Event Summary:

• Date: September 22-23, 1861
• Location: St. Clair County, Osceola, Missouri
• Adversaries: Brigadier General and U.S. Senator James Henry Lane with the 3rd, 4th, and 5th Kansas Volunteers vs. Missouri State Guard Captain John M. Weidemeyer and local militia and civilians of Osceola, Missouri
• Casualties and damages: At least 10 casualties (including nine executions after the raid ended) and approximately $1 million in building and property damage
• Result: The city of Osceola was left in ruins; Missouri bushwhackers sought retribution in the form of Quantrill’s Raid on August 21, 1863

The sacking of Osceola was a significant military engagement that took place during the early stages of the Civil War in Missouri. After losing the Battle of Dry Wood Creek near Fort Scott, Kansas, the Free-State leader, U.S. Senator and Brigadier General James Henry Lane guided his 3rd, 4th, and 5th Kansas Volunteers in the looting and sacking of Osceola, Missouri. A proud “jayhawker” and fierce antislavery supporter, Lane used his military status to impede the Confederate war effort in the border state.

Union General John C. Frémont originally ordered Lane and his men to cut off Confederate General Sterling Price and the secessionist Missouri State Guard north of Fort Scott, Kansas. Rather than personally pursuing Price and his Confederate troops after the Battle of Dry Wood Creek, Lane delegated Colonel Charles R. Jennison and some of his men to follow the Confederate general into western Missouri. Meanwhile Lane led his jayhawkers toward Osceola with intentions of raiding strong proslavery communities in the state.

Osceola's Board of Aldermen resolved in 2011 to request that the University of Kansas cease using the Jayhawk mascot and to use the lower-case to spell "kansas" and "ku," because "neither is a proper name or a proper place." 

Lane’s precise motivations for attacking Osceola are unclear. Local Osceola historian Richard Sunderwirth claims Lane targeted it because it was the home of one of his Confederate political foes, Missouri Senator Waldo P. Johnson. Other scholars, including Jay Monaghan, acknowledge the Johnson-Lane rivalry, but they assert that Lane’s chief purpose was to liberate African American slaves and squelch proslavery Missourians’ plans of secession from the Union. Indeed, before the sacking of Osceola, Lane stated, “Everything disloyal from a Durham cow to a Shanghai chicken must be cleaned out.”

Lane and approximately 2,000 of his troops arrived in Osceola, a port town on the Osage River, on September 22, 1861. In the early morning hours of September 23, Lane and his troops violently descended on the community. The so-called “Kansas Brigade” looted valuable goods and supplies from private homes, stores, the bank, and other businesses throughout the city, burning houses and buildings as they went. Lane and his men also “succeeded in capturing a heavy train of supplies destined for the armies of Generals [Gabriel J.] Rains and Price, together with $100,000 in money.” When the raid began, Missouri State Guard Captain John M. Weidemeyer and 200 Missouri militiamen fired their rifles and cannons at Lane and his men in an effort to protect the town and its citizens. Severely outnumbered and outmatched, however, the Missouri troops were soon forced to retreat to safety.

Brigadier General Lane and his troops left Osceola on September 23, many of them in a drunken state. Having plundered and burned almost everything in sight, including all but three of the town’s 800 buildings, the unauthorized jayhawker attack left Osceola in ruins. The October 11, 1861 edition of The Newark Advocate reported, “With his immense train of supplies, three hundred and fifty horses and mules, four hundred head of Price’s cattle, large droves of sheep and swine, with as many ‘contrabands’ [200 slaves] as he could employ, he [Lane] made his way to West Point [Missouri] unpursued.”Additionally, Lane stole 3,000 sacks of flour, 500 pounds of sugar and molasses, 50 pounds of coffee, and even the country records from the local courthouse. At least one of Captain Wiedemeyer’s men was killed during the raid and Lane executed nine other Osceola residents after giving them a hurried mass hearing.

From History to Pop Culture: In the novel True Grit, and in two movies of the same name, the character Rooster Cogburn was a native of Osceola, who joined up with Quantrill's Raiders after Jim Lane's Sacking of Osceola. The 1969 film featured John Wayne in the role, for which he won an Academy Award.

As the citizens of Osceola took stock of the extensive damage the Kansas Brigade had inflicted, many immediately called for revenge. John W. Fisher stated that the damage was “enough to make a man’s blood boil. . . . Men are anxious to go to Kansas and retaliate, [and] if we are permitted to go the retribution will be awful. Lane’s men were the destroyers and there will be no mercy shown them if we ever get a hold of them.” The formerly thriving port town never fully recovered from the attack.

The long-term consequences of the Kansas Brigade’s sacking of Osceola became evident two years later. On August 21, 1863, a group of 400 Missouri bushwhackers raided Lawrence, Kansas, killing between 160 and 190 men and boys and looting and burning much of the town. Commanded by William Clarke Quantrill, a proslavery guerrilla, the bushwhackers cited the sacking of Osceola as one of the primary justifications for their surprise attack on Lawrence. Brigadier General Lane was in Lawrence at the time of Quantrill’s bloody raid, and he narrowly avoided the wrath of the bushwhackers by running into a cornfield clothed only in his nightshirt.