Grimsley knew he was lucky. He didn't need everyone around him constantly saying it for him to believe it. He just knew. Although, if that luck could be classified as "good" or "bad," he wasn't quite sure.

After all, it was luck that he happened to drunkenly stumble into the one Nimbasa subway that traveled out to Castelia instead of the one to Driftveil. He honestly couldn't remember much from the day before, with the few remaining scraps of sober memories swirling in and out of his thoughts. He probably shouldn't have had so much to drink, but he couldn't object since it was free, offered up by a former college mate of his.

So now here he was, in Castelia with barely any money--where he used it all up, he had no clue--and a nasty hangover. Grimsley walked aimlessly down the streets, on the lookout for any open Pokémon Center. Despite having been to the city countless times, he was in no state to recognize the area.

Dark clouds loomed over the dreary streets, a telltale sign of an approaching storm. Grimsley groaned at that, knowing he would have to walk faster if he wanted to avoid the weather. The waves of people surrounding him all wore tired expressions, most likely they were leaving their jobs for the day and heading home to spend time with their families.

Grimsley couldn't recall the last time he had heard from his own family since the scandals started, but he didn't mind too much. They weren't much of a family to him. A mother and father by blood and lies. If anything, he was just born as a cover-up to them, an excuse for the "perfect family." Grimsley knew their secrets, and in a way, helped keep them. In his eyes, they were trash. Sure, his parents never hit him or called him names, but that's because they weren't there. They were always split apart, locked in their own separate paths of destruction. Out of sight, out of mind, and now out of money. A drunk mother, a cheating father, and a runaway son.

So, no, he didn't care to hear from them again. What he did care for was a warm bed and a bottle of painkillers.

As he followed the crowds of people nearby, Grimsley felt a body slam into him. The hungover male stumbled back a few steps, hands shooting up to grab at his throbbing head. His eyes narrowed at the sight of a scruffy teenager, who also seemed to have reeled back from their sudden collision. After a quick glance at Grimsley's irritated face, the boy gave a nervous laugh.

"Sorry, mister, didn't see ya there." And just like that, the boy was off yet again, already invisible as he darted back into the crowd.

Grimsley slowly moved his hands away from his head and continued to stay in place, looking at where the boy could have gone. Whatever hope he had of finding a Pokémon Center before it started to rain was now out the window, along with his patience. With a long and heavy sigh, Grimsley dug out from his coat pocket a Pokéball. The device had scratches here and there, but he didn't care that much. He gave up on appearances long ago.

With the simple click of a button, the device flashed as it shot out a beam of pure energy that formed into Liepard. The purple feline stretched her limbs at a leisurely pace, purposely ignoring her trainer's urgency. When she finally decided that she was ready, Liepard rubbed her head against Grimsley's leg. The man rolled his eyes but still took the time to pet her. "You know, if he steals my money, I won't be able to get you anything to eat."

That seemed to do the trick. The Pokémon instantly narrowed her emerald eyes, tail flicking at the thought of going hungry. Grimsley pointed in the direction of where the boy went and told her what he looked like. Liepard nodded and took off, her arching tail the only sign of where she was.

After following his Pokémon down a few blocks, Grimsley soon wound up in an quiet alley. Against the wall was the boy, who was trying to move as far away as possible from a growling Liepard. Although slightly out of breath from sprinting, Grimsley silently moved to stand behind the feline, a mocking frown on his face.

"So, if you didn't see me, how were you able to snatch my wallet from the inside of my coat?"

The pickpocketer paled even more at his words, now regretting who he picked to steal from. "I-I thought you were d-drunk."

"Yes, well, as you can see, I'm just hungover and now, thanks to you, broke." Grimsley knelt down to be at the same eye level as the boy. "And for me, having no money is quite unbearable." Liepard took her trainer's words as a sign to unsheath her claws, earning a whimper from the teen.

"Okay, okay, here, I'm sorry!" The boy fumbled around as he pulled out the wallet. He tossed it to Grimsley with shaking hands before pointing to Liepard. "Just get that crazy thing away from me!"

Grimsley ignored his plea, fighting the urge to laugh when Liepard hissed at the choice of words she was labeled as. "How about instead you answer some questions? What were you going to use my money for?"

The boy stayed silent, refusing to look him in the eyes. Grimsley smacked him halfheartedly with his wallet. "What, were you going to buy drugs or something? You'd need a lot more money than what's in my wallet for that, kid." He still didn't speak.

