Gary Heyward started as a normal jail guard fresh out of the marines. But after financial struggles and exposure to corruption from other corrections officers he soon began running a smuggling ring bringing in tobacco, drugs, and women to the inmates. This behavior eventually landed him in the role of inmate, completely changing his life.

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0:00 Intro
1:27 Growing Up In Harlem And The Polo Grounds Projects
6:07 Being Exposed To Corrupt Police At A Young Age
13:08 Hustler’s Relationship With Law Enforcement In Harlem
22:19 Joining The Marines
26:00 Decision To Be A Corrections Officer
29:17 This Episode Is Sponsored By PrizePicks!
31:22 Learning As A Rookie Corrections Officer
38:17 Being A CO With Old Friends As Inmates
46:21 Explaining How Dangerous Rikers Island Is/Smuggling Weapons
57:29 What Causes The Violence In Rikers
1:04:28 How The Drug Trade Operated In Rikers Island
1:08:37 Gary’s Introduction To Officer Corruption
1:15:14 Getting Started Smuggling Contraband And Making Money
1:22:36 Developing A Gambling Problem And Other Addictions
1:30:21 This Episode Is Sponsored By MAGIC MIND
1:31:14 Scaling Operations And Bringing In Drugs
1:42:54 Running A Cellphone And Bringing Women To Inmates
1:53:04 How Guards Encouraged Abuse And Assault
2:03:05 The End Of The Run And Getting Caught
2:17:57 Turning His Life Around After Prison And Wrapping Up