One by one, as Kansas Jayhawkers burned their homes and crops in Cass County, Missouri, John, Isaac, Joseph and Robert Hall joined Quantrill's Guerrillas. Kentucky born, they had strong Southern sympaties.They served with Quantrill throughout the war, in almost all major engagements.

With the war nearing an end, Quantrill decide to take the remainder of his band to Kentucky. Isaac (Ike), Robert, Joseph and John Hall were with the group. As they passed near Pocahantas, Randolph County, Arkansas, Joseph became ill with smallpox. He was left behind and John stayed also to take care of his brother. Joseph recovered but was killed later on in 1865. John went back to Cass County for his family and took them to Nelson County, Kentucky.

May 10, 1865 began as a quiet day at the farm of James Heady Wakefield in Spencer County, Kentucky. Quantrill and several other of the raiders, lulled by the rain hitting the barn roof, were peacefully sleeping in the hayloft. The rest of the men were engaged in other trivial pursuits to while away the boredom of hiding from Union patrols. Some of the Partisans were even having a mock fight with corncobs, as if they were a bunch of young boys. Since no trouble was expected, and no one wanted to be outside in the lousy weather, no sentries were in place to guard against surprise. 

The corn cob fight was what saved most of the raiders from death or capture. John Ross was getting the worst of the fight at this point. Unable to withstand, much less answer, the volleys of cobs from his friends; Ross found discretion to be the better part of valor, and fled the barn. What Ross ran into turned out to be far worse than the cobs he was running from. Facing better than two dozen charging guerilla fighters under Captain Terrell, Ross spun around and ran back into the barn screaming, "The Yankees are onto us!". 

With the fight already triggered, no one was left with any choice. Quantrill sprang from his nap in the hay and ordered the raiders to mount up, wheel about, and charge. He then hurriedly tried to mount his horse, but the stirrup broke and threw him off balance. The horse, reacting with the mounts of the other raiders, charged out of the barn doorway into the lot, with Quantrill desperately trying to correct his awkward situation. As Quantrill tried to pull himself upright in the saddle, at least three Yankees; Ben Kirkpatrick, Horace Allen, and John Langford took aim on him at the same time. All three men fired at roughly the same moment. Quantrill was struck by two of the three bullets from the Spencer carbines carried by the Union guerrillas. One of the bullets struck Quantrill in the hand, the death-dealing round entered near the left shoulder blade and lodged in the spine, paralyzing him from the waist down. Clark Hockensmith and Dick Glasscock both made desperate bids to save Quantrill, and were both killed for their trouble. Brothers William and Henry Noland were also killed in the brief, running 

fight. The rest of Quantrill's men made good their escape. 

Although the wounded man identified himself as Captain Clark of the Fourth Missouri Cavalry, Union Guerrilla leader Terrell was certain he had captured Quantrill. Terrell had the wounded man carried to the home of James Wakefield. They stayed there until his wounds were cared for well enough to move Quantrill to Louisville by wagon. While he waited, Terrell robbed Quantrill of all he had, and stole most of Wakefield's valuables. Once they arrived in Louisville, Quantrill was cared for at St. Joseph Hospital. It is said that, before he died on June 6 at 27 years old , Quantrill made a full confession and converted to Catholicism. 

After the fight at Wakefield, the surviving raiders scattered for a time. William Bassham, 

Thomas Evans (who was held in a Lexington prison until after the war, because he was 

suspected in the killing of a Union Lt. Cunningham.), Thomas B. Harris, and John Barnhill surrendered near the barn, or at Smileytown about a mile from Wakefield's farm; which one exactly is unclear since no date for their surrender is given. George Wigginton and John McCorkle surrendered later in May, 1865 at New Castle, Henry County, Ky. David Hilton and Isaac Hall hid in a pond to escape capture by Terrell's gang. Sometime before July 26, 1865, they rejoined the largest group of former Quantrill men under Capt. Henry  Porter, and surrendered to Capt. Young, US Army, at Samuel's Depot, Nelson County, Ky. In addition to Porter, this group was made up of David Hilton, Lee McMurtry, Alexander Franklin James, Randolph Venable, James Lilly, Andy McGuire, A. D. "Donnie" Pence, Bud Pence, William Hulse, Jim Younger, Payne Jones, Allen H. Palmer, Robert Hall, and John Harris. This was the end of Quantrill's raiders in the Bluegrass State. 

Most of the guerrillas went back to Missouri. Kentuckians by birth, Isaac and Robert Hall 

decided to stay and settle in Kentucky. In 1870, they were in Nelson County, as was their brother, John.