top of page
Loyalty Can Save You. It Can Also Keep You Trapped
Izell Leonard spent roughly 22 years incarcerated. His story is not only about prison or redemption. It is about the identities we build to survive — and what it takes to question them once they begin costing us more than they protect.
If you have just watched Izell Leonard’s story, I do not want to end it by telling you what to think. I want to leave you with the tension that stayed with me after we stopped recording: What if the hardest prison to leave is the identity that once made you feel safe, respected and needed? Izell spent roughly 22 years incarcerated. But prison alone does not explain who he was, why the life that led him there once made sense, or what it took to leave it. To understand that, you have to go back before the sentence. Back to Watts. Back to loyalty. Back to the rules that can make sense long before we understand what they may eventually cost us.
“I really need him to see me as the man that I am today.”
The Life That Made Sense
Izell described loyalty as something larger than a word. It meant family. Protection. Belonging. Standing by your people. Those values were not invented by crime. They were human values. But over time, loyalty became entangled with gangs, drugs, robberies, money and the streets. What stayed with me was that Izell did not sanitize that part of his life. He did not pretend there had been nothing attractive about it. There was excitement. Recognition. Money. The ability to provide. A feeling of importance. A sense that he mattered. That honesty changes the story. Because if we describe a destructive life only by what it destroys, we miss part of the reason people remain inside it. Sometimes the same pattern causing harm is also giving someone identity. Sometimes it offers status. Sometimes protection. Sometimes community. Sometimes purpose. And when a life is meeting those needs, telling someone simply to “make better choices” can miss the harder question: What are you asking them to give up along with the behavior?
Responsibility Without a Clean Redemption Story
In 1997, Izell received a 19-year sentence for armed robbery. He does not avoid responsibility for it. “I agreed that I should be in jail because I committed the crime.” But prison did not immediately transform him. That matters. He continued selling drugs inside. There is a temptation in stories about incarceration to search for one clean moment when the old person disappears and the new one takes over. Izell’s story does not give us that. Change came more slowly. And, in one important moment, through a question. A man asked him how old he had been when he first began committing crimes. Nine. Then came the observation that stayed with Izell: they were grown men still trying to remain loyal to decisions they had made as children. The word itself was familiar. Loyalty. What changed was what Izell could suddenly see inside it. The child makes the rule. The adult keeps obeying it.
When a Strength Becomes a Trap
That moment is important because Izell did not suddenly become less loyal. He changed what deserved his loyalty. That distinction stayed with me. We often talk about transformation as if becoming better requires destroying the person we used to be. But some of the qualities that once pulled someone into danger may also be the qualities that later help carry them out. Loyalty can become devotion. Courage can become responsibility. Resourcefulness can become leadership. The question is not always whether a trait is good or bad. Sometimes the more useful question is: Where is it being directed? Izell’s story made me think about how easily survival strategies can harden into identity. A way of behaving helps us through one chapter. Then the chapter changes. The behavior does not. And eventually something that once protected us begins limiting us. That is one of the most difficult forms of change because it requires more than giving something up. It requires questioning a version of yourself that once worked.
A Father and Son Meet Again
The meaning of that change became more visible when Izell spoke about his son. He had not seen him since his son was around five or six years old. Years passed. His son grew up. He became a father himself. And he became incarcerated. When Izell learned that the two of them might be at the same fire camp, he approached a sergeant. What he said was not simply that he wanted to see his son. It was: “I really need him to see me as the man that I am today.” That sentence stayed with me. Because there is a difference between wanting someone back in your life and wanting them to understand who you have become. The sergeant agreed on one condition. His son would work as a baker. Izell would teach him. And the place that had taken years of ordinary fatherhood from them became the unlikely place where father and son began getting to know each other again. They baked. They talked. They reintroduced themselves. There is something painful in that word. Reintroduced. A father and son who should have known each other having to meet again. Not because the relationship never existed. Because so much life had happened in between.
