Monthly Archives: November 2021

“Bushwhackers” and “Jayhawkers” Terrorized Jefferson County during Civil War 

Kansas and Missouri Guerilla Fighters Fought for Revenge

During the Civil War, a three-tiered suspension bridge (pictured) was built by U.S. Army engineers over the Meramec River near the site of today’s Arnold City Park. One of the first three-tiered suspension bridges ever constructed, the purpose of the bridge was to allow Union cavalry from Jefferson Barracks to reach Confederate encampments in Jefferson County and throughout Missouri. In reality, though, the bridge also was frequently crossed by notorious “Bushwhackers” and “Jayhawkers” galloping through Jefferson County to conduct brutal guerilla warfare.

Clint Eastwood’s movie “The Outlaw Josey Wales” reflects accurate encounters between Kansas “Jayhawkers” – also known as “Red Legs” – and is based on true experiences of Missouri “Bushwhacker” Bill Wilson (pictured) during the Civil War.

In the movie, Kansas “Red Legs” burn down Josey Wales’s farmhouse and barn, killing his wife and son. Southern sympathizer Josey Wales decides to kill as many “Jayhawkers” and Union sympathizers as possible.

The real Bill Wilson, like Eastwood’s Josey Wales, was a farmer in rural Missouri. He was wiry and trim like Eastwood, standing taller than six feet.

Like Josey Wales, Wilson always carried two 1847 Colt Walker .44 caliber revolvers in a twin holster. He was known to practice pistol shooting while riding a horse. In the movie, Josey Wales is a deadly straight shooter galloping on horseback.

Hollywood Bushwhackers

Hollywood has taken many liberties portraying Missouri “Bushwhackers” in movies, beginning in 1939 with two films about Civil War “Bushwhacker” Jesse James (pictured), who became a post-war outlaw.  The first movie starred Tyrone Power and Henry Fonda in serious, dramatic roles. In the other, cowboy singing star Roy Rogers and sidekick Gabby Hayes enjoy a rooting-tooting romp.

John Wayne (pictured in black hat) won an Oscar for portraying “Rooster” Cogburn as a Missouri “Bushwhacker turned U.S. marshal in the 1969 movie “True Grit.” Nobody forgets Rooster holding horse reins in his teeth at full gallop, guns blazing in each hand. Actor Jeff Bridges (pictured in khaki hat) played “Rooster” in the 2010 “True Grit” remake, said to be more authentic than the original because the script was based on real 1870s dialogue.

Yet no Hollywood movie can accurately portray the hellish brutality that Kansas “Jayhawkers” and Missouri “Bushwhackers” unleashed on their enemies and innocent homesteaders. Missouri was initially settled mostly by Southerners traveling up the Mississippi river.

Many brought slaves with them. Missouri entered the Union in 1821 as a slave state after Congress voted to make slavery illegal in most territories, except Missouri. This state was dominated by Unionists, not Confederates, because thousands of new immigrants came from Germany and other nations where slavery was not tolerated – most European settlers in Missouri were Unionists. Civil War guerillas were generally not enlisted in the military forces on either side but, like ‘Bushwhacker’ Bill Wilson, were farmers brutalized by Union soldiers or by “Jayhawkers.”

Vernon County’s Historical Society reports: “Most were citizens fighting the only way they knew how to protect their homes and families. Some were outlaws using war as an excuse for violence. The term ‘Bushwhacker’ was probably a consolidation of ‘ambush,’ defined as ‘a surprise attack from a concealed position’ and ‘whack,’ meaning to kill someone.”

“Bushwhacker” Bill Wilson

In summer 1861, Union soldiers ransacked Bill Wilson’s Edgar Springs home, abused his family, then set fire to the house, barn, and outbuildings. The Fannin County, Texas, Historical Commission reports:  “Bill moved his family to a one room cabin at his mother’s farm and started his quest as a Missouri ‘Bushwhacker.’

Sometimes disguised as a Union soldier, sometimes alone, sometimes with other ‘Bushwhackers’ (Arch Clements, Dave Pool, and Bill Hendricks pictured), Wilson was always lethal.  When alone, he claimed to have three friends with him: His best horse and two .44 caliber six shooters. He frequently practiced with his pistols from the back of a horse.”

One day, Wilson learned that four Union soldiers were looking for him.  He knew the trail they had to take to their encampment, so he rode fast through woods, arrived at the trail, and waited. When they approached, he drew both revolvers, shooting and killing all four men.  He left four dead bodies on the trail and rode away leading four government horses.

When another “Bushwhacker” – Jim Deem – was killed by Union soldiers, Wilson shaved his beard and hid near the Deem home. The “beardless disguise” was his edge. Soldiers came by the next day, asking if he had seen Bill Wilson. “You’re looking at him,” came the reply, followed by Wilson’s pistol blasts as he killed the four men, keeping their horses.

Often, Wilson would follow a Union supply wagon train. When the teamsters camped for the night, he would charge in on horseback, pistols blazing, killing every man he could as others fled.

After the war, Wilson moved to Texas with a troop of men (including Jesse and Frank James) who had served as Quantrill’s Raiders. Until William Quantrill’s death from battle wounds in 1865, Quantrill’s Raiders were Missouri’s biggest, most terrifying “Bushwhacker” group. The anti-slavery town of Lawrence, Kansas, outlawed them and jailed some of their young women. In August 1863, Quantrill led an attack on the town, killing more than 180 residents and burning down most of its buildings.

