Leo Leonardo is a Rhode Island native who got caught up in the system at a young age, facing repeated arrests that pushed him out of school and into the workforce—before turning to selling drugs when legitimate options fell apart. His path led to a federal drug case, time in both state and federal prison, and some of the harshest consequences behind the walls, including segregation (SEG) and maximum-security prison after continued trouble inside. After his release, Leo struggled to stay straight and was hit with additional gun charges, showing how hard it is to break cycles once the system has its grip. In this raw true-crime interview, Leo breaks down how the feds built their case, what life is really like in max prison and SEG, and the long-term consequences of early choices—an unfiltered look at crime, punishment, and life after prison.
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#PrisonStory #DrugRing #TrueCrimePodcast #FederalPrison #LifeAfterPrison #CrimeStory #ExCon #redemptionstory
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Thank you to PRIZEPICKS for sponsoring this episode:
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Hosted, Executive Produced & Edited By Ian Bick:
https://www.instagram.com/ian_bick/?hl=en
https://ianbick.com/
Shop Locked In Merch:
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Timestamps:
00:00 From Rhode Island Streets to Federal Prison
00:53 Growing Up in Rhode Island: Meet Splurge
02:42 Family, Childhood & the Environment That Shaped Him
05:16 Troubled Youth, Violence & Early Arrests
08:26 Juvenile Detention and Growing Up in the System
13:02 School Struggles, Dropping Out & Getting a GED
15:34 Trying to Go Straight: Trade School & Real Life
18:59 Back to the Streets: Drug Dealing & Survival
22:41 The Raid: Arrest, Indictment & Federal Charges
26:05 Facing the Judge: Court, Sentencing & Reality
28:08 State Jail vs Federal Prison: The Real Difference
31:57 Federal Transfer & Learning Prison Politics
37:20 Life Inside FCI Berlin: Isolation, Alliances & Trust
41:43 Prison Hooch, Contraband & Survival Tactics
43:00 Constant Transfers: Brooklyn, Oklahoma & More
47:08 Oxford Medium: Programs, Pressure & Prison Fights
51:12 Assaults, Box Time & Prison Discipline
56:41 COVID Lockdowns: Isolation & Mental Breakdown
01:03:04 Max Security at Kanan: Violence & Daily Routine
01:06:48 Prison Politics, Gangs & Loyalty Tests
01:13:00 Release, Relapse & Going Back to Prison
01:16:46 Education, Self-Improvement & a Decision to Change
01:18:39 Tattoos, Identity & Prison Regret
01:20:22 Making Amends & Breaking the Cycle
01:21:27 Final Advice & Hard Lessons Learned
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