Think Out Loud

‘Free’ illustrates enormous reentry challenges for those coming out of prison

By Allison Frost (OPB)
Aug. 16, 2022 6 p.m. Updated: Aug. 16, 2022 8:39 p.m.

Broadcast: Tuesday, Aug. 16

Free: Two Years, Six Lives, and the Long Journey Home captures the stories of individuals released from prison, who face multiple challenges to reenter society.

Free: Two Years, Six Lives, and the Long Journey Home captures the stories of individuals released from prison, who face multiple challenges to reenter society.

Courtesy Sourcebooks


Why do some prisoners who have been released from prison go back behind bars within just a few years — or in some cases, months or weeks? What social and economic systems contribute to or even drive those outcomes? Lauren Kessler answers those questions through the personal stories of six formerly incarcerated adults in her new book, “Free: Two years, Six Lives, and the Long Journey Home.” Two of those she profiles committed violent crimes as minors but were treated as adults as they were tried and sentenced. Kessler joins us to talk about the defeats and victories these six adults experienced as they reentered the outside world — and shares her insights into why and how their stories unfolded as they did.

Note: The following transcript was created by a computer and edited by a volunteer.

Dave Miller: 95% of people who are in prison are going to be released. But too often, the writer Lauren Kessler says, we focus on the outliers of reentry experience - the ex-con who robs a 7-11 hours after release or the one who becomes a famous attorney. According to Kessler, the truths about life after lockup are more interesting, more nuanced, more troubling and sometimes more triumphant than those headline grabbing stories. So she set out to write about six people who were released from prison, most of them in Oregon. They’re the focus of her new book. It’s called ‘Free: Two Years Six Lives and The Long Journey Home’. You start the book by writing about a woman named Belinda who was released from prison After serving 22 years behind bars and she went in when she was 18. Can you read from your prologue about what happened after that?

Lauren Kessler:  Sure. “Belinda and I sit in a booth at a chain steakhouse. She has allowed me to witness her release that day because we connected while she was still inside. I had interviewed her about her experiences with the prison’s Hospice where inmate volunteers sat with the dying as their lives ended behind bars. It was part of my research on incarcerated life that became my first book about life inside prison, ‘Group of Time’. I liked Belinda. She was tough. She had to be. But the hospice work had, I thought, touched a place inside her that maybe had not been touched before. I wanted her to do well on the outside. I thought I owed her at least a dinner for the time she spent answering my questions for honesty. So I had proposed this get together. Now sitting across from her, I take note that she has ordered the most expensive item on the menu plus three extra sides. The food on the plates in front of her could feed a family of four. Belinda hardly touches it. She’s not looked up from her phone since we sat down. A month ago, she had never held a smartphone in her hand. now she’s nonstop texting with her thumbs. She had gotten the phone three weeks before she had acquired a boyfriend. A week later she was in the throes of what sociologists call asynchronicity. While Belinda was in prison, her age cohort moved on. Inside time was frozen outside. Other young women acquired and dumped boyfriends or girlfriends, went to concerts, got and lost jobs, maybe went to college on the outside. Other young women moved to new apartments, new towns, new countries, had adventures, changed their look, had career aspirations that worked out or didn’t on the outside. Other women grew into their 30′s, found their place, lost it, reinvented themselves, settled in. Inside, Belinda had experienced a lot, but none of this at 40. She was still, in many ways, a teenager. She was a teenager with a new phone texting a new boyfriend. I watched her, her hair is dyed matte black, her eyes are thickly rimmed with black eyeliner. I can see a light etching of crow’s feet in the corner of her eyes. She has that hard look that women sometimes have when they’ve spent a lot of time in prison. She looks her age, maybe older. Prison does that to you. But she acts like a high schooler. I wonder what this disconnect might mean for her re-entry. That night, I offered to mentor her and be a sounding board, listen to her stories, take her out to dinner or lunch. She agrees. It didn’t happen. Belinda was consumed with this boyfriend and then with another one after that, with the miracle of the smartphone, with social media, with frappuccinos at Starbucks. She stopped texting me back.  She didn’t answer my calls. I never found out what kind of life she made for herself and that not knowing haunted me.”

