John Thrailkill Confederate Guerrilla Leader & Escaped Prisoner of War!

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The officers of quantrillsguerrillas.com are pleased to make available to our members a short profile of some of the brave men that rode with Colonel William Clarke Quantrill during the Border Wars during the Civil War. This is a service we take pride in but surprisingly we have discovered that every one of the histories that have been offered for the last several months share a common thread throughout their narratives and that is an account of cruelty and brutality from wanton attacks by Kansas Jayhawkers and Union officials before, during and after the war. Like other young men who chose to defend Missouri's right of sovereignty over the dictates of a central government the family of John Thrailkill suffered intolerably. Take a moment to look at the image below of the jaunty John Thrailkill.                                                                           

John Thrailkill was a six foot tall, twenty-three year old from Oregon in Holt County, Missouri. He first enlisted as a captain in the 1st Regiment, Missouri Cavalry, known as Gordon's Regiment, in the Missouri State Guard under General Sterling Price. Thrailkill was in charge of the skirmishers and sharpshooters in the command. The 1st Cavalry Regiment was formed during the summer of 1861. Many of its members had served with the Missouri State Guard. The unit fought at Elkhorn Tavern, then moved east of the Mississippi River and was dismounted. Many members of the regiment left with the understanding that they did not enlist in order to fight outside their native state.

Thrailkill was of Russian descent and known as a quiet, unassuming painter from northwest Missouri. He was born around 1838 in Livingston Co. and orphaned at a young age and living with a relative in Andrew County when the war broke out, He was destined to play a legendary role in the Civil War taking part in the most important battles and hairbreadth escapes. Thrailkill's relative's homes and possessions were burned out by Federals during the war. His friends and neighbors also suffered similar fates. When the war started he was engaged, but on the eve of his wedding, a militia patrol of twenty Federals rode to the bride’s home and killed her fifty-year-old invalid father on the doorstep in front of his daughter. As a result of this brutal assault she suffered an emotional breakdown and died shortly afterwards. To avenge her Thrailkill joined Quantrill, but not before making a solemn vow at his sweetheart’s grave: “Blood for blood; every hair in her head shall have a sacrifice.” Thrailkill eventually killed eighteen of the twenty men who caused his fiancée’s death. Thereafter Thrailkill became known as a ruthless killer all over Northern Missouri. Following this he became a guerrilla leader under Quantrill. It was said his only home was in the saddle.

During his illustrious career Captain Thrailkill fought in the battles of Carthage , Wilson ’s Creek, Dry Wood Creek, Lexington; Pea Ridge, Arkansas, Fayette, Centralia and several lesser engagements. He was captured on July 18, 1863 in Clinton County while on a recruiting mission and sent to the Myrtle Street Prison in St. Louis. Rather than take the oath of allegiance Thrailkill proudly boasted, “I am not ashamed to say that I am a Rebel and if I am shot in the defense of my country I will die in a glorious cause. And if I live through, I will never be ashamed to own up to the fact that I have been in the Rebel ranks.” For his patriotism he was then transferred to the Gratriot Street Prison in St. Louis before being transferred again to the Alton Military Prison, 25 miles away on the Mississippi River in Illinois.

Prison life was harsh and cruel. Gratiot was more of a clearing house for POWs in the Trans-Mississippi. Prisoners who were held a long time at Gratiot were officers who had been caught recruiting behind the lines, or engaging in other such illegal activities, spies, smugglers, and political prisoners. Many prisoners were sent on to Camp Douglas in Chicago or Camp Chase or were sent east for exchange and return south until exchanges were halted. In November 1862, Gratiot Street prison had 960 prisoners, many without bunks, when it’s maximum capacity was around 500 prisoners. The quarters were described as “a very dark, gloomy place, and very filthy besides.” The prison had a dungeon described as “the darkest pit of the prison,” and “a damp unhealthy hole, with a strong offensive smell.” The prisoners found that the Gratiot Street prison was a hard place and the “fare so rough, it seems an excellent place to starve.” In March of 1863 smallpox broke out among the prisoners causing them to wonder that “every disease under heaven does not break out in the lower quarters, half starved and crowded together as they are in dirt and rags.” In April two physicians were appointed by the Sanitary Commission and declared the prison to be a disgrace “to us as a Christian people. In these rooms the prisoners spent day and night, for the small yard of the prison is scarcely sufficient to contain a foul and stinking privy.... it is difficult to conceive how human beings can continue to live in such an atmosphere as must be generated when the windows are closed at night or in stormy weather. Here were persons lying sick, with pneumonia, dysentery and other grave diseases awaiting admission to the hospital.”

At the Alton Military Prison over 11,764 Confederate prisoners would pass through the gates. The prison was built in the style of a fortress, made of stone with walls 30 feet high. Initially the prison held 24 cells. The size of these cells has been determined to be 4 feet wide by 7 feet 4 inches long. Reports indicate there were 3 men in each cell. Of the four different classes of prisoners housed at Alton, Confederate soldiers made up most of the population. Citizens, including several women, were imprisoned here for treasonable actions, making anti-Union statements, aiding an escaped Confederate, etc. Others, classified as bushwhackers or guerrillas, were imprisoned for acts against the government such as bridge burning and railroad vandalism. While in the Alton prison, Thrailkill fared no better. Conditions in the prison were harsh and the mortality rate was above average for a Union prison. Hot, humid summers and cold Midwestern winters took a heavy toll on prisoners already weakened by poor nourishment and inadequate clothing. The prison was overcrowded much of the time and sanitary facilities were inadequate. Pneumonia and dysentery were common killers but contagious diseases such as smallpox and rubella were the most feared. The prison was so bad that it had been condemned two years prior to the war and it too had an epidemic of smallpox in 1863. Overcrowding in the prison made the disease impossible to control or eliminate. A prisoner's diary complained that "This is a much harder place than Gratiot-it is almost impossible to sleep on account of the rats, which run over us all through the night. There is much sickness, the small-pox is prevailing, and many are dying daily." Records indicate 1,613 deaths, but other estimates place the total as high as 5,000.

