eighteen of the number armed with Sharpe's rifles, was too great for Capt. Brown or any of his men to reasonably expect to win a victory, even if they had had plenty of ammunition. The most that could be done under the circumstance was to make a show of resistance, and to retreat across the Marais des Cygnes when their ammunition was exhausted, which they did.

Nothing was ever done by the Free-state forces to punish Gen. Reid for thus attacking and destroying a defenseless town, or to interrupt his return march to Missouri, except a faint feint by Gen. Lane, at which he was adept.

Soldiers Monument
The Soldiers Monument which was dedicated August 30, 1877 was paid for by friends and relatives to commerate those who died in the battle of Osawatomie. The names of the deceased are listed on it, who are Fredrick Brown, George W. Partridge, David Garrison, Theron Parker Powers, and Charles Kaiser. All of these men (except Charles Kaiser) are buried underneath the monument. John Brown's name also appears on the monument, but is buried in North Elba, New York.

A Contemporary History of the Battle of Osawatomie
By William G. Cutler (1883)
This was the most memorable battle of the Border War. It was fought August 30, 1856. Capt. John Brown, Dr. W. W. Updegraff and Capt. Cline commanded the defense, and Gen. John W. Reid the attacking party of 400 Missourians. Gen. Reid's command, after crossing the Marias des Cygnes, at Bundy's Ford, four miles northwest of Osawatomie, approached the town about daylight, Rev. Martin White acting as guide. Frederick Brown was making preparations to return to Lawrence that day, and on his way to Rev. S. L. Adair's, met Gen. Reid and Rev.

White with a small body of men in advance of the main force. He saluted them with "Good morning, boys; are you going to Lawrence to-day?" Rev. White replied:"Why, I know you!" and taking deliberate aim with his rifle, fired at Brown, shooting him dead in the road, about a mile west of town. This was twenty minutes before sunrise. Messengers were immediately dispatched to notify the people in town, and Capt. Brown, who was a half-mile east of town. He, Dr. Updegraff and Capt. Cline collected their men together as rapidly as possible.

At first it was designed to make use of the block-house as a defense, but learning that Reid had a cannon with him, this plan was abandoned and Brown and his men, forty-one in number, all told, took up their positions in the timber along the south side of the Marais des Cygnes, facing south; Capt. Brown, with seventeen men, on the right, Dr. W. W. Updegraff with ten men, in the center, and Capt. Cline, with fourteen men, on the left. There was also an independent command still further to the left, in the Emigrant Aid Company's mill, consisting of "Pap" Austin, an ex-regular soldier, and his large rifle, to which he had applied the fancy name of "Kill Devil", carrying an ounce ball.

When the forces were arranged in the woods the enemy was passing within about 600 yards of them, Mr. Holmes, a volunteer, advanced towards the top of the hill, on the southwest of the town to reconnoiter, and finding the enemy close at hand, fired at them, striking one of them in the mouth or chin and causing him "to bleed like a pig" as one of his companions afterwards expressed it. He then retreated to the woods, the enemy following him closely and forming a line from O. C. Brown's house to William Chestnut's premises-the high ground west of where the "John Brown monument"now stands. They then fired three guns, as they afterwards stated to Robert Reynolds, one of the prisoners whom they took, as a signal to the State force to surrender.

Capt. Brown had given orders to his men not to fire a shot until he gave the orders, but when these alleged signal guns were heard, the men became so impatient, believing the enemy had opened fire upon them, that they could not be restrained. Jason Brown raised his gun to fire, and the rest under Capt. Brown's immediate command did the same, although as one of the number states,"they knew it was contrary to orders." This first attack, which was made on the right wing of the Free-state line, was partially repulsed, when the enemy brought up their cannon and placed it in position within about 400 yards of the timber where Capt. Brown's men were stationed, at each successive shot moving it farther east to scour the timber.

The cannon was loaded with grape shot but did no damage, the missiles passing over the heads of the men. During this time the Free-state forces kept moving east and returning the fire of the enemy, who finally ceased firing the cannon, dismounted and made a charge in to the timber when the main body of the Free-state men, having gallantly held their ground for an hour against ten times their number, were compelled to surrender or retreat. Most of them escaped across the Marais des Cygnes, some swimming and others in a skiff. Robert Reynolds, H. K. Thomas and Charley Keiser were taken prisoners by Capt. Warren Harris, of Platte county, MO and taken under guard to the town.

