The Prince of Chicago

Chapter 6

Angelo

I could hear the doors to her room slamming shut from my forcefulness as I advanced down the hall. I couldn’t shake the fearful look she gave me moments before. There was a part of me that was excited by it, knowing I could have control over her like that. What I hadn’t expected was her standing up to me. Most people in my life wouldn’t dare defy me like she had. And while she didn’t know the whole truth about who I was, I was sure she knew I was dangerous at the very least, yet she still stood her ground. The girl had guts, and I had to admit there was a part of me that was excited by that too.

I ducked into my office and sat down behind my desk. I needed to look these friends of hers up to make sure they weren’t connected to any of my enemies. God knows I have a lot of them. I also wanted to look more closely into her, too. I was up into the wee hours of the morning after bringing her here, using that time to run her name, look through her social media, and learn all the preliminary info I needed to be able to question her once she woke up. But I still wanted to know more about her; it was like I craved it.

After my late-night dive into the life of Isabelle Bradford, I was almost certain she had no ties to anyone that would make her dangerous to keep around, but you never could be too careful in my line of work. As I looked into her friends, it was very clear they, too, were harmless to me. I was relieved to find this out, I had been avoiding thinking of what would have to be done if I learned Isabelle was connected to any of the families we were at odds with, be it by herself or through her friends or family. She seemed to be clean though.

I had found last night that she had just moved to Chicago and was the only child of a single mother in Iowa. But I had only taken the time to run her mother’s name against the names connected to our enemies and their known aliases. Now, as I dove further into Isabelle’s family, I realized that her mother had passed away four years prior, and her death had been a tragic accident. Drowning was the cause, it appeared she had slipped and fell in the bathtub, hitting her head and falling unconscious in the water. I wasn’t much in the way of an empath, but it almost made me feel sorry for her. That's a terrible way to lose a loved one, especially your own mother.

The night before I also tried to find a father’s name, but there was nothing on the birth certificate, no record of any male presence claiming fatherhood over Isabelle. And even after some more digging, I came up empty. I took this to mean whoever her father was, he wasn’t aware of her existence. After this discovery and learning that her mother was no longer around, I realized that Isabelle had almost no one in the way of family. This could work, I thought to myself, an idea brimming up in my mind.

We were already in the predicament of what to do with her; even though she wasn’t a threat to my family, we couldn’t turn her out on the street. She was still a witness, and I couldn’t risk her implicating me or anyone else in the execution she had stumbled upon. But she was also right, I couldn’t keep her as a prisoner forever either. The only solution that seemed clear to me was to tell her who I really was, and invite her to work for the family. Once she was loyal, I would know she wouldn’t turn on us and she would no longer be a prisoner. She was a perfect candidate, most of my men and other employees were void of family too; people with no relatives to fall back on were the ones who needed the kind of family I offered them the most. In my mind, it was the only way to deal with her. And it came with the added bonus of keeping her close to me for quite a while.

The decision was made, I would bring her into the crew. I called in Marco, one of my top men, and coincidentally one that Isabelle had seen in the alley, to inform him of my decision. We’d call a small meeting with my uncle and the handful of other high ranking men I had at the penthouse, and then I’d go speak with Isabelle to inform her of her new job.

* * *

Isabelle

After Angelo left, I tried the doors. Unsurprisingly, they were locked from the outside once again. I paced around the room, trying to figure out what to do. I knew Angelo or one of his men would come back at some point; they at least had to feed me, right? Seeing as though there was nothing left to do in the present moment, I decided to explore the room a bit. An intimate knowledge of the space they were keeping me in could come in handy, and maybe I’d even find something to help unlock those doors.

I started opening the drawers of the two dressers with the vanity attached. They were all empty besides a set of bedsheets, which I assumed were a second set for the bed in the room. I rifled through the vanity too, but found nothing except an old comb. Then I moved on to the desk. There were standard office supplies in there: post-it notes, pens, erasers. I found a paperclip which I thought I could use to pick the lock, but after inspecting the door, I realized there was no internal keyhole to pick the lock from. And besides, I didn’t have any experience picking locks, so that route would’ve been almost impossible.

