On a riverboat casino headed down the Manessissippi River, a pure white stallion with a pair of dice for a cutie mark walked the deck, looking for ponies to carry out conversations with. Spotting one, an orange Earth pony with a carrot cutie mark, he sauntered over to her.
Leaning up against the Blackjack table she was playing at with the dealer and a light blue earth pony mare, he gave her a low-lidded look and said in his most honeyed voice, “Why, hello there, ma’am. I couldn’t help but feel that it’s an absolute crime for a mare as lovely as yourself to be here all alone.”
Sweeping off his fedora with a flourish and bowing slightly, he introduced himself. “My name is Lucky Streak, but you can just call me Lucky. And what lovely name belongs to such a beautiful mare?”
She giggled at his introduction, not in derision, but in nervousness. “My name is Carrot Top,” she said finally, beginning to blush at the sudden attention from the colt, distracting her from her game completely.
There was no denying that Lucky was handsome, and he knew it. But his accent was what really sold his personality. It was fine, cultured, and undeniably upper class, leaving listeners with a heady sensation reminiscent of drinking champagne. It wasn’t a Canterlot accent, but from a place far older than the Equestrian capital. No, he was from New Poneleans. In combination with his looks, he cut quite the distracting figure to many a mare, making his job of distracting patrons that much easier.
While the mare was occupied with listening to the flirtatious comments being made to her by the stallion, his associate running the Blackjack table, a gray Earth pony with black dappling across his coat grabbed some of her casino chips, while his other associate, the blue pony he had stationed at the table, switched one of her cards with Carrot Top’s that would no doubt make Carrot lose this hand. It was done so quickly and efficiently that, had Lucky not been looking for it out of the corner of his eye, he would have missed them both.
With an experienced eye and a quick glance, he took in what just happened. As usual, the dealer had performed excellently, taking just enough chips to make an impact but not too many as to be noticed. The planted player had also done well, switching cards that were of the same suit, but giving Carrot a card one count lower than the one it replaced.
He wrapped up the conversation with the mare, finishing with, “I’m sorry, but I’ve got to go now. How’s about you leave me your number, though, and we’ll see if we can meet up for a drink sometime, hmm?”
The mare murmured her agreement, wrote down her number on a bar napkin, and handed it to him with a wink. Nodding his thanks to her, he took her hoof, kissed it, and left. He waited until the Blackjack table was out of sight, and then ducked into a door labeled “Owner.” He closed the door behind him, and then sat down behind his desk in the center of the office to do paperwork. An hour later, he felt the bump that announced that they had arrived back at their starting point, and heard the shuffle of ponies’ hooves as they exited down the gangplank onto dry land.
As the bouncers closed and locked the front door for the night, Lucky heard a knock at his office door.
“Come in.”
The two ponies from the Blackjack table earlier came in and sat down in the chairs in front of his desk.
“Ash! Sapphire! Great to see you. So tell me, how did it go today?” he asked leaning his chin on one hoof as he waited for the good news.
“Well between the two of us, we were able to win two thousand bits today,” replied Ash with a satisfied grin.
“And how many did we earn the ‘questionable’ way?” asked Lucky with a knowing smile.
“Half of that,” replied Sapphire. “It’s really amazing what ponies won’t notice being taken right out from under their noses.”
“Sure enough,” replied Lucky. “Well, I do believe y’all have earned your keep for tonight. Here’s your cut for the day.”
He dropped ten bags containing the thousand bits they had swindled from their patrons that day. “Now y’all go out and enjoy yourselves. I think we’ll take a break for a week or before moving on to richer waters.”
“Where are we headed next?” Ash asked excitedly.
“Well that mare from earlier, Carrot Top, said she was visiting friends in Manessissippi. She said she was from Ponyville. If they’re all as easy to play as she was, I think it’d be a great idea to pay a visit to the little town,” replied Lucky with a smirk.
“Anyway, y’all get going. Go on, enjoy yourselves!” he said, playfully shooing them out the door.
“Thanks, Boss!” said Sapphire as she and Ash scooped the bits into their saddlebags.
“Please, I’ve told you before, just call me Lucky,” he called out to them as they walked out the door.
After the door closed, Lucky sat back down at his desk and looked at the papers he was working on.
