August 17, 2026
I Was a CIA Operative for 25 Years — Then I Got Set Up & Sent to Federal Prison | Michael Wayne
Michael Wayne grew up in Mississippi, attended the Naval Academy, left after his father died, built a career in business and investments while running a hedge fund for fifteen years, spent twenty-five years as a clandestine CIA contractor operating across some of the most sensitive and most dangerous missions available — and then went to Ukraine after the 2022 Russian invasion to organize humanitarian aid, evacuate women and children from combat zones, train Ukrainian soldiers, and deliver equipment to the front line before discovering widespread corruption tied to Ukraine aid that he says reached powerful US politicians. In this episode of Locked In with Ian Bick, he shares what twenty-five years as a CIA contractor actually looked like from the inside, what changed after 9/11 in the intelligence world, what the Ukraine work actually involved, what the corruption he discovered actually implicated, and what the DOJ prosecution that followed his decision to push back against that corruption actually produced — including a wire fraud conviction, a federal prison sentence at FPC Montgomery, and what he believes was a deliberate government effort to make him a convicted felon before he could become a whistleblower. _____________________________________________ #TrueCrime #espionage #cia #prisonstory _____________________________________________ Thank you to CASH APP for sponsoring this episode: Download Cash App Today: https://capl.onelink.me/vFut/ksjh06pb #CashAppPod Cash App is a financial services platform, not a bank. Banking services provided by Cash App's bank partner(s). Prepaid debit cards issued by Sutton Bank, Member FDIC. Cash App Visa® Debit Flex Cards issued by Sutton Bank, Member FDIC, and The Bancorp Bank, N.A., pursuant to a license from Visa U.S.A. Inc. See terms and conditions for the Sutton prepaid card, Sutton debit flex card, and Bancorp debit flex card. Discounts and promotions provided by Cash App, a Block, Inc. brand. Visit cash.app/legal/podcast for full disclosures. _____________________________________________ Connect with Michael Wayne: Instagram: https://www.instagram.com/officialmichaelwayne/ Website: https://officialmichaelwayne.com/ _____________________________________________ Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/ _____________________________________________ Timestamps: 00:00 Intro and Guest Introduction 01:31 Family and Entrepreneurship 05:00 The Call to the Naval Academy 12:42 The Challenges of the Naval Academy 15:17 Leaving Annapolis After Two Years 17:51 The Tragic Loss of His Father 21:41 The Funeral and a Call from the Captain 24:23 Choosing Family Over Country 28:55 Rethinking Leaving Annapolis 31:14 The Plan to Return Falls Apart 36:24 The Decision to Stay Out of the Military 37:57 Mississippi State and Running the Family Business 41:17 Sponsor Break: Cash App Security 44:27 College Life and Degrees 55:36 Buying Properties and Developing a Strategy 01:00:20 Moving to Atlanta and Sports Betting 01:03:30 The Unexpected Call from an Agency 01:08:40 The First Interview for a CIA Contractor 01:14:40 The Path to Becoming a Contractor 01:19:03 Interviews and the Training Invitation 01:24:05 Paramilitary Training and Selection 01:29:07 Understanding Classification and Compartmentalization 01:34:55 The Intensity of the Initial Training 01:39:19 Field Exercises and Testing Survival Skills 01:47:26 The Importance of Knowing Your Limits 02:01:20 Working as a Paramilitary Contractor 02:04:20 A Career of Off-the-Books Missions 02:07:09 Getting Shot and the Impact of 9/11 02:12:30 The Post-9/11 World and the War on Terror 02:24:03 A Screenplay That Predicted 9/11 02:31:10 Transitioning to a New Role and Grad School 02:37:50 Living as a NOC (Non-Official Cover) 02:42:10 The Intensity of the NOC World 02:47:51 Running a Hedge Fund as Cover 02:57:21 Making Money and Helping a Nonprofit 03:02:41 Volunteering in Ukraine After the Invasion 03:05:00 The Corrupt Side of Humanitarian Aid 03:10:34 Protecting Aid and Empowering People 03:15:14 The Hidden World of Powerful Elites 03:21:18 Learning You're a Target 03:28:08 The Plan to Discredit Him 03:34:55 A New SEC Inquiry and the Missing Questions 03:39:01 The Target Letter and the DOJ 03:44:37 Attempting to Investigate the Management Company 03:50:59 The Reverse Proffer: The DOJ's Show of Force 03:57:20 Realizing the System Can't Be Beaten 04:01:44 The Threats That Forced His Hand 04:03:42 The Strategic Choice to Plead Guilty 04:08:35 The Courtroom Deal and Sentencing Guidelines 04:12:00 The Aftermath of the Guilty Plea 04:16:08 The Hit to His Reputation 04:18:24 The FBI Agent and the Press Release 04:22:47 Dealing with the PSR and Sentencing 04:27:44 The Leak and the Fallout 04:31:14 The PSR: A Document Full of Falsehoods 04:35:35 The Sentencing Hearing 04:40:20 The Judge's Unusual Statement 04:45:36 Getting a Year and a Day 04:50:00 A Trip to Federal Prison Camp 04:56:30 The Confusing Charges and the Real Crime 05:04:20 The Plea Deal and the Missing Documentation 05:09:30 The Sentencing Hearing and a Shoutout to the Judge 05:12:10 The Camp: A Place for the Forgotten 05:16:08 Life After Prison and the Supervised Release 05:21:01 The CIA and the Burning of Bridges 05:25:20 Finding a New Path Post-Prison
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