On October 12, 1906, he murdered five members of the same family, including three young children, during an argument over a horse saddle.
His father, James Buchanan Hamilton, was a very religious Christian preacher who always carried a Bible.
Two years later, he was kicked in the head by a mule, giving him a permanent scar over his left eye.
Several years later, Hamilton was taking care of mules when one kicked him in the chest, knocking him unconscious.
Hamilton eventually returned to Missouri by himself, where he started working for Carnell "Carney" Parsons, a sharecropper.
[2] When Hamilton was 20, he fell in love with a 16-year-old girl named Mae Thompson, who he'd met shortly before he left for Kansas.
Carney pressured Hamilton, saying he knew it was stolen and would report the theft to the local sheriff.
The shotgun broke into three pieces afterward, and Hamilton fatally struck Carney in the head with the barrel.
He then loaded the bodies into the wagon and hid them in a river, before fleeing with one of the Parson family's mules.
When the bodies were discovered and the news spread to the congregation, he made an excuse to leave and fled to Houston, Missouri.
Under the cover of a dark early morning, the police transported Hamilton to Carthage, Missouri to protect him from the mob.
A lynch mob nearly caught Hamilton at the local jail in Springfield, which he had been transported from a few hours earlier.
Under Missouri law at the time, nobody who confessed could be executed without a trial, and the judge was reluctant to take full responsibility for sparing the life of a mass murderer.
He called Hamilton's brother to the stand and asked him about the head injuries he suffered as a child.
The judge then sentenced him to death, with an execution date set for December 21, 1906, exactly two weeks after Hamilton's 21st birthday.
James Hamilton petitioned Governor Joseph W. Folk to stay the execution, claiming he was insane.
He was allowed to inspect every component of the gallows at the Houston County Courthouse, and test the trap door.
Asked if he had any last words, Hamilton sang a song:"Companions, draw nigh, they say I must die, Early the summons has come from on high; The way is so dark and yet I must go, O, that such sorrow you never may know.
Sad the regret, we have never learned how To come before Him, who only can save, Leading in triumph thro' death and the grave.
"Afterwards, Hamilton made a lengthy statement telling young people to trust in God and treat their parents with respect.
As the sheriff bound his arms and legs, Hamilton continued to ask God for mercy.
This time the knot held, breaking Hamilton's neck, and he was pronounced dead 13 minutes later.
James Hamilton took his son's remains and buried him in the Allen Cemetery, next to his dead mother.