Miller:  That’s Lauren Kessler, reading from her new book, ‘Free’.  Lauren, as you mentioned early in that segment, you’d written an earlier book about life inside prison called ‘A Grip of Time’. How did that book lead to your new one?

Kessler:  I learned about life inside from 10 men who were part of the prison writing group that I had started at Oregon State Penitentiary. They taught me what their life was like. And the more that I learned about that, which is not the Hollywood version, the more that I understood the kind of person that you had to become when you’re incarcerated to stay sane and to stay safe and how that kind of person is, in many ways, ill suited to go out into the world upon release. And when I found out, during the research, that 95% of people who are incarcerated get out, I thought I have to really look at what happens to those folks when they get out. That was my connection with Belinda and Belinda disappeared. So I needed to find other people that would graciously and honestly allow me into their lives.

Miller:  You quote a former inmate who now works for the ACLU. His name is Lewis Conway and he says this. “I thought serving my time in prison was my punishment. I didn’t know I was facing a life sentence after leaving prison.” What does he mean?

Kessler:  I think it means many things. There is a stigma to having spent time inside that you carry with you, that a person carries with them their whole life. That stigma is internal but it also affects, externally, the kinds of jobs that you can get, the sort of housing that you can get, the community that you come back to. And depending upon how you are released, the kind of parole restrictions that you have, your “imprisonment” can last many years longer than your actual incarceration.

Miller:  Inside you note that according to the American Bar Association, there are about 45,000 federal and state statutes and regulations that restrict a convicted person’s freedom after they have been released. And yet, in a survey by the Urban Institute, three quarters of inmates said that they thought that reentering society was going to either be pretty easy or very easy. How do you explain that?

Kessler:  It is very difficult to explain. I mean part of it is just you want to admire the optimism there. You want to admire the energy and optimism of thinking that once you get out of the gate, everything’s going to be different and the sun is gonna shine and it’s going to be wonderful. And I think it’s so important to feel that way. But because very little is communicated back inside about reentry, those expectations are overblown. So I don’t exactly know what to say about that other than you don’t want to dash people’s expectations, but you want to be able to give them some realistic view of what faces them and especially a road map that helps them navigate that terrain.

Miller:  As you mentioned, you focused on six people in this book. How did you choose them? What were you looking for?

Kessler:  In one sense, I had a checklist, which I’ll tell you about.  But besides that it had to be people that allowed me into their lives and that trusted me and that I trusted them. So that probably was the main consideration. But what I wanted was a mix. So I wanted a mix of men and women and I needed more men than women because there are far more men incarcerated than there are women in our country, well in the world. So I thought that 50-50 was not a good idea. I wanted people who had been inside for a considerable amount of time. Because their re entry would be more challenging than somebody who had spent maybe two years or three years inside. I wanted a racial mix. So the six people are black, white and brown. Um what else? Uh yeah, I think that would be it.

Miller:  Could you tell us some of the basics of Arnaldo’s story? He’s one of the six you followed, starting with his childhood?

Kessler:  Arnaldo, yes, is one of the six. And he was born and raised in a border town in Texas. His mother and father were Mexican americans. And after big domestic issues between his parents, his mother moved the family to Eastern Oregon to do agricultural work. So Arnaldo and his brothers moved there and he joined a gang and became a leader in that gang. [He] became involved in violent acts and the other things that the gangs were involved in and found himself at Oregon State Penitentiary with a 20 year, I believe, sentence for murder.

Miller:  His violence, as you note, and I should say you don’t pull any punches in terms of what these men and women have done. You’re very clear about their crimes. You also note that after Arnaldo got to prison, the violence didn’t end. He was a pretty ruthless gang leader and enforcer behind bars, which often led to his being put in the hole - in solitary confinement. But then, while in prison, he went through some massive transformations. What happened?

Kessler:  So this can happen. People think in prison isn’t it great if people get an education and that is excellent. Or isn’t it wonderful that they might learn a trade like welding or whatever and that’s excellent. But the real work, the hard work, the important work is the internal work. And that’s what Arnaldo did in his connection with the restorative justice movement inside prison, inside Oregon State Penitentiary and especially with something called transforming trauma or trauma transformation - dealing with that awful ugly stuff inside of you, some of which you exhibited in your behavior and transforming it to something good, something powerfully good, which is what Arnaldo did and what his friend Sterling Cuneo who was also a character in the book and also did. [He] brought Arnaldo actually into the restorative justice, trauma transformation movement within the prison.