On June 10, 1864 Thrailkill managed to escape from the Alton Military Prison and return to Missouri and rejoin Quantrill where he commanded a group of guerrillas while maintaining he was a regular Confederate officer. Captain Thrailkill operated in numerous missions with Quantrill’s men namely those with Lieutenant Fletcher Taylor with Frank and Jesse James. Thrailkill was with Fletcher Taylor when they were ambushed and where Taylor lost his right arm by a blast from a double-barreled shotgun on August 4, 1864 near Missouri City along the Missouri River in Jackson County. The militia reported that they also wounded Captain John Thrailkill in the head, but if so it was a slight wound as Thrailkill continued in the saddle leading the guerrilla's advance.

In the fall of 1864 Thrailkill had only 16 men in his command but was known throughout the border as a desperate fighter. As the guerrilla bands began to head towards Boonville to meet up with General Price on his invasion of Missouri Thrailkill was in charge of the advance scouts under Captain George Todd as they made their way across the Missouri River on September 13, 1864. Three days later they engaged a militia company in Ray County. Leading George Todd’s advance, Thrailkill’s company often skirmished with Federal militia. George Todd had forty men along with Captain Dave Poole’s thirty men. They made a long-range patrol through the counties east of Kansas City and toward Howard County, where they knew Quantrill was staying and waiting for their arrival. With Todd and Poole Thrailkill attacked the Federal garrison in Tipton and killed its garrison of forty militiamen. Leaving Moniteau County, the guerrillas next raided the town of Boonville in Cooper County eliminating Federal resistance prior to Price's arrival.

During the skirmishing the guerrillas lost some of their best fighters. Riley Crawford was shot from his saddle by a load of “buck and ball” fired by a militiaman in ambush from a fence corner along the Lamine River. Not yet seventeen years old, Riley had witnessed the hanging of his father and the murder of his two sisters by Federal troops. Because of his youth, Riley’s death was much lamented by his fellow guerrillas. In revenge, they fought ferociously, and the result of their raiding soon claimed 114 Federal militiamen killed and 80 horses captured, 50 recruits gathered up, and half a million dollars of Federal property destroyed.

Following the guerrillas disastrous setback where they were repulsed by the small Federal garrison at Fayette on September 20, Thrailkill headed east with Todd and Captain Bill Anderson where they camped outside the little town of Centralia. Unbeknownst to the guerrillas Maj. A. V. E. Johnson, in command of the Thirty-ninth Missouri Militia, mounted around 155 men and were in the saddle looking for the guerrillas. Johnson’s advance scouts ran into Anderson’s company around noon on September 26, 1864. Anderson, not wanting to bring on an attack, slipped into the darkness just outside Centralia. He rejoined George Todd’s command along with John Thrailkill’s and other small guerrilla units camped on the Singleton farm four miles south of Centralia. Here they gathered with a combined strength of more than 225 men. The guerrillas had just received word of Sterling Price’s reentry into Missouri with twelve thousand troops.

That day the sky was blue with the chill of early fall in the air. The ground was covered with prairie grass, long and coarse, bending in the afternoon breeze. Major Johnson's men had followed a group of Anderson's men back towards their camp. Todd ordered his men to saddle up. The outcome of the battle was determined before the action began. The guerrilla warriors sat their horses, armed to the teeth. Many were only teenagers but still veterans of numerous battles the North called massacres because of the overwhelming death toll the guerrillas inflicted on the enemy. The men under Captain John Thrailkill threw down a fence and advanced along a small creek branch to the west of their camp. To the left of the little branch rode the commands of George Todd and Silas Gordon. Bill Anderson was assigned the center of the battlefield. David Poole arranged his men behind Anderson, slightly overlapping his line. The only guerrillas visible to Johnson was Anderson’s company. When Anderson saw that the others were in place, he waved his hat three times as a signal. Poole’s and Thrailkill’s forces soon appeared. Anderson’s company was on line and began a slow walk toward the enemy. It was four o’clock in the afternoon. The sun was beginning to set, and the guerrillas knew that they must make short work of the fight ahead of them. Jesse James had a watch and timed the fight. In exactly five minutes 123 of Johnson's men including Johnson were dead upon the battlefield.

Following Centralia, Thrailkill undoubtedly continued aiding General Price in his invasion of Missouri as he headed towards Kansas City taking part in the 2nd Battle of Independence and the Battle of Westport and he continued to ride with General Price as he pulled his forces back south into Texas. When the war ended Thrailkill went to Mexico with Gen. Joseph O. Shelby and joined with the dictator Porfirio Diaz. Diaz was probably the only dictator to improve his country. Diaz offered the ex-Confederates land knowing they would improve the economic conditions of his country. As a result Thrailkill became quite wealthy becoming successful in the mining, cattle and railroad business. Thrailkill died in Mexico City in 1895. 

Article submitted by Paul R Petersen–2009 quantrillguerrillas.com."Permission should be requested and agreed to before using this or copyrighted essay and/or image."