How Has Your Life Changed Behind Bars? - Daily Love with Mastin Kipp

How Has Your Life Changed Behind Bars?

TheLastMileBy Tommy Winfrey

San Quentin State Prison


I remember that moment when the gavel dropped all too vividly. I had just turned 20 years old and there really was no doubt in my mind that I was going to be found guilty. I remember being numb to what was happening. A few weeks later, when I went back to the sentencing phase of my trial, the judge gave me a 25 years to life sentence.

Many people would think that a 20-year-old with his whole life ahead of him would be crushed by the sentence. But I wasn’t. The bailiff took me back to the holding cage and asked me if I would be okay. I said I was fine, but he didn’t want to believe me. He told me he was going to put me in a cage by myself so I could have some time alone. I told him that if he wanted to help me, he could get me an extra sandwich. I don’t think he understood that I didn’t care. I didn’t value my life, and a life sentence didn’t mean anything to me. Up to that point in my life, I didn’t understand what life really meant. Mine had been miserable and I didn’t see much point to it. Looking back now, I see that I overlooked a lot of good things in life. I let my emotions affect me in some pretty bad ways. I did this because I didn’t understand them. I couldn’t see that isolating myself was just making me feel lonelier and lonelier. I couldn’t see that the feelings of unworthiness were driving me to do things that made me see myself as unworthy. I was hurting everyone around me because I was hurt. The worst part of the whole situation is that I believed nothing mattered.

I kept that attitude for a long time after coming to prison. I perpetrated a huge lie on myself and others. The truth is that everything mattered to me. The reason I said I felt numb is because I was hiding from myself. I didn’t want to deal with the pain that I felt I was causing others. Today things are much different.

I have really started to understand my emotions and feelings. This had led me to some amazing breakthroughs in life. I appreciate life and value what I have been given now. I really understand my actions and how they affect others. I feel sad for that 20-year-old boy who stood before that judge and didn’t care that he was going to prison for 25 years to life. But I feel even worse for the people I hurt to get that sentence. So much has changed for me during my time behind bars. I am happy with where I am at in life, even if it is behind razor wire.

I see that life should not be all about what you don’t have or what you have lost. Life should be about finding peace with what you do have. (Tweet-worthy!) Whether it is millions of dollars or a 6’ by 9’ cell there is beauty to still be found in life. Prison taught me to appreciate these things. A hard lesson for sure, but one I desperately needed.


All communications between inmates and external channels are facilitated by approved volunteers since inmates do not have access to the internet. This program is part of The Last Mile San Quentin. Twitter: @TLM