The Fighting Webbs of Jackson County, Missouri

Following the Revolutionary War scores of families migrated west. Many of those from Virginia took their families and settled in Kentucky and Tennessee. Subsequent migrations saw many of these settlers move on to the greener pastures of Missouri. As extended families moved as one unit whole neighborhoods soon developed that were based around a single family unit. This was true for one 53 year old Asaph Asa Webb who settled in Jackson County, Missouri in 1844. Along with Asa came his brother, Allen and his family. Also in Jackson County lived Asa's cousin Larkin Webb who settled in Oak Grove and whose farm later served as a rendezvous for Quantrill's guerrilla company. Asa Webb's family, consisting of a large group of aunts, uncles and cousins all lived close to each other farming the rich fertile land in the Valley of the Little Blue just south of Independence, Missouri while the Larkin Webb family lived along the Sni-a-Bar Creek in eastern Jackson County.

During the Civil War the Webbs were true Southerners. Asa's sons, Hewitt "Press" Preston, Thomas Bridges, William Huston and Joseph B. Webb rushed south to join General Price in the Missouri State Guards enlisting in the 8th Division, Shank's Regiment, 12th Missouri Cavalry, Company C, along with their many relatives, serving in the company commanded by their cousin, Captain George Brown Webb.

The vacuum caused by the absence of Southern men incited Kansas Jayhawkers to raid into the county knowing there would be no armed threat to oppose them. With only women and children in their path the Jayhawkers freely stole whatever could be carried off then burning down the homes of those left behind. While the Webbs were away fighting Jayhawkers attacked their neighborhood. Jayhawkers set fire to their homes and drove all their stock back into Kansas. During one attack Jayhawkers shot Thomas and Preston's younger brother, John in cold blood. When their mother took a pillow and placed it under the head of her dying boy, the Jayhawkers tore it  away and threw it in the flames, with the threat that if she did it again they would throw the body in also.  Below is a war-dated image of Black-Tom Webb AKA "Lefty."                                      

Thomas and Preston Webb fought in all the early Missouri battles at Carthage, Wilson's Creek and Lexington. While fighting at the Battle of Lexington Press Webb advised General Price that the position of the Federal troops could not be taken by storming the heights around the city which were fortified and defended with cannon. He, and his brothers, advised the general to execute a flanking movement, in much as a direct assault upon the city would result in disaster. When Price ignored his advice, the Webbs left to join their local partisan organization.

After returning home Thomas and Preston joined Colonel William Clarke Quantrill in his guerrilla company taking part in such notable battles as the First Battle of Independence, the Battle of Lone Jack and the Lawrence raid as well as the battle at Baxter Springs and Centralia along with many others. Thomas Bridges Webb, known as "Black Tom" was born July 3, 1839 in Jackson Co. Missouri. He was wounded in action at Wilson's Creek. Missouri. He was captured while fighting in Jackson County on May 28, 1862. At about the same time Preston was captured by a regiment of Federal troops while he was spending the night at his parent's farm. On Dec 27, 1862, Thomas and Preston Webb along with their cousin George Brown Webb, were sent to the Gratiot Street Prison in St. Louis by order of a Lt. Col. Dick. There they took the Oath of Allegiance on January 7, 1863 and by January 14, were released after each posting a $1,000 bond. During Quantrill's raid on Lawrence, Kansas, Thomas's horse was shot out from under him during the guerrilla’s withdrawal. He had $3,000 in his saddlebags. Thomas was saved by jumping up and riding behind Cole Younger.

Hewitt Preston Webb, also known as "Press" was born July 6, 1836 in Missouri. All of Preston Webb’s relatives and neighbors had suffered from Federal atrocities. After joining the guerrillas Preston Webb became one of Quantrill’s best scouts. It was said that, “He had the eye of an eagle and the endurance of the red deer. He first taught himself coolness, and then he taught it to others. In traveling he did not travel the same road twice." Press Webb fought at the 2nd Battle of Independence just prior to the Battle of Westport. It was there that the gallant Captain George Todd was killed. Webb helped carry his leader’s body to the city cemetery for burial.

