"We're here, Ma'am. Welcome to Chicago." Sean, her driver for the day, told Alison in his shy, low voice waking her.

Rousing from a shallow sleep, Alison groaned before removing her sunglasses and looking out the window of the sleek black car Tom had sent for them. The familiar landscape of North Side greeted her, the sky gloomy and dark, with the dark waves of the water crashing violently against the docks. Despite the weather, there were still men lined at the docks, gathered at a table playing a game of poker. Just like that, Alison knew that one of those men was the man she was looking for, the man she needed to befriend-- Vito Sallieri. How did she know he was there from just one look?

Simple. Vito Sallieri was a notorious 'businessman' in Chicago, owning the docks and other less-than-legal practices, including ammo supply, which is why Alison needed to meet with him. Another thing he was famous for? His gambling habits. According to a few little birdies, Sallieri would visit Las Vegas at least once a month to visit the casino and lose tons and tons of cash over craps, blackjack, anything he could bet on. He doesn't know when to quit, and Alison knew it was her way in.

Easy to say, it didn't take a genius to know that he was one of those rowdy men hunched over the game of poker with chips lined up.

Before getting out of the car, Alison smoothed her dress and made sure her signature red lipstick was still on point. She winked at Sean as she opened the door, saying "Wish me luck, Seany boy. I'm about to play poker with the devil." And with that, she was off.

Clicking her heels towards the group of men, most of them ogled her and devoured her with their eyes-- all except one. "May I speak to Signor Sallieri? Privately." She asked sternly, with a small smile. The man who ignored her looked up and put down his cards, a look of annoyance across his face.

"What do you want, kid? We're in the middle of a game here, so make it quick and worth my time." The man said, his age showing in the lines around his eyes as he shooed the other men away. The old man gestured for her to sit down across him, waiting for her to speak.

"Mr. Sallieri, let me cut to the chase. My name is Alison Allport and I work for Tom Shelby, I understand you did business with him before, yes?" Alison asked him.

Sallieri let out a heart laugh. "First of all, please, call me Vito. Secondly, yeah I know Shelby. Always looked like trouble. He's your boss now? Guess the bastard made it big in Vegas." He said before laughing again.

Alison nodded and faked a laugh, playing along with his humor. "Oh yes, indeed. Anyway-- Mr. Shelby has recently opened an ammunition business down in Vegas and he sent me here to buy some stocks from you. I hear you have the best weapons in the country."

"Oh, stop flattering me, Alison was it?" He asked, to which Alison nodded. "And you heard right. Come, come with me, my warehouse is just around the corner."

Alison stood up as she gathered the deck of cards on the table and gestured for the man to go first. "Lead the way."

--

"Viola," Vito said proudly as he opened the gate to reveal piles and piles of weapons on the floor and lines of guns on the walls. "Real beauty to look at, huh?"

Alison nodded, trying to hide her appreciation for the collection. "Indeed... I'll take it." She said, looking square into his eyes.

"The whole lot? Sorry Miss, but I doubt you could afford it." He said with a laugh.

Alison rolled her eyes but tried to suppress her annoyance. "I believe I can, after all, you're giving me a discount right?" Alison said with a sweet smile as she rested her hand on his shoulder gently.

Suddenly, Sallieri got serious and took Alison by the shoulders. "Lookie here, missy. This is a business I'm running, and no amount of googly eyes and pouty lips could make me give you a discount. Shelby ripped me off enough for this shit dock, I'm not about to let him do it again. So take it full price, or get the fuck out of here." 

Alison smiled right in his face before shaking out of his grasp. "I understand. I can't afford it." She simply stated before continuing. "But let me cut you a deal."

Pulling a deck of cards from her purse, she presented it to Sallieri. "High card wins. If I win, give the lot to me half price. If you win, you could keep everything and I'll give you the money Tom sent me and whatever cash and jewelry I have on me. Deal?"

Sallieri smiled a wide, cheeky grin. "I'm starting to like you, Alison. You got yourself a deal. Let me shuffle the cards." He said, snatching the deck from her hands and shuffling it in mid-air. "Ladies first." He told Alison.

