April 22, 2026

The Best Part of Prison: Jesse Crosson's Story of Healing and Hope

The Best Part of Prison: Jesse Crosson's Story of Healing and Hope

Send us Fan Mail Send us Fan Mail In this powerful episode of Living the Dream with Curveball, we welcome Jesse Crosson, the founder of the Second Chancellor Foundation and author of the memoir *The Best Part of Prison*. Jesse shares his extraordinary journey of transformation, detailing his struggles with addiction and the life-altering consequences that led to a 32-year prison sentence. Through resilience and hard work, Jesse turned his life around, earning a pardon after 19 years and...

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Send us Fan Mail

Send us Fan Mail
In this powerful episode of Living the Dream with Curveball, we welcome Jesse Crosson, the founder of the Second Chancellor Foundation and author of the memoir *The Best Part of Prison*. Jesse shares his extraordinary journey of transformation, detailing his struggles with addiction and the life-altering consequences that led to a 32-year prison sentence. Through resilience and hard work, Jesse turned his life around, earning a pardon after 19 years and dedicating his life to helping others navigate their own paths to redemption.
Jesse opens up about the pivotal moments that shaped his journey, including the importance of self-reflection and the role of support systems in fostering change. He discusses the motivation behind his memoir, which aims to inspire those currently incarcerated and remind them that they matter and have a future. We also dive into the work of the Second Chancellor Foundation, which focuses on empowering at-risk youth and providing them with the resources and opportunities they need to succeed.
Throughout this episode, Jesse emphasizes the notion that no one is defined by their past mistakes and that redemption is possible for everyone. His story is a testament to the power of transformation and the impact of believing in oneself. Tune in for an inspiring conversation filled with hope, resilience, and a call to action for those who feel trapped by their circumstances.
What You’ll Learn in This Episode:
- The significance of self-reflection in the journey of change
- How storytelling can empower individuals in prison
- The importance of support systems for successful reintegration
- Why everyone deserves a second chance, regardless of their past
- How Jesse's experiences can inspire hope in others facing adversity
For more information on Jesse Crosson and his work, visit jessicrosson.com or second-chancer.org.
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>> Curtis Jackson (also known as DJ Curveball):

Welcome to the Living the Dream podcast with Curveball. If you believe you can, achieve. Welcome to the Living the Dream with Curveball podcast, a show where I interview guests that teach, motivate, and inspire. Today's guest is someone who understands transformation from inside out. Jesse Crosson is the founder of the Second Chancellor Foundation. He is the author of the memoir the Best Part of Prison and a criminal justice advocate who understands transformation from the inside out. Jesse found drugs at a young age, and it spiraled out of control. But now he has transformed from the inside out, and we're going to be talking to him about his life and his story and everything that he's up to and gonna be up to. So, Jesse, thank you for joining me.

>> Jesse Crosson:

Thank you for having me.

>> Curtis Jackson (also known as DJ Curveball):

Why don't you start off by telling everybody a little bit about yourself?

>> Jesse Crosson:

Sure. So I was, you know, like a lot of kids, kind, of struggling on the inside growing up. Felt like other kids knew something or had something I didn't, and ended up chasing everything that made me feel like it was an answer, chasing a sense of belonging, chasing, you know, kind of a family or a group outside of me that would accept me or would support me. And one of the places I ended up chasing that was straight into drugs. Because I remember the first time I did drugs, the first time especially I did cocaine, but even before that, with alcohol and marijuana, I suddenly felt like I was enough. It felt like all the lack or all the doubt or all the insecurity just kind of faded away. And I felt like that was what I wanted to feel like for the rest of my life. And then solving that one problem of being insecure and being anxious created a million other problems. And as I continued to chase them, I got deeper into drugs, I got deeper into trouble. I started carrying a gun. I, ended up committing a robbery and a shooting just after my 18th birthday. So I was arrested, I pleaded guilty, and I was sentenced to serve 32 years in prison. So at 18, I thought my life was over. And I really felt like this was kind of a validation of that deep insecurity I'd always had, that I wasn't good enough or something was wrong with me or I didn't belong. And yet, with support, with guidance and with a lot of hard work, I managed to turn my life around while I was inside, to be accountable, to focus on amends, to focus on healing, to focus on making a change going forward with my life.

>> Curtis Jackson (also known as DJ Curveball):

Well, after receiving that 32 year sentence, did, you have to serve the whole thing and what were some of the turning points that changed you during that time?

