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The moon shone in through the window. The big man in the sleek black suit wrapped his lips around the cigarette and inhaled deeply. There was a knock on the door. As he sat down and put his feet up on the desk, Jimmy entered the room.
“Hey chief. You wanted me?”
“Have a seat.”
Jimmy, with his blue pinstripe suit and greased back hair, slowly lifted his fedora off his head and sat opposite the big man. The boss held out his pack of cigarettes and Jimmy accepted. He struck the match with intent, and while exhaling a puff of gray smoke asked, "whaddya need, boss?"
The captain was silent for a moment, staring Jimmy straight in the eye, as if to determine whether he was fit for the task. Jimmy glared right back at him, and his eyes met the boss' even through the heavy fog from cigarette smoke. Clearly he was ready to accept the challenge.
"There's this singer over at the Fat Cat Café, Ruby something-er-other. Very talented. Real beautiful doll. Anyway, word on the street is she’s been gettin’ herself into trouble. I heard through the grapevine that she's got a second job performin' at a speakeasy somewhere. We have no word of where this juice joint is. You're one of the best we got. I want you to go down to the club and on her way out follow her over to the speakeasy. When you see her walk in, take note of the address, find the nearest payphone and call me. I'll take care of the rest.”
“Atta boy. What are you still doing in my office? You better get over to that night club before it closes.”
“Right away, boss. I"ll call ya.”
Jimmy placed his hat back on his head with confidence and swaggered out of the room. He was the most dedicated man on the force, and he was determined to complete the assigned task.
As he entered the Fat Cat Café, the thick aromas of cigarette smoke and perfume were wild. The lights were dim and the music was loud. Jimmy took a lap around the joint and finally had a seat at the bar, eyes up on stage waiting for Ruby to finish her act and leave the joint. “Gimme a scotch,” he said to the bartender as he was watching the singer through the thick clouds of smoke.
Before he knew it, his target was on the loose, and he put the drink down, placed his hat low down to cover half of his face, and followed her.
She was a good amount ahead of him, but he could still see her perfectly well, even through the late night New York City fog. He saw how she was all dolled up and her little black dress clung to her body as she took each step. Clack. Clack. She walked with a slight bounce in her step, and her hair went along with it-- bobbing in the slight breeze. Clack. Clack. The sounds her high heels made on the pavement began to entrance him Clack. Clack. Clack. She began to walk faster. He was getting too close. So Jimmy hung back, lit a cigarette, and kept on following her. Clackclackclackclack. Still, she walked even faster. She didn't know by who, but she knew she was being followed.
She glanced behind her briefly and all she saw was some good-looking John in an expensive looking suit and hat smoking a cigarette. So, she kept on walking, but this time more calmly. Finally, as she approached a building she came to a stop. She took out a tissue from her bag, scribbled something on it, and pressed it up to her lips, leaving a red lip stain. She nonchalantly dropped the tissue on the ground, knocked on the door of the building, and turned around to give her late-night stranger a flirty wink. Jimmy couldn't take his eyes off her as she walked inside.
He walked up to the speakeasy, picked up the tissue, and saw three words written on it: Joe sent me. He walked up to the door, but to his right, not so far away, he spotted a payphone. His head moved back and forth, glancing at the door then at the phone. Finally, he proceeded forward, and with a knock on the door and the utterance of three short words, Jimmy swaggered into the building, disappearing from the night.