The Hustlers

The Hustlers

A Supernatural story by Ariana @arianaspn61497

A new entry in the second wave of the #SPNWishList fic and art challenge! Ariana is on a roll, responding to the prompt: "Dean's memories of hustling pool," inspired by "The Heroes' Journey."  Ariana told me she had around Season 5 as the setting for this memory... and I can totally see it. It's from a time when Sam was more angry, unpredictable and brooding. What a transformation he has made. Enjoy.  -- Jennie

Dean was so excited to find this lucky pool hall. 

He had always been proud of his ability to hustle pool. It not only gave them spending money, but it was something he could do for fun. Dean spent most of his time hunting or traveling. He couldn’t remember when he first started learning to play, but he did have very early memories of smoky bars and his dad smiling as he made his shots.

Pool was fun for him, but playing pool with Sam? Now, that was his happy place. Sam never realized how good at everything he was. Sam just thought he was good because Dean told him so. 

Sam always idolized Dean. Dean was the only constant in his life, and the one person he always counted on. So when Sammy was learning from Dean and they traveled together, he always kept his best games for hustling.

Sam didn’t want to beat Dean too much. Dean would always seem to lose some of his bravado when he lost to Sam. It was like his little brother was so good, and that wasn’t the way of the world. Big brothers were supposed to be better at everything. Dean kept that tucked away deep inside, but somewhere he always knew Sam was special.

Dean had talent at shooting pool, but he was even better at getting people to want to beat him or Sam. They always wanted to wipe that smug grin off Dean’s face. Sam liked to use the drunk card and then beat someone soundly for hundreds of dollars. Dean was the straight man making the deals most times, because he was good at it. 

Dean had watched “The Hustler” a lot with his father -- on the rare occasions John would actually relax. John admired the movie because in the end Fast Eddie got what he wanted, even if he had a hard road to travel to get there.

Dean liked it because, no matter what, Eddie kept going. He didn’t give up, and even after personal pain and suffering, he won. Dean imagined himself to be Fast Eddie a few times when he played, though he didn’t say it out loud. Sam always knew, but he decided keeping his mouth shut was better than Dean getting that sad look he got when he felt like someone was making fun of him.

Dean could remember one time he and Sam were on the road together, in between jobs and bored. Dean decided a night of bar-hopping might be fun. They settled in by the pool tables.  They nursed beers and watched the players, seeing if there was a chance to fleece anyone.

 Dean was watching a nearby table of big burly guys playing for beers. He decided to start a conversation and maybe see if they could be beaten. 

Dean walked up and looked them over. There were four guys, all in biker leathers, with lots of worn patches from all the places they had traveled.

They were all in their early 40s and fit looking. The one who seemed to command respect was huge -- almost as tall as Sam -- and had hair braided to his waist. His hair was black, streaked with gray, and his face was clean shaven. He had rugged good looks and sparkling blue eyes.  His smile was easy, and he looked like he might be a good guy under all that leather armor. 

The guy caught Dean staring, and his eyes turned hard. He walked through his pals, right up to Dean.
“You got a problem with me?” He was toe-to-toe with Dean, and he had to admit, it was a little intimidating. But Dean was used to Sam’s height, so he just shrugged and gave a half smile.

“Nope. I just like to play pool, and you guys look like you might be good at it.”  Dean took a slow swig of his beer, watching the leader’s eyes. He could see the other men forming up behind the leader, so Dean kept his stance casual.

“Oh, really? I don’t think you’ve been watching long enough, buddy. The name’s Mike, and these are my friends: Ron, Larry, and Joe.” Mike pointed at each man, and they nodded at Dean, with caution in their eyes.

“My name’s Dean, and my brother Sam is over at our table.” Dean pointed to Sam, who didn’t look up. Dean turned back with a huge grin and held out his hand to Mike.

Mike looked Dean up and down, trying to decide if this kid was selling something or hustling them. He shrugged and shook Dean’s hand with a firm grip, watching for a reaction.

Dean worked hard to keep the wince out of his face and saw Mike nod -- as if saying the kid must be OK.

“All right, Dean. I assume you didn’t come over here just to butter us up, so lay it on me. I don’t have all day.” Mike leaned back against the pool table and waited.

“I just want to play a game against anyone but my little brother. He can’t play for squat, and I am starved for a good game. If I lose, I could buy the next round...”  Dean gave his winning smile, the one that made most people trust him, and waited to see if they would bite.

“What do you want if you win, Dean?” Mike stood up straight again, his voice lowering a bit.
“Just the privilege of kicking some ass.” Dean felt his heart beating faster. They looked ready for his game, but Dean had an ace up his sleeve. 

