Chapter 7: The Gambler

(8 Days before Orientation Day)

"And let me tell ya, that's when I knew I was never gonna gamble again," Ron declared, his voice quivering as he recounted his tale of woe. He was a burly, bearded figure, eyes glistening with a mix of regret and relief, seated within the small circle of fellow degenerates at the Gambler's Anonymous meeting that frosty morning.

The assembly was sparse, consisting of just five individuals who had braved the aftermath of a Boston snowstorm. Despite the chill outside, Jack McCoy was there. At 37, Jack McCoy was a captivating mix of Irish and Italian descent. Towering slightly over six feet, he had thick raven-black hair that reached down to the middle of his neck. His light blue eyes emanated a welcoming warmth when he smiled. The young man was not at the meeting out of any sincere belief that he belonged, but more for the promise of warmth, donuts, and free coffee – a trifecta of comfort that he couldn't find at home, where he’d lost his rights to electricity for failing to pay the bill. 

"Thank you for sharing, Ron. And hey, maybe someday your daughter will look past the college fund fiasco and give you a shot at redemption," chimed Aaron, offering a mix of empathy and skepticism, his eyebrows slanted in two different directions. "Now, is there anyone else who wants to talk this fine morning and wrap this up?" He locked eyes with Jack, practically challenging him to contribute.

Jack's gaze lingered on his scuffed and dirty boots, remnants of a snowy journey to the meeting. With a sigh that carried the weight of a thousand bad decisions, he finally lifted his head. "Look, I get it – I've probably said this before but hear me out. I think this might be my last fucking meeting."

The group hushed, a collective silence broken only by a snicker from Vic, who sat on Jack's right. The snicker bordered on incredulous disbelief, a sound so distinct it could've been bottled and sold as mockery.

In response, Jack shot Vic an irked glance, then turned his attention to the others. "This morning, folks, I woke up to find this damn eviction notice plastered on my door. Can you believe those fucking bastards?" He paused, frustration etching lines on his forehead. "I can't stomach the thought of being homeless. I refuse to be another statistic. I've got to fight back – do it the hard way, cold turkey."

Aaron sat up a bit taller in his chair, a hopeful grin tugging at his lips as he directed his encouragement toward Jack. "You've got this, Jack. Remember the old saying – if you don't rein yourself in, life's gonna come along and slap some sense into you." With a final authoritative nod, the group leader rose to his feet. "That's a wrap for today, everyone. Thanks for coming out. Now scuttle back home before the storm decides to get feisty again."

After the meeting concluded, everyone departed, leaving Jack as the lone inhabitant of the room. The meeting had infused him with a renewed sense of hope. His pal, Vic, who shared his gambling woes, had excitedly rambled on about a seemingly "golden opportunity" before the meeting had started. This peculiar prospect involved an advertisement Vic had stumbled upon on Craigslist. The ad hailed from a laboratory seeking individuals willing to take part in an experimental drug study, with a tempting compensation of $300 per day.

"Can you fuckin' believe it, Jack? Three hundred bucks a day! That'll get those fucks off your back!" Vic exclaimed with an enormous grin plastered on his face.

Jack raised a skeptical eyebrow. "You sure it's not some kind of scam? What if it turns out to be a con?"

Vic shrugged off his concerns, laughing. "Ah, come on, dumbass! What do you have to lose, you fuckin’ loozah?"

Jack contemplated the eviction notice haunting his door and found it hard to present a convincing counterargument. He took a gulp from his Styrofoam cup, or as he liked to call it, "black sludge," and made a face at the subpar coffee. He and Vic spent the next hour dissecting the opportunity in depth. Eventually, they shook hands, united in their hopes of participating. Jack, an old-hand gambler laden with debts to some unsavory characters, saw this as a much-needed "get out of jail free" card.

Leaving the meeting, Jack devised a plan: he would kick his gambling habit, snag a Sunday newspaper to scour job listings, and then throw his hat into the ring for the drug trial. If he managed to secure a spot in the trial, his intention was to line up a job for after its conclusion, hopefully steering his life back onto a more normal course.

