Jack was kneeling down in front of the door. A bobby pin in his hands, he was attempting to pick the lock of the mayors office. He knew that the drunken bastard had fallen asleep on his chair, like he did at 6pm everyday. It was like a routine for the wanker. DeanWinchester had called upon Jack to break into the mayor of Philly's office, and get the job down. What was the job you ask? It was simple really. Jack needed to blackmail the old fucker into allowing The Devil's Trap to use this office to run certain rackets that were frowned upon by law.

These rackets were the kind of activity that men killed over, and it made people filthy rich. Drugs were a powerful weapon, almost as powerful as money, and when you get the greedy corrupt bastards in office using and abusing, then you got yourself a racket. Blackmail, extortion, murder, trafficking, and heists were Jack's department. He was extremely gifted at these rackets, which was why Dean usually called upon him for them. Dean just knew that Jack was the fella who could get these jobs done.

So there he was, lock picking the door, about to confront the mayor. He finished up, and he heard a cough coming from behind him. It would be the security detail that was on guard duty for the mayor that day. He must have been running late for his shift, as he should have been there an hour ago. Jack quickly hid behind the small statue next to the door, and waited for the guard to take his position. Jack pulled out a piece of copper wire from his jacket pocket, and he grasped it tight in his hands. He crouched down and sneakily crept towards the guard. He threw himself at him, grabbing him around the neck with the copper wire. It took only 20 seconds to choke this motherfucker to death, and when Jack heard the man stop breathing and kicking, he knew it was time to let go.

Jack dragged the corpse behind the small statue, then proceeded into the mayors office. There he was, fast asleep on his chair with his feet up on the desk, his fedora covered his face to block out the light from outside. Jack turned and closed the door. He walked over to the mayor, pulled out his silenced gun and tapped it on the mayors foot. Not even a twitch from the miserable fuck. Jack slapped him on the leg, and he woke up. Looking startled, the mayors eyes widen, and he thought he was going to die. He quickly tried to grab his gun from the desk, but Jack was far too quick for him. He pistol whipped the mayor around the head, and he fell to the floor holding his head.

Jack crouched down, and they looked at each other. Flashing the mayor a smile, Jack held his gun to his face and stared at him. This was the kind of thing that Jack lived for!

"Good evening, Kyle. I think you know why I am here." Said Jack to the mayor. Indeed he did know why Jack was there. He knew he had fucked up, and he knew that Jack would have evidence about what he had done.

You see, the mayor had sex with some fella from the accounting department. If word ever got out about this, then the mayor would be finished and most likely killed for being run out of office. He was on too many payrolls to be a nobody, and he knew it. Dean Winchester also knew this, and that's why he needed something from the mayor.

"We need to talk. Sit down." Exclaimed Jack. He pointed to the seat in front of the desk, while Jack went and sat down in the mayors seat. He placed his gun down on the table, just as the mayor sat down, still holding onto his head.

"Dean Winchester sent me. You see, we have certain photos that you probably don't want getting out to the general public. If I was you, I'd co-operate with us. You know who we are, and you know what we can do, pal." Jack leaned in a little closer, and grimaced a mean look at the mayor. "Mr Winchester will be along any second now with a few others. He'd like to have a word with you, Kyle. Pour us a drink while we wait please."

Lily had to make her way to Philadelphia for a business meeting, JackRuby had told her that she needed to go persuade a certain politician. Well not just any politician but the mayor. Jack had given her an envelope, she had specific instructions not to open it until she had gotten into Philly. So she stuffed it in her bag and proceeded on her way. Initially she was thinking about flying down there but had decided to take the train instead, figuring it would give her a couple hours to finally get some sleep. She had one of Jack's drivers bring her to the station where she bought the next ticket to Philly. She was hoping she would be able to spend more then just enough time to get the job done. There were a couple of her mothers old friend out there that she wanted to visit. Plus the cheese steak, the only place in the country that you really can get one. 

Getting to the train station she stepped out of the car and tipped her hat to the driver. She made he way inside walked straight up to the teller.

"One way ticket to Philadelphia please."

Without hesitation the lady printed her ticket out and placed it on the counter. "That will be..." Before she was able to finish Lily placed a couple bills on the counter. "Anyone asks you haven't seen me here, ok?" The lady counted the money, it was quite a bit more then the ticket. With a nod and a smile the lady agreed.

Lily waited for the train to arrive, only took a couple minutes. Seems she somehow timed it perfectly, not like she was trying to but things like this happened to her often. She handed her ticket to the conductor and quickly found her seat. She propped herself up against the window and sprawled her legs across the seat so no one else could sit next to her. She watched the people boarding the train for a couple of moments until her eyes started getting heavy. Her blinks got longer and longer, before she knew it someone was tapping on her foot. She sprung up.

