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Sir!Jackson masterpost
Perhaps his father, the King, was traveling during the war, and fell for Jack's mother while in her village? They spent some time together, enough to fall for each other and conceive a baby, before he was called away again. They both knew they couldn't work, but still.
Once Jackson was born, his mother sent a letter to the King telling him what happened. He couldn't claim Jackson as his son, but sent her help so she would be able to manage. They made the story that she didn't have a child out of wedlock, that she'd eloped with a Knight in secret, but he'd had to go off to war before the child was born and was killed. She'd have rights and the child would be looked after. The King also sent his most trusted Knight to the village to help look after them in secret. (Probably North and Bunny c:)
Jackson grows up not knowing who his father really was, and aspired to become a knight himself, like the father he thought he once had. He goes through training as a soldier under the watch of Sir North. He only just achieves his knighthood as the war escalates.
During the war though (Probably some barbarians or something trying to take over), the King is killed by Pitch. Maybe his brother or someone who would have claim to the throne once the king was gone. He takes over, and starts to rule with an iron fist. Perhaps the barbarians that had been constantly raiding the land worked for him too, and now serve as his own personal bully force/army. However since no one could prove foul play, he goes unchallenged.
A revolution starts up. Trying to take the land back from their new tyrant. Jackson gets caught between serving his King, and serving his people. He tries to protect the people as best he can without disobeying direct orders, and he still travels with North, who now wants to find a way to prove Jackson's lineage.
I'm thinking Pitch finds out that the King had an heir, and decides to try to track the child down. So Jack eventually starts getting hunted by Pitch's Soldiers. He eventually has to go into hiding, but gets hurt at one point. North takes him to a secret village, where he knows there are healers. They can hide them from the soldiers for a time as well. The healer is probably Rapunzel, but there are other magic users there too. Most people with magic had to go into hiding many many years ago, and has been starting to fade into rumor and myth. But Jack likely befriends some in the village who decide to help him.
So Punzie is likely the magic healer. Aaaaand I want Elsa to have magic as well :D
I want Jackson and Elsa to have a special encounter of some kind. But I'm not sure yet.
Also we're going to pull a King Arthur/Stardust thing for Jackson's proof of lineage. There'll be some kind of enchanted object that will only react for the true heir.
I'm thinking that Jack's given a special sword while he's at the magic village too. Made from sky metal (Meteor or moon rock) that channels magical power. That could be the thing that reacts to him. Though I'm not sure how at this point.
I was also thinking that the magical side of the land was kept separate from the rest of it. Like, most of the people in the land fear magic due to not understanding it, so they're often treated with suspicion and are mistreated.
Also magical creatures. Because. Magical creatures.
I like the idea of the royal line having magic in their blood, but only the Heir's can use it. Like, they have to go through an Awakening to gain access to it, and only the heirs are put through that. The Kings and Queens would use their abilities to protect the kingdom, and as such, were the only magic users that the people trusted. So perhaps Jack has the potential to use magic, but just doesn't know it. And perhaps an "unoficial" Awakening could happen if he was put under enough stress that triggered his abilities.