Chapter Text
In a world filled with cartoon magic and next to zero scientific logic, there was one fact that remained certain: Cuphead was incredibly lucky.
And not just in a “Oh, I found a coin on the street!” kind of lucky. He was the kind of guy to walk head-on into danger, behave completely reckless, and come out with little injuries and an interesting story to tell. People could only look at him in disbelief before choosing their own sanity and ignore the very obvious sign that the universe seemed to have favorites—and it was Cuphead.
Even at a very young age, during his first introduction to gambling, all dice usually landed how he needed them; cards would fall into place like they wanted him to win. Heck, even mistakes or accidents seemed to work in his favor!
The only time he ever lost to anything was when he wagered his and his brother’s souls to the Devil. It could be said that the bet was rigged—never meant to be won by anyone other than Devil himself. But even so, Cuphead and Mugman came out victorious in the end, even uncovering possibilities beyond what they ever imagined.
Many may call his luck a blessing.
Cuphead would just shrug it off and continue on to the next betting table.
Many years have passed since then. Cuphead and Mugman now willingly work at the Devil’s Casino as waiters, fighting their way through afternoon rushes rather than waves of bloodthirsty minions. On one fateful day, the clinking of dishes and chatter of patrons filled the busy casino. The two brothers leaned against one of the less populated counters, finally having their breaks after long hours of taking orders, running drinks, and clearing tables.
Sitting near were some of their other co-workers: Chips, Wheezy, and Pip and Dot—all taking their own breaks.
Cuphead wiped his hands clean with a rag, exhaustion clearly displayed on his face as he sat down on one of the stools. “Man… I don’t think I can carry another tray tonight.”
Mugman, on the other hand, looked a bit more composed—though admittedly just as tired as his brother. He sighed and took his own seat beside Cuphead, “Come on, just rest for now, the rush’ll be over soon.”
Before Cuphead could form a reply, a sudden burst of noise came from a different area. In one of the more crowded areas of the gambling tables, sounds of cheering, groaning, and scraping of chairs could be heard.
“What’s goin’ on at that table there?” Cuphead asked, straw tilting toward the sound.
Chips looked to where the noise came from. “Oh, it’s just one of the dealers winnin’ a fortune again,” he said casually, “That guy has been on a roll for quite some time now.”
Cuphead’s grin spread instantly. The exhaustion previously plastered on his face was now replaced by something closer to an ‘Is that so?’ expression. It was a look Mugman knew all too well and, unfortunately for Cuphead, he had a say in his brother’s plans.
Mugman groaned, pinching in between his eyes as a headache started to form. “No. No, no, no—you’re not going there, Cuphe—”
Too late. As Mugman opened his eyes, his brother was nowhere in sight. He shot an annoyed look at the cartoony dash-trail that his brother left off in his haste. Turning his attention to his co-workers, his mood soured. Wheezy and Pip and Dot were laughing at his expense, while Chips made a shrugging gesture.
Meanwhile, it didn’t take long before Cuphead reached the packed table. Across from him, he was met with the sight of two men facing each other down. One looked wealthy, based on his attire, though disheveled and had a devastated look on his face as he recently lost all his money to the dealer. Cuphead crossed his arms together with a low whistle as he watched the scene, “Welp, break time just got interestin’!”
The dealer, confident and composed, laughed as he took his prize money from the pitiful man. He pocketed the money and stacked his chips with practiced ease.
Seeing as though the previous round was over, Cuphead pushed his way forward. “Hey.”
The dealer glanced up and raised a brow. “You? Aren’t you one of ‘em waiters? We’re not here to order anything.”
Cuphead planted his hands on the table, not letting the snidey comment ruin his fun. “Nah. I’m here to gamble,” Cuphead said with a smirk.
His words got a few murmurs from the crowd.
The dealer leaned back slightly, eyeing him with a snort. “Pffft, what? I’ve heard the stories about you, kid,” he taunted, “Did the last time you pulled this shit not enough of a lesson? You plannin’ to sell your soul again?”
“What? No!” Cuphead scoffed. He knew what this man was trying to do. Cuphead may be viewed as dumb or reckless by many, but he knew when someone was attempting to rile him up. He does know what to do when it comes to gambling. Besides, it’s a common tactic to provoke your opponent before the rounds begin, so that they wouldn’t be able to think straight and act purely on irritation or anger.
