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Shadows of the Underworld

Summary:

A Mafia AU.

Richie is one of Chicago's most notorious crime bosses. His organisation, The Bear, have their hands in just about every illegal activity in the city. Nothing comes in, OR out of Chicago without Richie's knowledge. Nothing except for maybe Sydney.

Notes:

This is my first time writing fanfiction. I'm not particularly happy with how the first chapter turned out. I'll probably keep changing things here and there. The story is going to be a slow burn. I want to take my time with building up the different relationships between the characters, as well as "build up" the world around them. I'll do my best with keeping everyone in character, so not too much OCC.

(See the end of the work for more notes.)

Chapter 1: The Numbers Game

Chapter Text

Chapter 1 – The Numbers Game

The faint glow of the sun’s afternoon rays cast eerie shadows across Richie's office as he sat behind his mahogany desk. The air thick with the scent of cigar smoke and anticipation. His righthand man, Carmy, stood by the window, his expression stoic as he surveyed the city below. The office was nestled within the towering skyscrapers of Chicago's business district, hidden amidst the maze of corporate headquarters and financial institutions that dominate the city skyline. From the outside, it appeared to be just another nondescript building, its sleek glass facade blending seamlessly into the urban landscape. But behind the unassuming exterior laid a world of power and intrigue, where Richie holds court as the undisputed crime boss of the city's underworld. His office, located on one of the upper floors of the building, was a fortress of secrecy and security, known only to those who have earned his trust.

The office was a testament to Richie's status in the underworld, adorned with lavish furnishings and opulent décor that spoke of wealth and prestige. The mahogany desk at which Richie sat was a commanding presence in the room, its polished surface gleaming in the dim afternoon light. Richie cherished the mahogany desk almost as much as he cherished his own daughter. Most people who laid their eyes on it would simply just see a piece of nice furniture and nothing more. But for Richie the desk represented so much more. It was a symbol of loyalty and brotherhood, reflecting years of memories and secrets shared with his long-departed best friend, Michael “Mikey” Berzatto. The word “best friend” was perhaps not the best word to describe the relationship between the two. He was more akin to a sibling, a partner in crime, his dear brother in arms. When Mikey had fallen in the line of duty, defending their empire against a rival faction, Richie had inherited not just his responsibilities, but also his brother’s mahogany desk.  As Richie sat behind the desk, his fingers tracing the familiar grooves and scratches etched into its surface, he felt a pang of nostalgia wash over him. The furniture held a lifetime of memories, both joyous and sorrowful, and it was a constant reminder of the sacrifices they had made, and the bonds that had been both forged, and paid back in blood. Though Mikey was gone, his spirit lived on in the very wood of the desk, a silent guardian watching over Richie as he navigated the treacherous waters of the underworld. He knew he would do whatever it took to honour Mikey's memory and protect everything they had built together.  

Lost in thought, Richie's mind drifted back to the night that Mikey had acquired the desk. He had gotten the desk in a high-stakes poker game that took place years ago in the back room of a quite notorious and seedy underground casino. Richie and Mikey had been regulars at the casino, using it as a hub for their operations while indulging in the occasional game of chance. On this particular night, however, the stakes were higher than ever, with rumors circulating of a rare antique desk up for grabs as the grand prize. The general vibe in the room was quite tense, quiet, with only the occasional sound of clinking glasses. In a dramatic twist of fate or luck? It came down to a final hand between Mikey and the reigning champion, a ruthless gangster known as Ebraheim. Richie did not know it back then, but Mikey, like the bastard he usually was, had actually put their restaurant, – The Beef – , up as collateral. It wasn't until they were walking out of the casino, the antique desk in tow, that Mikey revealed the truth with a sly grin. 

"You sneaky son of a bitch," Richie had exclaimed, a mixture of shock and amusement. 
"You risked everything on that game?" 

Mikey had simply shrugged, his grin widening. "Hey, didn’t Zach Galifianakis once say;  it's not gambling if you know you're gonna win, right?" 