>> Jesse Crosson:

people have this idea of an 80s movie montage where you change something and then you do this routine and everything's better. And it was never that much of a straight line for me. There were moments where I would turn around. There was a moment in the jail where I remember I went in, I was emaciated, I was hungry, and I stole a milk from someone. And because I was stealing from someone who didn't have anything, it wasn't something I could justify. It wasn't something I could understand. It really forced me to reflect on that in a different way than I probably had in the world where I would just keep running and doing other things. And that was one of those moments where I realized I was living in a way that I couldn't justify or I couldn't be okay with. I didn't like myself. there were also times where I gave up. You know, when they told me I was going to spend 32 years in prison at 18, I gave up. I thought my life was over. But then from that place of collapse, from that place of surrender, I was able to start building back and making different decisions and living a different life. And, I did a lot of things. You know, I got a college degree. I was really fortunate to have family support, be able to do that. Became a journeyman electrician. I helped start a peer support mental health program. I mentored people, I tutored people, I wrote articles for publication. Did all these things. So much so that after 19 years, the gun of Virginia said that the Commonwealth of Virginia was better off with me out of prison than in it, and granted me a pardon and released me. And in the same way as that judge giving me such an extreme sentence, which was twice the high end of the sentencing guidelines at the time. It's. That judge made me feel like I wasn't worthy. Like a validation of that fear. The governor granted me a pardon. Releasing me gave me some inkling or belief that maybe I am worthy or maybe I am enough, or maybe, maybe I can live a good life. And it was a really. It was a counterbalance to what I experienced with the judge. And it really was the beginning of my second chance and the chapter that I'm on now.

>> Curtis Jackson (also known as DJ Curveball):

Well, speaking of that, let's talk about your memoir, the Best Part of Prison. That is a, provocative title. So talk to the listeners about the book and talk about what that title means and what you want readers to take away from your book.

>> Jesse Crosson:

So I started you know, writing essays, recording things, doing things while I was in prison, because I thought one day maybe I would have a blog or I would. We didn't have blogs when I went to prison. That wasn't a thing. But I thought one day I would share my writing. and I really wanted to get an understanding. So writing the book was about trying to better understand how I had become the person I was at 18, who committed that robbery and committed that shooting. It was just this, like, ball of pain and anger going through the world, causing so much destruction. Then I also wanted to understand how did I turn my life around and heal and grow better in a place that often leaves people more broken? Like, what was the difference? about the approach or about the experience? And the. The third reason that I started writing the book was I remember the first time they allowed a formerly incarcerated person to come back in to speak to us at one of the prisons, because before that, it didn't matter who it was. They couldn't come back in. They couldn't talk. But they let this guy come in who had spent 22 years trying to get out of prison, and he decided that the most important thing he could do with his day was to go back into prison to tell us that we were not forgotten, that we mattered, and that we had a future if we took certain steps now. And I was in a gymnasium full of guys crying because I don't know that anybody had ever told us that. Definitely not somebody who had chosen to come back into this traumatizing environment. And I remember how good that felt. And so when I was writing a book, I wanted to be able to do that for someone else or hopefully as many other people as possible. Like, I want people in jails and prison to be able to read this book and know they do still matter. They're not forgotten, and they do have a future. That was why when I got this, this contract, 500 physical copies and unlimited digital copies are going into jails and prisons free of charge. Because I want people to be able to pick this book up and read it and remember and know that they matter.

>> Curtis Jackson (also known as DJ Curveball):

Well, when you were released, you started the second chance of foundation. So talk about what gap you were looking to feel. And how does your foundation help people coming home from prison?

>> Jesse Crosson:

Yeah, I. I recognize that I experienced a lot of privilege with friends, with family, with just good luck. And so I had a lot of support and I had a lot of opportunities, both while I was in prison and when I got out that other people around me didn't have, you know, getting a college degree over 15 years was one example. Like, it wasn't. It wasn't easy. It took a lot of time. It, you know, took a lot of, you know, writing by hand and sending in through. Through the mail. But it was an opportunity that not many people had. So I looked at that and I said, yeah, I did do a lot of hard work, but I had that support and I had those opportunities. So what if we were to give that support and those opportunities to other people? We'd probably have a lot more success stories. Like, I wouldn't be the success story. I would just be the norm. So I wanted to figure out a way to do that. And we've gone through a bunch of different iterations. I won't. I won't bore you with the details, but we've tried to figure out how we can do storytelling inside prison to help people begin to see themselves in different ways. Because what I found inside is that changing my life is not difficult or it's not complicated. It's not necessarily easy at the time. But that's the far simpler part. The harder part is beginning to believe that I'm capable of it or that I'm deserving of it or worthy of it. Because I see people all the time who don't take the steps because they don't see a point in it, or they don't feel like they would belong if they did, or they don't feel like they're worthy of it. And so sometimes the storytelling is going inside and helping people see themselves in a way where they begin to believe that they can change, that they're worthy of change. We also do some direct services. We're working on a video game to give people the opportunity to practice life skills before they're released. We just do a lot. But, the whole idea is I want to try to create the same conditions that I had so that other people who do the work can find success.

>> Curtis Jackson (also known as DJ Curveball):

Well, take us back to the moment where Governor Northam granted you a conditional pardon after 19 years. what. What was that moment like?

>> Jesse Crosson:

You know, pardons are not often given in. In any state, but especially in Virginia. so when I filed, like I said, the. The sentencing guidelines had called for from eight to 13 years, and they were modified to 10 and a half to 16 and a half years. So the maximum the state of Virginia said I should have gotten was 16 and a half years. And I didn't feel any way justified in applying for a pardon before I had done those 16 and a half years. Because it felt like. Well, no, like I. I should have to do that. I just have to do the Max. I messed up, I caused a lot of harm. But at 16 and a half years, I wrote this pardon petition. I got some letters, I put it all together and I submitted it. And I didn't think it was going to be granted. I just thought that I would be able to rest at night knowing that I had done everything in my power and that I wouldn't be second guessing for the rest of my time inside. So I submitted it, basically forgot about it. And then two and a half years later, they called me into the counselor's office one day. And I woke up that morning not thinking anything was different. I made my coffee, I got on the phone, I went to work, and they called me in the counselor's office and someone on the speakerphone said, Mr. Cross and are you sitting down? And I looked around, I thought that was kind of strange. And they said, because you've been granted a pardon, you're leaving Coffee Wood today. So literally, in a moment, my life changed. The trajectory of my life changed from having 10 years left in prison to walking out an hour and a half later and seeing my mother for the first time in a year and a half. Because Covid meant there were no visits, there was nobody coming into the prisons. And it was such a monumental shift and I just wasn't ready for it.

>> Curtis Jackson (also known as DJ Curveball):

Well, through your foundation, you work with at risk youth. So talk about why working with young people is so important to you.

>> Jesse Crosson:

It's, you know, I had a, the art teacher for a local juvenile detention center reach out to me. And we got coffee and about five minutes in she just started sobbing and she said, jesse, I need help. Because these kids are so smart and they're so capable and they're so creative. And then they get out and they go back to the same home or the same community and they get arrested or they shoot someone or they get shot themselves. And I need your help. And it really called me because I remember what it is to be that kid who's lost and angry and trying to compensate and looking for belonging. And so I could relate. So we started going in and we started doing kind of a fact finding mission of basically saying, hey, we want to know about your life. We want to know what it is you want, what is it you need, what is it you're missing or you're excited about and how can we provide those resources? And that was really where I realized, like I said, the storytelling piece. Because every time I would bring in academic opportunities or work opportunities or vocational, the kids would tell me, either with their words or with their actions, that they didn't belong. They'd say, yeah, that that school is great, but not for someone like me. Or, oh, yeah, that job would be great, but people like me can't do that. So I started bringing speakers in who look like them or come from the background they come from, or come from the neighborhood they come from, or have some other similar experience. Because I want the kids to begin to believe, like, have that light switch of opportunity, flip and start to believe maybe I do belong. Maybe that is a possibility for me. Because I know as a kid, I felt trapped. Like. Like even before I went to prison, I felt stuck. And it wasn't that I was physically stuck. It's. I didn't feel like I belonged anywhere. I didn't feel like I was good enough to do those things. I didn't feel like I was capable of doing those things. So if I can switch or, flip that switch in a kid's life, all of a sudden, the world really does become open because they've been shutting them off from. They've been shutting themselves off with this. This failure of imagination to imagine that they could belong in a different place. And if we can flip that switch, all of a sudden, the world opens up for them. They tend to take a different path.

