Hear the incredible story of Carlos Rebollo, who was incarcerated at just 15 years old and served 24 years in adult prisons. If you have a loved one in prison, then Carlos’ story will give you hope. If you never knew anyone who was incarcerated (or thought you didn’t), this story will humanize the prison experience. Carlos will take you on his journey from being an angry young man to growing into the man he always knew he could be.
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Listen to the podcast here
Part I – Carlos Rebollo Incarcerated At 15 Years Old
Before we start, I would like to remind you that Prison: The Hidden Sentence is offering workshops to help families support their loved ones through incarceration and release as well as workshops on self-care and empowerment. Go to PrisonTheHiddenSentence.com or email Contact@PrisonTheHiddenSentence.com. This is where you will find the tools to help you get the information you need when a loved one is in the carceral system. Enjoy the episode.
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I’m here with Carlos Rebollo, who has been released from prison after serving 24 years. Carlos was incarcerated when he was fifteen years old. He survived the criminal justice system. He obtained an Associate’s degree in Psychology while he was incarcerated and is now working towards a Bachelor’s degree in Multi-Platform Journalism. Someday, he’s going to be interviewing me.
In the first part of this episode, Carlos will take us on his journey of being incarcerated at such a young age and will provide helpful information for families on how to survive the prison system. The second part of this episode will bring us up to date on his release and how he’s thriving in the world post-incarceration. Carlos, thank you so much for being here. I can’t even imagine what it would be like to be incarcerated at such a young age. Can you take us on that journey?
Thank you for having me so much, Julia. It’s an honor. It was very difficult. I remember the first time I entered prison. I had all these ideas about what it would be like. In my mind, I thought that I would be corrected and set on the right path. I would get examples of what being responsible is like because I came from a chaotic, abusive, and senseless environment. Coming into prison and being met with the same violence, senselessness, and chaos wiped away whatever sense of responsibility I thought I would encounter.
It was difficult for me at the beginning. There was no direction or guidance. There were few people I could trust. I remember that I was sent to the general population the next day after my admission into the prison. A few officers came to get me and told me that I couldn’t be in the general population because my bond was $500,000 and I had a serious violent crime. I was fifteen years old.
I was sent to solitary confinement, where I was given a lime green jumpsuit. I stayed there for a week. They transferred me over to a security risk group unit where there were older gang members. You can imagine what happened once I was admitted into that unit. I’m fifteen years old. I’m in a cell by myself. I’m surrounded by men who thrive off of violence.
I remember that I had no property at all. My family didn’t know how to contact or support me. I remember that out of boredom, I started to peel the paint off of the door. By the time I was done with it, it was completely gray. You can only see the metal of the door. I received the Destruction of Property ticket. Two weeks after that, I received two tickets because I had a fight with two other gang members that were there. They sent me to chronic discipline.
Within a month, I had already been through so much violence and solitary isolation that I was already getting the idea that my life was in shambles. Chronic discipline consisted of 23-hour lockdowns. Whenever we would be released from this cell, we would have to put our hands through a slot where we would be handcuffed and remain handcuffed outside of this cell. I would also be required to take a shower while handcuffed. I would have to put a shirt over after the handcuffs, go out to use the phone in handcuffs, and take a shower in handcuffs.
That lasted for three months because there are two phases. You have to be compliant for the first three months to get to phase two and then remain compliant to complete the program and be released back into the general population. I remember that I was compliant but going toward the third month, the very last week, I was given a ticket for being non-compliant. When I went before the captain and the staff and asked them what the non-compliance was for, they told me that I didn’t smile enough and that I didn’t have a positive attitude. To get that last compliant evaluation, I would have to smile a little bit more.
You can imagine what the thought process was like for me. I asked him, “Is this a joke?” He said, “You have to change your attitude.” Here I am, fifteen years old. I have little support. I’m in the cell 23 hours a day. I’m being handcuffed while outside the cell and I’m being told that I should smile more. It speaks to this disconnect that was going on between custody and mental health issues or care that was going on at the time. This was in 1998. I completed the program.
Instead of going to the general population, they sent me to a prison that houses inmates who have high bonds, and because I couldn’t be in a cell again with older men, they put me in the unit with them. I was surrounded by men who were facing murder. They were 30 years old and 40 years old. They knew about my case. They knew that it was violent and that I would potentially serve a long prison sentence.
