For Brothers Together, we won’t have this scenario showing up. It’s possible it may appear in a different AU, but it’s a difficult type of scene to write and the setting and the emotions have to fit.

With Oscar and the younger Winchesters, bullies usually pick on easy targets, which is why Sam had such trouble in school. He’s a scrawny kid. Dean might be the type to get into fights, but in this scenario he’s not looking for trouble. He’s keeping his head down in order to keep Sam safe, and he’s a dangerous enough looking guy that no one wants to go after him first.

And I doubt that Oscar would ever come out of the motel again if he was involved in a fight.

Ah, yes, Oscar really would have quite a time outside! Everything is so open and the air is full of fresh smells that never make it into the dusty walls of the motel. Before meeting Sam and Dean, it certainly wasn’t a safe possibility for the tiny little kid.

We’ve got plans for Oscar going outside in a short Brothers Together mini-story. Here’s a snippet of A Day at the Park:

Oscar swept his gaze all around, watching the field of grass with pure awe on his face. He could see the shimmer in the green expanse as wind washed over it, creating soft waves and a faint rustling above them. It was a tranquil scene, not something he’d have expected from the wide, dangerous outdoors.

He twisted around to look past Dean’s face at the leaves shading their spot. A real tree. Oscar was certain it’d be impossible to count so many leaves, all waving and showing both sides in the wind. He traced their shapes, and his eyes trailed over the paths of the branches. “It’s … it’s so tall! ” he muttered.

The wind even tugged at his hair and shirt and Oscar had to close his eyes against the air flow when the breeze picked up. He shuddered once, but the chill didn’t last.

“Even taller than me when I’m done growing,” Dean said with a grin. He slowly knelt down, keeping his speed to a minimum for the two kids in his hand.

The place he lowered them down to was only a foot away from the trunk of the oak tree. Its roots formed a barrier on each side, trailing down into the earth only to vanish under Dean’s feet. Sam hopped off the hand, landing down in the small dirt clearing. There was just enough space around him so he’d be able to see over the top of the grass as it wafted in the breeze.

Once he was certain of his footing, he glanced back at Oscar. “You coming?” he called back with the biggest grin, excited to explore.

Oscar hesitated a second longer, craning his neck to peer at the ground from his safe place on Dean’s hand. The grass ringing in the clearing really was taller than Sam, and a lot taller than Oscar. He was amazed and nervous all over again. He could get lost in there.

He glanced back up, staring at the trunk of the tree above them and the way it stretched out high overhead. Then, he looked back at the smile on Sam’s face, and stood with his bag clutched in his hands. “Okay,” he answered, taking far more hesitant steps to get down from the hand.

He’d get annoyed eventually, and probably storm off and give Dean a heart attack. Eventually, with all the time they’d spend together, they’d come to some type of agreement, probably “Give me time to myself, damnit!”

Dean trying to find a tiny Sammy in the walls, though.

Sam probably wouldn’t have much of a problem. He’s big enough that Dean would hear him if he shouts, and one hand can scoop him back up. If he ever did temporarily get lost, Sam would need to find his way to an abandoned cell phone or hijack a house phone and give Dean a call.