Prologue: O Brother, where art thou?

Whoever appeals to the law against his fellow man is either a fool or a coward. Whoever cannot take care of himself without police protection is both. It is as cowardly to betray an offender to justice, even though his offences be against yourself, as it is not to avenge an injury by violence. It is dastardly and contemptible in a wounded man to betray the name of his assailant, because if he recovers, he must naturally expect to take vengeance himself ~ The code of Omertà.

Vale: Three months after the Battle for Beacon.

Saphron Cotta-Arc stared out the window of her hotel room at the glittering lights of Vale highlighted with an orange sunset sky. It was almost difficult to believe that a month ago this was a city under siege. Here and there, however, she had seen the signs of the battle as she traversed the city. Buildings damaged by Grimm or explosives set by the White Fang terrorists, fires that had left homes piles of ash or blackened concrete facades, and piles of rubble left over to be picked up and disposed of.

Though thankfully, it could have been worse. Much, much worse. It was one thing everyone seemed to agree on. Every bit of information going around about the attack was vague at best or at worst, highly suspicious. The Vale Council had been laying the victory on the well coordinated efforts of the police and military, but everyone was casting doubt on the official story. The truth of how a potentially cataclysmic attack was avoided was in truth irrelevant to her- she had come here for different reasons.

She looked down at her Scroll and opened it to see a pair of bright blue eyes and a goofy grin staring up at her. Jaune. She had been showing anyone and everyone this picture of him hoping that someone could lead her to him. So far, she had no luck whatsoever.

Moving past the image she pulled up her contact list and selected her home number. It rang three times before it clicked and she heard her wife's voice greet her. "Hey, Saph."

"Hey, honey," she sighed, feeling relaxed just hearing her voice over the line.

"I'm guessing you didn't have any luck again today, huh?" Terra asked her.

"No," Saphron said, her mood immediately dimming again. "Honestly, I don't know WHERE to look anymore! Beacon's in ruins and the new Headmistress hasn't exactly been forthcoming. Downright cold was more like it. I know Jaune managed to enroll and pass initiation, but she says they have no record of a Jaune Arc even attending."

"I don't mean to upset you, hon, but, well, Jaune was the one that told you about passing initiation," Terra said. "He could easily have lied."

Saphron, unseen by her wife, shook her head. "I don't think he would have lied about that," she stated. "Besides, I have no doubt that he at least went through initiation. Even if he'd failed, you'd think they would have some record of him."

"I suppose you have a point," Terra conceded. She then paused for a second before asking her carefully, "Did you… Did you recheck the casualty list again?"

"I did," she answered with a sigh. "And there was still nothing. Honestly, I don't know if that's a good thing or not." The growing list of dead had been the hardest to check. Thankfully her brother's name had yet to appear. Unfortunately, that meant little as every day, more and more corpses were recovered and identified. She had checked with the morgues but that too had been fruitless. The idea of her brother dead and unidentified, or worse, buried under some pile of rubble somewhere and rotting chilled her to the bone.

Saffron rubbed her eyes as if her exhaustion could be cured so easily. "I wanna come home," she said. "I don't know what else to do or where else to look. It was bad enough not hearing a word from Jaune before all of this, but after all this... I don't know what I'm going to tell Mom and Dad."

"Tell them their son misses them," Terra explained to her, "and that your wife misses you and that you've done everything."

"I just… feel like I'm giving up on him," Saph told her, tears beginning to leak out. "What would you do if I had disappeared like this?"

"Babe, I'd turn over every stone in Vale for you," Terra said. "And I wouldn't rest until I found one know whether you were alive or not." She then sighed and said in a soft voice, "Just take as long as you need. Only know that Adrian and I need you too."

Hearing this, the tears began to come in earnest. However, they were more happy tears at the fact she'd married such an understanding woman. "Thank you, sweetie," Saphron sniffed, unable to hide her smile. "I won't stay too much longer, promise. A few more days at the max to make sure I've looked everywhere."