The advice that I started to get from these men was that I should capitalize on pretending that my mental health was declining. They would tell me to cut myself, jump off the second floor, try to commit suicide, or get on some type of medication to give the impression to the court that I wasn’t mentally stable. I was surrounded by this on a constant basis. I refused to. I was beyond what I was capable of doing. I ended up going to trial. That didn’t seem like it was going to turn out in my favor. I agreed to a plea bargain deal where I would cop out to 45 years and seek parole at 85% of that sentence.
It’s so hard to imagine that at fifteen years old, you’re going through that no matter what the crime was at that time and that you were treated that way and not given guidelines, “You had to smile or change your attitude. We think you’re violent, so we’re going to keep you handcuffed.” However, they’re not telling you what you need to do so that you can be released. Twenty-three hours of solitary for anybody is crazy. It’s amazing that you got through that part and that you didn’t do things and become mentally unstable.
To be able to keep strong during that time at that age pays tribute to where you are. It’s the strength that you had back then even though you didn’t know it was going to help you now. You were fifteen years old. You were put with other people that were incarcerated. Was there anybody else that was a minor? Was there anybody else that you could talk to or anybody else there?
There were other juveniles there that were being charged as adults and also sentenced as adults. I remember one particular young man. He was fourteen years old. He was facing 40 years in prison. He ended up receiving 40 years in prison. They were other guys who were 16 and 17. These were victims of this idea that was being proposed and pushed in 1995 by two authors, John DiIulio and William Bennett. It’s the idea of the super-predator where society accidentally braces itself for these juveniles who packed guns instead of lunches and were flaunting all the rules and laws of society.
This created this moral panic when legislatures went into action and started passing these harsh laws that started handing out severe sentences to juveniles. I was surrounded by all these young men in prison. Sadly, there was no way we could support each other. There was no us-against-them and trying to figure out how to navigate the system. We were there trying to figure out where our place was. It ended up in a lot of chaos for us. Particularly, before my first year, I already had ten fights. It was a result of being placed in violent environments, but because I was a criminal at the time, everybody thought that I was violent naturally and that I should be punished more severely as well.
Not to put you on the spot, however, what do you think could have been done differently? Let’s stay with young people that are being incarcerated for violent crimes. What can we do differently? What could have been done differently for you?
I have been in units. For example, I know about this unit in Cheshire Correctional Institution that’s called the TRUE unit. It was implemented to emphasize humanity, not only in inmates but also in the relationships between correctional officers and inmates. That space allows them to interact like no other unit in other prisons allows for. They can play cards together. They can sit down and engage in dialogue. During certain groups, they can reach out for personal conversations.
There’s this rule that’s against correctional practices called undue familiarity. It states that officers cannot engage in personal behaviors with inmates because it might lead to other stuff, but this program and this unit have proven that no such danger exists at all and that it’s perfectly safe and even healthy to engage in these personal relationships with inmates. The problem with that is that when you isolate this one space and say that only in this specific area are we going to allow for this humanity, it sends a message to the rest of the department of corrections that they can act with disregard for that humanity.
The kind of units that I’ve been in have been filled with that disregard, but fortunately, I went to one where I ended up meeting two men who were cellmates for eleven years. They focused on reading, challenging each other, and improving themselves. They built curriculums, instituted programs, and wrote books. They took me under their wing and provided me with guidance and a philosophy of life that began to have a great impact on my life. It sustained me to this day.
I want to let everybody know that Carlos is feeling a little under the weather. I wanted to let you know that he was nice enough to continue because this was so important to him and me too to get his story out there. I want to thank you. We did talk a lot about your story. At what age were you when you met these gentlemen? I want to go back to the first eight years. How old were you at this time when you met them?
I was 23 years old. I started doing programming after eight years because I was incarcerated in 1998. Eight years later, I was 23 years old. I met them. I was doing programming. I started to have certain achievements. One of them came up to me and said, “You look like you have a lot of potentials.” I gave him some essays that I had written. He said that I could become great and thrive if I started to focus on honing those good qualities of mine. I befriended him. He became a great friend and mentor. We’re still in contact to this day.
