Bleeding Kansas & the Missouri Border War

"Bloody Bill" Anderson

“Bloody Bill” Anderson

Anderson’s greatest fame came as a result of a massacre and battle with Union soldiers at Centralia, Missouri, when on September 27, 1864, he led a band of about seventy men into the town. Wearing Confederate uniforms, the ruffians showed no mercy to the Centralia residents as they systematically raided homes and stores, raped, and murdered. In their final act of wanton destruction, the entire town was reduced to a burning ruin.

After the Centralia Massacre, a Union detachment chased the fleeing guerrillas, who turned on them killing 114 of their pursuers. On October 11, Anderson’s Bushwhackers sacked Boonville, while their leader joined Quantrill to capture Glasgow. Todd, riding with Jo Shelby’s cavalry division, was killed in battle near Independence on October 21, 1864, and Anderson fell 5 days later in a skirmish near Orrick.

In mid-September of 1864 Confederate General Sterling Price made a last-gasp raid across the state hoping to capture Missouri for the South. The Civil War had raged for nearly 3 1/2 years, and Price, a former Missouri governor, had been actively engaged throughout. Leading pro-Confederate Missouri State Guard troops at the Battles of Lexington, Wilson’s Creek and Pea Ridge, Price was a favorite of his troops and was affectionately known as “Old Pap.”

Forced to bypass St. Louis because of its overwhelming Federal strength, Price’s troops struggled past Hermann, Boonville, Glasgow, Lexington and Independence filling his ranks along the way with fresh volunteers in preparation of an invasion of Westport (now part of Kansas City.) On October 23, 1864, his troops suffered the worst Confederate defeat in Missouri at Westport, which allowed the Union to finally gain control of the state. Westport was the last major Civil War battle west of the Mississippi River.

Exhausted, the fleeing wagon train, retired south down the state line. However, hot on the Price trail was Union General Samuel R. Curtis.

After crossing into Kansas, Price and his weary troops camped near a trading post on the night of October 24th. The next day the Rebels, stalled by their wagons crossing the ford, had formed a line on the north side of Mine Creek. The Federals, although outnumbered, commenced the attack as additional troops arrived during the fight.

Colonel Sterling Price

Colonel Sterling Price

They soon surrounded the Confederates, resulting in the capture of about 600 men and two generals – Brigadier General John S. Marmaduke and Brigadier General William L. Cabell. Having lost these many men, Price’s army was doomed. Retreat to friendly territory was the only recourse.

Meanwhile, in an attempt to regain his prestige, Quantrill concocted a plan to lead a company of men to Washington and assassinate President Abraham Lincoln. He assembled a group of raiders in Lafayette County, Missouri, in November and December 1864 with the idea of completing this task. However, the strength of Union troops east of the Mississippi River convinced him that his plan could not succeed. Quantrill turned back and resumed his normal pattern of raiding.

On April 9, 1865, General Robert E. Lee formally surrendered at Appomattox, effectively ending the Civil War. However, while peace was brought to the rest of the land the violence in these two states would continue for years to come.

Fearing capture and execution, Quantrill and his men headed east. In May 1865, a Unionist irregular force surprised his group near Taylorsville, Kentucky, and in the ensuing battle, Quantrill was shot through the spine. He died at the military prison at Louisville, Kentucky, on June 6, 1865.

Conquered Banner of the Confederacy

Conquered Banner of the Confederacy. Click for prints & products.

The divided state of Missouri suffered the third-largest number of engagements during the war at 1,162. Only Virginia and Tennessee had more. 40,000 Missourians joined the Confederate ranks, while nearly three times that number joined the Union Army. When it was over Missouri lost 27,000 of its valiant sons.

Kansas contributed 20,097 men to the Union Army, a remarkable record since the population included less than 30,000 men of military age. Furthermore, Kansas suffered the highest mortality rate of any of the Union states. Of the black troops in the Union army, 2,080 were credited to Kansas, though the 1860 census listed fewer than 300 blacks of military age in the state; most of them came from Arkansas and Missouri.

Members of the guerrilla bands, having tasted the excitement of gunplay, were in no mood to lay down their arms meekly and become model citizens, and their resolve to continue their outlaw ways was strengthened by the knowledge that surrender meant the hangman’s noose. Men like Jesse and Frank James and the Younger Brothers merely shifted their field of endeavor from the political to the financial. Continuing to apply their hit-and-run tactics, bank robberies and train holdups now became endemic, effectively beginning the advent of the Wild Wild West and its many outlaws.

© Kathy Weiser/Legends of America, updated March 2020.

Author’s Notes:

What an interesting piece of history to explore! Did you know that most historians believe that the Civil War began as a result of what has become known as “Bleeding Kansas?” When the Kansas-Nebraska Act allowed the Kansas Territory to be settled and eventually become a state, there were a lot of people who fervently believed that by the state becoming a “Free-State,” the tides could be turned in the ongoing issue between pro-slavery advocates and abolitionists.

Another interesting point was that while doing the research for this article, how we received varying stories when visiting Kansas and Missouri sites.. When we visited the Mine Creek Civil War Battlefield in Kansas, we were told that the hostilities between Missouri and Kansas still exist to this day, albeit to a much lesser degree. Though Legends of America is based in Missouri, we are not native to the area and were surprised to hear this. However, when we began to do our research on this fascinating story, we found evident disparities, where the sentiments of the Civil War generation have been passed down for well over a century.

For instance, when doing an internet search, you will get a very different story when searching for “Bleeding Kansas” than you will get if you search on “Missouri Civil War .” Many of the books that are available are no different. Though most lean toward the Kansas side of the conflict due to its anti-slavery sentiment, Missouri cannot be ignored in its contribution to history and its heavy losses during the Civil War. Officially, a Union State, Missouri was internally divided between its pro-slavery sentiments and its obligation as a Union State. Never officially entering the Civil War, Missouri fought its own internal battles between the Federal Officers and its own State Forces.

Bleeding Kansas Fight

Jayhawkers and Bushwackers fight it out over Kansas becoming a Free-State or a pro-slavery state.

Even when we visit the historical sites of Kansas and Missouri, we got a different impression in the “telling.” Kansas sites will focus on the great battle of Mine Creek, where the Union Forces won the skirmish against the Confederates at immense odds; the Lawrence Massacre by Quantrill’s Raiders, or, upon John Brown, the fanatic abolitionist, and his actions to defeat the Missouri Bushwhackers.

In Missouri we heard the stories of the burning of Osceola by Lane’s Kansas Brigade, the attack upon the Missouri building that killed many innocent women and children, and the forcible evacuation of Kansas City area counties that displaced many Missourians and turned the area into a desolate “No Mans Land.”

Also See:

The Civil War

Civil War Battles By State

Lawrence, Kansas – From Ashes to Immortality

Osceola, Missouri – Surviving All Odds


Birth of Freedom DVD

Birth of Freedom DVD, available at our General Store

Blackmar, Frank W.; Kansas: A Cyclopedia of State History, Standard Publishing Company, Chicago, IL 1912.
Cutler, William; History of the State of Kansas, A.T. Andreas, Chicago, IL, 1883.
The Kansas Collection
Kansas Memory
Kansas State Historical Society
National Park Service
Territorial Kansas

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