AI Challenge #5 / May 2026
The alley reeked of wet brick and yesterday’s gin. I was tucked in the shadows under the fire escape, Lucky Strikes burning low between my fingers. The name's Jack Harlan, private dick.
I’d been tailing Frankie Malone for three days - small-time muscle for the Blue Room Lounge. Tonight he’d slipped out back with a fat envelope. I was waiting for him when she stepped into the light.
She was the only splash of color in the night. Red satin dress, black gloves, veiled hat, lips like fresh blood. She moved past the garbage like it wasn’t there, heels sharp on the wet cobblestones, chin high, shoulders back. Whatever she carried in that small black purse had Frankie’s name written all over it.
I flicked the cigarette into a puddle, following closely and keeping to the dark.
In this business, when the dame in red walks away, you don’t ask questions. You tail her. And you hope the bullets don’t have your name on them yet.
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