How A Gang Leader Survived America's Worst Prison System

Diaz Aguilar went to prison at 23 years old and spent the next 22 years inside Mississippi’s notoriously violent prison system. In this episode, Diaz sits down to tell the unbelievable story of how he survived decades behind bars while navigating gang politics, corrupt prison staff, brutal violence, and a massive underground contraband economy. Diaz explains how inmates worked with guards to bring in marijuana, tobacco, liquor, smartphones, and other contraband worth enormous amounts of money inside the prison system. He describes guards cooperating with gangs, violent conflicts between prison factions, years spent in segregation, and the abuse he says he witnessed and experienced at the hands of correctional staff. He also breaks down the case that sent him to prison. Diaz maintains that he was convicted of manslaughter despite no DNA, fingerprints, or physical evidence tying him to the murder weapon. Over time, Diaz became a powerful figure within the prison gang hierarchy and helped operate an organized contraband business that could generate more money than many street hustles. But after spending nearly half his life behind bars, Diaz eventually had to face an entirely different challenge: learning how to live in the free world again. Today, he is rebuilding his life, pursuing professional certifications, working in management, and sharing his story through his memoir, Rosecrans. This is a story about prison corruption, gang politics, survival, institutionalization, and what it takes to start over after 22 years behind bars. Go Support Diaz! IG: https://www.instagram.com/diaz_santiago_55/ TikTok: https://www.tiktok.com/@diaz_santiago75 Book: https://a.co/d/00doiiEd This Episode Is #Sponsored By The Following: Freecash! Sign up at https://signupfreecash.com/theconnect and get a $10 bonus! Hit the link, grab your bonus, and start getting rewarded for stuff you're already doing anyway. Shopify! If you’re ready to launch your business before Black Friday, go to https://shopify.com/mitchell to start your free trial. Cloaked! See if your SSN is for sale right now. My sponsor Cloaked will tell you for free in 2 seconds at https://cloaked.com/connect Join The Patreon For Bonus Content! https://www.patreon.com/theconnectshow 0:00 Intro: 22 Years in Mississippi Prison 6:51 Corrupt Guards & Brutal Prison Conditions 13:22 How the Contraband Operation Worked 18:20 This Episode Is Sponsored By Freecash 19:53 Cash, Money Orders & the Prison Economy 25:14 Cell Phones, Contraband Laws & Prison Education 33:37 Growing Up Puerto Rican in Compton 39:48 Gang Life & the Road to Mississippi 44:56 Why He Stayed in Mississippi & the Vice Lords Network 49:01 This Episode Is Sponsored By Shopify 50:11 The Fight That Led to 22 Years in Prison 57:05 The Evidence, Trial & Case Against Diaz 1:03:44 Anger, Isolation & Learning to Survive 1:09:03 This Episode Is Sponsored By Cloaked 1:10:54 His First Years Inside Mississippi Prison 1:17:52 Security Threat Status & Abuse by Guards 1:24:21 Handcuffed, Beaten & Prison Violence 1:30:49 Gang Wars, Stabbings & Prison Riots 1:36:17 Spending Four Years in Solitary Confinement 1:42:05 Prison Weapons & Building Connections With Guards 1:48:03 Smuggling Contraband Through Prison Guards 1:55:44 Rising to the Top of the Contraband Operation 2:02:33 Hidden Stashes & Making Money in Prison 2:08:48 Weed Markups & the Prison Liquor Racket 2:15:57 Smuggling Contraband Through Maintenance Trucks 2:22:03 Adapting Prison Survival Skills to the Free World 2:28:13 Life After Prison, Career Plans & Final Reflections Learn more about your ad choices. Visit podcastchoices.com/adchoices