The city streets were coated in a fresh layer of snow, a scene that was both mesmerizing and bone-chilling. The cold penetrated to his core, leading Jack to question the wisdom of not hitching a ride with Vic. As he trudged on, he mused about how long he could survive in a wintery climate if forced to live on the streets. He also thought about living with his drunken mother but banished the idea immediately.

Fifteen minutes into his journey, Jack arrived at "Brown Street Goods," a small market that promised temporary warmth. With determination, he cleared the entrance of snow and managed to get the door open against the wind's resistance. The bell above the door jingled merrily as he stepped inside, and the door slammed shut behind him, shutting out the cold winds.

In this haven of warmth, Jack's mood improved significantly. He felt the blood returning to his frozen extremities, and he couldn't help but smile. With a sense of relief, he removed his earmuffs and stowed them in his pocket, ready to tackle the next part of his adventure.

The store had a charmingly worn look, a dingy tile path leading to the register. Flanked by double-sided shelves holding familiar items – candies, chips, toilet paper, cat food, and the beloved canned Beefaroni and Spaghetti-O's. Classic convenience store goods, though triple the grocery store's prices. The aroma of freshly brewed hazelnut coffee tickled Jack's senses, inviting him to grab a cup alongside the newspaper.

​Guilt nibbled at him as he noticed the trail of slushy footprints he'd left behind. When he reached the counter, he rubbed his frigid hands together and cleared his throat, facing William, a seasoned silver-haired clerk. The elderly man welcomed Jack with a sly wink and a small grin nestled beneath his bushy mustache.

"How's it going? Cold enough for ya?" the clerk chimed in.

"Tell me about it, it's downright brutal out there. This winter's a real piece of work. Sorry about tracking in the mess," Jack replied, rubbing his hands together to stave off the chill.

"Don't you worry, son. Cleaning's become my main form of entertainment these days. Looking for some smokes?" the clerk inquired.

"How 'bout a job?" Jack threw back, a half-smile gracing his lips.

"Well, if only business were booming. Economy's not exactly throwing a party right now. How long you been on the job hunt?" The old clerk's curiosity peeked through the mustache that adorned his weathered face.

Jack frowned and sidestepped the question, focusing on restoring feeling to his frozen nose. "Just give me a pack of those Camels, and if you've got a Sunday paper left, throw that in too."

The seasoned clerk nodded and retrieved the cigarettes. "Single pack or doubling down? You know, you get a deal with two."

"Just one for now," Jack answered.

William placed the cigarettes on the counter and leaned over to fetch a slightly used Sunday paper. "Eight bucks for the smokes and the paper's on the house. Just finished reading it," he said as he rang up the order.

Jack's face brightened, appreciating every chance to save a few bucks. As he reached for his wallet, his eyes caught the display of scratch tickets to his left. He'd spotted them upon entering the store but quickly averted his gaze to stave off the temptations that haunted him. Jack was determined never to waste money on gambling again, but then an idea flickered into his mind. "Hey, Sir, how much would that paper really cost me?"

"Two bucks, but don't sweat it, kid," the old man grinned, offering a wink.

"Well, that's not quite where I'm headed with this. I'm thinking of taking your kindness and testing my luck. How about a two-dollar scratcher?" Jack suggested with wide-eyed enthusiasm.

"Hmm, alright. Which one's your pick, son?"

"You make the call, old man," Jack responded promptly, his eyes locked on the case. He couldn't help but notice the ticket promising "$2,000 a week for life," and his mind painted a vivid picture of the dream life it offered. Still, not wanting to jinx himself, Jack decided to let the clerk choose for him. As expected, the old man selected a different ticket, not the one Jack had felt particularly "good" about. Yet, he decided to stick with the clerk's choice, reasoning that his luck had never exactly been a winning streak. The ticket landed on the counter, a penny placed atop it.

"That's ten bucks, all in," the clerk stated.

Jack pulled out a well-worn debit card from his wallet and handed it over.