Miller:  What was the work that they did with fellow inmates? I mean, what does restorative justice mean in practice within the walls of a prison, as opposed to between people who committed crimes and save their victims. Because it seems like a lot of what they were doing was with people that they were incarcerated alongside?

Kessler:  I think that’s a really good point that it can work the story of justice. We outside most often think about someone who has done harm being able to sit in a room with facilitators and the person to whom the harm was done and talk about it and work through it and see what they can do. But people do harm to each other and to themselves inside prison. And so [regarding] restorative justice inside prison, the difference between being harmed and being the one who harms is a thin line. It’s a very thin line.

Miller:  What do you mean by that? Because I guess they seem like such different ends of action and intent and effects that, I’m not sure what you mean by ‘the thin line’?

Kessler:  I understand what you’re saying. The research shows though, that very, very many people who are in prison come from backgrounds that included a significant amount of harm. So they were harmed and then they did harm. That would be the connection. And when you don’t deal with that, when you try and cover up the harm that was done to you, whether we’re talking about growing up with a parent or parents who are substance abusers or growing up in a neighborhood where violence is just an everyday aspect, or having some sort of domestic or sexual violence committed against you - if there’s no help for that, if you don’t recognize it, you can go on and often do go on to do harm. So that would be the connection that I’m talking about.

Miller:  For Arnaldo, how did the work he started doing internally, then with fellow inmates, while incarcerated - how did that affect his life upon reentry, his life outside of prison?


Kessler:  In a truly transformative way, I would say. Moving from using his cred inside as a gang leader to being the person who can de-escalate, can recognize violence before it happens and can help de-escalate that violence, that’s what he did in prison. He unlearned what people have called toxic masculinity, which is kind of how you often have to be in prison in order to stay safe. When he left, after a while, he moved into a job in Portland working with at-risk Latinx youths, very similar to who he was back then. Because he knows the road they’re traveling, he can help them navigate it, he can help them. So in his professional life, he’s specifically used those skills. And in his personal life, he has become a father. And it has been a truly lovely thing to watch him interact with his son and with his partner, Nicole.

Miller:  The person you followed who really seems to have had the most difficulty upon re-entry, you call her Vicky. Can you give us a sense for the cycle of reoffending that had really defined her life for decades?

Kessler:  Thanks for asking about Vicky because she, of the six people, is the only one who did not commit a violent offense. And you would think that re entry would be easier if you weren’t carrying the incredible guilt and burden and shame of having taken another’s life, right? And that’s what five of those six people have, that carrying of guilt. So with Vicki, you would think it would be easier for her. But it wasn’t. And the answer, I mean it’s too simple I guess, but I will just say drugs. She is, was an addict with two serious substance abuses and had been for almost all of her life. All of her crimes for which she got stretches of four or five years, I think maybe seven years was the most, they’re all paper crimes, as they say. Forgery and stealing identity and kiting checks and that sort of stuff.

She continued to do that to support her double drug habits and continued to reoffend when she got out. She was released to the same place that she always lived in with her street family right there and all of the triggers that triggered her her whole life right there. And I mean, how many times can you be triggered before your defenses just go down. She’s worked very, very hard to stay off of drugs. But it has been a struggle. She’s not back in prison. None of them are. They are all doing okay. Vicki is probably doing the least okay of them because she’s still battling those demons.

Miller:  For so many of your books, you immerse yourself in the world that you’re writing about. In this case it meant that you didn’t just report on these people as they’ve been reentering society. You were also a teacher or a mentor or a volunteer or in some cases a friend. Did you have competing interests as a helper on the one hand and as a chronicler on the other?

Kessler:  I wouldn’t say competing although in my training, my very conservative training as a journalist, I would’ve said competing. But the more work that I have done embedding myself in people’s lives and worlds, the more I don’t see that as competing. The more I see that as really intertwined. I think that it is enormously important to make a personal and enduring connection with people who are so generously letting you into their lives. You have to give back in some way and being an editor of their writing, being a person who buys them a cup of coffee, being, in Vicki’s case, a mentor, that’s the way of me paying back the time. And the honesty they’ve given me.