I moved onto the closet next, but that was empty too besides a single stray tie and one sock without a partner. The thing was massive though, I didn’t own enough clothes to fill a quarter of it. I sat down at the bench in the center of the space, imagining what it would be like to fill each and every inch with beautiful, designer clothes. It was a lovely image in stark contrast to my current situation. All I had were the clothes I wore to the club, and they were starting to get very uncomfortable. I laid back on the bench with my feet hanging off the end. I decided that I’d need to ask the next person who came in, whether it was Angelo or one of his men, to get me some personal items. I was dying for a proper shower and a pair of sweats. I allowed my mind to drift at that point, and eventually, I must’ve fallen asleep.

Some time later, I heard the doors opening, waking me from my nap. I sat up and peeked through the doorway of the closet to see it was Angelo, carrying a plate of food. It was dim in the room, it must have been evening time.

“Isabelle?” he called out. I stood up slowly and emerged from the closet, not looking forward to whatever confrontation awaited me. Last time we spoke, he threatened my life. I didn’t see how whatever he had to say to me this time could be much better, unless it was an apology.

“Doing some exploring, I see,” he said casually. I just stared back at him. He set the plate down on the vanity. “I bet you could fill that closet pretty quickly if you had free reign over some of the high end shops here in the city. We have a lot of things here you just can’t get in Iowa.”

This time I rolled my eyes and stood, casually sauntering out of the closet and toward the chaise in the middle of the room. Here he went again with the random facts about me that he just seemed to know with no explanation. I wasn’t going to play this game with him again.

“I brought you some dinner,” he said, walking over to me. “My chef here is top tier, and I’m sure you’re hungry.” He was now standing a few feet from me, but I didn’t look up at him. “Soon enough you can take meals with me in my dining room, I’m sure that will be more comfortable than eating in here.”

Was he being serious? I wouldn’t dare share a meal with him, not as his prisoner. The audacity of this man, talking as if I’d just be hanging around, taking meals with him at his leisure. No, I was getting out of here the first chance I got.

“Isabelle,” he said sternly. I sat myself down gingerly on the chaise, still ignoring him. “Look at me when I’m talking to you!” He raised his voice, clearly ruffled by my silent treatment. Good, I thought. All of a sudden, I felt a rough hand come to my chin and yank my head upward. He was bent over, face a few inches from mine, forcing me to meet his gaze. Him being so close sent a thrilling chill down my spine. Focus, Isabelle!

“You WILL respect me,” he said in a low tone, icy eyes piercing my own.

“Why should I?” I said back coldly, shooting my own daggers into his baby blues. I was waiting for another threat, or perhaps something worse, but all he did was let go of my chin, stand up, close his eyes, and run his hand through his hair, sighing loudly. Though he wasn’t forcing me anymore, I kept my gaze on him.

“Look, I met with a group of my high ranking men today, and we’ve decided what to do with you,” he said back, clearly irritated. Panic sprung up in me, what were they going to do with me?

“Calm down,” he said, noticing my fear. “Nothing bad is going to happen to you, I promise. We have a job for you.” A job? What, was he going to send me out to shoot someone too?

“What makes you think I’d work for you?” I said back, genuinely curious to hear his response. Instead of answering my question, he posed another.

“Have you ever heard of Al Capone, Isabelle?”

“Sure,” I responded. Who hadn’t? He was only one of the most famous American mobsters of the 20th century.

“Capone ran a faction of the Sicilian Mafia called the Chicago Outfit,” continued Alngelo, looking at me pointedly. “My great great grandfather worked closely with him for years, smuggling alcohol into the city during the Prohibition. After Capone went to prison, my family continued to work with the Outfit. About ten years ago, the leader retired in poor health, and my uncle, Salvatore DeLaurentis, took over operations.”

