From Judge to Prison: Jessica O'Brien's Fall and Rise

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Nightmare Success In and Out

brent cassity

202 episodes

3 days ago

What happens if your worst fear becomes your reality? Brent Cassity was a successful CEO working in a family business that grew to a national company that was recognized by the media of being the pioneers in their industry. Brent had it all and lost it all. He found himself standing at the gates of Leavenworth Prison to serve a 5 year sentence. Brent's podcast explores the stories of inmates who were in and now out of prison. What was life like before they went in, life inside prison, and life now that they are back home. These conversations are deep, sad. often funny, but always interesting.

Self-Improvement

Education

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Self-Improvement

Education

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From Judge to Prison: Jessica O'Brien's Fall and Rise

Nightmare Success In and Out

1 hour 50 minutes 21 seconds

3 months ago

From Judge to Prison: Jessica O'Brien's Fall and Rise

In this powerful and revealing episode of Nightmare Success In and Out, Brent Cassity sits down with former Illinois Judge Jessica O’Brien—the first Filipino-American elected to the bench in Cook County—who went from a respected courtroom authority to a federal inmate. Jessica opens up about her stunning journey through the justice system:the decision to go to trial that led to a conviction for mortgage fraud, the surreal experience of trading her judge robe for a prison uniform, and how she rebuilt her identity from the inside out. With raw honesty, she reflects on the shame, isolation, and loss of purpose she faced, and how she found resilience and redemption in the most unlikely place. Now an advocate for second chances and systemic reform, Jessica shares how her experience has reshaped her understanding of justice—and her mission moving forward. She is still diligently fighting to overturn her conviction. This is a conversation about resilience , surviving, and the courage to rewrite your story. A must-listen for anyone who believes that rock bottom can be the beginning of something new.

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