James Montgomery was twenty years Jennison’s senior. He was born in Ashtabula County, Ohio, and moved to West Liberty, Kentucky, in his early twenties, where he taught school and became a minister in the evangelical Disciples of Christ—often referred to as the “Campbellite”—denomination. His first wife died, after which he married the daughter of a slave owner. While in Kentucky, he purchased a large plot of timberland, then built and operated a sawmill on the Licking River until several floods washed out his operation. In 1851, he sold his timber business and moved his family to eastern Missouri. In 1854, shortly after the passage of the Kansas-Nebraska Act, he landed in Mound City, Kansas. By the time Montgomery arrived in Mound City, he was a radical abolitionist. He was constantly harassed by pro-slavery settlers, who burned his house when he refused to leave the area. He responded by building a new house that was nearly impregnable, which he dubbed “Fort Montgomery.” Soon he became the leader of like-minded antislavery settlers called the “Self-Protective Company,” who retaliated against the pro-slavery Border Ruffians.228
James Montgomery. Kansas State Historical Society.
Of all the free-state military leaders, James Montgomery might well have been the most skilled and the most clever in guerrilla tactics. He never read nor heard of the ancient Chinese classic—Sun Tzu’s The Art of War—which inspired twentieth-century guerrilla leaders like Mao Zedong and Ho Chi Minh, but he understood and practiced Sun Tzu’s principles as if he carried a copy with him into his engagements. “Let your plans be dark and impenetrable as night,” Sun Tzu wrote, “and when you move, fall like a thunderbolt.” This was Montgomery’s strategy, and his men followed him without question because he intuited another piece of Sun Tzu’s advice to “treat your men as you would your own beloved sons. And they will follow you into the deepest valley.”
Montgomery’s tactics included harassing pro-slavery settlers on both sides of the border between Kansas and Missouri, ridding the area around Mound City of pro-slavery settlers, and seeking revenge for Border Ruffian incursions into southeastern Kansas. In 1856, the notorious pro-slavery leader, George W. Clarke, led some four hundred men on a sweep of Linn County—where Mound City was located—in which they “plundered, robbed, and burned out of house and home nearly every Free-state family in Linn County, while [Clarke’s] hands were steeped in innocent blood, and the light of burning buildings marked his course.”229 To get even, Montgomery went into the area in Missouri purported to be Clarke’s headquarters, claiming to be an unemployed teacher. He was hired for a teaching post, and from that position, he pieced together the names of twenty of Clarke’s associates. After several weeks, Montgomery, the teacher, mysteriously disappeared, but then reappeared later as Colonel Montgomery, leading his Self-Protective Company. He and his men systematically visited each of the twenty Border Ruffians on his list and took each man’s money, horses, cattle, weapons, and anything else of value, and rode back to Kansas.230
When “Doc” Jennison joined forces with Montgomery, it was—in many ways—like mixing oil with water. True, both men were passionate in their desire to eradicate the institution of slavery, but otherwise they were quite different. Montgomery was a teetotaler; Jennison drank heavily. Montgomery never swore, and chastised any of his men who did; Jennison often cursed a blue streak. Montgomery tried to restrain his men from excessive violence; Jennison often encouraged more violence. Not surprisingly, the two men eventually had a parting of the ways.
