Sam sat at one end of the bar. He was facing the entrance, nursing a drink as he waited for the after work crowd to morph into the regulars, the serious drinkers and those looking for a good time. Dean had had most of their cash on him when he got dragged into the portal, so Sam was there to hustle some pool or darts and earn enough to pay for a few more nights at the motel. He had a scammed credit card in his wallet, but it was too risky to use it for such a long stay.
The youngest Winchester stared into the amber depths of his glass, the sounds of the bar filling up barely registering. His mind was on Dean. Well, actually on all the times when Dean wasn't there. Sam seemed to only drink whiskey alone when his brother was dead or missing. He snorted a soft sardonic laugh as he thought about how frequently that had happened.
The first time Dean had died had been in Florida after that horrible time loop that Gabriel had tortured him with. Sam remembered kneeling in that damp parking lot, cradling Dean's body in his arms. He'd been so certain that he'd close his eyes and wake up again to that damn song and Dean's jaunty "Rise and Shine Sammy." But he hadn't. He remembered the pebbles under his knees, the damp January breeze on his face, and the strange feeling of Dean's muscles lax and limp under his hands. But he had almost no memory of the paramedics or police. He must have given someone Bobby's number at some point, because the grizzled hunter had arrived later that day and took Sam somewhere quiet and dim and then placed a double shot of whiskey in front of him. Bobby had done his best to help him, but Sam had been too angry, so determined to hunt down the bastard that had stolen Dean from him, that he'd distanced himself from the only person left who cared about him.
A lot of years had passed since then, but Sam still remembered the hunting machine he'd allowed himself to become. He had strictly ordered his life, giving into the cold fury in his gut in order to avoid his grief. He'd killed every evil thing he could, risking his life in a way that would have been called reckless if he hadn't been so efficiently and coldly driven. The only variance to that military, robotic life had been the whiskey he allowed himself each night. He hadn't let himself have too much, not wanting the warmth of the alcohol to dull his icy rage, but the booze had been the only thing that allowed him to catch some sleep during those dark months.
A shrill laugh from what looked like a bachelorette party roused Sam from his thoughts. He downed the rest of the glass that he had been swirling in his hand and signaled for another. It was a fine line that he walked. Sam knew that he had to be alert enough to successfully hustle, but the golden liquid helped release some of the tension he had been holding in his body since Dean had disappeared. While he waited for the bartender, he scanned the bar, looking for an appropriate mark. It was still a bit early, but Sam knew how to be patient. His thoughts drifted back to the dark days after the next time Dean had died.
If Sam had been a bundle of controlled fury for the 6 months before Gabriel had reversed the time loop, he was anything but controlled once the hellhound had dragged Dean to Hell. Thinking back, one of his greatest regrets came from how deeply he had crawled into the bottle once he and Bobby had buried his brother's body. It was a marvel that he hadn't died of alcohol poisoning back then. At the time he had felt completely adrift. He was afraid of who he had become back in Florida. And more importantly, he was tormented with guilt. He'd failed to save Dean, and knowing that the person he loved more than anyone or anything was suffering eternal torment because of him, to save his pathetic, undeserving ass...well it destroyed him. In his heart, he knew that if Ruby hadn't showed up when she did, that he would have either drank himself to death, gotten himself killed hunting drunk, or put his own gun in his mouth.
The bartender put a fresh glass in front of him with a thunk. The bar was filling up rapidly. Most of the tables were occupied now and the bachelorette party was in full swing, dancing and singing up a storm. Making eyes at the ladies, was a group of tough looking young men who were settling in at one of the pool tables at the back. Bingo. He watched the group in the mirror over the bar as he sipped his drink.
Dean was a master at hustling pool and had taught Sam his technique. Sam couldn't pull off Dean's good natured con. Dean could fleece anyone while pretending to be happily drunk. He'd charm his mark while flirting with the closest women and at the end, he'd walk away with several hundred dollars in his pocket and a half dozen phone numbers. That was assuming Dean didn't head out with some hot chick under his arm and a "Don't wait up, Sammy" tossed his way. Sam had to smile. He couldn't do that, he didn't have Dean's easy charm, but he'd been playing the wide-eyed newbie with wicked beginners luck since he was 16. He only wished his brother was there to watch his back and provide his usual color commentary on Sam's performance. Sam swallowed the last of his drink and slid off his stool towards the pool tables. He had a job to do.
A few games later, Sam was taking a break, waiting for his next mark to show up. He stepped up to the crowded bar and asked for a beer. All the stools were full, and he had to slightly lean over a petite woman to get his drink. He was about to go back to the pool tables when he felt a small hand grab onto his shirt. The girl he had leaned over had spun on her stool and was pulling him closer by his shirt, she slid her other hand underneath to stroke his stomach. She looked up at him with the glassy, unfocused eyes of someone who was one drink on this side of too many. "Oohhh….muscles" was all she said. Sam was instantly uncomfortable. He didn't like being touched at the best of times, much less being pawed by some drunk chick. Still he smiled tightly and pulled away, gently dislodging both her hands in one of his, making it clear he wasn't interested. He was about to go back to the pool tables when someone gripped his shoulder and spun him around.
The guy wasn't as tall or as big as Sam, but he was still a bulky guy. He wore a green polo shirt and a mean look on his face. "Whaddya think you're doing with my girlfriend?" The guy's face was flushed red from drinking, and his eyes were heavy and droopy, maybe from some other intoxicant. The last thing Sam needed was trouble.
"Sorry man, she grabbed me." Sam held his hands up, one still gripping his beer bottle. He didn't want to antagonize the guy. "She's all yours." Sam did little to hide his lack of interest in the girl. Green polo guy put one hand on Sam's chest, holding him in place while he snapped out his other beefy mitt and dragged the young woman off her stool.
"You telling me you don't think she's hot? 'Cause she's damn hot!," the guy said angrily shoving her up against Sam's body. The girl giggled, a sappy look on her face as she slumped against him. She was pretty in a lush, obvious way, dressed in a tight pair of jeans and a frilly tank top, but certainly not Sam's type, even if she wasn't drunk and taken. Sam just wanted to get out of this stupid situation, wishing again that Dean was here to help diffuse the situation.
"Um, sure. She's not my type, but you two make a cute couple," Sam tried to smile and extricate himself from the woman and her roving hands. He shoved her back towards the guy, eager to get away. He had barely used any force at all, as she wobbled on her high heels, but the girl looked hurt at his rough handling and turned her pout towards her boyfriend. The guy's hand had still been resting on Sam's chest, but he pulled it away as if we was burned.
"You some kinda faggot?," he glared, as if he'd discovered that Sam was poisonous. Green polo wiped his palm across his jean covered thigh and Sam saw his opening.
"Yeah, sure, that's it," the youngest Winchester said flippantly, tossing his words over his shoulder as he broke away from the pair and pushed his way back into the crowd. Sam made his way around the pool tables, being sure that the guy hadn't followed him. Agitated by his encounter with the annoying couple, he leaned against a wall and sipped his beer. One or two more games and he would have enough money to cover more than a week's expenses. Scoping out the pool players, Sam found a new target and turned his brain to studying the way his chosen mark played and the best way to hustle some more cash.