I knew it, he was connected to organized crime! Now the whole ‘enemies of the family’ thing and Angelo knowing random facts about me made sense. Surely he had checked into my background, making sure I wasn't some spy from a rival crime family. This left me in a dangerous predicament though, I was sure now that the murder I witnessed was a mafia execution. I suddenly realized getting out of here may be much harder than I originally hoped.

“My parents died when I was young, and my uncle raised me as his own. He never married or had kids, so I kind of filled that bill for him,” he chuckled as he said this, like he was reminiscing on fond memories from his childhood. “I grew up around the Outfit; they became my family. Once I became a teenager, my uncle started teaching me all the inner workings of the organization, grooming me to take over one day.”

“So you’re the leader of the Chicago Outfit, then?” I asked.

“Almost,” he responded. “My uncle is still technically in charge, but his health is declining. I do pretty much everything. I’ve been trying to convince him to retire, to officially hand everything over to me. But he’s stubborn, he likes his power,” Angelo chuckled again.

“So you will be the leader of the Outfit?” I asked again. I wanted him to confirm it in no uncertain terms, so I could process what I was up against.

“Yes,” he said back. “They call me ‘the Prince of Chicago’. And soon, I’ll be king.” He smiled in a kind of goofy way as he said this. I liked this side of him, he seemed almost warm, like someone I could joke around and get a beer with. I had to remind myself who I was dealing with, though. He was a mob boss, head of a major crime family. I couldn't get too comfortable.

“So let me guess, this ‘job’ is working for the Outfit?” I asked. He nodded.

“It was the best solution. You’re still a witness, Isabelle. But no harm will come to you this way,” he answered back. “Besides, I think you’ll like it here. I know you don't have family of your own anymore, after your mother passed. The Outfit could be a new family for you.”

How dare he bring up my mother’s death. And to suggest I’d find a ‘new family’ in the arms of the mafia? Ludacris.

“No,” I said coldly back.

He stared at me, his expression, which had softened as he recounted his story, went sharp again.

“Well, sweetheart, you don’t really have a choice.” Here he went again with the ‘sweetheart’ thing. I rolled my eyes. “Look,” he said sharply. “We have a job set up for you. You’ll stay here with me in the penthouse, at least for the time being, and we’ll make sure you’re well taken care of. You’re going to work for the Outfit, and that’s final.”

“I am not becoming a criminal!” I hissed back. Angelo laughed, a deep belly laugh as if I had just said something incredibly funny. I shot him an irritated look.

“No one said that,” he replied, trying to stifle his laughter. “You have a business degree, no?” I nodded. “I want you to run my office. I own a number of businesses, including the club you were at last night, and I just don’t have the time to keep everything organized. You’ll oversee the books for those businesses and general operations. You’ll be helping manage everything for me.” So he wanted me to be his assistant, essentially.

“How do I know this is safe, to work for you?” I asked back hesitantly. “Don’t you have, like, people after you all the time?” He smiled in that goofy, warm way again.

“You’ll be working out of an office here in the apartment, sweetheart. My office is right next door, and I have at least a half dozen of my men here at all times, if not more. Trust me, you won’t be put in harm’s way. I… I wouldn’t do that,” he finished, after trailing off.

“Somehow I don’t believe that, considering you threatened my life a few hours ago,” I said, looking him square in the face. I was surprised I had mustered the courage to say such a thing. His expression flattened.

“Look, Isabelle, I was frustrated, and the situation was tense. I was trying to find a good solution to our predicament, and I’m not used to people being… uncooperative with me,” he said. Not really an apology, but at least he acknowledged it. “As long as you behave, we won’t have any issues.”

So I was still a prisoner then. Yes, I’d get a job, and yes, I’d get more freedom around the apartment, but I still wasn’t going to be free. I still had to ‘behave’, as he said. Realizing that arguing was futile, I decided to give in. Having more freedom around the penthouse would be a good thing, I may figure out a way to run if I could study where his men were and the layout of the place. I sighed, and then gave him my answer.

“Well, I’m going to need some more appropriate clothes if you expect me to be working in an office”