Richie had laughed, shaking his head in disbelief at his friend's audacity. But deep down, he couldn't deny the rush of exhilaration that came with their victory.  

It wasn't until the next day that the repercussions of their victory, if you could call it that, truly became apparent. Ebraheim, the rival gambler who had lost big in the poker game, was unable to pay up the debt he owed Mikey. The word spread like wildfire through the underground network, whispers of Ebraheim's failure reaching even Richie's ears. Normally, Richie would have had no sympathy for a man who couldn't pay his debts. But there was something about Ebraheim's predicament that struck a chord with him, a sense of empathy born from the knowledge that he had once been in a similar predicament himself. Unable to turn a blind eye to Ebraheim's plight, Richie made a bold plea to Mikey. Rather than demanding payment in cash, he convinced his best friend to offer Ebraheim an alternative: his loyalty and allegiance in exchange for forgiveness of his debt. It was a risky move, one that could easily backfire, but Richie trusted his instincts and believed that Ebraheim could prove to be a valuable ally. To both of their surprises, Ebraheim accepted the offer without hesitation, grateful for the opportunity to wipe the slate clean. And so, a new friendship was forged in the unlikeliest of circumstances, the bond between Richie, Mikey, and Ebraheim growing stronger with each passing day.

Lost in the memories of their past triumphs, Richie was abruptly pulled back to the present when Carmy cleared his throat. 

"Boss, sorry to interrupt," Carmy said, his voice brisk and businesslike as he held out a stack of papers. "But these just came in, and I think you'll want to take a look." 

Richie blinked, shaking off the remnants of his flashback as he focused on the papers Carmy held out to him. With a nod of acknowledgement, he took them from Carmy's outstretched hand, his mind shifting gears as he delved back into the complexities of running their empire. 

"Cousin, these figures don't add up", he remarked, scanning once more just to make sure. "We should have pulled in twice as much this month."

Carmy's jaw tightened, his eyes narrowing as he studied the papers over Richie's shoulder. "That's strange," he muttered. "I made sure all the collections were on point. There shouldn't be any discrepancies." 

Richie drummed his fingers impatiently on the desk, his mind already racing with possibilities. "Get Marcus on the phone immediately! The new waiters he hired better not be skimming from the top!!!," he ordered, "He's in charge of that territory. Find out what's going on”. 

Without a word, Carmy nodded and reached for his phone, dialling Marcus' number. As the line rang, Richie leaned back in his chair, his gaze fixed on the city skyline beyond the window. Marcus had been with them for over six years now, a loyal soldier who had climbed the ranks with determination and skill. Richie trusted him with his life, but even the most trusted men could falter under pressure. 

After a brief conversation with Marcus, Carmy hung up the phone and turned to face Richie with a troubled expression on his face. "Marcus says everything's running smoothly on his end…He swears there haven't been any hiccups in the collections”.  

Richie's lips formed a thin line as he processed the information, "Then someone's lying!!!,"his eyes flashing with anger. "I want to see for myself. Put on your coat cousin, we’re going on a little field trip". 

 

***

 

Their destination was a nondescript bakery nestled in the heart of Marcus' territory, a front for their money laundering and coke operations. As they entered the establishment, the aroma of freshly baked bread filled the air, masking the illicit dealings that took place behind closed doors. 

Marcus greeted them with a tight smile, his demeanour betraying none of the tension that hung in the air. "Boss, Carmy," he said, nodding respectfully.  

Richie's eyes narrowed as he studied Marcus, searching for any signs of deceit. "We've noticed a discrepancy in this month's finances," he explained, his voice cold and clipped. "Care to explain?" 

Marcus' expression remained unchanged, but Richie could see the flicker of uncertainty in his eyes. "I assure you, boss, everything is under control," he insisted, his tone steady despite the sweat glistening on his brow. 

Richie exchanged a meaningful glance with Carmy, both men silently communicating their suspicions. Something wasn't adding up, and Richie was determined to get to the bottom of it. 

