The El train rattled overhead, its metallic shriek drowning out the muffled sobs of the dame huddled in the corner of my office. Chicago in July was a special kind of hell, the kind that made you wonder if maybe Ma Barker had the right idea, trading this sweatbox for a cool cell in the pen.
I peeled myself off the cracked leather of my chair, my silk blouse sticking to my skin like a second-rate grifter to a fresh mark. “Start from the beginning, sweetheart,” I growled, fishing a Lucky Strike from a crumpled pack. “And this time, try leaving out the bullshit.”
She looked up, mascara-streaked cheeks glistening in the harsh light filtering through the venetian blinds. For a moment, I saw something in those eyes – a flicker of steel beneath the carefully crafted vulnerability. It was gone in an instant, replaced by a fresh wave of tears that did nothing to douse the fire her gaze had ignited in my gut.
“It’s my brother, Ms. Callahan,” she whimpered, voice catching on every other word. “Tommy… he’s mixed up in something bad. Real bad.”
I lit my smoke, the bitter taste of tobacco filling my lungs like a familiar lover. “Sweetheart, in this town, ‘something bad’ could mean anything from skimming off the top at the corner store to making deals with the devil himself. You’re gonna have to do better than that.”
She flinched, whether from my tone or the truth of my words, I couldn’t tell. Her eyes darted to my lips, lingering a beat too long to be accidental. “The unions,” she whispered, glancing nervously at the door as if saying it too loud might summon them like demons. “Tommy… he found something. Papers, ledgers. Names that shouldn’t be there.”
I exhaled a plume of smoke, watching it curl towards the ceiling like the tendrils of desire snaking through my veins. Unions. Of course it was the fucking unions. In Chicago, they were the poison and the cure, the disease and the snake oil all rolled into one.
“Let me guess,” I said, stubbing out my cigarette in an overflowing ashtray. “Tommy boy thought he’d play hero. Threaten to expose the whole racket. And now he’s in the wind, leaving you to clean up his mess.”
Her eyes widened, a mix of surprise and something else – a heat that mirrored my own. Like she was glad someone finally understood the depth of the shit her brother had waded into, and wasn’t afraid to wade in after him.
“How did you–”
I cut her off, closing the distance between us. “Sweetheart, I’ve been in this game longer than you’ve been turning heads. I’ve seen idealistic schmucks like your brother come and go. Most of ’em end up face down in the Chicago River.”
She blanched, the last of the color draining from her face. It only made the red of her lips more enticing. “Please,” she whispered, reaching into her purse. “You have to help him. I can pay.”
I watched as she pulled out a wad of bills, neatly bound and probably fresh from the bank. It was enough to keep me in whiskey and smokes for a month, maybe two. But something didn’t add up. The clothes, the money, the rehearsed damsel-in-distress routine – it all stank worse than the stockyards on a hot summer day.
“Keep your money, doll,” I said, moving towards the door. “I don’t like the smell of this any more than I like the stench coming off the river. Your brother made his bed. Let him lie in it.”
Her facade cracked, just for a second. A flash of anger, quickly masked by another sob. She stood, closing the gap between us. I could feel the heat radiating off her body, smell the expensive perfume that barely masked the scent of fear and desperation.
“Please,” she tried again, her voice low and husky. “You’re my last hope.”
I paused, hand on the doorknob. Every instinct screamed at me to throw her out, to wash my hands of whatever mess she and her brother had stirred up. But something – call it curiosity, call it a death wish, call it the way her dress hugged every curve – made me turn back.
“Alright, sister,” I sighed, reaching for my hat. “You’ve got one hour. Take me to where this all started. But I’m warning you now – if I smell even a whiff of a setup, you’ll be wishing you’d never darkened my door.”
She nodded, relief flooding her features. As we stepped out into the sweltering Chicago night, I couldn’t shake the feeling that I was walking into something bigger than union skimming and idealistic whistleblowers. This city had secrets, layers upon layers of them, each one dirtier than the last.
The El roared by overhead, and for a moment, I could’ve sworn I heard it laughing. At me, at this dame with her crocodile tears and bedroom eyes, at this whole damned city rotting from the inside out. One thing was certain – before this night was through, blood would be spilled. The only question was whose.
I flicked my lighter, the flame dancing in the humid air. As we walked, the shadows seemed to grow longer, darker. Chicago at night was a beast all its own, hungry and waiting. And I had a sinking feeling I was about to be served up as the main course. But with the way this dame’s hips swayed as she walked ahead of me, I found myself thinking that maybe, just maybe, it might be worth it.