In November 1860, Jennison and his men captured Russell Hinds, a slave hunter operating in Missouri and Kansas. There was no question that Hinds made his living tracking down runaway slaves and returning them to their owners to make his living; there also was no question that what he was doing was not only legal, but sanctioned by the US Constitution and the Fugitive Slave Act of 1850. But Jennison wanted to use Hinds as an example to scare slave hunters out of Kansas, so the Jayhawkers tried Hinds in a kangaroo court, sentenced him to death, and hanged him. Montgomery probably disagreed with Jennison’s way of dealing with Hinds, but he begrudgingly conceded that Hinds was “worth a great deal to hang but good for nothing else.” Eventually the breach between Jennison and Montgomery was complete; in 1862, Montgomery said the doctor was “an unmitigated liar, black-leg and Robber.”231
Although Montgomery and Jennison were most commonly associated with Jayhawkers, James Lane managed to have his name connected with them as well. Lane had kept a low profile for several years, settling into his law practice in Lawrence. After he was introduced to Abraham Lincoln during his visit to Kansas, however, Lane became a staunch supporter of the future president. Whether from his encounter with Mr. Lincoln, or whether the political bug bit him again, Lane soon re-entered the political arena, and when Kansas was admitted to the Union in 1861, he successfully campaigned and won the election in the new state legislature to the US Senate.232
When Lane arrived in Washington as a senator, he quickly ingratiated himself to the new administration by recruiting a security force called the “Frontier Guard” to protect the president and the Executive Mansion. For his efforts, Lane was authorized to raise and command two regiments in Kansas. He accepted the offer, but he did not officially accept the rank of brigadier general, with concerns that it might force him to resign from his Senate seat.233
In several speeches before the Senate, Lane made it clear how he intended to prosecute the war on the Kansas-Missouri border. In a speech before the Senate, he said “that the effect of marching an army on the soil of any slave State will be to instill into the slaves a determined purpose to free themselves.” He continued, “I do not propose to make myself a slave catcher for traitors and return them to their masters.”234 Lane made it clear that freeing as many slaves as possible would constitute a significant part of his strategy and tactics.
When Senator Lane arrived back in Kansas with the commission to raise two regiments, he started recruiting volunteers who came to Fort Leavenworth for training. Enough men showed up—about two thousand—to form the 3rd, 4th, and 5th Kansas Volunteer Regiments. He moved his base to Fort Scott and decided that his strategy would be to harass Confederate forces and pro-slavery sympathizers in the border area. On September 2, 1861, Lane and a contingent of six hundred of his cavalry met Confederate Major General Sterling Price’s and Brigadier General James S. Rains’s substantially larger force near Fort Scott in an engagement near Big Dry Wood Creek. Although Lane and his men surprised the Confederates, the latter’s numerical superiority soon determined the encounter’s outcome. They forced Lane’s men to retire and captured their mules.235
Next, Lane decided to move against Osceola, purported to be a Confederate stronghold, as well as the home of Waldo P. Johnson, a US senator from Missouri who would soon be expelled from his Senate seat for his support for the Confederates. Lane’s brigade attacked Osceola on September 22–23, 1861. The attack, more appropriately called the Sacking of Osceola, was important—not because it was a major or significant strategic battle, but rather because of how it was later interpreted. There is no question that the Jayhawkers attacked Osceola, that they freed and took some slaves with them, that they burned parts of the town, that they inflicted some casualties, that they captured some military supplies stored there, and that they consumed, stole, and destroyed a certain amount of liquor, salt, bacon, and other commodities. These were the facts of the raid.
On the rumor side of the story, the Confederates reported that three hundred Jayhawkers were so drunk that they had to be carted out of town in wagons. Between one thousand and two thousand residents were driven out of town, and over one hundred buildings were burned. Lane and his men stole thousands of dollars in cash and valuables. James Lane alone was reported to have stolen a piano, silk dresses, and other valuables. The story seemed to get bigger and bolder with each telling. But the real significance that transcended the stories was that Osceola was a civilian—not a military—target, which played into the hands of secessionists and secessionist sympat
hizers. They condemned the attack as an act of barbarism. Osceola became a symbol and an excuse for Confederate soldiers and guerrillas to attack their military or nonmilitary targets in the border areas with brutality. Eventually, the attack on Osceola would have a direct impact on Lawrence. Two years later, when William Clarke Quantrill led his guerrilla band into Lawrence, he and his men were reported to have shouted “remember Osceola” as they ransacked the town. Their main objective was to find and kill James Lane.