Miller:  We’ve been talking with Lauren Kessler, the author of 15 books of nonfiction including ‘Free: Two Years Six Lives in the Long Journey Home’. Kessler is a creator of a writing group for lifers at the Oregon State Penitentiary and an affiliate professor at the University of Washington. Lauren, I wonder if you could read us another excerpt from near the end of this book?

Kessler:  Sure. This is a very short passage here. “When researchers survey ex-felons to evaluate their post incarceration lives, they ask, ‘have you found a place to live? Have you found a job? Are you clean and sober?’ They might ask about family but they very rarely ask about the way life is being lived day to day, about ordinary activities, the simple ways of being and doing that. Most of us take for granted the scores of small decisions we make, everyday choices we face with relative ease, our casual interactions with others, our fluency in reading body language, the way we effortlessly navigate space, our composure in crowds, our curiosity about the new and the novel. These are behaviors we have learned and honed and internalized as citizens of the free world. They do not come naturally to those who spent decades behind bars where they have learned and honed and internalized an entirely different set of behaviors. The success of those who do not recidivate is most often measured by the metrics most easy to measure housing and employment and not by the subtler and far more difficult to accomplish feats of psychological and psychosocial reintegration.”

Miller:  For the six people that you followed, I’m wondering if there is an example that comes to mind of how these subtler aspects of social or interpersonal skills, where you saw them either lacking these skills upon re entry or through their own hard work or good luck actually getting these skills.  How did these show up for the six people that you followed?

Kessler:  In many ways. I think interacting with others who have not also been incarcerated, who you don’t know from the past, new people in your life, is a real challenge. I’m thinking of one of the characters in the book who had a really difficult time reading other people. So when a stranger starts a conversation, what are they after? Are they just being friendly? Do they want something? Are they scoping you out in the way people might do in prison as friendly? How do you judge when somebody is being too friendly? The person I’m talking about is a man who went into prison a long time ago as a closeted gay man and then came out of prison at a time when one does not have to be closeted anymore. And when there’s same sex marriage and when you can interact in different ways that he knows how to interact. And that has been and continues to be an extraordinary challenge.

Miller:  It’s such a poignant example that you bring up. And there’s a really heartbreaking section where you describe him going to a park and a man comments on his car. And as you said, he’s not sure how to engage and what this man’s intent is. And [whether] he wants to be friends, if he just likes the car, if he’d maybe want a date. He has no idea. And it made me think that there’s a lot that could happen. And we will talk about offerings, in terms of classes and support groups that can happen while people are still incarcerated that can give them more of a sense for how to function outside of prison walls. But it’s not clear to me, for this particular example, what could be done ahead of time, teaching people to interact in myriad social ways. I mean, what could happen inside prison to provide some of these interpersonal skills that you’re noting are so important and also so subtle?

Kessler:  Um, so I think a couple of things. One is, the more volunteers that are allowed in prison, volunteers from “the free world” as they say. The more non prison people that people inside can see, observe, interact with, the better. So there are prison officials, there are guards, there are recreational specialists. There’s a big staff in there. And then of course there’s families who come to visit. There can be people who come in to teach. That’s a very particular kind of relationship. That’s a power relationship, teacher-student. But volunteers just who come in. It doesn’t even make a difference why they’re coming in. I mean, you have to come in for a purpose. But just that kind of interaction, I think more of that is really important and it is relatively difficult to become a volunteer and to stay a volunteer inside.

The other thing that I think is important that is being done, a little bit, here in Oregon and in other places I have heard better, is bringing back into the prison people who have been released and have spent a year, six months, three years outside to have very candid conversations about these kinds of issues, straightforwardly. It’s hard to look somebody in the eye and know what to do to be able to have those conversations with people that they trust coming back into prison. If you want good re-entry, it starts in prison. It doesn’t start when you put your foot outside the gate, regardless of the kind of support you might get out there. It has to start inside. And for most people, it does not start inside.

Miller:  You’ve said that people in prison, correctly, learn not to trust other people. I’m really interested in your use of ‘correctly’ there. What do you mean?

