Ok, so The Ransom of Red Chief is basically like 19th century Dennis The Menace. So, bear with me, cuz I’m about to do this with my headcanon:
Because the guy in the top hat is the other guy’s great-grandpa
So, firstly, here’s my flimsy evidence for the exact date, as O Henry published the story in 1907 without telling us when it took place. There’s a line in the 1998 movie where Andy asks his dad to take him to Buffalo Bill’s show in the “capital city next week.” This being set in Alabama, that means Montgomery. The only other thing O Henry gave us is an Autumn setting. Well, lookit this:
Those circled dates are Christopher Lloyd’s birthday (Oct 22) and mine (Oct 18). That’s a sign. It’s gotta be one of those years. At least the movie setting does. Mrs Dorset’s dress and the women “protesting a saloon” helped me narrow it down to 1895.
Now, Switchblade Sam turns up in Wichita, Kansas by jumping out of a boxcar. Sam Howard, in the movie (which is the only canon we’re using for this) turns up in the fictional Summit, Alabama sitting on the front of a train with his ‘buddy,’ Bill. (They’re disaster bisexuals and I will die on that hill.)
Already, we’ve got a family penchant for trains. Howard is a lot nicer than Switchblade, and actually bonds with the impulsive, aggravating boy he kidnaps. While neatly managing to ensure Bill is the one stuck with him lol…but he likes the kid. Doesn’t try to kill him and even gets pissed off thinking Andy is unappreciated by his father. So I don’t think he’d abandon any of his own on purpose. But! There’s a line when he’s having a minor tiff with Bill that ends in the joke “Your honor, I didn’t know she was married, I swear!”
He claims to have met Bill in an orphanage where they grew up together. So here’s what I think. They are, for all intents and purposes, life partners who run harebrained schemes together without ever managing to get ahead. They mean well, but they aren’t all that educated and people keep taking advantage of them instead of the other way around. From time to time, one of them has an affair with a woman in the towns they pass through, not really thinking much of it. They’re men, men are meant to sleep with women. But ultimately they only care about staying with each other.
At some point in recent history, Sam Howard got a married woman in a lot of trouble. Unfortunately, he’s gone and untraceable before finding out just how much trouble she was actually in. Not just cast out for adultery, but pregnant. He’s happily settled as a model citizen in Summit, knowing nothing about it. She’s left in poverty to raise the girl on her own, leading to an unprotected young woman who gets taken advantage of by a man who promises everything and gives her nothing.
The resulting daughter will go on to sink even further, forced to support herself the only way a “fallen” woman was allowed to. In 1938, at the age of 23, she has a little boy with an unknown father and names him Sam after the man who has become a bitter cautionary tale handed down through generations. She takes care of the kid as best she can because it’s expected and sometimes even thinks he’s almost sweet when he’s not making a nuisance of himself. But he’s just one more mouth to feed, her clients don’t like him being underfoot, and more often than not she sends the kid off out of the way.
He falls into a bad crowd, learning to steal in order to keep himself and his mother fed. Learning to fight to keep what he’s stolen. She dies when he’s around 13 or so, leaving him without even that pitiful excuse for a roof over his head. He tries, but there’s nothing in town for him. No one who wants to extend any help to “that dead whore’s thieving son.” He takes off on a train, fully aware he’s following in a long lost somebody’s footsteps and figuring it was meant to be.
Maybe he tries again, from time to time, to make an honest go of it, but he already looks like…what he is, basically. His face when the sheriff calls him over suggests he’s used to being hassled by cops. At some point, he decided it is what it is and just accepted this was his life.
The fact he goes on to be defeated by a little boy he’d kidnapped and considered killing, with a much less happy ending than the one he doesn’t know his great-grandpa had, is just the perfect narrative symmetry to my headcanon.
