Battle of Osawatomie, Kansas
The year 1856 in the Kansas Territory was a crucible, forging the path toward the American Civil War. Tensions between those advocating for a "Free-State" Kansas and those supporting the expansion of slavery had reached a fever pitch. Armed groups from both sides roamed the eastern part of the territory, skirmishes were frequent, and the air was thick with fear and animosity. The events of that summer, particularly in the small settlement of Osawatomie, Kansas, exemplify the brutal struggle that earned the territory the moniker "Bleeding Kansas."
Following the infamous Sack of Lawrence, an event where pro-slavery forces attacked and looted the Free-State town, a wave of terror spread throughout the territory. Pro-slavery factions declared their intent to expel all Free-State settlers, and Osawatomie, Kansas, became a focal point for this campaign of intimidation. The residents, including the family of the staunch abolitionist John Brown, lived in constant apprehension, fearing the complete destruction of their homes and livelihoods.
The first taste of this orchestrated terror came early in June. A contingent of approximately 150 men from Missouri, led by John W. Whitfield, descended upon Osawatomie, Kansas. Finding the majority of the Free-State men occupied elsewhere, they met with little resistance. While they refrained from widespread destruction, the Missourians plundered homes and absconded with livestock, leaving the residents in a state of heightened anxiety.
From that point forward, the inhabitants of the region stretching from Mound City to Fort Scott, and westward to Lawrence, lived under a cloud of uncertainty. The presence of "border ruffians," as the pro-slavery Missourians were often called, made life precarious; neither person nor property was safe from their depredations. The constant threat of violence and the arbitrary nature of the attacks created an atmosphere of pervasive fear.
By mid-August 1856, the situation had deteriorated further. The Missouri-Kansas militia escalated their activities, engaging in widespread plundering and acts of violence in the vicinity of Osawatomie, Kansas. On August 25th, a force of around 150 Missourians established a camp near the town, intending to launch a surprise attack. However, the Free-State men, acting swiftly, managed to capture the camp, routing the pro-slavery force. This victory, however, proved to be short-lived.
Unbeknownst to the Free-State settlers, a larger and more determined attack was on the horizon. On the night of August 29th, a force of approximately 400 Missourians, commanded by General John William Reid, departed from Bull Creek with the objective of reaching Osawatomie, Kansas, under the cover of darkness and launching an assault at daybreak.
The morning of August 30th dawned with impending doom. Frederick Brown, son of John Brown, left Osawatomie before sunrise, heading towards the home of S.L. Adair. Tragically, he encountered Reid and a small advance guard led by a minister named Martin White. The pro-slavery force had crossed the Marais des Cygnes River at Bundy’s Ford, about four miles northwest of Osawatomie, and were approaching the town when White recognized Brown. Without hesitation, White raised his rifle and fatally shot Brown on the spot.
The sound of the gunshot served as a grim alarm, alerting settlers in the surrounding area. Messengers were immediately dispatched to notify the residents of the village and Captain John Brown, who was located half a mile east of town. In a frantic effort to organize a defense, Dr. Updegraff and Captains Brown and Cline rallied their men, formulating a plan to resist the impending attack.
Initially, the Free-State men considered utilizing the town’s blockhouse as a defensive stronghold. However, this plan was abandoned upon learning that Reid’s force possessed a cannon. Faced with this disadvantage, Brown, with a force of just 41 men, opted to establish a defensive position in the timber on the south side of the Marais des Cygnes River, facing south. Brown positioned himself with 17 men on the right flank, Dr. Updegraff with ten men in the center, and Captain Cline with 14 men on the left wing. An independent company was stationed further to the left, near the Emigrant Aid Company’s mill.
As the Missourians advanced, they passed approximately 600 yards in front of the Free-State defensive line. A scout, sent to observe the enemy’s movements, fired upon the approaching force before retreating to the main body. This act triggered a premature engagement. The Missourians formed a line on the ridge west of where the John Brown monument now stands and fired three guns, signaling the Free-State men to surrender.
Despite explicit orders from Captain Brown to hold their fire until given the signal, the Free-State defenders, believing that the enemy had initiated the attack, unleashed a volley of shots. The Battle of Osawatomie, Kansas, had begun.
The Missourians focused their initial assault on the right wing of the Free-State line. After being partially repulsed, they brought their cannon into action, positioning it approximately 400 yards from Brown’s command. With each shot, they moved the cannon further east, attempting to sweep the timber with grapeshot. Fortunately, the grapeshot passed harmlessly over the heads of the defenders, causing minimal damage.
The Free-State forces gradually retreated eastward, maintaining a steady rate of fire. The Missourians, eventually abandoning their cannon, dismounted and charged into the timber, where the main body of the defenders was located. After holding their ground for over an hour against a force ten times their size, the Free-State men found themselves in a precarious position. They were left with the choice of surrendering or retreating.
The majority of the Free-State men managed to escape across the Marais des Cygnes River, but a few were killed or captured. The Missourians then entered the town and commenced a systematic campaign of pillage and arson. They targeted the blockhouse, where several men were stationed, and set fire to all but four of the town’s houses. When the pro-slavery force departed, they left with two wagons filled with their wounded and ten wagons laden with plunder stolen from the homes of the citizens.
Reid and his force initially intended to cross the Marais des Cygnes River near the mill, but the men stationed there opened fire. Uncertain of the strength of the remaining defenders, the Missourians retreated from the town along the same route they had taken to arrive. The surviving Free-State men, including Brown and Updegraff, regrouped at a log house north of the river. The following day, they began fortifying a new camp on the south side of the Marais des Cygnes, but the camp was never fully completed.
The Free-State men suffered approximately six casualties, either killed or captured, and several more were seriously wounded. The Missourians are believed to have sustained a similar number of casualties, although the exact figures remain unknown.
The Battle of Osawatomie, Kansas, though a defeat for the Free-State forces, became a symbol of resistance against the expansion of slavery. John Brown’s courageous defense, despite being heavily outnumbered, cemented his image as a fearless abolitionist and further fueled the growing conflict that would ultimately engulf the nation. The ashes of Osawatomie, Kansas, served as a stark reminder of the brutal reality of "Bleeding Kansas" and the sacrifices made in the fight for freedom.