Meeting Charlie Madagan: Part 1, Chapter 10

“Kyler! Kyler, wake up!”

Kyler groggily wiped at his eyes. The room around him was still dark. This wasn’t all that uncommon with the limited daylight of December in the Midwest, though this lack of light was far more pronounced than usual.

“Kyler!” Riza shouted again. “Wake the fuck up.”

He felt her shake at his arm, her breathing hurried and panicked.

“I’m up, I’m up,” Kyler grumbled. He felt around for the light on his nightstand, clicking it on and blinding himself in the process. The clock on his dresser read 5:17 am, but Riza was dressed for the day. Judging by the bag at her feet and the winter coat she was wearing, she was ready to leave.

“Where are you going?” Kyler asked.

“I got a call,” Riza said. “My dad. He’s…he’s not good.”

“Oh my god. Did he get in an accident?”

“No, nothing like that. It’s cancer.”

The room fell silent. Kyler expected Riza to be a sobbing mess. Not because that’s the type of person she was — in fact, Kyler wasn’t sure he remembered a time where he’d seen Riza cry from anything other than laughter. Riza was always the strong one, be it in conversations, in an argument, or just in life. At the same time, her dad had a serious disease. That knowledge made Kyler upset and uncertain, as he’d known Delmon Andreesi for much of his life. For Riza not to be sobbing or choking back tears was astounding to Kyler.

“I’ll come with you,” he replied. “Or I’ll drive down after my last final this afternoon, I mean. I should probably take that.”

“You should,” Riza said. “Weren’t you spending the weekend here?”

“Yeah, but that was before –”

“We’ll be fine. Just come visit us on Monday or Tuesday. Whenever you’d planned on coming back anyway.”

“Are you sure?” Kyler asked. “I can drive down right after.”

“I am,” Riza replied. “He’s apparently known for a few months. We need to have a talk about why he didn’t tell me before now.”

“I’m sure he just didn’t want to put that on you mid-semester. Especially with you being one semester away from graduating.”

“It’s not his place to decide what I can handle and what I can’t. Really though. Take your final. Get trashed with Troy or whatever you plan on doing. We’ll see you next week. I’ll even talk him into taking us ice skating.”

Riza gave Kyler a hug goodbye, then left the apartment, quietly shutting the door behind her. Though Kyler tried to go back to sleep, Riza’s unexpected news kept him wide awake. If her dad hadn’t told her about the cancer until now, it had to be for a reason. Maybe it was relatively minor. Maybe he was already cancer free. Maybe he really just was trying not to stress Riza and add onto the mental load that her accelerated college plan gave her. Whatever it was, Kyler would figure it out when he went home.

With sleep eluding him, Kyler got dressed and made his way to the coffee shop just off campus. It wouldn’t be open until 6 am, but if he walked slowly enough, he should get there just as it opened. While most small towns tend to be dead just before the sun comes up, that reality was even stronger when the small town doubled as a college town. Even the occasional street lamp or pair of headlights couldn’t stop Kyler from having to adjust his eyes, not to mention wondering why anyone would voluntarily wake up this early.

Kyler’s phone began to ring, the sound practically screaming through the early morning air despite being in his pocket. He fumbled the phone open and hurriedly answered.

“You okay?” he asked.

“The fuck you talking about, Kyler?” came the voice from the other end of the line. It wasn’t Riza as he’d suspected. It was Charlie.

“Sorry. A friend of mine got some bad news and just had to rush home.”

“That explains why you answered,” Charlie replied. “Listen. What are you doing this weekend?”

“I’ve got a final this afternoon,” answered Kyler. “Then I’m probably hanging out with my roommate until I head home Monday. Why?”

“You got $100?”

“Yeah. Why?”

“Wanna go to Vegas?”

“Doesn’t it cost more than $100 to go to Vegas?” asked Kyler.

“You put up with this old man for a whole semester while I told you my life story,” replied Charlie. “No one gives a shit about how I’m happily married with kids. That’s not what makes me interesting. Let me show you a good time. Think of it as a thank you.”

“I don’t k–”

“And before you try to talk your way out of it,” interrupted Charlie, “that $100 is in case you want drinks on the plane. Couldn’t line up a flight that takes cards. Everything else will be paid for.”

“I mean, that sounds awesome,” replied Kyler. “When do we leave?”

“Our flight leaves at 6am tomorrow. It’ll take an hour for us to get to the airport. I’ll pick you up at 4.”


“Sleep on the plane if you want. You’ll want to be well-rested for your first time in Vegas.”


“I can’t wait to see The Strip!” Kyler said excitedly. “My parents told me it was one of the most surreal places they’ve ever been.”

“Yeah, we’re not going there,” replied Charlie. “At least not tonight. Too flashy. Too touristy. We’ll still go there tomorrow if you want. But I think you’ll enjoy yourself more with my plan.”

“So where are we going then?”