"WHAT?"

A weary conductor was standing there looking at her kind of shocked.

"I'm sorry ma'am but we are in Philly now, it's time to get off"

She chuckled to herself, she had been a sleep the entire train ride. Collecting her stuff and fixing herself up quickly is disembarked the train. Finding the nearest bench she sat down and pulled the envelope out of her bag and opened up it. It had a name and address on it along with some other key points she needed to bring up in conversation. Reading the name in her head "Kyle - Mayor" she was taken back for a moment. Has she worked her way up that much that she is dealing with mayors now. A smile beamed on her face, as the excitement to get her first real assignment was setting in.

Walking out of the train station, she wondered how she was going to get down the center city. Luckily there was a row of cabs awaiting fares. Walking right up to the cab she got in, told the driver where she wanted to go and she was off. The driver tried to make some chit chat with her but Lily couldn't be bothered she had more pressing issue going through her head then to talk to some driver that she will more then likely never see again.  After a couple minutes he got the hint and the two spent the rest of the drive in complete silence. After about 15 minutes the car suddenly stopped.

"Here we are."

Lily pulled some cash out of her bag handing it to the driver, again it was more then the fare.

"If anyone asks, your fare this evening was a nice married couple. Got it?"

He counted his stack of cash and smiled. "Yesss, ma'am!"

There Lily stood in front of the mayors office, the letter that was in the envelope stated that there was only one guard on duty but that he usually hangs out in the back. The front door is a simple lock and can be picked with a bobby pin, same with his office door which is on the first floor it is the one with a massive statue next to it.

Lily took a deep breathe before digging in her bag to find a couple bobby pins she always carried with her. She looked around to make sure no one was looking, when she was confident no one was she casually made her way to the door. With a slight of hands and a little jiggle of the bobby pin she was inside.

It was awfully quiet in the building, she could tell no one was there. Well no one but the one guard and the mayor. She slowly walked down the hallway and hooked a right until she noticed the statue in the hallway. Though there was something a bit wrong with this picture, she spotted the guard. He looked dead. Lily quickly pulled her gun out of her bag and slowly made her way to towards the mayors office. Upon reaching the statue she glanced down at the guard who was quite obviously dead. She instantly noticed the strangle mark on his neck. 

She wasn't quite sure what to do and was about to leave until she overheard someone speaking to the mayor. It was a voice that she thought she had heard before, she decided to muster the courage to find out what was going on in the office. The door was slightly cracked open, as if whomever was in there was expecting someone else. Lily with gun in hand slowly pushed the door open. The first thing she saw was the mayor on the ground with a bit of blood trickling down his forehead, quickly she looked to her right and pointed her gun.

"Drop the gun, NOW!" Lily shouted

The man was facing the other direction, he gently placed his gun on the shelf next to him.

"Turn around!"

The man slowly turned around.

"Jack.... JackFranco... What are you doing here?"

About 20 minutes went by, and there was still no sign of DeanWinchester or anyone else from Philly coming to the mayors office. Jack wasn't entirely sure as to how much longer he needed to wait, or whether he should take matters into his own hands. If he had his way then the mayor would already be dead, and he'd take charge of rigging the election to bring a new mayor into office. But Dean didn't want Kyle to be killed today. He wanted to wait until we had him on our payroll. We had the evidence but it was a matter of 'if we can break him' kind of thing.

Jack sat there in silence remembering how things used to be before they went all professional. He would be given a job, and it was up to Jack as to whether or not he'd kill the target. Blackmail was always fun, but there was something about murder that gave Jack a thrill. Maybe he needed to see someone about that when he got back home. There was definitely something sinister inside of Jack that shouldn't be allowed to see sunlight. Jack hadn't always been that way, but ever since he become one of Dean's Captains he had become more dangerous than ever. He took nothing for granted, and never let people take the piss out of him or his associates.

He was already wanted by the cops out in Jersey. He had been sleeping with a police captains wife, and when he was caught in the middle of fucking her, the police captain tried to shoot him. Luckily for Jack he was too quick on the draw, and he shot the police captain in the dick and made him bleed to death in the middle of his own street. Poor bastard never even stood a chance against Jack. Even though he was only the rank of Wise Guy, Jack was already showing the potential of a Capo. He was tough, and most people knew it. 

"I'm only prepared to wait another 10 minutes there, Kyle. If Dean doesn't show, then I'm afraid you'll have to be having this conversation with me, pal." Jack told the mayor. He knew that he should wait for Dean, but then again, Dean knew exactly how good at this shit Jack actually was. It was his passion and he'd been doing it for many moons now.

