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On September 23, 1861 a raid conducted by pro-Union guerrillas known as "Jayhawkers" led to the destruction of most of the city by fire and the killing of at least nine Missouri men. This attack was part of a series of atrocities committed by pro-Confederate and pro-Union men in the early stages of the Civil War and are related to the earlier period known as "Bleeding Kansas" that saw several skirmishes, raids, and even cold-blooded murder resulting from conflicting views about the extension of slavery into Kansas Territory. This attack on Osceola was the most infamous of the attacks conducted by Jayhawkers and was not authorized by the Union or any officials in Kansas. In this attack on Osceola, men under the leadership of self-proclaimed "General" James Henry Lane looted the city before putting it to the torch. The result was the destruction of nearly the entire town of Osceola.Of an estimated eight hundred homes and other buildings, only three were left standing after the raid. When Lane and his men left town, nine Missouri men had been killed (some were likely executed after their surrender, and the once-thriving port town on the Osage River was left in ruins.


  • Confederate Memorial Monument erected on the burial site of the men who were killed in the Battle of Osceola.  The monument is available for viewing year round from dawn to dusk.
  • An artist's rendition of the burning of Osceola by Brigadier General James Henry Lane on September 23, 1861.
  • Brigadier General James Henry Lane, the general who led the attack on Osceola, Missouri.

Union General John C. Fremont called on volunteers to confront the forces of Confederate General Sterling Price who were moving through Missouri, often terrorizing Union loyalists and confiscating property. Instead of following these orders and confronting Price's men, Lane sent Charles R. Jennison and his men to follow Price and his Confederate troops westward into Missouri.  Lane then led a force to Osceola, which had an approximate population of 2200, and mirrored Price's actions of commandeering supplies and terrorizing Confederate supporters. However, Lane's attack on Osceola took a deadly turn in the early hours of September 23, 1861.  

General Lane and his troops advanced on Osceola and quickly overran Guard Captain John M. Weidemeyer and his 200 Missouri militiamen. The pro-Confederate defenders were outnumbered made a speedy retreat. The city was now left to the mercy of Lane and his Jayhawkers, but little mercy was shown as they looted homes, stores, robbed the local bank, and raided businesses throughout the town. After taking what they wanted, the troops laid torch to nearly every structure in sight.

Demonstrating the unclear line between theft and attacking the resources of the enemy, Lane and his men managed to seize many supplies that would have aided pro-Confederate partisans in Missouri, including a train loaded with supplies that were intended for the Confederate Army. “Lane had commandeered some 300 horses and mules, 400 cattle, numerous hogs and sheep, 3000 sacks of flour, 500 pounds of sugar and molasses, 50 pounds of coffee, 200 slaves and $100,000 in money.” ¹ During the siege and plundering of Osceola the brutal Jayhawkers used violence and destruction to terrorize the citizens of Osceola. The worst was yet to come. “Nine male citizens were given a speedy hearing before Lane executed them.” ³

To commemorate the Burning of Osceola and the men who died at the hands of the Jayhawker militia, a monument was placed on the exact burial site where the men were buried following their execution. The monument is located in the Osceola Cemetery.

1. Paryzek, Scharla. "Civil War on the Western Border: The Missouri-Kansas Conflict, 1854-1865." Sacking of Osceola. Accessed May 29, 2016. http://www.civilwaronthewesternborder.org/encyclopedia/sacking-osceola?nopaging=1. 2. "Missouri Jayhawking Raids 1861 by Albert Castel." Missouri Jayhawking Raids 1861 by Albert Castel. Accessed May 29, 2016. http://www.civilwarstlouis.com/History2/casteljayhawking.htm. 3. "Burning of Osceola Monument." - Freedom's Frontier National Heritage Area. Accessed May 29, 2016. http://www.freedomsfrontier.org/Visitors/Sites/Comments.aspx?id=112.