"I can put the cigarettes on the card, but for the ticket, I need cold cash."

"Damn it… got an ATM around here?" Jack asked through gritted teeth.

"Sure do, it's in the back. But there's a three-buck charge, mind you. So, this ticket's setting you back five bucks," the clerk warned.

"Well, let's hope I hit the jackpot then!"

Jack hustled to the back of the store, inserted his card into the ATM, and reminded himself not to let the gamble spiral beyond the "free ticket" he was getting. The state of Massachusetts had been coughing up $300 a week in unemployment benefits, yet like clockwork, every week he'd squander it all at the casino. He entered his pin number, hesitating for a moment. Should I even be withdrawing money right now? he pondered. For an instant, he considered abandoning the ticket idea and walking out. His eyes flitted to the front of the store and his thoughts played out the repercussions of his impending decision. He almost cancelled the transaction, but then his gaze fell on a luminous digital sign that shouted, "$40,000,000," the -Lottery Jackpot-. Right beside it, a white sign chipped in, "You can't win if you don't play." Jack's mind was made up.

"Ah, screw it," he mumbled.

"WHAT?" the old man's voice boomed from the counter.

"Nothing!" Jack yelled back.

Facing the ATM, Jack contemplated how much to withdraw and decided he might as well get all the funds out to avoid future fees. He reasoned it was smarter to take the hit just once. He withdrew $280, leaving a measly $17 in his account. Jack pocketed the wad, except for a twenty-dollar bill needed for the ticket and smokes. Returning to the counter, he handed over the twenty, receiving a ten-dollar bill in return.

"May luck be on your side," the clerk grinned.

"Thanks, Sir. Mind if I scratch it here? Just in case I win?" Jack inquired, eyeing the ticket and mindful of the cold trek back to his apartment.

"I already picked out your penny." the old man replied with a wink.

Jack's smile broadened as he picked up the penny and started scratching off the ticket's coating. After a moment, he checked it, checked it again, and once more. He had lost.

"Damn. I was really hoping for something to break my way," Jack muttered, stowing the smokes in his pocket and grabbing the paper.

"It was worth a shot, son," the old man chuckled.

"Sure was," Jack replied with a disappointed expression.

About to leave, Jack's gaze fell upon the ticket that had caught his eye initially: "$2,000 a week for life." The statement lingered in his mind, prompting a moment of reflection. Why does that ticket seem to be calling to me? he wondered.
"What the heck, I've got no use for this ten-dollar bill anyway. Give me five of those tickets over there," Jack declared, tapping the glass case.

The seasoned store clerk fetched five tickets as requested. "Here you go. Feeling lucky now?"

"I don't know, but for some reason, that ticket is whispering to me. It's like it's trying to tell me something. I've got a good feeling I might just win big," Jack said, setting the paper back down on the counter.

"Alright then, here's to your win," William responded as he took Jack's payment.

Jack proceeded to scratch the tickets in rapid succession, each time his frown deepening as the truth unveiled itself: they were all losers. Disappointed in himself for being lured back into gambling's clutches, he hastily discarded the losing tickets in the trash and retrieved his paper. He shot the clerk a grin. "Here's your penny..."

Jack examined the penny the old man had handed him for the tickets. Something felt off, and he checked the date: 1990. It was one of those newer, cheaper alloy pennies they'd started producing after 1981. Jack tossed it into the air, catching only a faint tick. He grinned, realizing the source of his bad luck. "Mind if I pick my own penny from the cup?" he asked, placing the paper on the counter.

"You got some kind of penny superstition, huh?" the old man chuckled.

"Sort of. These newer pennies are like magnets for bad luck," he commented while rummaging through the cup. He pulled out a darker penny and cradled it in his palm. The year read 1978, his birth year. A sign. He flicked it upward, the metallic ping confirming its high copper content. A smile formed. "This one's my lucky charm. Give me ten more of those tickets." The clerk shrugged and handed Jack a fresh batch of ten tickets.