“Fremont Street. Some of the oldest casinos in the city are there. Security isn’t quite as tight there, so you can have a bit more fun.”

“Fun how?”

“You’ll make your own fun,” Charlie replied. He pulled their rental car up to the red light then turned to look at Kyler. “I’m not one to say what you should and shouldn’t do. But I am willing to make a suggestion.”

“Which is?” asked Kyler.

“You’re young. You’re healthy. You’re single. Just enjoy yourself. Don’t say no when opportunities come your way. And always aim higher than you think you can attain.”

“That might be the most profound thing I’ve ever heard you say.”

“Then let me say it a way that’s a little more direct,” continued Charlie. “Don’t stick your dick in ugly.”

Kyler looked at Charlie, stunned at the sentiment that had just cpewed forth from his lips.

“Just because you think someone’s ugly doesn’t mean I will,” replied Kyler. “We could be into different things.”

“My type is attractive women,” retorted Charlie. “If you don’t think that’s your type too, you’re either vastly underestimating yourself or you lied to me about having a girlfriend. If it’s the latter, I’ve got a guy out here who can get you in touch with the right people. If it’s the former, have some fucking confidence in yourself. The fact that you don’t is exactly why you don’t think some hot girl will be into you.”

The rest of the car ride to the hotel was spent in silence. Had Kyler really been underestimating himself? He really hadn’t had any relationships to speak of throughout high school. Even the ones he had weren’t particularly long, nor were they with girls that his classmates regularly referred to as pretty, hot, or whatever the physical appearance compliment du jour was. Sloane was certainly a conventionally attractive woman, and he did manage to date her for two years. Kyler certainly had no intention of trying to find a relationship so quickly after Sloane broke up with him. But maybe Charlie was right, he reasoned. After all, Sloane wouldn’t have stayed with him as long as she did if he wasn’t deserve it. There had to be some truth to what Charlie said, even if Kyler didn’t fully believe it.

After a short stop at their hotel, Kyler followed Charlie to the first casino on their loose itinerary for the evening. Charlie’s logic seemed sound enough. The casinos around Fremont street largely surrounded a pedestrian area, meaning there would be no risk to crossing the street in front of a car should one of them have a bit too much to drink. And though this wasn’t the famed Strip that Kyler had heard so much about, the glitz and the lights certainly caught his eye. No sooner had they entered the building than Kyler had a drink thrust into his hand by Charlie.

“Martini,” said Charlie. “If it’s not your thing, ask one of the cocktail waitresses. Tell them to put it on my tab. You see that brunette over there with the curly hair?”

Charlie pointed across the room to a busty brunette who was carrying a tray of drinks between a pair of roulette tables. She glanced there way and gave Charlie a small wave with her free hand and a big smile.

“That’s Misty,” he continued. “She’s off-limits. Anyone else you want to take back to your room, patron or staff, is fair game.”

“Why’s she off-limits?” Kyler asked.

“Misty and I have an arrangement. When I visit The D, she visits the d.”

“So she’s a hooker?”

Kyler had barely finished his sentence when he felt himself being pulled toward Charlie by the collar of his shirt. He stopped inches from Charlie’s face, finding himself staring into Charlie’s cold, steely eyes.

“Rule number one of spending time with someone who is paying for your entire trip,” Charlie snarled, “don’t insult them.”

A tall, wide-bodied security guard was quickly by their side.

“Is something wrong, Mr. Madagan?” he asked. Kyler stared up at the guard. There weren’t a ton of people who made Kyler feel like a child, especially not since Kyler crossed the six-foot tall mark. But this man was massive.

“Not at all,” replied Charlie, his voice calm and upbeat. “His shirt collar is too stiff. I tried to fix it and yanked a bit harder than I meant to. Sorry about that.”

Charlie let loose of Kyler’s collar, taking the time to straighten it out as he did so.

“Understood,” said the security guard. “If there’s anything you need at all, please let us know. Will you be using your private room tonight?”

“I might,” said Charlie. “Though Kyler here might have more use for it than me. It’s his first time in the city. I want to show him a good time.”


“Fifteen,” said the dealer. “What do you want to do?”

Kyler stared at his card, the jack of spades and five of hearts peering back up at him from the table. He’d lost six hands in a row — and with that, more money than he felt comfortable admitting to Charlie — but things had to turn around at some point. All three of the other players at the table had won more recently than him, including the man to his left having hit blackjack on this very hand. Still, with the dealer showing a three of clubs, Kyler liked his odds better now than in most hands.

“Hit,” he said.

The dealer flipped a card over.

“Ace of hearts,” she said. “Sixteen.”

Kyler felt his rising frustration spread across his face. On one hand, at least he didn’t bust again. On the other hand, this wasn’t much of an improvement in his position.

“You should hit,” said the woman to Kyler’s right. “You’ve been on a bad run. It’s got to end sometime.”

“Anything above a five and I bust,” replied Kyler.

“I know.”