Heart pounding and sweat beading on her forehead, Alison drew a card in the middle of the deck. As she turned it over, a huge smile creeped on her face. "Queen! Yes!" She said as Sallieri furrowed his eyebrows in worry.

Slowly, he drew his card, and as he turned it over, he looked up at Alison and grinned again. "Darling, I believe that was a premature celebration because..." He showed Alison his card, and she felt her world collapse. "The King always wins. Pay up, doll."

Alison's head was spinning and she felt like she was going to faint-- she'd lost millions of Tom's money and no way to pay him back, at least not for a long period of time. Knowing Tom, she'd probably be swimming with the fishes as soon as she told him how badly she fucked up.

Suddenly, a thought crossed through her mind. She had her gun with her, and none of Sallieri's goons were around. If Sean is as good as a getaway driver as Tom said he was... maybe, just maybe, they'll get out of there alive and with Tom's money intact. Never mind the god damned weapons, the important thing is for her not to lose the money that isn't even hers to begin with.

"Unless..." Sallieri spoke, interrupting her train of thought."You want to raise the stakes. Double or nothing. You win, you get the whole lot for free. I win, you give me Shelby's and your money, that sweet little car you rode in, and you'll work for me instead of that goon Shelby. And by work, I think you know what I mean." He said with a lick of his lips.

With her face contorted in thinly veiled disgust, Alison considered the offer before nodding. "Alright. D-double or n-nothing." Alison picked a card and felt her heart get crushed when she found that it was a measly 7.

"Oh dear, a seven, that's quite a shame. My turn." Sallieri said, eyes wide and crazed with the thrill of the gamble. When he turned it over...

It was a 6.

Alison screamed of joy and tossed the deck, causing the cards to fly in the wind. Sallieri let out a string of expletives and curses, begging her for another round. "Come on, Alison! Another round-- double or nothing! If you win, you could have the damn docks back!" He cried, basically on his knees.

"Hmmm..." She pretended to consider his offer before laughing in his face and tossing her hair over her shoulder. "Tempting offer, but I'm afraid I'll have to pass." Alison told him coldly, a sly smirk on her face. "Have it delivered to Mr. Shelby's shop within two days."

"Fuck you! Fuck Shelby-- I ain't delivering shit!" He said, full of bitterness.

Alison sighed and reached for the gun under her skirt. She pressed it to the middle of his forehead before kicking him in the groin, causing him to double over in pain. Still aiming the gun at him, he tilted her head and pouted her lips. "I hate playing bad cop, but you made me do this, Vito. A deal was a deal" Alison crouched to meet his crippled frame, and caressed the butt of her gun to his cheek. "I'm off to Vegas now. And please-- don't make me come back and pull the trigger. Trust me, neither of us want that. Understand?"

Through gritted teeth, he agreed. "You play tough, Allport. But you're right, a deal's a deal. I understand-- shit happens, bad luck has me today. As for the weapons... I'll have it delivered by tonight." He said as he regained his balance.

"Good. Pleasure working with you, Vito." Alison stood up and smoothed her dress before blowing him a kiss goodbye, as she always does after a job well done.

--

As Alison got into the car, Sean nervously asked her how it went. Alison told him the story of how she almost got both their asses killed by losing the money the first try, after which Sean pulled over, just looked at her, mouth agape before going apeshit.

"A-are you out of your mind, A-Alison? Y-you could've lost everything-- the money, the car, your body! You c-could've been his slut by now!" He screamed at her. 

"Jesus, calm down boy! I knew... I knew I was going to win." She said smugly.

He took a few deep breaths before regaining his composure. "How? How were you so sure?" He asked, calmer now.

Alison smirked as she shook her head. "You naive boy-- I was sure because I did my research, dear Seanny. I asked around the casinos in Vegas, and they all told me one thing-- Sallieri never knows when to quit. He'll keep raising the stakes until he loses everything. Every gambler's problem." She stated smoothly. "Long story short-- if you lose against a man like that... keep doubling the stakes until you finally win."

Sean let out a nervous laugh before driving again. "You're insane, Miss Alison."

Alison shrugged before closing her eyes, retiring to sleep. "It's a game of chance, darling. High risk... high reward."