Union leaders were upset by Lane’s actions as well. Union Major General Henry Halleck wrote that “the course pursued by those under Lane and Jennison has turned against us many thousands who were formerly Union men. A few more such raids will make this State unanimous against us.”236
Since Lane had received his military authority directly from the Lincoln Administration, he took this as a license to act independently, often to the consternation of Union commanders. Whereas Union generals had difficulty controlling Lane, they did their best to manage “Doc” Jennison and his Jayhawkers. He was given his opportunity when Kansas Governor Robinson recommended him to Major General John C. Frémont for a commission. Frémont was the Commander of the Department of the West. His abolitionist views were in line with Jennison’s, so he appointed Jennison as commander of the 7th Kansas Cavalry. Daniel Anthony, Susan B.’s brother, and a member of the first Emigrant Aid party to Kansas, was second in command. John Brown Jr., who as the name implied was the eldest son of his namesake, joined the regiment and recruited a number of abolitionists from Ohio into the ranks.237
Jennison’s Seventh Cavalry was assigned to protecting Union wagon trains in the border area. If Confederates attacked the wagons they were assigned to protect, Jennison and his men quickly retaliated. As with Lane’s men at Osceola, they often attacked civilian rather than military targets. They burned the areas around Pleasant Hill, Dayton, and Columbus in Missouri, stole livestock, freed slaves, and generally wreaked havoc everywhere they went. President Harry S. Truman often told the story that Jayhawkers attacked his family’s farm near Independence, Missouri, stole the family silver, killed and butchered the hogs, and burned the barn full of hay.238 His mother, who suffered during the war as a Confederate sympathizer, was reported to have refused to sleep in the Lincoln Bedroom the first time she visited her son in the White House because it reminded her of the Yankee soldiers.
In part because the 7th Kansas stirred up so much resentment, the regiment was ordered into camp in Humboldt, Kansas, at the end of January 1862, and then to Lawrence at the end of March. At that point, Colonel Jennison chose to (or was forced to) resign as commander.239 With Jennison’s departure, Daniel Anthony was elevated to regimental commander. Because Jennison and his men had made such a nuisance of themselves and had stirred up so much resentment in western Missouri, the regiment was sent to Rienzi, Mississippi, where it arrived on July 23, 1862, to help shore up the Union forces near Corinth, Mississippi. On its journey south, and before the Seventh arrived in Mississippi, Colonel Anthony was removed as commander. While stationed in Tennessee on the way to Mississippi, Anthony issued an order that if any of his officers or men did anything to assist in the capture and return to slavery of any fugitive slave, he would be severely punished. Since he did not have the authority to issue that order, he was dismissed.240 Stephen Z. Starr, author of Jennison’s Jayhawkers, concluded that “no other regiment in the Union army had so bad a reputation” or “worked so diligently to deserve it” as Jennison’s Jayhawkers.241
The Seventh remained in the Mississippi/Alabama/Tennessee region through most of the remainder of the war. Other volunteers from Kansas joined, including a seventeen-year-old who joined in 1863 as a teamster. He already had more adventures under his belt than most men of his era would experience in a lifetime—prospecting for gold in Idaho and riding for the Pony Express. This young man would remain in the Seventh for the remainder of the war and go on the great fame and fortune afterwards. His name was William—later Buffalo Bill—Cody.
The Jayhawkers were fierce fighters. But Union leaders faced the constant challenge of trying to control them. Major General Henry Halleck tried to implement a two-pronged strategy. On the one hand, he marshaled the forces under his control to rid Missouri of Confederate soldiers. Union Brigadier General Samuel R. Curtis successfully drove the Confederates out of Missouri. Then on March 6–8, 1862, he won an important victory at Pea Ridge in northwest Arkansas. Curtis and his troops were outnumbered, but they defeated the Confederates under the command of Major General Earl Van Dorn in this two-day battle. This part of Halleck’s strategy worked well.
The second part of Halleck’s plan was to do everything in his power to keep Missouri in the Union and to remove any reason for its fence-straddling citizens to side with the Confederate cause. This strategy was much more difficult to implement because he had such a difficult time keeping the Jayhawkers from raiding across the border into Missouri. Dealing with Lane’s three regiments was complicated because of Lane’s political clout. But while Lane was in Washington, fulfilling his senatorial duties, Halleck moved quickly and placed Major General David Hunter in charge of all Union forces on the border area, including Lane’s three regiments. When he found out what Halleck had done, Lane returned to Kansas in January 1862 and tried to wrest control of his brigade from Hunter. He also offered to resign his Senate seat if he was granted the rank of major general and given command of a force of thirty thousand men to raid the South and free as many slaves as possible. He was neither given the command to execute his grandiose scheme nor was he able to regain control of his brigade. With Lane in check and with the 7th Kansas Cavalry out of the region, Halleck started making progress on the second part of his plan.
