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Criminal Mastermind

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It’s not enough.

It’s never enough. Dean looks down at the crumpled five dollar bill in his hand, all that’s left of the cash John gave him for the week. They still have three days left. He didn’t plan well enough.


He knows what he has to do, and hates himself for knowing exactly how to do it.

He makes sure Sam is set up with the TV and the last of the cereal, and orders him to stay put.

“I mean it, Sammy. Don’t move a muscle until I get back. I’m going to buy groceries,” he lies, pulling on his jacket and heading out the motel room door, locking it behind him.

It’s cold outside, the winter wind piercing through the thin material of his jacket. He turns his collar up and jams his hands into his pockets, trying to ignore the numbness that slowly creeps across his skin. As long as he keeps moving, it’s easier to ignore the cold than it is to ignore the hunger, the emptiness in his stomach. He really hopes this works, for his own sake as much as for Sam’s. Last night’s dinner of half a peanut butter sandwich is quickly becoming a distant memory.

He walks down the busy road to the nearest shopping center, and once he arrives, surveys the layout with a grin. He lucked out with this place. The hill at the edge of the parking lot is a great vantage point, not too close to be noticed, but not too far away to pull this off, either.

He sits down in the grass with his back pressed against a tree, and subtly watches people entering and exiting the Wal-Mart at the edge of the strip mall, keeping his posture casual like he’s just another bored teenager with no better place to be. He needs a good target, and so he waits and watches, scanning the rows of cars until his eyes land on a woman walking towards the store, only halfway paying attention to where she’s going as she digs through her huge purse for something.


He gets up, chilly breeze ruffling his hair, and walks down the hill until he’s between a couple of parked cars. With no one looking, he takes off running towards the entrance of the store, weaving in and out through lanes of cars so that he’s headed on a collision course with the woman. As she nears the front of the parking lot, still distracted with her purse, he dashes out from between two cars and crashes right into her, making her yelp and drop her purse in surprise. Sure enough, everything goes flying, tumbling out of the unsecured opening of the bag and rolling out onto the pavement.

“Oh my God, ma’am, I’m so sorry!” he blurts out quickly, his hands on her coat as he keeps her from falling. “I’m so sorry!”

She pulls away from his grip, answering sharply, “What’s wrong with you, kid? Your mom never taught you to watch where you’re going?” She glares at him and crouches down to begin picking up the contents of her bag.

Now’s his chance.

Dean gets down on the ground next to her, positioning himself in the middle of the chaos so he’s blocking her view of some of the things that had tumbled out. “I’m sorry, I didn’t mean to,” he repeats his apology, picking up a rumpled pile of junk mail and handing it to her. “I was racing with my friend and I just didn’t see you…”

“You shouldn’t be running in a parking lot, anyway,” she admonishes him, flipping her dark hair over her shoulder as she turns away to retrieve a makeup bag, frowning at the scratches that the pavement has left in the shiny patterned vinyl.

“I know, you’re right,” he agrees, making sure her back is still turned as he grabs a handful of cash from her wallet, a big pink thing that had come unclasped during its fall from her purse. He stuffs the bills up the sleeve of his jacket and gathers up some things from the ground, turning back to hand her the wallet, a packet of tissues, and a tube of lipstick. “Here you go,” he says in his best helpful voice, looking sheepishly apologetic. “I’m really sorry, ma’am.”

She still looks annoyed and angry as she takes the things back from him, shoving them into her purse before hoisting the straps up onto her shoulder and tucking it under her arm. He gives her his best puppy dog eyes and stands back up, reaching out a hand to help her to her feet. She accepts, and he pulls her upright with another string of apologies, which she waves off in haughty annoyance, turning to walk away without another glance back at him.

Dean darts back between the cars, putting a couple of lanes of distance between the two of them before he slows his pace and saunters away from the parking lot, casual as can be. He pulls his hand up into his sleeve, fingers brushing against the bills tucked against the fabric.

Twelve years old and he’s already a great pickpocket.

His stomach grumbles again as he walks down the street, reminding him of his purpose. With one last backwards glance at the shopping center to make sure no one is coming after him, he pulls the money out of his sleeve and quickly counts it.

Twenty-eight bucks. He can absolutely work with that.

He keeps an eye out for the grocery store on the way back to the motel, relieved that he’s going to be able to eat today, after all.