“I’m down nearly four hundred bucks.”

“And if you win, you’ll make up half that,” the woman replied. “If I’m wrong or you lose, I’ll cover your bet.”

Kyler looked back at the table. The old man on the far side had bust. It was back to him. The dealer’s card stared back at him.

“Hit,” he said.

“Ace of diamonds,” the dealer replied. “Seventeen.”

“I should stay now,” said Kyler.

“No!” the woman quickly replied. “One more and stay under twenty-one and you automatically win.”

“We don’t have a 5 Card Charlie rule here, ma’am,” the dealer replied. “The only automatic wins are twenty-one with any count of cards and blackjack.

“Still go for it,” said the woman. “I feel your luck is about to change.”

Kyler knew very little about blackjack before tonight. One of the few things he did know was that the dealer is required to stand when they hit seventeen. It should stand to reason that he should too. But the more the woman to his right spoke, the more he was convinced he had a chance to win.

“Hit,” Kyler said for a third time.

“Three of diamonds,” said the dealer. “Twenty.”

“I’ll stand!” Kyler said emphatically. The woman nodded her head.

The dealer flipped over her second card, the king of clubs. She drew her next card — the eight of spades.

“That’s twenty-one,” the dealer said stoically. “Dealer wins.”

“Goddammit,” Kyler muttered under his breath.

Kyler picked up his last chips and walked away from the table. Even if he would have been better off leaving the game a half hour ago, the next best time to leave was now. He’d passed a few tables when he heard the sound of footsteps running up behind him.

“I wasn’t kidding about paying you for your bet if you didn’t win,” said the woman from the table.

“It’s really fine,” replied Kyler. “You have to know when to stop. That was my time.”

“At least let me get you a drink. If you wouldn’t have listened to me, you’d be better off.”

“I would have lost standing at seventeen or eighteen.”

“Let me try this again,” she said. “Hi. My name is Matilda. I think you’re good looking in a casino filled with people who are decidedly not. I would like to buy you a drink and see where the night takes us. I suggest my room, but I’m not picky.”

Kyler checked the time on the front of his phone. 10:35 pm. He had no idea how it’d gotten so late. It was still before dinner when he got her with Charlie.

“Deal,” said Kyler. “But let’s get some food first. I’m starving.”


The sunlight cutting over the desert skyline darted through the gap between the curtain and the wall, placing itself squarely in Kyler’s eyes. He squinted and tried to pull the blankets over his eyes, only to find they weren’t there. A plain white sheet covered his legs from the thigh down, but the blankets had migrated to the other side of the bed.

Kyler got his first sober look at Matilda as she slept beside him. She had a very attractive face, though she was much older than Kyler remembered her being. Her red hair was dotted with flecks of white and gray. She certainly wasn’t near his age and though Kyler didn’t have a problem with that, he couldn’t remember much of anything from the night before after leaving the casino to know if he’d enjoyed himself.

He grabbed his phone off the nightstand, happy he’d managed to put it close by despite not being in his own hotel room. The voicemail icon was lit up on the screen, along with an alarming twenty-two missed calls.

“What in the fuck?” Kyler mumbled.

He dialed into the voicemail and listened to the first message.

“Kyler. Charlie here. Listen, I see that broad you’re going home with. Good for you! Never took you as one for older women, but you could do a lot worse. Let’s meet up for lunch. We’ll see what worked and do what we can to make tonight better. Our hotel. 12:30 pm. Wear a blazer if you brought one.”

Kyler sighed and deleted the message. The next one started playing, Riza’s frantic, sobbing voice coming through the speaker.

“Hey. Pick up. Pick up please. I need to talk to you. I’ve tried calling ten times and you’re not answering. Something bad happened. Please call me back.”

Kyler deleted the message and went back to his call log. Charlie’s call came in at 10:40 pm, not too long after he remembered leaving with Matilda. Beginning at 12:09 am, Kyler had twenty-one missed calls. Nineteen were from Riza, two were from Troy.

The next message played.

“Dude,” said Troy’s voice. “I know you’re in Vegas, which, awesome, you owe me stories when you get back. But if you’re awake or alive, answer your phone. Riza’s calls me twice panicking. And I’m doing my best. But you’re her best friend. Answer if you can.”

The fourth message started.

“Hey. Me again. Troy says you’re in Vegas. So I know you can’t get back here. But please call me. Dad…he…”

The message trailed off before ending. The next one quickly began.

“He’s not going to make it, Kyler. I found him. *a long silence* He was barely breathing. I…I didn’t even know he owned a gun.”

Kyler deleted the message and shut his phone. He wasn’t sure how many more messages he had, but there was a good chance none of them were good. He felt Matilda stirring beside him, wrapping her arms around his naked waist.

“Well good morning,” she purred.

“Morning,” replied Kyler somberly.

“Rough wakeup?” she asked.

“Something like that.”

“I’m sorry. How about I make it a little better?”

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