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

Nightmare Success In and Out

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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