King Pin,
Today's profits are lower than yesterday's. I take it as a sign that we need to change venue a small bit, so my associates and I will be moving temporarily to a small town named Ponyville. I would like to inform you that we are now fifty percent of our way towards the set price, and I wish to remind you that once you receive the agreed upon sum, our business will be concluded forever.
Sincerely,
Lucky Streak
Working for a benefactor he knew nothing about was a little troubling, to be sure. But this pony did set him up with ponies who taught him everything he knew about casinos, and had set him up with his own casino to run. He just wanted to pay off his debts to the pony so that he was out from under the hoof that loomed over him.
Early the next morning, Lucky was finishing up preparations for their trip to Ponyville. He went about the deck, stowing loose articles left out from last night. As he picked up a pair of reading glasses left behind by some careless patron, he heard the scuff of a hoof behind him. He turned to see one of the security guards walking dazedly towards the bar area that doubled as their dining area.
The pony in question was a gray Pegasus with a long, orange mane and goatee. The Pegasus looked over to Lucky and mumbled a groggy, “G’mornin, Lucky.”
Lucky nodded to him with a smile. “Mornin’, Ymber,” he replied amicably. Lucky liked the pegasus, he was a good kid with a smart head on his shoulders. He finished picking up, and sat down across the table from Ymber, since they were the only two awake at the time, excluding the cooks.
“So where are we headed now?” asked Ymber as he munched on a muffin. “Somewhere interesting, I hope.”
“Well, I heard about this lovely little town from a mare yesterday,” replied Lucky. “It’s a bit far upstream, real close to Canterlot, but worth it, if they all gamble like she did,” he explained with a lazy grin.
“Well, don’t keep me waiting, where is it?” asked Ymber, eyes brightening exponentially at the thought of a town full of easy marks.
“Calm down, now,” Lucky chuckled. “The town’s called Ponyville. Hay, it even sounds like an easy job.”
Ymber’s excitement, palpable one moment, vanished the very next, and his eyes darkened.
“Not to be a wet blanket, boss,” he said slowly, as if it pained him to say the words. “But I’m from Ponyville.”
Lucky stopped, processing and filing this information away. This could potentially cause some complications. The first was the risk that somepony could recognize the colt, which would lead to questions, which, if answered, would lead to their work being discovered. Another problem that could rise was that Ymber, surrounded by the familiar faces that once made up his home, may accidentally grow a conscience, and end up losing them all their business. He slowly turned back to the stallion in question.
“Are you going to have a problem with us working in your hometown?” he asked carefully.
“No, I won’t be all that bothered by it,” he said, shaking his head. “I just worry that I’ll be recognized.”
Lucky smiled and nodded. “Don’t worry about it. We just won’t have you work while we’re there. That way you can catch up with family and friends while we do business. Sound good?”
Ymber nodded in return. “So when are we leaving? Soon, I hope,” he asked, obviously excited to see home again.
“Well, I figured we’d leave after everypony woke up and had breakfast,” he replied, leaning back in his chair. He heard the hoofsteps that announced another pony, and looked to see Ashen stumbling into the room. As he came and sat down with them, Lucky grinned. Ash was obviously hung over, and that was one of Lucky’s favorite times to mess with the earth stallion.
“Well, hey there, Ash!” he exclaimed as he slapped the gray pony on his back. Ash moaned in return, most likely in pain, but from the sound, light, or slap he couldn’t be sure. “Aww, are you all right, buddy?” he asked quietly, leaning down to look Ash in the eye. He received a bloodshot glare in return.
“Go to Tartarus,” Ashen growled, bringing a smile to Lucky’s face.
“Aww, don’t be like that, Ash,” the white pegasus said with a chuckle. “Be happy! We’re headed off to a new venue, after all.”
“Oh, yeah, I forgot,” Ash replied.
“Well, I would too, if I was that hungover,” Lucky murmured to Ymber so only he would hear, earning him a chuckle from the gray pegasus.
They continued to pass the time, reminiscing over past jobs and going over the plans for Ponyville. As they did, more of the staff awoke and joined them in the dining area, until all had assembled. Lucky stood on a table and surveyed the ponies around him; his trusted colleagues.
“Well, everypony,” he began. “It looks like this town has begun to dry up.” This remark was met with a few groans and mutterings. “But don’t worry, I’ve heard about this nice town up North a little ways that’s just full of new marks.”
