As a computer science student in Brooklyn, I’ve trained models to predict game outcomes—yet I’m haunted by a deeper question: if an algorithm forecasts your loss before you even bet, does that mean choice is an illusion? In this essay, I blend data analysis with philosophical reflection on Aviator-style games, exploring how machine prediction challenges our sense of agency. Using real-world volatility patterns and emotional risk metrics, I reveal what algorithms can—and cannot—see. This isn’t just about winning; it’s about who we are when machines know us better than we know ourselves.