In this episode of Me, Myself & AI, Casey asks a bold question: Why am I always rooting for the underdog? From the Toronto Raptors proving the world wrong—again—in the 2026 playoffs, to Stephen Curry completely changing how basketball is played, to Zohran Mamdani challenging power through housing and economic reform, to Kanye West forcing his way into an industry that didn’t fully see him—this episode explores what makes underdogs so powerful, so necessary, and so unforgettable. Casey and Jay unpack the systems, the setbacks, the culture shifts, and the uncomfortable truths behind people who weren’t supposed to win… but changed the game anyway.