>> Curtis Jackson (also known as DJ Curveball):

Well, I know you've built a following of over a million people on social media by sharing your story, honestly. So talk about why you feel like your. Your story resonates with so many people.

>> Jesse Crosson:

You know, I think I started telling stories. I got out right in the middle of COVID and everybody was on their phone, everybody was on social media looking for something interesting. And I think prison, you know, exists behind these walls. And these walls are both to keep people inside the prison, but. But also to keep people on the outside from being able to get in or be able to see in. Because I think if people saw what was happening in prisons on a daily basis, they'd be horrified. But so I think people have that interest of what's behind the wall or what's really going on or what's, this world that I don't know about, but also, what is this world that is somehow relatable enough that it's interesting to me? So I think I showed up at a time that everybody was on their phone and they wanted to hear a story, and people wanted something they could be interested in, but again, relate to. Yeah, I remember Feeling stuck or I felt out of place, or I've questioned whether I was deserving. And all of a sudden, people begin to see themselves in. When I wrote the book, that was what was so bizarre. Because, again, I wrote this book thinking about people in prison, people that were directly affected. And all of a sudden, I started getting letters and emails and DMS from people who had never been to prison, who had never been arrested. But tell me, hey, I see myself in this book, and I know exactly what you're talking about, and I feel like you're talking to me. And that was when I realized that being trapped is not just about having handcuffs around your wrist. Being trapped is a place that a lot of us live without even realizing the prison we're in.

>> Curtis Jackson (also known as DJ Curveball):

Well, what do you want someone who has never thought about criminal justice reform to take away from your story?

>> Jesse Crosson:

I want people to know, both people in prison and out, to know that no one is just the worst thing they've ever done. No one is just one thing. We are. We're all far more complex than that. And for the individual, I want them to know that we can change. We can find freedom, we can move in that direction. And it starts today. Like, today is the first day of the rest of our lives. And what we do today and what habits we feed into today, what energy we spend today, will go to pay dividends in the future. So it really, it. It behooves us to pay attention to where we're putting our energy now because it will shape who we are in the future. And that can be for better or for worse. But it really is one of those things that, you know, I went through most of my youth feeling like kind of, a victim of the universe. Like, I felt like I was responding to everyone and everything instead of actually making a decision and choosing what direction I wanted to go in. And so I know what that is to feel stuck. And I want people to know they can choose that direction. They can move in the direction they want to live in. They can move in the direction to being the person they want to be. And it starts today.

>> Curtis Jackson (also known as DJ Curveball):

For listeners who have someone who is incarcerated or someone in their lives who feel like they are beyond redemption, what would you say to them?

>> Jesse Crosson:

I know what it is to feel like I was beyond redemption. And here I am, having earned a conditional pardon, having helped a lot of people in prison, having helped a lot of people since coming home, having been accepted, having seen the value that I have to offer the world, and having the opportunity to be a friend to, to be a mentor, to be support for people in the world. And when somebody feels like they're beyond redemption, it's one of those places where we feel stuck. And I love the idea that, you know, when we're feeling sorry for ourselves, the best thing we can do is go help seven people, go buy them a cup of coffee, go pat him on the back, go lend him an ear, go do something. And every time I felt unworthy or every time I felt kind of self pity or I felt lost when I did something for someone else, all of a sudden I felt a lightness and I begin to see the value that to offer the world. So I think people who feel like they're beyond redemption can start with one small thing today for one other person.

>> Curtis Jackson (also known as DJ Curveball):

Well, after walking out of prison after 19 years, what surprised you most about the outside world?

>> Jesse Crosson:

I wasn't ready for the technology. There were cellular phones when I went to prison, but there were no smartphones. There was no YouTube there. Netflix was actually on DVDs. It was a different world. And I remember getting out and it felt like every room I walked into, no one was looking at each other or talking to each other. Everyone was staring down at their phone. And that felt alien to me. I couldn't imagine being in this like prism all day and like being stuck in the same way. I kind of felt stuck in a prison cell. And it wasn't long, especially with social media and all the projects I was doing that I started being that person, started being tied to my phone just like everyone else. And I think it surprised me. And I think it's one of the things that if I miss anything, what I miss about prison is the simplicity and the lack of demands and the lack of confusing, like being pulled in a million directions. Because in a simple life, I knew how to live a simple life. And out here in the world, it's a lot more complicated. And it can be hard to kind of bone down to what the really important things are.

