Kansas Jayhawker in South Carolina

Hailed in Kansas as a hero, James Montgomery moved from Ohio to Mound City, Kansas during the tumultuous border strife between Missouri and Kansas. In personal character he was resolute and self-confident, but coarse and unscrupulous. By 1857 Montgomery became the chief agitator along the border establishing himself as a leader of a local freebooter gang. They would chase proslavery settlers back into Missouri. When Missourians returned to reclaim their property Montgomery considered them claim jumpers having already sold the claims and making a handsome profit. His crimes became so numerous that territorial Governor James W. Denver dispatched U.S. Army soldiers to restore order. In 1858 Montgomery joined forces with terrorist John Brown cooperating with him on his raids of plunder and murder in Missouri. After Brown's arrest for his insurrection at Harper's Ferry, Montgomery devised a scheme to rescue Brown which ultimately failed.

While in Kansas Montgomery threatened and ran off the Federal judges attempting to hold court in the territory. Another of Montgomery ’s schemes of putting down “rebellion” was to steal ballot boxes in proslavery settlements in Kansas . He had already committed several murders against Kansas settlers regardless of their political sympathies. Another Kansas citizen wrote to Governor Denver complaining about “Montgomery and his murderers, & robbers." He believed, “If the officers of the law will arrest Montgomery and his men we will have no trouble keeping the peace among the people in this region."       

In April of 1858 Montgomery ’s gang attacked a squad of Federal troops killing two and wounding four. A month later he drove all proslavery settlers from Linn County, Kansas. When proslavery settlers retaliated Montgomery struck again going so far as to free convicted murderers from prison simply because they espoused antislavery sentiments.

Montgomery boasted, “We feed ourselves at proslavery larders and our horses at proslavery corn cribs." A. J. Hoole, who lived just outside Lawrence, remembered how Montgomery's gang treated their own neighbors. “Only last week a party of desperadoes went to a man’s house, dragged him out of bed, and gave him fifty lashes on his bare back, telling him that, if he did not leave in ten days, they would kill him. They have also threatened others in the same way…The reason they have been treated thus is because they would not join (his) band, but served on the jury in trying some of his robbers.”

During one Missouri raid Montgomery killed a citizen named David Cruse robbing him and two other men of eleven Negroes, seven head of horses, two mules, two wagons and a yoke of oxen valued at fourteen thousand dollars. The government put a $3,000 reward out for his arrest. Despite his criminal activities Kansas radicals flocked to Montgomery ’s company. Using the subterfuge of an iterant preacher Montgomery crossed the border reconnoitering wealthy Missouri farmers that would afford the best opportunity for a lucrative raid. Montgomery vowed he “would first exterminate every vestige of pro-slaveryism in Kansas , and then invade Missouri for the purpose of kidnapping and freeing slaves, murdering slave owners and destroying property.” It was before the war when William Clarke Quantrill was attacked and robbed by Jayhawkers under Montgomery. After recuperating from his wounds he joined Montgomery's band in order to discover the identities of his attackers. When Montgomery sent his gang into Missouri to rob wealthy Missouri farmer Morgan Walker Quantrill went along to revenge himself of the last of the gang who had attacked him.

Once the war started Montgomery became an officer in Lane's Jayhawker Brigade. He ordered the plunder and destruction of Butler and Papinsville , Missouri. A week later, Jayhawkers sacked and burned Columbus in Johnson County, Missouri, then ventured back into Cass County and plundered Pleasant Hill. In nearby Kingsville eyewitnesses counted over 160 houses on fire.  Later the same month Jayhawkers again struck Cass County burning 150 homes in Chapel Hill. Continuing the depredations Jayhawkers sacked Morristown near Freeman in Cass County in July killing several citizens. On September 17, Montgomery returned and burned Morristown to the ground and killed three of its citizens.

On September 23, 1861, Montgomery entered Osceola, Missouri with the Lane Brigade. There wasn’t a Confederate soldier within miles of the town. A few residents fired on the Jayhawkers, so the order was passed to shell the town. After the Union guns had reduced the town to rubble, nine male inhabitants were brought to the town square for a drumhead court-martial and shot. Most of the remaining residents were women and children. The stores, warehouses, and homes were ransacked then set on fire. Of Osceola’s eight hundred buildings all but three were turned to ashes. The plunder included 350 horses, 400 head of cattle, 200 kidnapped slaves, 3,000 sacks of flour, 500 pounds of sugar and molasses, and 50 sacks of coffee. Property losses were estimated at more than a million dollars. Three thousand people were left homeless.

Montgomery had been competing with Charles Jennison to be the leader of the first organized black regiment. Jennison’s candidacy was tainted by his brutal reputation, and Montgomery ’s criminal background worked against him. The command went to another. By December 1862 Montgomery departed the border in disgust. Heading east Montgomery became colonel of the Second South Carolina Colored Volunteers. His Jayhawking expeditions in Missouri gave him the experience he put to use terrorizing the populace by burning, raping and murdering along the South Carolina coastline. Montgomery attacked the undefended town of Darien, Georgia on June 11,1863. The town had no strategic importance. It consisted of 2,000 residents, eighty homes, five churches, a school, a hospital, twelve stores, a few mills and storehouses. First Montgomery order the shelling of the town before the residents had time to flee. Montgomery, leading his 400 Negro troops looted then destroyed the town, including the homes of the black residents. The First African Baptist Church was destroyed along with the rest of the town. What livestock that was not taken was shot down in the streets. With all the stores destroyed all means of livelihood were gone. The docks along the coast were destroyed. Also destroyed were the jail and the court house and with it all legal protection and all semblance of justice.

Robert Gould Shaw whom the North praises for leading the Negro troops of the 54th Massachusetts Regiment aptly portrayed in the contemporary movie, Glory, took part in Montgomery's destruction of Darien. Shaw called the raid a "Satanic action". In a letter to his family that he asked not to be made public Shaw relates the decision he had to make: whether to report Montgomery's crimes or remain silent. "Remember not to breathe a word of what I have written about this raid, for I have not yet made up my mind what I ought to do. Besides my own distaste for this barbarous sort of warfare, I am not sure that it will not harm very much the reputation of black troops and of those connected with them....After going through the hard campaigning and hard fighting in Virginia, this makes me very much ashamed of myself. There are two courses only for me to pursue: to obey orders and say nothing, or to refuse to go on any more such expeditions, and be put under arrest, probably court-martialed, which is a serious thing." History will attest that the North made a martyr of Shaw despite the fact that he made a self-serving decision rather than the moral and honorable one.

The day after the destruction of Darien, General David Hunter, Montgomery's commanding officer was relieved of command. Lincoln removed him not only for the destruction of Darien but for earlier raids and burnings of towns in similar circumstances. Montgomery was left to idle when in September 1864, he resigned his commission and returned to Kansas. He ended his military career as colonel of the 6th Kansas Jayhawker Regiment that saw action in October against Confederate General Sterling Price at the Battle of Westport.  

Article by: Paul R. Petersen - Author of Quantrill of Missouri, Quantrill in Texas, Quantrill at Lawrence and Lost Souls of the Lost Township.     

Below is wedding photo of James Montgomery and his wife. You see how thrilled she is now that she has realized that she is married to the Jayhawking monster.                       




References: Castel, Albert E. A Frontier State at War: Kansas 1861-1865

The Letters of Lieut. Col. A. J. Hoole, Kansas Collection, Kansas Historical Quarterlies, May, 1934, vol. 3, No. 2, pg 145–171

Spencer B. King, Jr., Darien - The Death and Rebirth of a Southern Town.                        

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