Taking a deep breath, Jack separated the tickets with care. Slowly, he scratched each one, his attention laser-focused, diligently revealing the potential winners. When he was done, he held onto only three cards that had secured him a total of ten dollars – half of what he'd paid.

"These ones not living up to the hype?" the clerk teased.

"Give me ten more," Jack requested, fishing out a twenty from his pocket.

"You... sure about this, kid? Ain't you supposed to be on the job hunt?"

"Don't worry, old timer. I've got savings," Jack fibbed.

"Well, alright then. Let's have a bit of fun."

The old man handed over the tickets and pocketed the twenty. He cashed in Jack's previous winnings and asked if he wanted the cash or more tickets. Jack opted for new tickets as he scratched away at the ones already in front of him. Lost in his own world, Jack's focus was singular: hope. He ventured into a realm where his life could transform at any second, where everything could turn for the better. Bills paid, a new apartment, a shiny car, all debts wiped clean. Jack's world was about to shine brighter, he could feel it.

An hour later, Jack stood before the counter, one ticket unscratched. He had lost all his money, the store clerk snickering, assuming the young man was having a bit of lighthearted fun. For Jack, it was no amusement. He had just squandered his week's income, leaving him without enough for food, rent, or the overdue electric bill, which brought the mocking eviction notice to the forefront of his mind. The gambler was broke, again. But this time, it was dire. With rent 37 days overdue and no power... Jack realized his misstep. He should have used the money for food or to pay the electric bill. His face drained of color, eyes dimmed with the weight of his compulsion's aftermath.

"Feeling lucky with that one, son?" the old man asked.

Jack flinched, met the clerk's gaze, and let out a sigh. "I hope so. Really, damn well hope so."

With a heavy heart, Jack scratched the card, the sting of defeat sharp and unrelenting. As expected, it was another loser. Like Jack himself. He tossed the scratch card into the trash, along with the pile of several hundred others. He closed his eyes, rubbed his face, and embraced the cold, hard truth. All he wanted was to cry. He turned to the door, his exit marked by the clerk's shout.

"Your paper!"

"Keep it."

Jack trudged through the dim and icy evening, his head hung low. A cigarette dangled from his lips as he meandered the desolate streets of Boston. The realization that he had a mere $17 left on his card hit him like a punchline, meaning he was stuck with another week of raw Ramen noodles. He ambled toward his apartment building, pondering how he'd dig himself out of yet another self-made mess. A glimmer of hope warmed his thoughts as he recalled his buddy Vic's "golden opportunity." Checking his watch, he noted it was just past 5 pm – he had a tight window to apply for the trial online at the Boston Public Library before it closed in two hours. Jack's optimism was fragile; his life was running low on chances, and he needed a game-changer, pronto.

As Jack started to feel almost like a functioning human again, a silver Buick SUV pulled up beside him, giving him a nudge just strong enough to knock him over. Out stepped Jimmy and Tony Rizetto, offspring of the infamous mob boss, Carlos Rizetto.

"Hey, Jacky boy, did ya miss us?" Tony quipped, sporting a grin. Both were decked out in dark jeans and leather jackets.

"Did you have to use your car as a battering ram, you dick?" Jack shot back.

They burst into laughter. "Oh, poor Jack, got a little ouchie? Gonna cry, baby?" they teased. "Where's the cash you owe, Jack? It's been over a month – you owe us over $5,000, and the boss is tired of waiting."

"If he only needs $5,000 for his gender reassignment surgery, why not apply for a loan?" Jack quipped, instantly realizing he'd regret it.

Jimmy's fist collided with Jack's gut, sending him sprawling back onto the snowy sidewalk.

"Okay, okay, I just need a few more days," Jack began, cut off as Jimmy delivered a kick to his stomach. Jack lay still on the ground.

​"You've got one week, Jack, or you'll be experiencing a very painful session, capisce?" Tony barked. They both retreated to their vehicles and left Jack in the snow, staring at the sky as snowflakes gently drifted onto his face.

NEXT CHAPTER