Missouri outlaws loom large in both history and fiction. The myth of Jesse James like that of Robin Hood, Billy the Kid, Dick Turpin, and Ned Kelly is apt to mix the factual with the fantastic. In the case of the James brothers and the Younger brothers, open conflicts helped shaped both the legends and the reality.
The question in the 1850s was whether the territory of Kansas would enter the Union as a Free or Slave state. Northern abolitionists sent money and Sharps rifles to like-minded settlers. As Missouri accepted slavery, some of its residents sought to spread the plague to Kansas. The result was the Border War which gave impetus to men like John Brown, James Lane, William Clarke Quantrill, and William T. Anderson.
The fictional Missouri farmer Josey Wales rode with the very real Bloody Bill Anderson who was involved in two different events named for the small central Missouri town of Centralia: the Centralia Massacre and the Battle of Centralia. September 27, 1864 was not a good day to be a Union soldier in that neighborhood. According to some stories, the guerrillas were shocked to see Johnston's troops dismount to fight. The Union soldiers' muzzleloading rifles were no match for the mounted mobility and firepower of multiple revolvers and/or multiple loaded cylinders deployed by Anderson's men.
Quantrill's fictional protege Rooster Cogburn gained his famous eye-patch from a wound sustained in the Battle of Lone Jack. Cole Younger, depicted as meeting Mattie Ross at the end of the 2010 version of True Grit, really was at Lone Jack for the battle.
(My ancestors were not part of this. They came in later from Indiana, Nebraska, and Tennessee and tended to be sympathetic to the Union cause, abolition, and Republicans.)
The University of Missouri and the University of Kansas, which is in Lawrence, KS, were, until Missouri left for the SEC, conference rivals in the Big Eight and Big Twelve. The meetings, especially on the basketball courts, between the two teams were considered a (usually) less bloody continuation of the Border War.
If you want to read a little more about the strife that foreshadowed the death and destruction of the American Civil War, I can suggest a couple of books -- War to the Knife: Bleeding Kansas by Thomas Goodrich and Bleeding Kansas: Contested Liberty in the Civil War Era by Nicole Etcheson. I have read Goodrich's book, and, though the Amazon reviews are unfavorable, I thought it was good. I have been trying to get hold of Etcheson's book, but I never order anything from Amazon.
Another book, primarily about the Youngers, which I read and enjoyed is Marley Brant's The Outlaw Youngers.
It is good to know the past events and pressures that helped to shape the present. I don't know if those who ignore history are doomed to repeat it. Perhaps if we know how we got here, it might help us figure out where we are headed. At least we might recognize where are when we get there.
History is always a sifting of facts that become a narrative, depending, often, on who is better at wholesale bloodletting. Thus, the sacking of Osceola by the despicable and cowardly James Lane gets a lot less play than Quantrill's retaliatory Raid on Lawrence.
While hardly historically accurate, I still enjoy something like Warren Zevon's "Frank and Jesse James". History is the chronicle of what happened, sometimes through wisdom and courage, just as often through foolishness and perfidy. Legend is the way it should have been, and, unlike the accidents of history, legends may tell us who we are.