Richie's suspicions lingered like a shadow as he glanced around the restaurant, his keen eyes taking in every corner and crevice with a sense of scrutiny. The familiar sights and sounds of the bustling establishment provided a comforting backdrop. As he inspected the faces of the patrons, searching for any signs of deceit or betrayal, his gaze wandered to the window, where the lively city streets stretched out before him. Perhaps someone was pressuring Marcus, he thought. Suddenly, his eyes caught the view of something he hadn’t seen before. A new bakery located directly across from them. The establishment stood out like a sore thumb. Its storefront was adorned with pastel-coloured paint, whimsical designs, and cartoonish characters that seemed to dance and frolic across the windows. The name, "Sydney’s Delightful Sugar Sprinkles" was written in playful, swirling script, adding to the overall….charm of the enterprise. How hadn’t Richie noticed the store up until now? And more importantly, could this bakery be connected to Marcus' sudden troubles? It seemed unlikely, but Richie had learned over the years that one should always expect the…unexpected.  

Turning back to Marcus, Richie's expression hardened with resolve. "I want you to look into that bakery," he said, his voice low and commanding. "Find out everything you can about who's behind it and what their intentions are. We can't afford to overlook any potential threats to our territory. Me and cousin are going to go over and have a look around it”. Marcus nodded, his earlier uncertainty replaced by an unwavering determination. "Consider it done, boss," he replied, "I'll get to the bottom of this, whatever it takes." 

Leaving Marcus behind, they stepped out of their bakery and approached Sydney’s Delightful Sugar Sprinkles. With each step they took, Richie's mind buzzed with thoughts of the potential dangers that awaited them. With a shared nod, Richie and Carmy entered the bakery, the tinkling of a bell announcing their arrival. Inside, the air was thick with the scent of sugar and baked goods, the walls adorned with colourful decorations and cutesy artwork. Suddenly Richie's senses went on high alert as he felt the weight of dozens of eyes gazing upon him and Carmy. The sudden shift in attention was palpable. It felt as if the air had thickened with suspicion and curiosity. The workers had even stopped their tasks in order to fully observe their new guests.  

Carmy tensed beside Richie, his hand subtly moving closer to the concealed weapon at his side. Carmy's whispered words cut through the tense silence like a knife, his voice barely audible. "Boss," he murmured, his tone low and urgent, "I'm ready to shoot if things go south." 

Richie's eyes widened in alarm at Carmy's declaration, "Cousin, are you out of your fucking mind??? Keep that damn thing in your pocket" he hissed back, his voice a sharp whisper. Despite the urgency in Carmy's voice, Richie knew that resorting to violence would only make matters worse. They were outnumbered and possibly outgunned. A confrontation could easily spiral out of control with disastrous consequences. 

Taking a deep breath to steady his nerves, Richie placed a reassuring hand on Carmy's shoulder, his grip firm but comforting. "Calm down, Carmy," he said, his voice loud enough for everyone to hear. "I’m sure they sell gluten free cookies in this fine establishment. No need to get so nervous”, then he looked at the cashier and said, “These new age fairies can be so damn dramatic about their damn keto diets”. Richie's attempt to diffuse the tension with humour was met with a subtle shift in the atmosphere of the bakery. Some of the workers exchanged uncertain glances, while others suppressed amused smiles at Richie's quip. The cashier, caught off guard by Richie's remark, blinked in surprise before composing herself. "Actually, sir, we do offer a variety of gluten-free options," she replied politely, her voice tinged with a hint of amusement. "And keto-friendly treats as well." 

Richie grinned, pleased that his attempt at distraction seemed to be working. "See, Carmy?" he said, nudging his righthand man playfully. "No need to worry. We're in a health-conscious establishment. Can't be too dangerous, right?".  

