AI Challenge #5 / May 2026
The alley reeked of wet brick and yesterdayโs 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.
Iโd been tailing Frankie Malone for three days - small-time muscle for the Blue Room Lounge. Tonight heโd 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 wasnโt there, heels sharp on the wet cobblestones, chin high, shoulders back. Whatever she carried in that small black purse had Frankieโs 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 donโt ask questions. You tail her. And you hope the bullets donโt have your name on them yet.
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