The Tables Are Turned: An Informant's Prison Story & the Comeback

Barry Oberholzer has interviewed everyone else from a helicopter. Now the tables are turned.He's been a confidential informant for U.S. intelligence, a sanction buster moving $2 billion in Iranian deals, and a prisoner in two countries. He spent 97 days in solitary confinement. He was burned by the very governments he served. And he came back.In this episode, Barry sits in the guest seat for the first time and tells his own story: the arrests, the prison time, the isolation, the betrayal, and the choice to rebuild.From the cells of South Africa to the federal prison in Sheridan, Oregon, this is the full unfiltered account of what it took to survive and what it cost to come back."Comebacks are hard, but comebacks are doable."The Flying Felon is the world's first podcast in the sky. No scripts. No rules. Raw truth. Real redemption.IN THIS EPISODE:- The wire fraud case, the DOJ, and the plea deal- Entering federal prison: Sheridan, Oregon and the Birdcage- Race segregation, prison economics, and the phone raid- 97 days in solitary confinement — and the first sunlight after- Unsent letters and surviving inhumane conditions- Transfers, Victorville, and violence inside- The Iran connection: sanction busting and $2 billion deals- "Just a chess piece": the U.S. government's double game- South Africa: the bribe, the burn notice, and the second arrest- The old prison: the overdose plan and the family visit- The Gulfstream extraction: DHS gets him out- The tech startup con, the lawsuit, and why The Flying Felon existsFollow The Flying Felon:Instagram: @theflyingfelonTikTok: @theflyingfelonYouTube: @TheFlyingFelonThe Flying Felon is a conversation series about redemption, resilience, and real life. Filmed entirely in real helicopter flight. No studio. No scripts. No rules.