Gambling Recovery: Taking Back Your Life

Gambling. Drugs. Alcohol. For Rob, addiction started young and grew into years of lying, chasing losses, broken trust, and escaping the pain he carried inside. In this episode of Gambling Recovery: Taking Back Your Life, Rob shares how childhood insecurity and trauma shaped his journey, and how his addictions fed off one another. From arrests and overwhelming debt to nearly losing his marriage, he opens up about the moment he finally surrendered and accepted help. We talk about stopping versus staying stopped, working the 12 steps, making amends, and rebuilding trust through action. We also discuss addiction’s impact on families and warning signs loved ones can look for. This episode hits deeper for me. Rob and I share lived experience and a passion for helping others. We both went through our own personal hell, and today we use those experiences to give someone else hope. Rob also shares how that mission led him to build Right Choice Recovery. After visiting the facility, I felt the family he’s created there. Our partnership means a lot because we believe in each other and our work.

Bob had a successful career, a wife, and a family—but behind it all was a gambling addiction that nearly cost him everything. Years of chasing wins, hiding losses, and keeping secrets eventually brought him to his knees in a hotel room in Cleveland. His wife, Karen, lived through that same addiction from a different side: the confusion, the half-truths, the broken trust, and the fear of what it meant for her family. Today, Bob and Karen join me together to share both sides of their story—and the work it took to begin healing. From facing the truth to setting boundaries and rebuilding trust, their journey shows how deeply gambling addiction affects an entire family, and why each person’s recovery matters. This is a conversation about love, accountability, and finding hope after years of pain. Welcome to Gambling Recovery: Taking Back Your Life.  

I grew up in the Little Italy neighborhood of Chicago, where sports, competition, and betting were part of everyday life. As a kid, there were parlay cards, survival pools, and pitching quarters. By high school, I had a bookie. What seemed like fun became years of debt, broken trust, and an addiction I could not control. Gambling changed my character. It turned me into someone my parents didn’t raise me to be. I had a big ego. I became a master manipulator and a liar, and I hurt the people who cared about me most. In this first video episode of Gambling Recovery: Taking Back Your Life, I share my story—from asking my mother to cover a gambling loss, to going in and out of Gamblers Anonymous, to serving time in jail and gambling again after I got out. My last bet was February 9, 2012. Recovery began when I finally accepted that stopping for a while wasn’t enough. I had to change how I lived. I’m sharing this for the person who feels trapped by gambling and for the family trying to understand it. You are not alone, and change is possible. If you need guidance on where to start, email me at [email protected]. Follow Gambling Recovery:
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I’ve been quiet for the past two weeks because I’ve been working on something I’m excited to share with you. I’m building an in-person podcast studio in Chicago, and the first video episode of Gambling Recovery: Taking Back Your Life launches Tuesday, September 29, at 6:00 a.m. Central. You’ll find it on YouTube at Gambling Recovery with Jimmy Morris. I’m also taking the podcast on the road to 13 cities over the next three months. If you believe your story could help someone, email me at mailto:[email protected]. To everyone who has listened, shared an episode, or supported this mission: thank you. We do this together. ❤️

Craig Dempsey joins the podcast from the United Kingdom to share his lived experience with gambling addiction, recovery, and rebuilding his life.

Craig is the founder and host of The Calm & Steady Show, where he uses his experience to raise awareness around gambling harm and mental health.

In this conversation, Craig opens up about addiction, family, fatherhood, and the people affected beyond the gambler.

An emotional and vulnerable conversation about gambling, recovery, and what matters most when rebuilding your life.