Episode 76

How Failure Became My Greatest Teacher with Ryan Leaf From Putnamville

RYAN LEAF OPENS UP ABOUT HIS
FALL FROM NFL STARDOM TO PRISON,
THE LESSONS HE LEARNED IN
REDEMPTION, AND HIS MISSION
TO INSPIRE CHANGE.

About The Show

Ryan Leaf is a former NFL quarterback turned advocate for criminal justice reform, recovery, and second chances. Once known as one of the biggest “busts” in NFL history, Leaf’s career spiraled due to addiction and legal troubles, leading to his incarceration. Since his release, he has transformed his life, becoming a motivational speaker, media analyst, and mentor to incarcerated individuals. Through his work with organizations like The Last Mile, Leaf has dedicated himself to helping others break cycles of incarceration and rebuild their lives with purpose.

“Ninety percent of success is just showing up when you’re supposed to, even when you don’t want to. The last ten percent is hard, but showing up is everything. The discipline to keep going, to be where you’re supposed to be, even when it’s uncomfortable, is what separates those who move forward from those who stay stuck. Every small step in the right direction builds momentum toward something greater.”

In this deeply personal speech to some of the men within the Putnamville Correctional Facility, Leaf speaks candidly about his fall from grace, the harsh realities of life behind bars, and his journey toward accountability. He shares how his initial release from prison was met with stigma and isolation, but a pivotal moment—helping fellow inmates learn to read—shifted his perspective on service and redemption. He delves into the importance of rehabilitation, the failures of the prison system in providing real opportunities for change, and how programs like The Last Mile are creating pathways to success for returning citizens. Leaf also discusses his battle with addiction, the power of personal responsibility, and the long road to self-acceptance.

Episode Outline

(00:00:00) Introduction
(00:02:00) Life After Prison: The Harsh Reality
(00:06:00) A Wake-Up Call from a Fellow Inmate
(00:08:30) The First Step Toward Change
(00:12:00) Masculinity and Vulnerability
(00:15:30) The Power of Service to Others
(00:18:45) Breaking the Cycle of Incarceration
(00:22:30) Accountability and Self-Reflection
(00:27:00) Addiction, Shame, and Recovery
(00:30:45) Finding Redemption Through The Last Mile
(00:35:00) Perspective Shift: From Victim to Leader
(00:38:00) The Importance of Second Chances
(00:42:00) Closing Reflections and Call to Action

Episode Resources: (Prompt) (GPT Page)

Behind The Scenes

JOIN OUR E-LIST

Want to know when we have new behind the scenes content available, or a big upcoming episode? Sign up for The Last Mile radio e-mail subscription to learn the latest

Name(Required)
This field is for validation purposes and should be left unchanged.

Ryan Leaf wants to hear from you

The power of this show is the strength of our audience and it's impact on the justice system. Which means, we want to hear from you. If you have any questions, feedback or suggestions, leave us your name, email and a brief description.

Name
This field is for validation purposes and should be left unchanged.