Kessler:  Well, you need to protect yourself physically. Prison is a very odd place in the sense that it’s, on the one hand, sort of stultifying routine. But on the other hand, anything can happen at any moment. Anything can happen at any moment. So you have to be on high alert. And the only analogy that I can make in my own life is a woman walking along alone on the street in the city. You are on high alert. You are looking on both sides of the street. You’re hearing what’s going on behind you. You are wondering if somebody’s going to cross the street and do something. You’re on high alert and you need to be on high alert inside to protect yourself. So, I think maybe ‘correctly’ is just being a strong word there. But you evaluate everybody in your sphere to see if you’re safe. and then over time you trust certain people and you stay just with them. and when new people come in that you are on high alert about them.

Miller: And then eventually you get released and there are new people all around you?

Kessler:  Correct. Absolutely.

Miller: Another big issue that you touch on is the question of freedom itself, of choices. Because one of the most central facts about life behind bars, in addition to the bars, is how restricted and constricted your life is, how little you can do without permission. And then, you get outside and there are absolutely, as we mentioned earlier, a ton of restrictions depending on the circumstances, based on someone’s individual parole situation. But nevertheless you get to decide when you’re going to eat or where, to some extent, you’re going to go. How do people handle that explosion of choice?

Kessler:  That is such a good question. I don’t remember now, but I looked up, at one point, how many individual tiny choices a human being makes in 24 hours? And it is astonishing. I mean, it’s absurd how many. And most of them, we don’t pay attention to at all - those of us who are used to making those choices. So it is, I think, a habit acquired over time. In the book, there are two stories of the first moments after release that are about this.

One is the guy that I was just talking about earlier who is working on having relationships outside. He gets taken to breakfast like right out of the gate, gets taken to breakfast at a place that everybody knows right outside of the prison. And he has a menu and the guy hasn’t seen a menu in 35 years and it has choices. Do you want coffee? Do you want something in your coffee? How would you like your eggs? And it’s overwhelming. He just shuts down and somebody has to order for him.

The other thing is Catherine. We haven’t talked about Catherine. Catherine was the youngest person in the United States, not a very good distinction, to have been tried as an adult for murder. She was 13 years old. She gets out when she’s 31 and she and her father stop at a gas station to get gas and there’s a 7-11 or some kind of store. She goes in and thinks she’s going to get a candy bar, which would be like the first candy bar in 18 years. And they have to pull her out of the store because it’s 15 or 20 minutes later and she can’t make a decision. That’s just way too much in front of her. She just shuts down.

Miller: I want to go back to what you said earlier about the lack of preparation within prison for life outside of prison. It doesn’t seem like that’s an accident in U.S. society. It seems like there’s something deeply embedded in our culture that says that prison should be a time of deprivation, that simply being locked up is not enough, and that things that make life more bearable or better shouldn’t be available to people who have done terrible things. Corrections officials wouldn’t say this. They would say the opposite. But when you just look at the way prisons are set up in this country that seems to me like an inescapable truth. It seems like it’s embedded in our culture and it’s different than in other countries, including nordic countries.  What do you think it would take to change that aspect of our society? The way so many of us seem to think about what prison should even be?

Kessler:  Boy. That big question. And I know that your show and OPB in general covered the journey that some department of corrections people made to Norway to look at their prison system. Their idea is rehabilitation first of all, and that you prepare somebody for the life they are going to live outside prison on the very first day they go to prison. That’s just their mission. That’s the mission. And so part of the preparation is cooperation and decision making. So you’re depriving them of their family, their home, their privacy, all of that kind of stuff. But you are helping them become the kind of people who will be welcomed back into their community. And that’s the lesson that we can learn from Norway in particular, but other countries. What would it take?  To me, understanding that 95% of people who are incarcerated are going to be coming back to our communities, is an even more powerful statistic than the 2.3 million that we incarcerate. So what kind of life are we creating for those 5, 10, 15, 35 years? What kind of people are they becoming? And then we let them out. So we can be selfish about it. Instead of thinking we’re going to be soft on these terrible people who do these terrible things. What about being kind to our families and our neighborhoods and our communities by not creating 600,000 men and women who come back to us creating the kind of difficult transition that they’re going to have because of life in prison. So to me, it’s almost selfish, in a good way, to change our attitude.

Miller:  Lauren Kessler, thanks for your time today and for this wonderful book.

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