A knock at the door pulled her attention away from her phone. "Oh, that should be my room service," Saphron told Terra. "After searching all day I'm starving, so I'll eat and call you back, sweetie. Give Adrian a kiss for me."

"Alright, babe," Terra said. "Talk to you soon. Good luck and I love you."

"I love you too," Saphron said. She closed her Scroll and, as she took a tissue from the bed stand to wipe her tears, she stood to walk to the door. Looking through the peephole in the door however, she saw that it wasn't room service. Instead, a tall brown haired young man stood waiting on the other side dressed in a dark suit wearing a fedora. She assumed that she had simply knocked on the wrong door and opened up to tell him as such. What he said next though dispelled the "wrong room" thought.

"Saphron Arc?" he greeted, extending a large hand for her. The fact he knew her name stunned her as she'd never seen this person in her life. However, her dad always said that if you want to figure something out, you have to grab it before the chance flies away. She then looked down at the hand for a moment before noticing that a large flanged mace hung from his belt.

"It's Cotta-Arc actually," she corrected, finally taking hold of his calloused hand and giving him a firm shake. She saw the man wince a little. She may not have been a Huntress, but she was still plenty strong. Now he knew if he tried anything with the mace. "Who are you?"

"Cardin Winchester, ma'am" he said, politely introducing himself and giving her a friendly smile, all while pulling away his hand and flexing it subtly. "I work for your brother."

"Jaune!?" She exclaimed. "Where is he!? Is he safe!?"

"Calm down, please," Cardin said, raising his hands up in a placating gesture. "He's fine, honest. I'm supposed to take you to him."

"I don't understand. If he's fine then why can't he come here and see me himself?" She asked Cardin, taking a step back into her room but kept the door open.

Cardin rubbed the back of his neck. "It's... complicated," he told her.

"So explain it to me!" Saphron demanded in a tone that showed she was getting more frustrated by the minute. She gave another glance at the mace on his hip. "Are you a Huntsman?" She asked. He looked a little young to be a Huntsman, but the weapon he carried certainly looked like something a hunter of Grimm would carry.

"No," he said shaking his head holding his position outside her door. "Not anymore at least. And it's Jaunie's job to explain this all to you. He just wanted me to get you for him."

She narrowed her eyes at the tall man that loomed in her doorway. Her instincts were screaming for her to slam the door, lock it, and call the police before he possibly busted it open with that big-ass mace of his. She couldn't just trust a stranger and simply leave with him. Then again, as stated, she had no doubt this guy could pull her kicking and screaming out of here and she would be helpless. Again, as stated, she was strong but if the guy went whole hog and was prepared for her, there was almost nothing she'd be able to do. Plus, this was the first person she had met who seemed to have any idea of where her brother was. But what if he was lying for whatever reason?

"What if I... don't want to go with you?" She asked him slowly, voicing her paranoia.

Cardin tipped his fedora to her. "Then have a good night, ma'am," he said, turning and walking away down the hall.

She watched him leave as her mind churned with her options. She'd been here looking for Jaune for weeks and here she was letting her first lead simply walk away from her! What was she going to do next? Keeping checking morgues only to possibly not find him? Keep showing his photo to strangers only to receive shakes of heads?

"Wait!" she called down the hall for him. He stopped and turned to look at her. She let out a resigned sigh, not daring to believe she was actually doing this. "Let me grab my coat," she told him, closing the door to do just that.

When she came out, he was still waiting for her and they left together, taking the elevator down to the parking garage. "So... you said you work for my brother?" Saphron asked him, replaying his words in her head.

"That's right," Cardin answered, stepping out and leading her through the garage.

Saph left out a scoffing chuckle. "Since when does anybody work for Jaune?" she asked him as her heels clicked against the pavement.

Cardin smirked. "It's kinda a long story," he told her.