“How far North?” questioned one of the cooks.
“Oh, don’t worry, you all,” assured Lucky. “It’s not too close to Canterlot, so there won’t be that much of a chance we’ll be caught.”
He thought about the stories he and the rest of the group had heard about swindlers and cheats being punished harshly by the guards to prevent future incidents. Beyond scared straight didn’t even begin to describe how the ponies were once they came out of the dungeon. In reality, the town was actually quite close to Canterlot, but Lucky didn’t see the point in worrying the crew. No harm in a little white lie. And besides, why would Canterlot guards be in Ponyville, anyway?
The crew was in various states of wakefulness, but the common attitude was one of excitement, or at the very least happiness to be off to another town. He heard various murmurs and whispers, all positive, before Ymber jumped on a table and yelled, “Well, what are we waiting for? Let’s get moving!”
With joyous cries of assent, Lucky made his way to the wheel with a chuckle. He put the boat to full forward, and settled in, hooves resting lightly on the wheel, occasionally maneuvering the surprisingly agile vessel through rocks on the way up the river. He would stay there until the small hamlet of Ponyville was in sight.
“Sapphire!” he called to the blue pegasus mare. “Go and see about finding us some space at their docks, yeah?”
She gave a lazy salute and smiled, taking off after a graceful dive off the ship, flaring her wings just before plunging into the water.
Half an hour later, the Horseshoe anchored in the middle of the river, waiting for clearance to dock. Waiting for them was Sapphire, deep in heated conversation with an aged, tan mare with a scroll for a cutie mark, probably the head of the village. It looked like the conversation wasn’t going well for either party, at the moment. Calling Ashen over and handing him the wheel, Lucky took off towards the mares, landing in a trot to kill extra speed.
“Is there a problem here, Saph?” Lucky asked the mare.
“The mayor doesn’t want to let us dock,” replied the blue pegasus with a huff.
“It isn’t to be inhospitable or anything,” defended the mayor. “We just aren’t sure how well your establishment would fit in in our village.”
Lucky stepped in front of the mayor, dazzling smile on his face. “Now Miss Mayor,” he said, voice dripping with charm. “It isn’t as if we’d be the first business to set up shop here, correct? You must have nightclubs, of course?”
“Well, yes, we do,” responded the earth pony.
“And would it really make that much of a difference if the citizens of Ponyville had another place to let their manes down for a while?” he asked sweetly, giving the mare a lazy smile
“W-well, I suppose not…” the mare said quietly.
“Then is there really any reason not to let us dock here?” he asked innocently.
“No, I don’t suppose there is,” the mayor replied after thinking it over to herself. “I hope your business works out well for you, Mr…”
“Streak,” Lucky replied, offering a hoof. “My name is Lucky Streak. It’s been a pleasure speaking with you Mayor…”
“Mare,” she finished, shaking his hoof.
“Wait, so your title is Mayor Mare?” Sapphire asked from behind Lucky. Lucky quickly put a hoof over the blue pegasus’ mouth before she ruined what he had just gained them. “If that will be all, Miss Mayor, we’ll be returning to our ship now.”
The mare nodded and smiled at Lucky and trotted off, after shooting a glare in Sapphire’s direction. Lucky turned back to his colleague with a small smile. “See, Saph? It’s not that difficult to get what you want. You just have to know how to ask.”
Sapphire rolled her eyes in response. “The only reason you get anything done is because you give every mare you need something from bedroom eyes and flirt shamelessly,” she teased.
Lucky laughed. “And that’s my way of asking,” he replied. “Now come on,” he said. “I don’t trust Ashen steering the ship for very long, and we need to set up shop.”
King Pin,
We have pulled into the town of Ponyville. There was a slight misunderstanding with the mayor for a few minutes, but it was quickly handled, just as I was taught. We open shop tomorrow night, and are looking forward to easy pickings among the simple folk living here. Some of my employees who went into town today came back and mentioned that the citizens here are extremely trusting. They were welcomed with smiles regardless of where they went, and some even got gifts from an eccentric, white unicorn, who said that their clothes were “rags not even a filthy manticore was fit to wear. Expect another letter soon. Details on the town will be included.
In your debt for now,
Lucius Streak