Richie smoothly turned towards the cashier, his charming smile in place as he approached the counter with a casual air about him. "Hey there," he greeted warmly. "I couldn't help but notice your bakery from across the street. It looks like you've got quite the selection here”. "Thank you!" she replied. "We pride ourselves on offering a wide variety of treats to satisfy any sweet tooth. Is there anything in particular you're interested in?". Richie's smile widened as he gestured towards the array of pastries and confections displayed behind the glass case. "I must admit, I'm quite intrigued by those cupcakes. They look absolutely delicious. What flavours do you have?". As the cashier launched into a detailed description of the bakery's cupcake selection, Richie listened attentively, nodding along as he made a mental note of her explanations. "As the owner, what would you recommend?", Richie asked. The question caught the cashier off guard for a moment, but she quickly composed herself, "Well, I have to say that all of our treats are top-notch," she replied with a smile. "But if I had to recommend one thing”, she continued, “It would have to be our signature chocolate fudge cupcakes. They're a customer favourite and always a hit!”. Richie nodded appreciatively, his smile seemingly widening at her enthusiastic response, "Sounds delicious! I'll have to give them a try sometime then”.  

Richie's attention on the cashier faltered slightly as they were interrupted by a voice coming from the backroom of the bakery. "Tina, could you give me your thoughts about this crème brûlée pistachio recipe I found?". He glanced in the direction of the noise, noting the slight furrow of Carmy's brow as they both exchanged a curious look. “Tina, are you at the register?”, the voice continued, sounding as if the person attached to it was moving closer. Tina nodded, her expression tinged with a hint of apprehension. "Yes, I'm here," she called back, her voice wavering slightly.  

Suddenly, emerging from the backroom a figure in all white. Wide eyes looking straight at them, “Oh Hi! We have customers!”. Richie's attention was immediately drawn to her vibrant energy and warm demeanour. She wore a crisp white chef's coat that accentuated her petite frame, and her long black braids swayed with each eager step she took. As she approached, her smile widened, and she extended her hand to greet both Richie and Carmy with firm handshakes. Richie winced inwardly as he felt her grip, a bit too strong for his liking. But he quickly masked any discomfort with a polite smile, returning her handshake with equal firmness. As she released his hand, Richie caught a fleeting glance in her eyes, a knowing spark that seemed to flicker for just a split second before vanishing. It was so subtle that he almost missed it, but it left him with a lingering sense of unease and…excitement?  

Richie's eyebrows raised slightly in surprise as she introduced herself as Sydney. He studied her carefully. Isn’t she too young to own a bakery?  

"Sydney, huh?" Richie repeated to himself, his tone neutral as he processed the new information. "Nice to meet you cutie--- I mean Sydney". 

Richie's cheeks flushed slightly as he realized his slip of the tongue, the word "cutie" escaping his lips before he could even think to stop it. He felt a pang of embarrassment wash over him as he saw the widened eyes of Carmy, Sydney, and even Tina, who had been quietly observing the interaction. 

But before the tension could escalate, Sydney broke the awkward silence with a hearty laugh. "Freudian slip? It happens to the best of us, Richie," she remarked, her tone light and playful as she brushed off the awkward moment. 

Richie felt a wave of relief wash over him at Sydney's reaction. “Right, of course," he replied, his smile returning as he quickly regained his composure. "Thanks for the cookies. We'll see you around." 

With a hasty nod to Tina and a polite farewell to Sydney, Richie made a swift exit from the bakery. He walked so quickly that Carmy had to practically run to keep up with him. Richie came to an abrupt halt, his mind racing with thoughts and questions. "Cousin... She called me Richie," he mused aloud, turning to face Carmy with a furrowed brow. 

Carmy looked at him dumbfounded, his expression mirroring Richie's confusion. "Yes," he replied simply, his voice tinged with uncertainty. "When in any point of our conversation did I mention my name?". Carmy’s eyes widened in realization. Maybe Sydney's seemingly innocent slip of the tongue, wasn’t so innocent after all..a lot things were not adding up, but Richie was not quite able to put his finger on the "how's and why's".

 

----

 

To be continued ~~~ hopefully

 

Notes:

I feel like the scene at Sydney's bakery, when Richie and Carmy walked in, was quite unrealistic. But I had a lot of fun writing it.

And to be quite honest, going forward, you'll probably have to suspend a lot of your disbelief in order to enjoy the story for what it is. I'll try to keep everyone "in character" as much as possible, however everything else is fair game.