The door was suddenly thrown open, and a woman had come in pointing a glock pistol at Jack's face. He didn't recognise her at first because she was shouting at him, and she was also attractive. Jack had always been a sucker for a pretty face. He just loved to fuck, and he was always thinking about doing it. This was no exception. Jack never got scared, even when there was a gun being held to his face by death himself. Jack laughed the last time someone did this to him, and he ended up doing the actual killing.

Jack tilted his head a little to the left, and he realised that this was none other than Lily, a Wise Guy from New York City. He had met her a few times on occasion, and even had dinner with her once during a business meeting. Why he did not recognise her before shocked him, but it was probably because she was so beautiful, and had a body like Rita Hayworth. Jack had always had a thing for Rita Hayworth, and this brought up some old feelings for him. He looked Lily up and down, before looking at the gun she was holding. Lily had obviously recognised Jack too, because she had said his name in complete surprise.

"Are you going to be putting that gun away any time soon, Lily? Or do you plan on shooting me with it?" Asked Jack with a smile on his face. He didn't understand why she was here, but he knew he needed to find out.

"You sit the fuck down, Kyle!" Shouted Jack angrily to the mayor, who decided that making a break for it was the smartest move to play. Jack shot up, grabbed the mayor by the back of his jacket, and threw him onto the desk, knocking the desk fan onto the floor. The lit cigarette that Jack had left issuing from the ashtray he placed it in also went flying onto the floor, scattering ash everywhere. 

Jack stood above the mayor, grabbed him by his shirtand tie and headbutted him in the face. The mayor was knocked out cold instantly. Jack fixed his hair, and straightened his tie. Turning back to Lily, he flashed her another smile, and ushered her into the seat that the mayor was previously sitting on. He went back, picked up the cigarette and ashtray that had flown onto the floor, and placed it back onto the table. He picked up the pack of smokes that he had on the desk, lit up another single and offered one to Lily. He took a few drags on the smile, and placed one hand on the desk as he crossed one leg over the other.

"So, tell me why you are here and we can try and get out of this awkward situation we now appear to be in, eh?" Exclaimed Jack. He was really pleased to see Lily, but he was still at a loss as to why she was even there in the first place. He leaned back in the chair behind the desk, took another drag from the cigarette, and listened to what Lily had to say on the matter. The mayor was still lying on his back on the floor, not knowing what was going on around him. His nose was clearly broken, and blood was beginning to trickle onto the floor. Jack didn't want to be around when the cleaning lady came into work later that night.

Lily stood there with gun in hand still pointed at Jack, she was trying to wrap her head around what was going on. For some reason even though she knew the man in front of her she was a bit reluctant at first to lower her weapon. It wasn't until she saw that playful smile on his face that she snapped out of her little trance and lowered her gun. The two of them had a couple run ins before this, mainly just casual though, except for that one business meeting that they met up for dinner to discuss...well that's for another time. 

The moment she lowered her gun the mayor tried to make a break for it. Without hesitation Jack halted that process, she watched as the mayor was flung over his desk. The fan fell on the floor and ashtray went flying in the air, Lily took a couple steps back towards the door just in case the mayor somehow got past Jack. She watched as he headbutted him knocking him out cold, Lily chuckled to herself. There was something about guys fighting that she got a rise out of.  

Lily listened to Jack as he spoke, and watched as he decided to take the mayors seat. She smirked at him and shook her head a couple of times before looking back down at the mayor then back up at Jack.

"I think that chair suits you pretty well."

She was about to go sit down until out of the corner of her eye she saw the door was wide open. With the mess that had just happened in that office it was better off to keep the door close, just in case someone decides to pop back in the building. She wasn't a huge fan of killing some random person that just happened to be in the wrong place at the wrong time. As she closed the door she turned around to see Jack giving her a bit of a funny look.

"What? You never know who might randomly show up, I'm just trying to cover all bases."

She walked back over to the mayor giving him a little tap in the ribs with her foot, to see if he really was out cold. The little tap did nothing so she gave him a harder kick and still there was no movement.

"I don't think you killed him but you sure as hell knocked him out, how am I supposed to convince him of certain things if he isn't awake to persuade?

Lily let out a big sigh, she looked up at the clock on the wall just as a force of habit. She knew she had no where to go but figured it would be good to play it off like she did. She looked down at Jack, she knew he was waiting on an answer to why she was there but she wasn't one to quickly give away her reasons.

She was about to go sit down in one of the chairs on the opposite side of the office but it just seemed way to far away for her liking. So she walked up to the desk Jack was sitting at, carefully stepping over the mayor and the small pool of blood that had formed around his head. She was wearing a pair of her nice shoes, a pair that she was against getting some blood on. She pushed herself up on the desk, sitting on the corner with her back slightly facing Jack. She crossed her legs and looked over her right shoulder.

"So you tell me why you are here first, then I may just tell you why I'm here."