Reflections on a Reentry Court

Kevin hesitates in the doorway before entering Courtroom 3. When Kevin was 26, he was tried and sentenced in this courtroom. The judge who presided over his trial and sentencing has since retired, but a massive portrait of her hangs high on the back wall, as if she is watching all below.

Being in this room, with the portrait looming, “brings back memories of something I don’t really want to remember,” Kevin said.

In 1991, a jury convicted Kevin of conspiring with several co-defendants to distribute narcotics. He was sentenced to serve more than 24 years, in part because his prior felony convictions rendered him a “career offender” under the Sentencing Guidelines. With a state sentence he received around the same time, Kevin was facing a total 26 years in prison. His impending term of incarceration, he noted, was the same length as his entire life up to that point.

Kevin survived more than a quarter-century of incarceration in nine different federal prisons by “staying focused” and “reading a lot of a books.” Last year, he emerged at age 52 and returned home to New Haven, Conn. He was welcomed by five generations of his family, from his 95-year-old grandmother all the way down to his grandchildren, who were born while he was locked up. Returning to a city felt strange after being incarcerated in rural areas for so many years. “When you’re in the mountains you don’t see people, you don’t see cars driving by . . . you just see a lot of snow.” Even more jarring were the enormous leaps in technology since 1991. One year after his release, he is still learning how to use the features on his cell phone.

When he came home, Kevin noticed that, despite the many changes in his community and in the world, “some people were still in the streets doing the same thing they were doing when I left.” He was determined to begin a new chapter. “I knew I didn’t want to be a part of that no more,” he said. “I’m not the type of person where I’m just going to be stuck in one spot for the rest of my life.” When his probation officer suggested that he visit the Reentry Court, Kevin agreed, despite some initial skepticism.

Now a regular and outspoken member of the program, Kevin considers Reentry Court a “blessing” — though he still sometimes wishes it took place in a different courtroom.

In this essay, we reflect on our experience with Kevin and other members of a federal Reentry Court program that began in the District of Connecticut in August 2016. One of us is the judge who presides over this Reentry Court, and the other is a law clerk who spent a year closely working with the Reentry Court and now works as a public defender. We don’t write this as an academic analysis of prisoner reentry, nor as an empirical evaluation of reentry courts in general or our program in particular. Our goals are more modest: to explain how our Reentry Court works; to share the stories and perspectives of some of our members (based on their consent to be interviewed); and to reflect on some of the values of a reentry court program that may not be readily susceptible to mathematical tracking or measurement.

The members of our reentry court are men who have very recently completed lengthy sentences in federal prison and are serving terms of supervised release in the District of Connecticut. Anyone on supervised release must communicate regularly with a probation officer, submit to drug tests and home visits, and comply with a litany of other conditions. Those who voluntarily choose to participate in Reentry Court agree to take on additional obligations and more intensive supervision for the one-year period of the program. Most importantly, they agree to report to court every other Wednesday to participate in Reentry Court sessions, which last about an hour and a half. In addition, they attend a cognitive-thinking group known as Moral Reconation Therapy (MRT), which is led by probation officers, meets weekly, and usually takes a few months to complete.

A Reentry Court session bears little resemblance to a typical court proceeding. Before the session begins, all the chairs in the courtroom are plucked from their usual places and arranged in a community circle around the two wooden counsel tables. The ten or so members arrive at 4:30 p.m. The first 15 minutes of the session are unstructured to encourage social conversation among the members and with the various members of the Reentry Court “team.” The team includes the judge, several probation officers, and representatives from both the U.S. Attorney’s Office and the Office of the Federal Public Defender.

As the judge who presides over the Reentry Court, I do not wear a robe, bang a gavel, or “take the bench” for any part of the Reentry Court sessions. A critical part of the Reentry Court is its informality, which allows all of us to step outside of our traditional roles and interact more naturally with one another. My own goals for each session are to be waiting by the courtroom door to greet every member as he arrives and to establish a person-to-person connection from the beginning.

After about 15 minutes of informal conversations, we all take seats around the circle. I go one-by-one to talk with each member about how things have gone for him since the last court session. Members share with all of us their successes — a job offer, praise from an employer, the birth of a grandchild — as well as their setbacks and disappointments — a failed driver’s license test, a break-up with a significant other, an eviction notice. If there is a success to report, I congratulate them and ensure that they are publicly recognized, as they should be for their effort. If there has been a setback, I ask them how they plan to respond, and I invite all the others gathered around to weigh in about how to troubleshoot the problem. Oftentimes, the best idea or inspiration comes from another member who has faced a similar challenge.

Even if one of our members has a serious setback, such as a positive drug test, we try to engage with him to reflect about what led to the choice he made and what consequences it can have. Naming and shaming don’t have seats at our table. The common goal throughout is to affirm, encourage, and inspire. We believe that building self-confidence and preserving dignity and self-esteem are vital to the success of every member, as they are for each of us in our personal lives and careers.

We challenge each of the members to articulate their short- and long-term goals, and the whole team works to identify concrete steps to be taken before the next court session. Between court sessions, the probation officers and the U.S. Attorney’s Office reentry coordinator frequently talk or meet with each member to help with following through on goals (reaching out to employers, signing up for testing programs, etc.). Almost every dialogue with each member ends with, “What else can we do to help you?” and then, “Does anyone else have other thoughts for Kevin?”

These individual dialogues last for about 45 minutes. The balance of each session is devoted to a different guest speaker each week. We have hosted a wide variety of speakers over the life of our Reentry Court, from prospective employers to a bank representative to a nutritionist. Frequently, our guest speakers are people who have served time themselves and can offer firsthand wisdom about the challenges they have overcome.

