Matthew Cox | Inside True Crime Podcast Insane Ways People Smuggle Things Into Prison
Nov 28, 2025
Dereck Jackson, a former inmate and reentry advocate, dives into the shocking world of prison life. He reveals bizarre smuggling techniques, including 'hooping' contraband, and shares the chaotic dynamics of prison politics. Dereck discusses the profound impact of prison culture on crime and survival strategies, dispelling myths around sexual violence and gang wars. His personal journey showcases struggles with reentry into society, the urgency for legal reform, and his efforts to support at-risk youth.
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First Robbery And Chaotic Getaway
- Dereck Jackson describes his first serious robbery and how a getaway went wrong when traffic trapped them.
- He smashed through cars to escape but was later caught after being linked by patterns and evidence.
Plea Deal And Humanity Switch
- Dereck took a plea for 20 years, eight months despite fearing a life sentence under career-criminal rules.
- He says his humanity 'switched off' when the gavel fell and he prepared mentally for a long prison stay.
Prison Reception Shapes Your Role Fast
- Reception in California prisons assigns newcomers to groups and enforces racial/political alignment quickly.
- Dereck learned prison 'lacing up' from lifers who taught survival, weapon-making, and politics.