Halleck continued with his strategy, and in February 1862, he sent a letter to Hunter, asking him to “keep the Kansas troops out of Missouri.” If Hunter did so, he (Halleck) promised “to keep the Missourians [meaning Confederates] out of Kansas.’’242 To further emphasize his intentions, in March Halleck wrote to Secretary of War Edwin Stanton: “I will keep them [the Jayhawkers] out of Missouri, or have them shot.”243
Foiled in his plan to lead a conquering army through the South, Lane returned to his Senate seat in Washington, DC, later in 1862. While there, John Speer, who was visiting at the time, reported that while walking down Pennsylvania Avenue, Lane casually mentioned that he had just received authorization to recruit three regiments of white and two regiments of colored soldiers. “When I asked in amazement to see the order to enlist colored troops,” Speer reported, “he informed me that it was a verbal promise from the President, that he [Lane] would see that they were clothed and subsided until such time as they could be brought into line, armed and equipped for battle.”244 There is no way to know if, indeed, President Lincoln gave Lane any such directive. Lane was a clever operator, and with this new “authority,” he enlisted James Montgomery to help, and he recruited former slaves who escaped to Kansas and slaves freed by the Jayhawker incursions into Missouri into a full regiment under the command of Captain James M. Williams. They were clothed and fed, and armed with Austrian and Prussian rifles and bayonets. Lane was careful to make sure everyone understood that his African American regiment was identified as a band of “laborers.”
Flag of First Kansas Colored Troops. Kansas State Historical Society.
Very quickly, Lane’s 1st Kansas Colored Volunteer Infantry was converted from “laborers” to soldiers. In October 1862, the 1st Colored Regiment was sent into Missouri in search of a large contingent of pro-Confederate guerrillas that were reported operating in Bates County. The regiment was accompanied by the 5th Kansas Cavalry, serving as scouts. On October 29, they found the guerrillas in an area called Island Mound. The bushwhackers—a term used interchangeably with guerrillas—knew the African American soldiers were in the area and were itching for a fight. By most accounts, the guerrillas outnumbered the 1st Colored Regiment—400 to 240. In Civil War military parlance, the engagement w
as not large enough to be called a battle but rather a skirmish. It probably would have gone unnoticed except it was the first engagement between black Union troops and Confederates, and, more importantly, although outnumbered, the African American soldiers won the engagement.245 Union casualties were minimal and the number of Confederate casualties was not known. In the following days, the skirmish at Island Mound drew national media coverage.246
Through the remainder of the war, the 1st Kansas distinguished itself in several battles. On July 17, 1863, the regiment was involved in the Battle of Honey Springs in Oklahoma (Indian Territory), which was the largest and perhaps the only battle in which whites were in the minority on both sides. The 1st Kansas, along with several contingents of American Indian soldiers on the Union side, fought mostly American Indian regiments on the Confederate side. The 1st Kansas was instrumental in the Union victory. A year later, on April 18, 1864, the 1st Kansas was nearly annihilated in the Battle of Poison Spring in Arkansas. The Union Army had discovered and captured a supply of corn held by the Confederacy. As the Union soldiers were transporting the corn, loaded in about two hundred wagons, they were ambushed by the Confederates. Colonel Williams placed the 1st Kansas between the wagons and the Confederate attackers. The 1st Kansas successfully repulsed two Confederate charges, but ran short of ammunition and tried to retreat. Nearly half of the regiment—almost 250—was captured. Rather than taking the black soldiers as prisoners, the Confederates murdered, mutilated, scalped, and stripped all who surrendered.
Although technically not Jayhawkers, to James Montgomery and James Lane, African American soldiers were as important in winning a Union victory as any white soldiers. In December 1862, after Montgomery assisted Lane in recruiting black soldiers, he was offered an opportunity by David Hunter to relocate to South Carolina to recruit, train, and lead African American soldiers there. Hunter was reassigned to a command in the Department of the South, and he was anxious to recruit former slaves to fight for the Union cause.247 Thomas Wentworth Higginson was given the command of the 1st South Carolina (African Descent) and Montgomery was placed in charge of the 2nd South Carolina regiment. Montgomery successfully recruited soldiers in Florida, Georgia, and South Carolina, but he was often criticized for his tactics, which not surprisingly resembled similar methods he had implemented with his Jayhawkers in Kansas.
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