They stopped when he reached his car. It was a sleek black luxury sedan that Saphron guessed cost more than she could ever hope to afford. He opened the passenger door for her and she climbed in. It still had that new car smell to it.

"I'm guessing you're not going to tell me this story, is that right?" she asked as he climbed into the driver seat and started the engine.

"Nope," Cardin said, pulling out of his parking spot and rolling out.

"Of course," she said, rolling her eyes.

She watched the city pass buy out the window trying. She contemplated jumping out if he drove her into a seedy neighborhood and running away. But then again, he would probably lock the doors before she had the chance.

"So what can you tell me?" Saphron asked him.

"I can tell you Jaune is safe and he's doing very well for himself," Cardin told her.

Considering Cardin's suit, car and other bling, Saphron found herself wondering if they were talking about the same Jaune.

Cardin soon pulled into a parking garage and they left for the elevator. Saphron watched as he pressed the button for the penthouse and they went up fifty floors.

The elevator dinged and they stepped out. The penthouse was roomy with hardwood floors and many big windows, giving a spectacular view of Vale's skyline.

"We're here, boss!" Cardin called out to the penthouse.

Saph began to wonder if this was some insane joke and was set to leave before she heard it.


She heard his voice and turned slowly to see him standing atop a stairwell staring at her. He looked different. He too was dressed in a suit minus the jacket. He wore black slacks and a vest over a blue button up shirt. A cigar smoldered between his fingers and a gold watch adorned his wrist. Her eyes widened as she saw a brown leather shoulder holster carrying a revolver in it at his side.

He wasn't just different in his attire either. Jaune looked worn, a little tired. Several scars ornamented his face, including what looked like a burn cutting into the hairline of his temple. He stood straight instead of slouching like he always used too, but he still wore the same goofy grin that was unmistakably Jaune's.

"It's so good to see you, sis!" he said, stepping down the stairs, his cigar leaving a swirling trail of smoke behind him.

Saphron felt a storm of emotions seeing him- happiness, relief, confusion. But seeing him alive and in front of her, she settled on rage.

In a few brisk strides she closed the distance to him and cracked her palm across his face. Jaune reeled back clutching his red cheek. "Jaunathan Arthur Arc!" she roared at him, feeling her own palm sting from striking him. "What the HELL is wrong with you?! I don't get so much as a text from you in months! You don't take my calls, and when I come here just to see if you're alive, you send this… this Beringel to bring me all the way here!"

She realized what she'd said and quickly looked back at Cardin. "Sorry. I meant no offence," she apologized to him. He had apparently been doing his job and didn't deserve to be called that.

Cardin held his hands up innocently to her. "None taken," he assured, clearly not interested in getting between the two of them.

"I deserve that," Jaune said, letting out a breathy chuckle as he removed his hand from his cheek and showed her the red handprint.

Hearing him chuckle made her want to hit him again. "You deserve a lot more than that!" Saphron growled.

"I do," Jaune admitted to her, giving her his goofy grin again. "Can your brother at least get a hug?" he asked, almost looking exactly how he used to when he was younger.

Saphron swallowed her anger and stepped forward, putting her arms around him. He returned her embrace. He stank of cigars, but she didn't care. He could smell like a skunk for all she cared and all that would matter to her would be that her little brother was physically in her arms at last.

After a few seconds, she reluctantly let go and decided to get down to brass tacks. "Jaune, what's going on?" she asked him. "Why didn't you call? And for Gods' sakes, since when do you wear suits and smoke cigars in penthouses!?"

"It's a long story," Jaune said, scratching the back of his head awkwardly.

"So I've been told," she deadpanned.

Jaune sighed and took a long drag off his cigar. "We should sit down. How about a drink?"

Saphron nodded as he led her back up the stairs and down a hall reaching an office. Jaune set his cigar down in a marble ashtray on a polished wood desk. He then went over to a little bar. "I don't think we've shared a drink since you let me tag along for that party," Jaune told her. "You remember that?"