While attempting to swim his horse across the river, George Partridge was shot. Samuel Wright sprang into the river on the same horse, swam across, and, by means of the bushes climbed the steep bank on the north side of the river and escaped. The Missourians, on entering the town, commenced to pillage and burn it, first firing on the block-house, in which were stationed several men, who escaped before the cannon was brought up. There were no women in town except those belonging to the families of Messrs. Chestnut and Sears. Every house but four was burned-Mr. Starkey's, Mr. Woodbury's and two small cabins. The invaders left town with twelve covered wagons, two filled with wounded men and a large part of the remainder of the plunder.

As General Reid's command approached the town in the morning, David R. Garrison and George Cutter, who remained in the house of Mr. Carr over night, attempted to escape to the timber along the Pottawatomie, and give the alarm to the town. A detail of Missourians was made to pursue them, Garrison was killed, and Cutter seriously wounded and left for dead. The invading force retired from the town about 10 o'clock a. m., taking with them as prisoners William Bainbridge Fuller, Robert Reynolds, Charley Keiser, H. K. Thomas, Mr. Morey, young Spencer Brown, who was taken prisoner at the burning of his father's house, and William Williams, from Miami Village.

Of these prisoners, Williams, formerly of Westport, Mo., which place he had been forced to leave on account of his free-state proclivities, was taken to the edge of the town site and there shot; Charley Kaiser was shot September 1-the second day following. Keiser was one of the party under Captain John Brown who captured F. N. Coleman, the murderer of Charles W. Dow, at the battle of Black Jack, and Coleman had then made threats against him. When therefore, Keiser found that Coleman was among his captors, he declared to his companions his belief that he would be killed. The party encamped, Sunday night, on the east side of Cedar Creek, on the old Sante Fe road, and Keiser was taken out on Monday morning to a guard of Kickapoo rangers and shot.

Besides the Free state losses mentioned, must be added Theron P. Powers, who was, at the time of the invasion, lying sick in a house near the timber. He crawled out of the house and into the woods for protection, and was lying there completely exhausted, when he was found by the ruffians and shot. Among those who participated in the defense of Osawatomie were John Brown, Sr., Captain; Dr. W. W. Updegraff, Captain; --Cline, Captain; Harrison Updegraff, Charley Keiser, Cyrus Tator, George Ferris, August Bondi, Robert Eaton, George Grant, George Partridge, William Partridge, Samuel Wright, J. M. Anthony, William Quick, Hugh Kilbourn, William A. Sears, ____Mills, R. W. Wood, D. W. Collis, Capt. Holmes, H. K. Thomas, James Clark, J. J. Holbrook, Jacob Benjamin, Caleb Shearer, __Baker, __Woodbury, Henry Kilbourn, Freeman Austin, Luke Parsons.

As before stated, Frederick Brown and David Garrison were killed on the approach to the town, and George Cutter badly wounded; George Partridge and T. P. Powers were killed during the progress of the battle and the retreat; William Williams on the outskirts of the town and Charley Keiser at Cedar Creek. Dr. Updegraff and D. W. Collis were wounded. The Freeman Austin, or "Pap Austin," alluded to, was encountered on the return march of the Missourians. After burning and sacking the town, they started eastward, with the purpose of crossing the Marais des Cygnes, in the vicinity of the Emigrant Aid Company's mill. Here they encountered Austin and the "kill devil" Austin opened fire upon them, calling out "Come on boys, plenty of men here," loading and firing as rapidly as possible. Not anxious to encounter :plenty of men" Reid faced about and left Osawatomie by the way he came, crossing the Maria des Cygnes at Bundy's Ford, four miles above.

The Free-state men who escaped re-assembled at a log house north of the river, Brown and Updegraff among them. The next day they removed to the south side, and commenced fortifying another camp, but were prevented by sickness from carrying out their design.

The losses of the Missourians are not generally known--probably not much greater than those of the Free-state men. There are numerous surmises and guesses as to what those losses were; but according to Reid's own statement, it was two killed and a few wounded. The disparagement in number-ten to one - and with but eighteen of the number armed with Sharpe's rifles, was too great for Capt. Brown or any of his men to reasonably expect to win a victory, even if they had had plenty of ammunition. The most that could be done under the circumstance was to make a show of resistance, and to retreat across the Marais des Cygnes when their ammunition was exhausted, which they did.

Nothing was ever done by the Free-state forces to punish Gen. Reid for thus attacking and destroying a defenseless town, or to interrupt his return march to Missouri, except a faint feint by Gen. Lane, at which he was adept.

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