I looked into the possible relationships of Quantrill, Hildebrand, and Thailkill and can answer your questions.

First, Sam Hildebrand operated only in southeast Missouri, his home, and did not even winter in the South, as did the west-central Missouri guerrillas like Quantrill. He based mostly in Greene County, Arkansas, just off "the Bootheel" of Missouri, so he could be close to his large extended family still living mostly in St. Francois and Jefferson Counties in southeast MO. Hildebrand's own memoir written I believe about 1868 some time before he was killed in a saloon in Illinois revealed that the furthest he strayed from SE MO was one raid that went poorly he conducted with a small band all the way to Panther Creek, which I believe is in southwest Missouri in Wright County. Therefore, I must conclude Sam Hildebrand, with all his accomplishments, never rode with Quantrill at least from summer 1862 when he began "the bushwhacker trail" through the end of the war.

Second, Captain John Thrailkill is I believe the same man by that name age 22 in the 1860 census of Holt County living with the George R. Cooper household in the far northwest corner of Missouri. This regular Confederate officer was instrumental in conducting the rear guard action for BG John S. Marmaduke's April 1863 raid in southeast Missouri during the withdrawal at the conclusion, and he was mentioned in dispatches for so doing. Captain Thrailkill took a recruiting commission from his superiors to recruit in his home region in the summer of 1863 and was captured by local militia in Clinton County on 19 July 1863 and sent eventually to the military prison in Alton, IL. A military tribunal in St. Louis during January 1864 sentenced Thrailkill to life imprisonment as a recruiter or partisan ranger. Evidently, they could not find enough evidence to convince them Thrailkill was a regular Confederate officer--which he really was! The captain escaped from the Alton prison 28 June 1864 and immediately made his way across the state to join the growing secret insurgency led by Confederate Lieutenant Colonel John Calhoun "Coon" Thornton in the Platte County area of northwest Missouri. The affable John Thrailkill quickly gathered his own company of irregulars, and, along with the bushwhacker band of former Quantrill members led by Charles Fletcher "Fletch" Taylor, formed the security for Thornton's large-scale operation. Thrailkill's and Taylor's guerrillas or irregulars handled any problems that arose and helped to keep LTC Thornton's uprising secure until Thornton brought it out in the open on 7 July 1864 with hundreds of southern men including scores of turncoat Union Enrolled Missouri Militia. When Thornton's expected help from Confederate troops such as Shelby's cavalry failed to come support his uprising, it failed, and Thornton was forced after being chased around eight counties north of the Missouri River for several weeks to infiltrate his remaining men across the Missouri River in groups of 100 to 150 and make their way south to the nearest Confederate forces in Arkansas. The unravelling of Thornton's uprising forced Thrailkill and his men out of their security screen job and they took to "the bushwhacking trail." Captain Thrailkill conducted his guerrilla operations during 1864 according to the rules of war as much as possible, refusing to murder prisoners and in some cases prevented "Fletch" Taylor's bushwhackers from doing so, too. Thrailkill paroled captured Union troops and asked for the surrender of towns using his actual rank as a Confederate captain. He actually rode with Quantrill for one day, September 24, 1864 when Quantrill and his bodyguard joined the amalgamated guerrilla group including Thrailkill's, Bill Anderson's, George Todd's, Dave Poole's, Bill Stewart's, and a few more about September 23 for the ill-fated raid on Fayette, Howard County seat, the next day.

You see, Captain William Clarke Quantrill (who was commissioned as a partisan ranger captain by Colonel Gideon W. Thompson in Jackson County during August 1862) was deposed at gunpoint in late May or early June 1864 by two of his subordinate leaders, Bill Anderson and George Todd, after extended disputes about some lapses in Quantrill's leadership practices that grew bitter during the winter of 1863 and 1864 while in the Sherman area of Texas. Quantrill with a small bodyguard of his most trusted men went immediately after this into a self-imposed exile to a woody camp in southwest Howard County a few miles northeast of Boonsboro. Quantrill only left his camp when he heard that most of the regional guerrillas were joining into an amalgamated group in order to conduct more effective operations against Union troops. Bill Anderson, the elected head of this group, and George Todd reluctantly allowed Quantrill and his several bodyguards to remain for the Fayette raid the following day. After the guerrilla leaders failed to respect Quantrill's advice not to conduct head-on, mounted attacks on the Fayette Union garrison behind fortifications, with disasterous results Quantrill left the group and returned with his bodyguard to his exile camp back in the woods. He only came out again in late October 1864 after Price's great Missouri raid left the state to gather his former guerrillas in the Kansas City area to prepare for their expedition to Kentucky in December 1864.

Back to Thrailkill: Thrailkill and his men remained with the group and especially George Todd's portion of it until after the Centralia actions of 27 September. The group split up to better avoid the expected Union counteraction and Thrailkill and his remaining men stayed with Todd's band over the next several weeks until during October 1864 when they became part of Confederate MG Sterling Price's great raid as it was passing through Lafayette County. During September and October 1864 while Thrailkill and his men rode with Todd's band, there is no evidence that Thrailkill exerted any influence to prevent the killing of captured Union soldiers or the killing of citizens as Thrailkill had previous to September, and Todd killed many during that time. Thrailkill may very well have, but I found no evidence of such clemency. All I can conclude is that during Price's great raid in Missouri during September and October 1864 many southerners in Missouri realized this was their last and best chance to "throw off the yoke of Yankee tyranny" from the state, and some of them went along with measures they would not have earlier. According to the 1886 History of Caldwell County on page 209 Thrailkill was re-admitted to the Confederate forces and restored to his previous rank of major in Shelby's Brigade. He passed out of Missouri with Shelby's command and after the war went to Mexico with Shelby. Therefore, Thrailkill only operated with Quantrill for about two days on 23 and 24 September during the attack on Fayette, and he did not operated at any time under the command of Quantrill.

And, as near as I can tell by research, neither did Sam Hildebrand.

Casey, does this answer your questions about Hildebrand and Thrailkill?

Bruce Nichols