Afterwards Thomas and Preston Webb accompanied guerrilla George Shepherd with a large contingent of Quantrill's men in taking their wives into Texas. In the spring they made their way back into Missouri. They resisted everything in their path. The advance element containing Press Webb killed more than twenty militiamen as they pushed toward Jackson County. At Kingsville in Johnson County, Missouri, they killed another ten Federals in a small skirmish. Thomas and Press eventually found their way into Lexington, Missouri where they surrendered on May 25, 1865.

Asa Webb's brother, Allen and his two sons, George H. and James Rowland joined the Confederacy. Allen was supposedly the oldest Confederate soldier in Missouri being born in 1808. While fighting in Missouri they were all taken prisoner. Allen was captured and sent to the Federal military prison in Alton, Illinois where he was murdered by the Yankees in 1862. His son George H. was taken as a prisoner of war near Warrensburg, Missouri and shot by his captors.   Below is a  war vintage image of "Press"  Webb is a Red battleshirt.                                                         

The intermarrying amongst guerrilla fighters held especially true in the Webb family. Thomas and Press Webb's sister, Louisa, married Joab Perry of Oak Grove. Jayhawkers went to the Perry farm and forced him to chop up his front porch steps for kindling wood then forced him to set fire to his own house. For this assault Perry joined Quantrill. Likewise, Press Webb married the daughter of John and Permelia Perry. George Webb married a sister of Thomas B. Webb's wife in keeping with the guerrillas propensity of intermarrying. In another instance John B. Webb married Mary Ellen Hockensmith, related to Quantrill's guerrillas Clark and Henry Hockensmith.

Larkin Webb, Asa Webb's cousin settled in Oak Grove, Missouri. Larkin's son George Brown Webb initially served as a captain in the 1st Regiment, Missouri State Guard, 8th Division, 12th Missouri Cavalry before joining Quantrill. Captain Webb died from wounds received in Price's 1864 Missouri raid.

Francis Webb, the grandson of Larkin Webb, also rode with Quantrill. Francis Marion Webb was born on October 17, 1844. In his own words Francis recalled: "I was 18 years old October 17, 1862 and on the night of December 3, 1862, I started to the army from near Chapel Hill.... We went from there to the Arkansas River through the Federal Lines by traveling at night and lying in the brush by day, and never were attacked, nor had any trouble of any kind. We landed there on Christmas Eve, and I was sworn in on 1st of January 1863. My first battle was on January 8th at Springfield, Missouri. I enlisted in Company C, Shanks' Regiment, Shelby's Brigade, Marmaduke's Division, Price's Corps, Trans-Mississippi Department of the Confederate Army. I continued in that command until the day of surrender at Shreveport, LA. I missed only one raid that Shelby made in Missouri, that was on account of sickness. I never was wounded, never was hit but once, but a ball went so close to my ear that it made it sting, that was at Mark's Mill, Arkansas, on Steele's raid.

Scores of Webb relations served under Quantrill and the Confederacy. Joseph Harrison "Harris" Webb also fought beside his relatives. He was reported taken prisoner at Vicksburg and never seen again. Another relative, Charles Webb served under Quantrill in George Todd's company while William W. Webb served with Quantrill in Bill Anderson's company. John A Webb, son of Allen Webb was a captain in the Missouri State Guards.

The Webb family fought in all the major battles in Missouri during the war. They gained fighting experience at Carthage, Wilson's Creek, Lexington, 1st Battle of Independence, Lone Jack, Cane Hill, Prairie Grove, Vicksburg, Lawrence, Baxter Springs, Fayette, Centralia, Newtonia, Mark's Mill, 2nd Battle of Independence and Westport. Gallant Southern fighters such as the Webb family kept alive the spirit of the Lost Cause long after the war ended.

Paul R. Petersen © 2013 Quantrillsguerrillas.com. "Permission should be requested and agreed to before using this copyrighted essay and/or image."


Reminiscences of the Women of Missouri, Missouri Division UDC, Reprint 2003, Morningside Books, pg 270–271;

Noted Guerrillas John Newman Edwards, Two Trails Publishing, 1996, pg 247, 252- 253 & 378-381

History of Jackson Co. Union Historical Company Pub. 1881.


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