This movie hardly lacks irony, but an intriguing possibility has occurred to me, which can you will see below. But first, the evidence:
When Grandma Sarah Turner meets Josey Wales in the film, she is not very fond of him, or the entire state of Missouri for that matter. She tells a shopkeeper:
"Anything from Missouri has a taint about it...Never heard of nice things from Missouri coming West"
And later, after being rescued from the Comancheros she tells Lone Watie "This Mr. Wales is a cold-blooded killer. He's from Missouri where they're all known to be killers of innocent men, women and children."
When they arrive in Santa Rio, where her late son's ranch was located, in the Saloon she tells Rose that her son "was killed in the Border War by Missouri ruffians. He died a proud member of Senator Jim Lane's Redlegs, fighting for the just cause!"
They camera then cuts to Josey, who has an especially pained look on his face.
The movie is in no way clear about this but I think it is entirely plausible that Josey Wales is responsible for the death of her son Tom. It's my guess that he was one of the soldiers in the redleg division that he gunned down with the Gatling gun.
Later in the movie when Grandma Sarah says grace before a meal she says "And thanks a lot for Josey Wales, who you changed from a murdering bushwhacker on the side of Satan to a better man in time to deliver us from the Philistines."
Has Grandma figured out by this point that Josey, her savior, is the very same person who killed her son? Or is she just referring to his checkered past? Impossible to say.
It would be just Clint Eastwood to set up this incredible scenario whereby he kills someone in the redleg division, one that that killed his entire family, then goes on to save this person's family from being killed by bandits, then helping them set up and defend their homestead from the same army division, creating a extended multicultural family and a new harmonious life for themselves. Its a complicated, conflicted yet redemptive conclusion to this incredible saga.
Am I crazy or does anyone else see this connection?
Many thanks to Global Moderator Matt for his post where I found the specific quotes was looking for: http://www.clinteastwood.org/forums/index.php?topic=2996.0