“Nothing I had gained was worth losing those years with my children.”
What Was It Worth?
At one point, Izell’s son wondered whether the money from his father’s former life had been worth it. Izell told him no. Nothing he had gained was worth losing those years with his children. That answer is easy to understand after the consequences are visible. It is much harder to understand when you are still inside the life that is giving you money, identity, recognition and belonging. That is one reason hindsight can be both clarifying and cruel. It lets us see the cost clearly. It cannot refund it. Eventually, both Izell and his son came home. And that could have been the ending. A father changes. A son returns. A business begins. Redemption. Roll credits. But real life kept going.
Freedom Is a Different Test
Prison can impose behavior. Freedom cannot. Outside, the old life was available again. That creates a different question: Who are you when no institution is forcing you to become different? Izell chose another direction. And one of the things he brought home from prison was unexpected: Baking. What had begun inside became part of a new life through Taste Bud Approved. There is something almost too neat about that transformation on paper. Prison. Baking. Business. Second chance. But reducing the story to that arc would flatten it. Because a new life does not erase the old one. And becoming different does not guarantee that life will reward you for it.
There Is No Contract With Change
In 2025, Izell lost his son. Before his son became a loss, he was someone Izell loved. That distinction matters because grief can easily turn a person into the worst thing that happened to them. His son was not only a tragedy in Izell’s story. He was a person. A child. A father. Someone Izell had lost time with, found again and loved. Transformation stories often carry an unspoken promise: Change your life. Become better. And life will give something back. But there is no such contract. Changing cannot return 22 years. Accountability cannot erase every consequence. Faith does not cancel grief. And becoming a different person does not protect us from what happens next. That is where Izell’s story stopped feeling like a story about whether people can change. The question became harder. Who do we choose to remain when change cannot protect us from loss?
“The strongest prisons are not always the things we hate. Sometimes they are the things that once made us feel safe.”
Loyalty or Captivity?
By the end of our conversation, I kept returning to loyalty. Not because loyalty ruined Izell’s life. That would be too simple. Loyalty gave him something. It helped organize his world. It told him who his people were. It gave him belonging. It gave him rules. And that is exactly why questioning it was difficult. The strongest prisons are not always the things we hate. Sometimes they are the things that once made us feel safe. That is what makes identity so powerful. We inherit rules from younger versions of ourselves. We keep following them because they once worked. Because they protected us. Because they helped us belong. And because abandoning them can feel like betraying the person we had to become in order to survive. But loyalty and captivity are not the same thing. Sometimes one can slowly become the other.
What Change Actually Asks of Us
There is a version of transformation that says: Leave the old person behind. I am not sure Izell’s story supports that. The man sitting in front of me did not appear to have erased every part of the person he used to be. Some qualities remained. Commitment. Loyalty. Drive. The desire to provide. The need to matter. What changed was what those qualities served. Maybe transformation is not always the construction of a completely new self. Maybe it is the harder work of deciding what deserves to survive from the old one. What should be redirected. What needs to be questioned. And what can no longer come with us.
What Remains
The Decision Room is not interested in the moment when a person becomes easy to understand. Human lives rarely offer that moment. We are interested in the point where an old explanation stops being enough. When survival becomes identity. When identity becomes a prison. When loyalty has to be examined instead of automatically obeyed. When the person we once needed to become is no longer the person we want to remain. Izell’s story begins with incarceration, but it does not end there. It asks something much larger. What do we owe the younger versions of ourselves who taught us how to survive? Do we remain loyal to their rules forever? Or can we honor what they protected us from without allowing them to decide the rest of our lives? Maybe transformation is not becoming someone else. Maybe it is learning to separate what once saved us from what is now keeping us trapped. And maybe one of the hardest forms of freedom begins with a question: What are you still loyal to that once helped you survive, but may now be keeping you from the life you could become?
bottom of page