That’s wonderful because when we talked prior to this, you were talking about how in the first eight years, you felt like you had no choices and that there was nothing in life for you. You were there. Things couldn’t be better for you, but then you got to a facility where you saw that people who were incarcerated there were smiling and laughing. That was a turning point for you. Something clicked in you. You opened up and then you got to meet these two men that changed your life and helped you see that there are choices.
That was very empowering for me because I had this mentality that nothing was up to me. I was a victim of all of my circumstances, and I had to adjust the best way I could. When I met these men who were serving 100-year sentences, and they look healthy, their eyes were glowing, they were smiling from ear to ear, and they were waking up every day with a purpose, I had to ask the question, “How is it possible? What is there to smile about?”
They told me that life doesn’t end. It continues to go. I could make of it what I wanted. It struck me in two ways. It struck me that I did have a choice and that you can still have a purpose while in prison. The burden was on me to choose where I wanted my life to go. In addition to meeting my mentors, it was incredible to witness prior to that. I never had anyone in my life that could set an example of consistency, integrity, and success. There were many instances where I had to look at myself in the mirror and say, “What are you going to do about your life?”
Life doesn't end. It continues to go. We can make of it what we want. We have a choice, and we can still have a purpose. Share on XIs that when you started going to school and getting your Associate’s in Psychology? What interested you in Psychology, of all things?
I want to backtrack a little bit because this brings in my childhood experiences. I grew up in a very chaotic environment. I remember being completely surrounded by a sense of inadequacy, as if I couldn’t understand anything about the world. I felt I wasn’t worth much at all. Something happened, though. When I went to school, I learned how to read.
You were learning how to read.
I got this sense, “I can understand something about the world, and it’s not me.” I began to read everything I could get my hands on. I remember going out into the street after school. I would read store signs, street signs, and everything that I could come across. I felt this sense, “My mind is capable of understanding.” The problem with that is then I would return to an environment where I didn’t know what was expected of me. It was so arbitrary and whimsical. I didn’t know when I would get attacked or when violence would break out. I felt this tension building within me.
The person that I loved so much couldn’t survive in that environment. I had a choice to make. Either I continued to fight for the person that I love or the studious and curious bright student versus the one who was being subjected to so much violence and thought that he would have to be violent to survive. I made a decision. I remember something to the effect of, “I can’t survive in this world. If this is what my parents want from me, then this is what I’m going to give them.” I went into this process of reversing my world, where I started to begin feeling affected by how much chaos I could create.
I remember my mother being shocked when she found out I was selling drugs at the age of twelve. For me, her shock was reinforcement that I was doing something better than she was because I was confused. I was the one that didn’t understand anything. You had the situation where you had psychologists, counselors, and all kinds of people reaching out to me and asking me, “What’s going on? Why are you behaving this way?” In my mind, the reinforcement is telling me, “You don’t understand what’s going on. Are you confused? Welcome to my world because I don’t understand anything at all.”
Going back into prison and answering your question, at the time when I was getting all of this evidence that it was up to me, I decided to see if that student or that curious, considerate, and bright young man was still there. I wanted to give him a chance. I began to set goals. I said, “What is one of the things that I’ve always heard responsible people do?” I remember that being independent is one of them. In 2005, when I was 23 years old as well, I said, “I need to be independent.”
I wrote a letter to my entire family and said, “I don’t want any more financial support. I want to see what I’m capable of and if I can do it on my own.” There were no money orders at all and financial help. I began to set goals for myself and said, “I want a degree in Psychology. What’s it going to take? I need to get a job.” I went to a commissary, which paid a good wage, but it was enough to make ends meet, and it wasn’t challenging enough.
I wanted to continue challenging myself while earning a good wage. I did that for eighteen months. I went to industries and worked in the carpentry shop under a master carpenter for seven years. Not only did I earn a good wage to pay for my Psychology degree, but I also learned how to build kitchen sets, countertops, tables, chairs, and all kinds of things that I never thought I would be capable of.
My geometry skills, spatial reasoning, time management, and work ethic improved. I was being guided and told, “This should not be isolated to your professional life. This is what you want to implement in every single area that you can in your life.” I started getting this impression that I could be successful in every single area of my life. It took me eight years to pay for my Psychology degree, but once I signed that last money order and got my degree, I was very proud of myself.