Mike laughed and smacked Dean on the shoulder. “You’re a comedian, buddy, but I’ll let you play. Joe, you up for a game?” 

Joe gave a short nod and got the balls together in the rack. Dean hadn’t watched all the guys, but he was pretty sure Joe was not their best player. Still good enough to test him, though. Dean went to the wall, chose a cue, and stood next to the table, waiting for Joe to break.

The rest of the crew backed up and took seats, acting casual, but they were all watching Dean with amusement. Dean could tell this didn’t happen to them too often; he guessed that most people just stayed away, assuming they were just tough hard-asses. Dean watched the other guys as much as the game. He wanted to get a feel for each one of them.

The game was a delicate dance between Dean and Joe. Joe missed a shot, then Dean sunk a few, before missing one too. Joe managed to win, but it went down to the last ball.

“Thanks for a great game, Joe.” Dean held out his hand with a half-smile, but his eyes were hard, as if challenging Joe to play him again.

Joe shook his hand but just nodded and walked away, letting Mike take over.

“I think you owe us a round, tough guy.” Mike looked to Dean like he knew it wasn’t over, but he wanted a few moments to strategize with his boys.

“I’ll be right back, fellas.”  Dean nodded, putting the pool cue back before heading toward his table.
Sam had been watching them in between drinks. He didn’t want to look too intent, but he needed to get the lay of the land. 

“Sammy, look alive,” Dean said. “I’m going to need your help soon. I’m going to fleece these biker boys good. I’m buying a round for them, and they’re gonna throw a better player at me, for money this time. Please be ready.”  Dean clapped Sam on the shoulder before heading to the bar to order beers.

Mike watched Dean until he headed out of ear shot, then walked over to his crew. They talked among themselves about how they could get the maximum amount of money out of this young punk. They were all smiling and laughing when Dean came back.

“The waitress is bringing the beers in a minute. Any chance for another game?” Dean asked Mike, out of respect to his standing as the leader. 

“Maybe, but I think we need to start putting money on this game. Can you afford that, buddy?”  Mike grinned and pulled out a roll of cash.

“Well, um, hang on a second.” Dean looked worried, but as soon as he turned away from Mike, he grinned. He walked over to Sam.

“OK, they want to bet with me. How much do you have?” Dean wanted to make sure they had enough.

Sam pulled out his wallet and handed Dean about $400 in five- and ten-dollar bills -- wadded up, small bills, so it looked like more.

“Here. It’s all I have. Don't use it all at once. What’s the play?” Sam watched Dean with excitement. This night might be fun after all, he thought.

“Thanks. I want to use you as the ace in the hole. They think you are a lousy player, and I want you to come in and save the day. Keep part of this just in case.” Dean handed back half the cash and pulled out his own stack. He saw he had $200, plenty enough for the first phase.  Dean put on his nervous face and walked back to Mike.

“Uh, how much are we putting up?”  Dean shuffled from foot to foot.

“I think $50 to start should be good. You OK, Dean? You look nervous.”  Mike grinned and patted Dean on the shoulder before peeling off his money and putting it on the edge of the pool table.

“I’m good. I can handle fifty.” Dean put his money on the table on top of Mike’s just as the waitress showed up with their round. Dean continued his nervous shifting as he looked over the cues on the wall, as if he needed the time to calm down.

Mike smiled, feeling like this might be his lucky day. He pointed to Larry and then waited for Dean to come back with his cue.

“Larry here has volunteered to play you. Ready, Dean?” Mike went over to his beer and leaned back, taking a long drink.

“Uh, yeah, I guess.”  Dean was still frowning, and he looked over to Sam as he waited for the game to start.

Dean turned back just as Larry broke. The game went like the first, but this time, Dean missed more shots. He set his face in a worried frown and saw Mike relaxing. Dean knew he looked like just a young guy with a lot to prove.

Dean knew that if he played better, they wouldn’t keep going. He tried to give Larry the confidence he needed to beat him. 

When Larry sunk the winning shot, Dean growled out “Son of a bitch!” in a low tone as he watched Mike pick up the money and pocket it.

Mike grinned and put an arm around Dean’s shoulders, pulling him towards his hip.

“Look, kid, don’t get upset. We aren’t playing for much, and you young guys can just ask Daddy for more money.” Mike laughed but missed the fire that lighted in Dean’s eyes.

Mentioning John was not a good thing. Dean realized this guy knew nothing about them, and that’s how Dean should like it, but anger simmered inside him anyway. He needed to calm down or he might blow the whole thing.

“Just dumb luck, old man. I bet you double-or-nothing I can beat your best player.” Dean stepped out from under Mike’s arm. He tried not to act mad, but he was beginning to see red.