Saphron took a seat in a leather chair watching her brother pour an amber colored liquid into a crystal glass from a matching decanter. "Yeah, I remember. You were so worried that our parents would know you had a sip of beer," she said, remembering it vividly as her and her friends pressured him into taking that sip. She snorted with a smile. "You thought it tasted like piss."

Jaune smirked as he paused in his pouring and sat the bottle to the side. "Yeah, and I spat it out all over that one friend of yours I had a crush on. You know, the black haired girl with brown eyes from Vacuo?"

The two shared a laugh. "Oh yeah, Magenta! Boy, she was pissed. Shouted at you and called you an idiot."

"Yeah, and then YOU socked her in the jaw and sprawled her out for insulting me. I lost my crush on her with that and she never did speak to you again."

"Honestly? She was always a bitch. I don't know WHY I hung out with her other than the fact that I kinda thought she was hot too," Saphron chuckled, to which Jaune joined her.

This felt nice. Laughing, catching up on old memories and old times like nothing had happened. She was almost tempted to believe that. But seeing Jaune now, she knew things had changed. Greatly. She was brought from her thoughts when Jaune spoke again.

"So, what will you have?"

"Oh! Same as you," she told him, wondering just what he was drinking. Considering this place, she wouldn't be surprised if the bar shelf was stocked with liquor and wines that cost thousands of Lien. She looked around the office as he poured her own drink. Behind in the corner hung a bowler hat and a cane. A rifle was framed in a case on one wall and the floor length window gave them a stunning view of the city. Plus, on the penthouse balcony was a pool! That did it. She had to get back on track and find out more.

"So… do you live here?" she asked him as he handed her her glass. The amber colored whiskey smelled smokey and petey and she felt buzzed just smelling it. The first sip burned with a harsh complex flavor.

"I do," Jaune told her.

"Your rent must be a fortune," she chuckled as she took another sip.

"I own the building, actually," Jaune clarified, taking a seat behind his desk and picking up his cigar. Saphron almost did exactly what Jaune had done all those years ago and spat out her drink when she heard that. "The property taxes are high though," he said, ignoring her wide eye stare at him as he stated so flippantly that he owned a likely multi-million Lien building

"How can you afford this!? This apartment, this whiskey, the cigars! Jaune, I will ask one more time: what's going on!?"

Jaune stared at her before setting his glass down and sighing, running a hand through his hair. "When I came to Vale to attend Beacon, things went very differently that what I expected," he explained to her.

"So tell me what happened! I mean, it's bad enough that you didn't answer my calls, but Mom and Dad are just as worried as I was! We didn't know anything! We thought you might be dead!" she exclaimed, tired of him beating around the bush.

Jaune stared at her for almost half a minute before finally sighing and looking guilty. "I… Saph, you gotta understand. It's not that I didn't want to contact you. It's just that I couldn't," Jaune explained. "It was for your protection, for everyone's protection."

"What are you protecting us from, Jaune!?" She demanded. "Were you in trouble? Are you still in trouble?"

"I'm fine," Jaune said. "Great even, but what happened after I left Beacon, I figured it was better to keep as far away from you and our family as possible."

"So what was it?!" Saphron demanded.

Jaune looked into his glass of whiskey and sighed. "I trust you've heard the rumors going around about what really happened that night the White Fang attacked?"

She narrowed her eyes at him. "I might have listened to Lisa Lavender's report," she stated. "She said the Grimm and the White Fang were fought off by a bunch of gangsters if you can believe it." She chuckled lightly, but stopped upon seeing Jaune's face. "I mean it is ludicrous, right?" She figured with Jaune's sudden vast wealth, he would probably know more than even the media.

Jaune was silent for a few minutes before sighing. "The Vale Council has been trying to keep the facts buried but... it's true," Jaune said in a slightly resigned tone. "That night, the Three Families of Vale stopped them and… Saphron, I was there with them."