>> Curtis Jackson (also known as DJ Curveball):

What would you say to someone who felt, who felt like someone who committed a violent crime doesn't deserve a second chance?

>> Jesse Crosson:

I would understand that. I think it's natural as human beings when we're hurt, when we see harm to, to lash back out or to want somebody else to suffer, want somebody else to punished. But the reality is that 95% of the people in prison are coming home, like regardless of what they've done, where they've been, the way the law stands, the way the policy stands, because people are going home. And if they're coming home. Do we want them to come home angry and broken and more traumatized by the system? Do we want them to come home healed and having been accountable and having made changes and created positive things in their lives? The other thing is when people say that they don't believe others deserve a second chance, what they're really saying is that they don't deserve a second chance for the worst thing they've done in their lives. And I believe people do. It's not given, but it's earned. And a lot of times when people reach out and they have some nasty comment for social media or send me some bizarre DM or bizarre email, what I see is this self loathing or this self hatred or this inability or unwillingness to forgive themselves or maybe believe that they are worthy of forgiveness or they are worthy of a second chance and rather than deal with that in themselves, they tend to lash out at other people. Because reality is we've all made mistakes, we've all caused harm. What we do with that or where we go with that is really what makes a difference.

>> Curtis Jackson (also known as DJ Curveball):

Tell us about any upcoming projects that you're working on that listeners need to be aware of.

>> Jesse Crosson:

you, I like I said with Second Chancellor foundation, we're working on this reentry video game that I'm really excited about to be able to make it, available free of charge to incarcerated people so they can practice the skills they need coming home. We've, got a bunch of speaking engagements coming up. We're maybe looking to go to Tribeca Film Festival. I feel like my day and my calendar is just about as insane as it can be because I'm here for a day and then I go to Hampton Roads and then I go to Chicago and then I feels like I'm just always on the road. But I'm grateful because I have the opportunity to spend my time and spend my energy helping people and sharing a message of hope and sharing a message of accountability and healing because I think we all need that more than we may realize.

>> Curtis Jackson (also known as DJ Curveball):

Though I should contact info so people can keep up with everything that you're up to.

>> Jesse Crosson:

Sure. You can follow me at jessicross&.com or second hyphen chancellor.org which is a nonprofit I run. I'm on social media as Jesse Crossing or A Second Chancer. yeah, we're out in the world and I love to meet people, I love to have experiences, I love to learn from other people and I love to highlight other people. So if somebody has a story to Share. If somebody has a question to ask, please reach out. I would love to respond, close this

>> Curtis Jackson (also known as DJ Curveball):

out with some final thoughts. Maybe if that was something I forgot to talk about that you would like to touch on or any final thoughts you have for the listeners.

>> Jesse Crosson:

I just think that in some ways the physical prisons that we see are the easy ones and the invisible prisons, the ones that we may feel in our minds or in our emotions or the prisons of trauma that we can't see are far more insidious because we don't necessarily know we're trapped. We don't necessarily know that we can be free. I guess my last message, or my only message to everyone is that you can be free from whatever is holding you, whatever is trapping you, whatever is keeping you stuck. You can be free. It's not going to be easy. You're going to have to put in the work. You have to have the discipline. You're going have to do one small thing every day. But I tell you it's worth the work because being on the other side, feeling a sense of gratitude, feeling a sense of connection, and feeling a sense of self forgiveness is, is the greatest relief and one of the greatest feelings I can imagine.

>> Curtis Jackson (also known as DJ Curveball):

All, right, ladies and gentlemen, jessicrosson.com or second hyphen chancer.org please be sure to check out that book. And if you know of someone that might be incarcerated and that can benefit, from Jesse's story. Follow rate Review Share this episode if you know of anybody, you know, might have somebody locked up, make sure you share this episode to as many people as possible. Also, for all things living the dream, visit www.craveball337.com Leave me a voicemail. It might get played on the show. Sign up for the newsletter if you haven't done so, leave us a review or drop a comment. Let us know. Give us some feedback on the show and share the website and the show to everybody you know. Thank you for listening and supporting the show and Jesse, thank you for all that you do and having the courage to share your story because it can help a lot of people. And thank you for joining me.

>> Jesse Crosson:

Thank you for having me and thank you for the work you do.

>> Curtis Jackson (also known as DJ Curveball):

For more information on the Living the Dream with Curveball podcast, visit www.craveball337.com until next time. Time Keep living the dream.