There are no heroes in this story.

The legend of the Sleepy Hollow is that a man named Ichabod Crane was looking to feed himself well and live a comfortable life, and he decided to do this by winning the heart of one of his singing students, a Miss Katrina, who was the daughter of an exceedingly wealthy farmer. The problem with this was that Miss Katrina was also sought after by one Abraham "Brom" Van Brunt, who was used to getting what he wanted and not having any of that shit and so told Ichabod the legend of the Headless Horseman, a figure that rides a black horse and has a pumpkin for a head and possibly reaps souls. Ichabod, being a coward who was only in it for the money to begin with, left the party early only to find that the actual Headless Horseman was out there and apparently waiting for a good laugh and a man to terrify and possibly, as we mentioned, a soul to reap, and so chased Ichabod down. All that was found the following morning was Ichabod's horse, and his hat, and some bits of pumpkin that were too ominous to make a pie out of and were probably later eaten by the horse.

Now, people think they saw our Ichabod getting busy later on way out in the countryside with a widow (for those unfamiliar, that used to be a bad thing), having seven little Ichabods just as lanky and long nosed and green eyed. Meanwhile, Brom, as it turned out, was all talk and could not "continue his lineage", so to speak, which would have made this whole ordeal a whole lot easier for Syc- but we'll get to that. Because it wasn't a coincidence that Brom told the story on the night Ichabod was scared away: Brom had in fact called in a favor from dear ol' grandad to "please, pa, I've never seen anyone as easily objectified as Katrina, you have to fix my problem for me," and Grandpappy Van Brunt grinned his pumpkin head and saddled up.

This became a problem when Grandpappy Van Brunt started getting tired. Reaping the souls of revolutionary war soldiers and those still obsessed with it was getting old, centuries passing, and "goddamn," he thought, "we're still at this?". The age of technology and the internet was his final straw- time to retire. They're making Ghostbusters episodes about him and now he's got nsfw art and he's seen enough. Time to pass the reins.

This is where it comes in that Brom never had any kids, no obvious choices for the next in line. However... the descendant of one of those seven little Ichabods who decided his family was weird and that he needed to go far away to West Virginia started getting really good at horseback riding. And Sycamore- "What kind of a name is that?," Grandpappy Van Brunt thought- seemed to already be unsteady with themselves and susceptible to some molding and persuasion.

Sycamore Payton Crane (born Christopher Payton Crane, after much confusion and deliberation from their parents) was an alright student with a tendency to throw themselves into their work, excelling more in stables, fields, and paddocks than classrooms, but trying just as hard at both. Unfortunately, having a major spirit latch to you at 10 years old tends to throw things off kilter.

Syc began hearing the voices of the Headless Horseman and the souls that follow him, having nightmares of chases in the woods where they swapped between being the one scared and the one pursuing, and dealing with becoming a person all at the same time did not go very well. And while their parents tried their best to support Syc, who was going to start going by that name in just a few years, in their hearts they had resolved that they wouldn't know what to do with their kid since the day they were born. Fortunately, Syc also happened to get very good at horseback riding in these years, creating an outlet and interest to bond to. And riding fast enough will sometimes even make the wind drown out the voices in their head.

Sycamore is 19 now and has an active tiktok account where they mostly post videos of the farm. Their face is always masked, clothes baggy and comfortable, and they have amassed a following because they fit a certain niche there and their farm videos are actually funny. Other than the nicotine addiction (Elfbars!), they cope alright with the haunting voices, even if they have gotten more aggressive over the years. It's fine, everything's fine, we're all fine. They figure they're schizophrenic and have accepted that in their podunk town, they won't be getting help for it, and have taken to telling the voices to fuck off whenever they're feeling up to it. Oh, and now Elfbars are discontinued, so they're switched to HighLights.

Still, things don't feel right. Syc thought they didn't feel comfortable in their head because of gender dysphoria, but they can't really convince themselves on it the way they have on schizophrenia. They fantasize, even or especially when they're riding, about their head simply falling off like ripe fruit from a tree, and the feeling they've gotten since they were 10 of being watched is still just as present as when it started.

Tl;dr: Syc is becoming the new Headless Horseman because the last one is tired of dealing with how he's portrayed now and Sycamore is the closest thing he's got to an eligible descendant. Sycamore does not know what's going on with themself and is currently of the opinion that they should drown out the voices in their head with nicotine, completely unrelated horseback riding, and the love of many pet wild dogs.