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From Juvenile Offender to Mentor: Bobby Bostic’s Redemption After a 241-Year Prison Sentence (ep. 624)

John O’Leary welcomes Bobby Bostic on the Live Inspired Podcast to share his journey in navigating an unlikely path to freedom, fostering a reconciling connection, and revealing the transformative power that liberates us from the shackles of our mistakes.

In 1995, a 16-year-old Bobby Bostic found himself caught up in a series of poor choices including robbery and armed criminal action. Judge Evelyn Baker, convinced he was a lost cause, handed down a jaw-dropping 241-year sentence on him, parole only becoming a glimmer of hope at the ripe age of 112.

While serving the longest sentence in Missouri for a non-homicide juvenile offense, Bobby didn’t crumble. Instead, he evolved, showed significant remorse for his actions and began reshaping what his future could hold.

Today, after serving 27 years of his sentence, Bobby is embracing his shot at redemption by teaching writing workshops at juvenile detention centers and using his story to mentor kids to keep them out of trouble.

Join me as Bobby shares his journey in navigating an unlikely path to freedom, fostering a reconciling connection with the judge who initially sent him away, and revealing the transformative power that liberates us from the shackles of our mistakes.

My friends, it’s easy to criticize others for their sins, crimes and missteps. And yet, when we delve into the narratives that precede those missteps, an empathic heart emerges. This episode is a reminder that our past doesn’t have to be our defining chapter. And that even in the face of adversity, the best is yet to come.

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  • “You will die in the Department of Corrections.” After serving 27 years, Bobby was reunited with Judge Evelyn Baker, the person who sent him away but also the person who helped advocate for his release. Watch their reunion here.
  • While being a “rebellious, hard-headed prisoner”, Bobby spent a lot of time in solitary confinement which is where he found a passion for reading and his awakening started.
  • “When everything gets taken away from you, that’s when you realize you need something bigger than you.” – Bobby on finding his spirituality.
  • “My pen was my satellite.” Hoping to give advice to his younger self, and in turn other young people, Bobby would write poems and essays, and send them to various publications. Read his advice to his younger self here.

Did you enjoy today’s episode? 

You’ll love my conversation with Becky James Hatter. As the former and long-time President and CEO of Big Brothers Big Sisters of Eastern Missouri, Becky helped propel a struggling program with a small budget and a goal of serving 300 young people into thriving organization serving more 9,000 young people and their families. It’s an incredible conversation that will spark unity + offer you concrete ways to be a change agent in your community. Listen to Becky James Hatter on ep. 59.


About our sponsor: Keeley Companies wholeheartedly believes that if you get the people right -the results will follow. They set themselves apart with a forward-thinking culture that empowers their people and fosters loyal partnerships. Keeley Companies are a proud sponsor, partner, and super fan of the Live Inspired Podcast. Learn more about Keeley Companies.



  1. Q. What is the best book you’ve ever read?
    A. The Autobiography of Malcolm X by Alex Haley and Attallah Shabazz Malcolm X.
  2. Q. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today?
    A. Hope beyond hope. He looked at the world and wondered why.
  3. Q. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be?
    A. My mother's picture. Her eyes tell me to keep going.
  4. Q. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be?
    A. A prophet.
  5. Q. What is the best advice you’ve ever received?
    A. Listen to your mother.
  6. Q. What advice would you give your 20-year-old self?
    A. Keep dreaming. There's more to come.
  7. Q. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read?
    A. A lost soul that once found himself. God gave him a certain call and he followed it.