Mike looked surprised, thinking he might have actually gotten a rise out of the guy. He held up his hands, palms out, backing up a step while his crew laughed.

“I think you might need to slow up there, Dean. You don’t have the chops to beat me.” Mike grinned at Dean as he saw more rigidity and anger in the younger man.

Sam walked up at that moment, weaving a little, and grabbed Dean.

“Dean, don’t do it. We don’t have much money. You can’t beat him, and you know it.” Sam slurred his words, his eyes unfocused. Dean turned to Sam and frowned, not sure what his little brother was up to. But he decided to let Sam take the lead.

“Sam, just go back and sit down. I don’t need your advice.”  Dean turned back with more anger in his face, but this time it was an act. It looked like Sam was ready to close this deal.

“Wait, now. Sam’s right, Dean. You don’t want to blow your diaper money.” Mike’s smile was bigger now, and he was thinking this could turn out to be more fun than he bargained for. These two might even be spoiling for a fight, he thought.

Sam grabbed Dean by the shoulder, spinning him around as if to drag him back to the table. Dean shoved Sam and gave him a small nod, giving Sam permission to hit him. This usually worked to get everyone off their guard.

Sam swung at Dean’s face and connected with his eye. Dean fell to the ground, grabbing his face. He was surprised Sam actually hit him. Usually it was just a pretend swing, and Dean sold it. This time it really hurt, and he couldn’t see out of that eye. He looked up at Sam and saw his brother grin. Then he knew Sam was going to kick ass.

Mike and Joe helped Dean to his feet, chuckling. It looks like little brother is a scrapper, Mike thought. 

“Whoa, Sam, no need to punch anyone. Dean, you OK to still play, or do you want out?” Mike watched as Dean’s eye was already swelling. Dean just shook his head. He walked toward the bar for some ice. He really did need to get some on it quick, or he could have problems for days.
Sam weaved a little as he watched Dean go.

“I’ll play you, old man.” Sam turned, with a wild look in his eyes. “I have $200 here that says you can’t beat me.”

Mike’s eyes went wide. This was too good to be true. He could make $400 off these punks easy.
“You sure you’re not too drunk, Sam?” Mike pulled out his money and laid it down first. He was so eager he missed Sam standing up straighter with a clear look in his eyes.

“Fuck you! Rack ’em!” Sam frowned as he wandered to the cue’s on the wall.

Mike laughed at Sam’s bravado and looked over at his crew with glee. They all nodded, pulled in, eager for the score. 

Dean came back with a bag of ice against his eye, his good eye glaring angrily at Sam.
“Sammy, you can’t do this!” 

“Screw you, Dean. Leave me alone.”  Sam stalked toward Dean as if he might swing again. Dean backed up a few steps.

“Whatever, dude. Just don’t screw it up.” Dean went back to the table to sit and drink his beer. 

As he watched Mike and his crew from afar, Dean was sure this would go the way they wanted.  Everyone was too eager, and Sam was playing up the drunk he was not. 

Mike broke, and sank quite a few shots before missing. Sam sunk a few but nearly fell down on his first miss. He had, however, set up a hard shot for Mike.

Mike saw his shot and frowned. He was good but not a wizard. He tried to sink his striped ball but missed and cursed under his breath. Sam grinned and staggered to his shot -- and proceeded to sink them all. His drunk swagger was still there, but anyone who could see his eyes would know he was sober.

The whole crew watched in shock. When Sam sunk the eight ball, he grinned and grabbed the money. He had almost made it back to Dean when Mike grabbed his shoulder.

“Look, asshole. That was impossible. I think you just cheated me!” Mike spun Sam around, but the look in Sam’s eyes made him stop, and his face went pale. He had never seen anyone look so angry before. Sam’s face was a mask of hate, and the fire in his eyes made Mike shiver.  This boy had something inside him that Mike didn’t want to mess with. 

Dean was already on his feet, dragging Sam toward the door. The rest of the crew filled in behind Mike and headed their way.

Dean and Sam took off at a run out the door. When they got outside, they saw the crew’s bikes, kicking them over before heading to the Impala. 

When Mike’s guys came through the door and saw their bikes, they ran for the car. Pissed. Dean had already fired up the engine, and it roared as they kicked up dust and pulled away. 

By the time Mike and his boys righted and mounted their bikes, Dean had stowed the Impala behind a dumpy motel. Sam and Dean watched as the bikes tore up the highway into the night. 

The Winchesters laughed hard, and both felt better than they had in a long time. It was a good night, and they both slept well for the first time in ages. 

Dean’s eye healed pretty quick, so by the time they went on their next hunt, he was back to normal.

Now, Dean grinned to himself as they pulled up to the lucky pool hall. He carried that happy memory as they headed for the door.