That’s wonderful. Having that Psychology degree is going to help in all aspects of your life and even your Bachelor’s degree as you’re doing multi-platform journalism. Having that in your pocket is going to be helpful. I can tell by the way you talk that it has been helpful because you get to the root of everything. People that might have questions can learn from you, especially their young ones. We talk about ACE or Adverse Childhood Experiences. You’re a prime example of that. Your environment is what led you to whatever it was that caused you to be incarcerated.
However, while you were incarcerated at such a young age, you were able to open up, learn, get this degree, and meet people. I want to go back to your parents because there are families that are reading this. There are two points I want to make. The first one is that even though you were in this situation with your family that was not ideal and chaotic, as you explained, was your family there to support you when you were incarcerated? Did they write? It seems like they did send you money.
In the beginning, they were concerned because it was very traumatic. I committed a heinous crime and got sentenced to 45 years at the age of fifteen. I had a son when I was fourteen years old. I was living with his mother. That was difficult for me, so I walked away. The last grade I completed was the fifth grade before I quit school out there. I was lost. My family never was supportive. We never were a cohesive and healthy unit, but it impacted all of us hard. They wanted to be there and they tried to be there, but it was toxic. It was difficult being in prison and me having so much time to think. This time, I’m bearing myself to ask questions I never asked and not receiving answers.
Along with my decision to stop receiving financial support, unfortunately, what happened was that I lost contact with my entire family, but at the same time, it allowed me to work toward establishing healthy relationships and being up against the wall where I was able to reach deep inside and try to find what I could hold onto to continue being better. I always say that I tell my son this, “You will never know what you’re capable of unless you can only depend on yourself sometimes because then you find out what your parents inculcated in you.”
Sometimes the analogy or the phrase is, “Let them fly to see what happens.” That’s what I did. I wanted to see if I could fly. Being apart from all of that put me in a position where I could improve myself and build the kind of character that was healthy. I started reaching out to my family after that and offering them positivity in return. I would write letters and ask one thing, “Can you be honest with me?” I wouldn’t force anything on them. I would show dignity, consideration, and patience and try to bring them toward the side of life that I was now living.
What is your relationship with them now?
It’s difficult because it seems like they’re still in 1998 when I was first incarcerated. It’s the same mentality and dysfunction. I’m coming into the picture. It’s shocking to me. Nothing has changed at all. All I can do is try to show them that there is a different way of living, caring, and loving. That’s what allows me to stay close.
We will talk more about that in part two when we continue. When we were talking for the first time, I was thinking, “He went in at fifteen. He probably doesn’t have any children.” You said, “I do have a son.” My understanding is that you’ve maintained a relationship with him and that you’ve been able to, even at such a young age, be a father to him while you were incarcerated.
That was an amazing experience because his mother made it a point for us to have a relationship while I was in prison. No matter what other relationship she was involved in, she would make sure that my son and I had visits and phone calls together. We were able to have a nice relationship throughout my incarceration. It went from her seeing this very violent young man to having my son say, “I need to see my father because I’m having difficulties in this area. I need some advice.”
It will turn into her also coming up and asking me for advice as well. I saw that the way I was living was starting to contribute positively to the lives of others. It was no longer, “Let me see him because he’s the father of my child. Let me bring my son up because he needs to have a relationship with his father no matter how dysfunctional he is.” It turned into, “He gives us this breath of fresh air, this motivation, and this energy to continue being excited about life and being able to face whatever challenges we may be going through out there.” That reinforced for me to continue doing what I was doing.
I saw that the way I was living was starting to contribute positively to the lives of others. Share on XI find it so interesting because I interviewed somebody else who has a life sentence. He was talking about how he raised his daughter even though he was incarcerated. That was the first time that I learned about that. It’s possible I’m hearing it more and more. When I interviewed his daughter, she was like, “It doesn’t matter where my daddy is. I love my daddy. He’s my dad.” As long as there are no circumstances where a family shouldn’t be together, it’s so important for children to stay in touch with their parents. You’re another prime example of that. He must be so proud of you. You’re living by example. You’ve turned it around.
