• Both Sides of the Bars
    Jan 26 2026


    Guest: Oak Smith, Former Acting Warden of San Quentin State Prison

    What happens when a formerly incarcerated man sits down with the warden who led the prison during his time inside?

    In this first episode of Basic Conversations, host Brother Boston welcomes Oak Smith - former Acting Warden of San Quentin State Prison - for a raw, honest conversation about faith, transformation, and second chances.

    Oak spent 27 years working through California's most dangerous prisons: Pelican Bay, Corcoran, Kern Valley, and San Quentin. He shares how he went from being an EMT who swore he'd never work in a prison to becoming a warden known for breaking down barriers and showing up as a human being, not just an administrator.

    What you'll hear:

    • Oak's first day at San Quentin signing release papers for a lifer
    • The reality of "checking your humanity at the gate" and how it nearly destroyed him
    • Why dehumanization happens on both sides of the bars
    • Unwritten rules that govern prison yards and how faith challenges those divisions
    • The moment Oak realized he'd been living as a "fake Christian" for 15 years
    • Why correctional officers have the highest suicide rate of any profession
    • How accountability sets you free
    • What it means to live out your faith when it's hardest

    This conversation goes deep into the psychology of incarceration for both inmates and staff. Brother Boston and Oak discuss anxiety, shell shock, the difficulty of returning to society, and the parallel experiences on both sides of the bars.

    At its core, this is about redemption - two men who found freedom in Christ and how that transformation changed everything.

    Guest: Oak Smith served 27 years with the California Department of Corrections, retiring as Acting Warden of San Quentin in November 2024. He's a man of deep Christian faith who believes in second chances and genuine transformation.

    Host: Brother Boston is the founder of B.A.S.I.C. Ministry and a recovery group facilitator at J.R.E.A.C.H. A former San Quentin resident, he's passionate about the transformation he found through Christ while incarcerated.

    Subscribe to Basic Conversations for real, honest conversations about transformation, second chances, and faith in the hardest places.

    Topics: Prison Reform | Faith and Justice | Transformation | Second Chances | Redemption | San Quentin | Rehabilitation

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    34 mins