Where It All Started! + A Look Back at My Conversation with Rosie O’Donnell

When You Know You Know · Jan 2, 2026 · 1h 6m

Today on Mea Culpa, I’m revisiting the very first episode of the podcast—recorded in September 2020, when I was fresh out of prison and still confined to my home—with my first-ever guest, Rosie O’Donnell. What began as a conversation between two people deeply harmed by Donald Trump became something more urgent: a documentation of character, cruelty, and power. We talk about Trump not as a political movement, but as a man—his brittle ego, his need for submission, and his use of humiliation and fear as tools of control. Drawing from my years as his fixer and Rosie’s experience as his first…