The other thing you didn’t mention that I found fascinating was when you said you wanted to be independent, “Don’t send me money. I’m going to work. I’m working in the commissary. I’m learning these trades.” You’re an entrepreneur. I’m looking at you now. Your hair is so nicely braided. You said that you learned how to braid. Do you want to talk about that for a minute? That’s a cool story.
When I wanted to become independent, I asked myself, “What are the things that I can do?” I remember that I was in the cell with this guy who taught me the basics of braiding. I never picked it up again. I left it. I learned something and said, “Let me see if I can do this.” I started offering my services, and I was horrible at it. I would punish these guys and pull their hair. They would flinch and squirm in their seats.
I would only charge them $2. I only would ask them one thing, “If you’re going to get your hair braided by me, let me do whatever design I wanted.” I was horrible. I didn’t know where to start. I didn’t know where to end. The braids weren’t compact and neat at all, but I continued to practice. I went from charging $2 to offering contracts where they would give me $20 upfront.
I would braid their hair six times whenever they wanted at their leisure. Sometimes I would go to a block and have ten clients. That alone was $200. It paid for my clothing, phone calls, cosmetics, and anything that I needed. It came to a point where I could even afford not to take all clients. It turned out to be very entrepreneurial on my behalf for choosing to be independent.
Excuse my ignorance, but how do they pay you? Do they put it on your account?
What I would do is I would have one guy who would buy my clothing whenever I needed it. I had another guy who would buy my cosmetics. I would never ask for food because I would be okay with my three meals a day. I didn’t waste money on that. For the rest, I made sure that all of the money went to the phone. They would have their family put it on the account so that I could always speak to my son and his mother.
You’ve been through a lot. I feel your warmth in sitting here and talking to you even though we’re not physically next to each other. I’m so proud of you and so happy for you that you’re smiling now. In the first eight years, even when you were handcuffed at fifteen, they said, “You’re not smiling enough.” Now, you’re smiling enough for everybody. It’s wonderful you’ve come so far. I would like to stop at this point and let everybody know that there will be a second part to this. We’re going to talk about getting ready to come home or wherever it is that you’re going.
I will let people know where you’re talking from and what your future plans are. Carlos, thank you so much. You’ve shared so much. Anybody reading that doesn’t have somebody incarcerated has learned a lot and humanized the experience. Anybody that does have somebody that’s incarcerated has come up with ideas of how they can support, promote, and mentor their loved one that’s incarcerated. You did it on your own. Luckily, you met those gentlemen we will talk more about in the next part of the episode. There’s always hope. You are proof of it. Thank you.
Thank you so much.
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For more information on what to do when your loved one is arrested, what you need to know about the court process, and information about incarceration, visitation, and most importantly, self-care, you can find all of this and more in the Prison: The Hidden Sentence book that can be purchased on Amazon. This book contains crucial information for anyone that has a loved one in the carceral system.
Important Links
- Contact@PrisonTheHiddenSentence.com
- Carlos Rebollo – LinkedIn
- Cheshire Correctional Institution
- Prison: The Hidden Sentence
- https://www.Audacy.com/wtic/blogs/todd-feinburg/todd-feinburg-introducing-carlos-rebollo
- https://www.MinutesBeforeSix.com/wp/your-painting/
- https://www.BridgeportCT.gov/MIRA
- https://www.WorthRises.org/team
- https://www.HangTimeRealTalk.com/
- https://www.YalePrisonEducationInitiative.org/
- https://www.CFSY.org/
- https://www.CFSY.org/what-we-do/ican-stories/
- https://www.PrisonFamiliesAlliance.org/
About Carlos Rebollo
My name is Carlos Rebollo. I was sentenced to 45 years in prison at the age of 15. I was recently released on October 31, 2022 after serving 24 years in prison. During my incarceration, I was able to achieve an Associate’s degree in psychology, and become a student of Yale Prison Education Initiative, The Second Chance Educational Alliance, and the University of New Haven. Today I am enrolled as a full-time student at the University of New Haven pursuing a bachelor’s degree in multiple platform journalism. I am also a member of the Campaign for the Fair Sentencing of Youth and of the incarcerated children’s advocacy Network. Our mission is to stop the injustice of sentencing children to excessive and life sentences.
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