As he opened his mouth to talk again, Grimsley felt rain drops land on him. He hated getting wet, and he knew that Liepard did as well. And just like he thought, the feline reacted immediately, ramming her entire body into the boy, who shrieked in pain. Grimsley didn't move an inch as he watched him gasp for air on the grimy floor. "Let's try this again, huh? What'd you want my money for?"

After shakily moving back into a sitting position, the boy clenched his stomach as he answered. "I wanted to go to a betting house, alright?"

Grimsley's eyes widened. He had heard rumors that hidden throughout Castelia were various places to gamble away money through games, but he never gave them much thought. But now, when he was broke and in need of money, the thought of testing his luck out seemed tempting to say the least. Grimsley quickly thanked Liepard for her work then returned her back to her Pokéball.

"What's your name, kid?"

"Huh?"

"Your name. What is it?"

"...Charlie."

"Well, Charlie, let me propose something to you."

|•|

The two were soaked from head to toe when they entered a dimly lit bar. Water dripped down from the leaking roof, landing in metal bucket. Soft jazz music played from hidden speakers and filled the ancient room. Dozing off in the corner of the bar was a Xatu. A few customers were spread out in tables, and a single bartender stood behind a scratched counter.

Grimsley cocked an eyebrow at their surroundings. "Not much of a betting house."

Charlie, now calm and collected with Liepard out of the way, rolled his eyes. "We're not there just yet, old man."

"I am twenty-seven."

"Yet you smell like you're fifty."

The bartender looked up at them with a wave, silencing Grimsley's response. "Hey, Charlie. Who's the guy with you?"

The boy shrugged as he glanced at the mentioned male. "He's a friend, Terrence. Said he wants to try something new."

As if Charlie had said some kind of secret code, Terrence's eyes lit up. "I see." Terrence grinned at Grimsley, who struggled to not let his confusion show. "Well then, you've come to the right place. Xatu? We have two guests."

At the sound of its name, the psychic bird's eyes snapped open, although the rest of its body stayed eerily still. Once Xatu's gaze landed on Grimsley and Charlie, its eyes emitted a bright pink light, blinding Grimsley for a few moments. The ground beneath him seemed to dip and fold away, leaving him floating in darkness. His head pounded just as hard as his heart, and he began to panic. He didn't know what was going on anymore.

"Hey, you can open your eyes now. We're here."

Registering Charlie's voice, Grimsley slowly regained his senses. His body felt stiff, as if he had been trapped in a small box for hours. When he could finally open his eyes, he saw a snickering Charlie in front of him. "Xatu's Teleport is always bad the first time you experience it."

"We were teleported?" And that's when Grimsley realized where they were.

They stood in the center of a massive room filled with people. Slot machines were neatly lined up in rows by the dozens, pool tables surrounded the walls, and a Blackjack tournament was taking place just a few feet away. Smoke hung over the crowd like a cloud, formed by the various cigarettes currently lit. Music could barely be heard over the sounds of people shrieking and machines buzzing.

But all Grimsley could hear was the sound of money.

"Are you okay, old man?" Charlie asked from behind him.

Grimsley whipped around, a look of pure amazement on his face. "Kid, this is heaven for me. I am definitely doing more than okay." The male gripped Charlie's shoulder with giddiness. "I am so glad you suck at pickpocketing. Now, I'm off try my hand at poker."

"You sure you don't want to start off with something easier?" Charlie shook his head in disbelief. "You're just gonna lose the rest of your money that way."

For some reason,Charlie's words triggered memories from Grimsley's childhood. He remembered growing up playing online games. Since he wasn't allowed to see many people, he made friends with the men that he gambled with through the computer. He learned how to lie in order to save the thousands of dollars he gambled away. And, most importantly, he learned how to tell when someone else was lying in order take thousands of dollars they gambled away. Did he need their money? Not really, he had plenty back then. Heck, he still had loads saved away in some family account. But Grimsley took money for the same reason he didn't touch his own: he was greedy.

Perhaps it was from years living with shallow elitists and being spoiled from a young age to do whatever he wanted without consequences. Perhaps it was because his parents weren't there for him. Perhaps it was because the men he befriended taught him to love money more than life itself. Perhaps it was all of the above. But no matter the reason, Grimsley just couldn't be satisfied if he didn't make it clear that the money he earned was thanks to him being better than everyone else.

Sure, he should probably head back to the League right now and help fulfill the dreams of young trainers by battling them. He knew Shauntal was probably waiting for him to return so she could show him her newly finished novel. He knew he had a responsibility as one of the Elite Four to stay strong and be smart. But honestly? Grimsley was a weak man with a crazed sense of winning.

For the first time in years, a small but charming grin poked out from Grimsley's lips.

"Let me tell you something, kid. I never lose."