Because of this, he remained calm. He couldn’t accidentally lose his cool and job to someone who was just trying to pick a fight with him. However, he now wanted to prove something to this dealer. “I’m obviously going to use my money! If I win, I get all your prize winnings. If you do, and I doubt you will, you can have my paychecks for the next 6 months, so—”
Somewhere behind the crowd, a very loud and horrified-sounding “WHAT!?” could be heard from Mugman. Cuphead paid it no mind.
The dealer’s interest sharpened. Slowly, he gestured to the empty seat. “Alright-y then… let’s play. I’ll explain the rules.”
The rules were shared and the game started. The first few rounds were small, with a few chips and coins passed around here and there.
Cuphead lost a round.
He won the next.
Lost again.
Took the win in another.
Honestly, it looked relatively fine. The crowd was starting to grow impressed at how smooth and balanced the game was currently, considering how poor the previous ones, who gambled with the dealer, did. Others were getting more curious on who would triumph in the end, placing their own bets on who would win between the two.
Then, the rounds got heavier and so were the bets. The casual pile of chips had turned into something more dangerous. Mugman, and the other staff members, watched with mixed emotions. The blue mug, who wanted no part of this in the first place, had forced his way to the front row to watch his brother, hands clutched on his head in panic.
“Cuphead, I swear to Satan himself, if you lose half of our finances over a stupid bet. I will personally—”
Cuphead didn’t even look back when he cut Mugman off, “Relax, Mugman! I promise, I know what I’m doing!”
Across the table, the dealer’s smile had grown just a little sharper.
“Are you, now?” he asked as he prepared for the final round. “Feeling confident, ey?”
Cuphead shrugged before smiling. He looked at his table for a moment, debating something in his mind, before he pushed forward every single chip he had. “All in.”
Silence befell among the crowd. Despite having a generous amount of chips from his own wins, Cuphead still didn’t have as much as his opponent. So, to pull a bold move just like that—
The dealer cackled; he couldn’t help but grin further. This was the perfect moment that he’d been waiting for.
What Cuphead didn’t know—what no one at the table knew, really—was that the game had been rigged the entire time.
The reason why no one else had beaten him at all during the high-stakes bets wasn’t because of some dumb luck. He made sure that all favors would be at his hands when he wanted them to.
The dealer slowly gathered his own pile. It was a far larger tower than Cuphead’s, made from the losses of countless others, and accepted the challenge.
With everything on the line, the dealer had Cuphead exactly where he wanted him.
“Roll,” the dealer insisted smoothly, handing the dice to Cuphead in a conceited way.
Cuphead took it without question, eyes held nothing but the thought of winning. He blew on the dice before shaking it with both hands.
Mugman closed his eyes. The crowd among them held their breath. Waiting. And waiting…
Then—Cuphead rolled the dice. It tumbled across the table and bounced twice, before ultimately stopping.
Silence.
The dealer, still looking smug, leaned forward—a taunting remark at the ready. His eyes caught the numbers on the dice and froze.
“…What.”
Cuphead blinked. Then, he looked at the results as well, before his mouth turned into a wide, triumphant grin.
“HAH!” he shouted. The cup stood up and slammed both of his hand on the table. “SUCK ON THAT, LOSER! I WON!”
The crowd erupted. Some cheered for the cup, some were in disbelief at what just happened, while others grumbled as the person they thought would win just lost. It was pure, utter chaos.
Mugman stared, speechless and not-fully there, yet.
Chips went in to pull the cup in a side-hug, saying, “Heck, yeah! I knew you’d do it.”
“No, you didn’t,” Wheezy said, looking and sounding slightly disappointed as the cup whooped in joy.
Amongst all the noise, the dealer still couldn’t wrap his head around the loss as Cuphead took all his money away from him. “B–But, how!?” The dealer asked, but no one seemed to listen to him.
How did this happen? His game was perfect. Flawless. Made to be in his favor at all times.
Yet, despite the impossible odds…
The dealer stared at his elated opponent. Cuphead now had his back turned, talking to his brother, all animated and proud as he held the bag of money in both hands. Mugman, a bit more collected now, was telling him off not to do that again, but had a smile of relief on his face.
The dealer really stared at him.
And he couldn’t figure out how he did it.