Saphron stared at him as if he'd grown a third head. "You? You fought Grimm with a bunch of mobsters?" She asked him dubiously. "Is this some kind of sick joke, Jaune? Because if it is, I swear to the Gods I'll-"

"It's NOT a joke!" Jaune assured her sharply. Perhaps a bit too sharply as Saphron winced a bit at his tone and Jaune sighed again. "I got booted out of Beacon and joined up with the mob."

"You became a criminal?!" Saphron couldn't believe what she was hearing- her sweet, goofy baby brother had apparently been kicked out of Beacon Academy for whatever reason and decided to join up with mobsters and hitmen! Had the world gone madder than it was already?

"I did," Jaune said calmly. "Though trust me. It's more complicated than that. I didn't join the mob because of money or sharp suits or anything like that, I was asked too by Ozpin."

Saphron blinked. The headmaster? The headmaster was the reason Jaune left Beacon and turned into a criminal?! Saphron then sighed as she rubbed her head. "I think you should start at the beginning," she told him wearily.

Jaune have a sigh of his own and took a gulp of his whiskey. "You're right," he admitted, taking a puff of his cigar and then dropping it into his ashtray to burn itself out. "The second I stepped foot into Vale, I lived a lie. And in many ways, sis, I'm still living a lie. You already know how this story started: I arrived at Beacon with fake transcripts, I barely managed to survive initiation, and I was made leader of Team JNPR."

She nodded and took another sip of the bitter whiskey, managing to taste a hint of sweetness as it burned her mouth. "That was the last I heard from you," she said to him, trying to wrap her mind about her brother being a mobster. "But things still seemed to be okay for you even with all that. So what happened after?"

"I was failing my way through the Academy," he explained to her in a depressed tone. "I was losing every fight in Goodwitche's class, I was failing every test, and to top it all off, I was getting bullied mercilessly by Cardin."

"That guy you sent to pick me up?" She asked jerking her thumb behind her.

"Yeah," Jaune chuckled. "Turns out he's actually a pretty decent guy. But I'll get to all that later," he explained before taking a long gulp of his drink. He then reached into his pocket and pulled out a new cigar. He lit it with a lighter in his other pocket and lighting it.

"My partner, Pyrrha Nikos, offered to help me and I let my pride get the better of me. Then I did something pretty damn dumb- I told her the truth."

"You mean?..." Saphron asked, leaning forward in anticipation.

" Yep. I shot down her offer and told her the truth. That I was a liar who'd never spent a day of his life in combat school and that my transcripts were forged." His face fell and he looked almost devastated. "She… she didn't take it very well and outed me to Ozpin."

Saphron watched as he took a long puff of his fresh cigar, the cherry glowing bright. He then turned his head and looked out over the city.

"That's where my story really begins."

So here we go! Finally after a month of resting and working in this fic at my leisure I'm back to posting. I hope all of you enjoy reading this fic as much as I have enjoyed writing it. I always wanted to write a mafia story so here I go. I have spent my time developing the various crime syndicates in Vale, from their history to their cultures I can confidently say I have put a lot of thought into making Vale's criminal underworld feel real. I will warn some of you that there will be OCs in this story I created to help flesh out the various crime families in this story as RWBY only gave me a handful of characters to work with in that respect. But Junior, Roman, the Malachite sisters and of course Neo all have prominent roles to play in this story.

I feel I should state for the record that it is by no means my intention to glorify or glamorize real organized crime. This is purely fiction nothing more and nothing less, the criminals that shall be portrayed are works of fantasy only.

I would like to thank Firefly25, MajorBrony95, and DrknssRules1 for every bit of help they gave me on this story. I cannot understate how much they helped me on this. You guys rock and I hope you enjoy every bit of this fic.

This prologue now has been adapted to a dramatic reading that can be found on YouTube. If you're interested in listening to it being read with nice calming visuals look up Fan x Fiction on YouTube and check out their video doing this prologue. I don't know if they're going to do more chapters in the future but what they've done is really cool so please support them and check out their channel.