Jesse and Frank James eventually returned to Missouri to become violent outlaws. In McKinney, Texas, Wilson was seen by two thieves as he sold a wagonload of apples, getting paid in cash. They followed Wilson, shot him dead, stole his money, then buried him. Wilson’s body was reportedly moved to Edgar Springs, 120 miles southwest of Arnold. Clint Eastwood’s movie “The Outlaw Josie Wales” has many parallels to “Bushwhacker” Bill Wilson’s life, and a revealing surprise near the end when a man tells two officers that Josie Wales’s real name is “Mr. Wilson.”

Bushwhacker Sam Hildebrand

“Bushwhacker” Sam Hildebrand’s family, including his brother Frank, lived 35 miles south of Arnold near the Big River in St. Francois County, before Sam killed and plundered his way across Missouri and southwest Illinois.

Sam and brother Frank were southern sympathizers that Kansas “Jayhawkers” wanted dead, so Sam and Frank began hiding in deep woods near their Big River homestead. In October 1861, Yankee vigilantes discovered Sam as he gathered supplies, yet he escaped into the woods. The next day, Sam moved his family to Flat River farther south in St. Francois County, but Frank was captured and lynched by the Big River Mill Vigilance Committee. In April 1862, vigilantes from Ironton ambushed Hildebrand at his Flat River cabin, shooting and wounding him. Sam escaped to the woods as vigilantes ordered his family from their cabin, burning it down with everything they owned.

In his autobiography, published in 1870, he wrote: “As I lay in that gully, suffering with my wounds inflicted by United States soldiers, I declared war. I determined to fight it out with them, and by the assistance of my faithful gun ‘Kill Devil,’ to destroy as many blood-thirsty enemies as I possibly could.”

“Kill Devil” was Hildebrand’s rifle. Whenever he killed someone, he notched the wooden butt. Some historians believe “Kill Devil” was a Spencer .52 caliber carbine or a .44 caliber Henry repeating rifle. Union calvary used both models in the 1860s.

Hildebrand soon visited Confederate General Jeff Thompson in Bloomfield. Thompson allegedly gave Hildebrand a Major’s commission saying, “Go where you please, take what men you can pick up, and fight on your own.” Hildebrand began recruiting masters of stealth, reconnaissance, and disguise for dressing as women or Union soldiers to sneak into camps and towns using rifles, pistols, Bowie knives, and firebombs to kill unsuspecting foes.

Hildebrand’s bloody exploits are chronicled in books including “Samuel S. Hildebrand: Renowned Missouri ‘Bushwhacker,” which he dictated to a pair of newspapermen in 1869. The authors made the illiterate Hildebrand look like a folk hero.

“In their memoirs, ex-guerillas cleanse their histories,” notes author Michael Fellman in his book “Inside War: The Guerilla Conflict in Missouri During the American Civil War.”

“They insist that they always acted exclusively in self-defense, that they avenged personal wrongs personally…and came to the aid of the weak and the downtrodden.”

Yet Hildebrand’s favorite solo tactic was to hide outside Yankee farmhouses early in the morning and, as family members emerged, pick them off with “Kill Devil” like shooting possums in the yard.

In May 1865, Hildebrand and five “Bushwhackers” began a rampage in Jefferson County. Between May 12 and May 17, they raged in Jefferson, Iron, St. Francois, Washington, and Madison counties, killing, robbing, and firebombing in Missouri and southwest Illinois. Hildebrand’s hideouts were caves in Jefferson County and St. Francois County. He kept robbing and killing Yankee sympathizers for seven years after the war ended in 1865.

On March 21, 1872, Constable John H. Ragland in Pinckneyville, Illinois, killed Hildebrand. Ragland was told by farmers that three bandits camped near Pinckneyville were committing brutal attacks and thefts. Ragland and two deputies rode to the camp and dismounted, surprising the outlaws at their campfire. Hildebrand tried to escape by stabbing Ragland with a Bowie knife, but Ragland shot him in the head. The body was taken to Pinckneyville where it was identified by the two men captured with him.

Buried in Illinois, Hildebrand’s body was later moved to Hampton Cemetery in Park Hills, St. Francois County, where he rests today.

President Lincoln

During the war, nearly 110,000 Missourians served in the Union Army and at least 40,000 in the Confederate Army. Many others joined pro-Confederate “Bushwhackers” or pro-Union “Jayhawkers.” It’s impossible to know accurate numbers of those guerillas in Missouri; some estimates range from 3,000 to 5,000.

Michael Fellman writes: “President Lincoln had long believed that bad men and badness in mankind had caused the strife in Missouri society and that Christian forbearance ought to pave the way for a social cure. Lincoln’s advice to every succeeding general and political figure in Missouri was that all good men ought to come to their senses.”

In a letter to Unionist Missouri Governor Thomas C. Fletcher, Lincoln wrote: “It seems that there is no organized military force of the enemy in Missouri and yet that destruction of property and life is rampant everywhere. Is not the cure for this within reach of the people themselves? It cannot but be that every man, not naturally a robber or cutthroat would gladly put an end to this state of things…And surely each would do this but for his apprehension that others will not leave him alone. Cannot this mischievous distrust be removed?”

Lincoln was exhausted when an angry Southern sympathizer appeared behind him on April 14, 1865, at Ford’s Theater in Washington, D.C., shooting the weary President in the head and silencing him forever.

Article by Jeff Dunlap for the City of Arnold

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