Reentry Court consists of four phases, with the entire program designed to take about a year. Every member must reach specific milestones in each phase before progressing to the next. If someone slips up — for example, if he fails a drug test, or misses a session without giving notice — he loses time credit, which means it will take him longer to progress to the next phase. In the end, those who graduate are celebrated with a joyous graduation ceremony and then have their term of supervised release shortened by one year. This reduction in supervised release is no doubt a “carrot” that prompts many of the members to join in the first place. But the benefits that members receive in the form of support and resources while in Reentry Court likely offer an even bigger return.

Leroy has been in and out of prison since he was a teenager. After serving an almost five-year federal sentence for illegal gun possession, he was released to a halfway house; within weeks, he was rearrested for violating his probation and sentenced to serve two and a half more years.

When he was released again in December 2016, he joined Reentry Court and quickly found work as a driver for a service that transports people to dental and medical appointments.

Leroy believes that “it’s a misconception that you can’t get a job” with a criminal record. “Does the record have an effect on it? A little bit. But there are a lot of places that will give you an opportunity — you just have to sell yourself.” During his first weeks in Reentry Court, Leroy brought in flyers with his employer’s contact information, encouraging jobless members to apply.

Despite his optimism, Leroy acknowledges that the process of applying for jobs can be intimidating. “I get nervous at interviews, because I’m not used to being questioned like that. My experience with interviews has mostly been getting interviewed by the police.” In job interviews, “I don’t want to say something wrong, or look stupid, or be judged. I already feel like I have an intimidating look because of my size, and then they see all these tattoos,” he says, motioning to his face and neck. “And then they see I got a record and it’s like, ‘Aw, man, I’m not going to get it.’ But you keep trying. You know, you’ve got to keep going. There is a place that will hire you.”

Leroy’s hours as a driver with the transport service have fluctuated. At times, work has “slowed down to the point where I almost didn’t have a job,” he says. It’s gotten slow again recently, so he has been looking for a second job; nothing has panned out yet. His long-term goal is to start his own business, but he knows there are a lot of smaller goals he has to achieve first. For example, he needs to build up his credit, which was non-existent after a lifetime spent either in prison or using only cash.

“I’d been trying to stop carrying cash all the time and start using a card, to build a little credit. I had a card for a while, but I never used it, because I didn’t know how. I was too embarrassed to say that I didn’t know how to use it, and I didn’t want to look stupid trying to use it, so I never used it. I just didn’t want to get up there and look like I didn’t know what I was doing,” he laughs. When he eventually relented and asked someone, he was surprised to learn how simple it was.

For Leroy, one of the hardest things about reentry has been having to ask for help. “I’m the kind of person where I like to take care of my own everything. So having to rely on people for a ride, or a place to stay . . . it’s tough.” But Reentry Court has given him a forum for seeking and accepting help. When his son’s mother refused to let Leroy spend time with his son, Leroy brought the situation to Reentry Court. The team connected him with a volunteer lawyer who handled his visitation case in family court pro bono, and Leroy was ultimately able to secure visitation rights. Though he considers himself a private person, Leroy became more comfortable talking about the issue with his son in Reentry Court after hearing other members talk about navigating similar situations with their own kids. “Going to Reentry Court,” he says, “I’ve seen that almost all of us had these issues.”

Like Leroy, Steve has been in and out of prison for most of his life. He came home two years ago at age 45, after serving 12 and a half years. In reflecting on his two-year “anniversary,” he mentions that, before now, he hadn’t been out in the world for more than two years at a time since he was 14.

Steve is soft-spoken and quick to smile. He jumped at the opportunity to join Reentry Court after his release. “For me, accepting help was a no-brainer,” he says, particularly because he had no legitimate work history. “Reentry” is in some contexts a misnomer, since a lot of people coming out of prison are making their first entry into the legal workforce. Holly, the U.S. Attorney’s Office reentry coordinator, helped Steve put together a resume and apply to jobs. He was hired as a “Downtown Ambassador” in New Haven, a role that is a combination of street cleaner, tour guide, and patrolman. His employer was so pleased with Steve’s work performance that he asked Holly for referrals for other potential employees.

At the team’s pre-meetings, the probation officers always update the team on what is happening with each member. Patrick, Steve’s probation officer, almost always began Steve’s update the same way: “Steady as he goes.”

Steve deflects praise for his achievements, attributing credit to the people he refers to as his “supporting cast” — that is, his adult daughter and three young grandchildren, with whom he lives. “A lot of people aren’t fortunate enough to have a supporting cast. My daughter opened her home to me, supported me, was basically taking care of me before I got a job.” And his grandchildren? “They think they’re my parents. They love to boss me.”

Although his relationships with family have remained strong, navigating relationships with friends has been one of his biggest challenges since coming home. Many of his friends “are not on the page that I’m on,” and although Steve feels strongly that it is “their prerogative to live life the way they choose,” he also believes he needs to keep his distance in order to avoid falling back into old habits. Distancing himself from these lifelong friends — relationships “built from the sandbox” — has been emotionally taxing and sad.

Last fall, Steve became the first graduate of Reentry Court. His daughter and grandkids attended the ceremony and gave speeches, as did his employer and even the judge who had sentenced Steve so many years ago.

Though members are sometimes isolated from their friendships for the reasons Steve describes, they provide moral support and inspiration to one another through Reentry Court and the Moral Reconation Therapy groups. In particular, older members like Kevin, Leroy, and Steve serve as role models for younger ones. Anthony, one of the youngest participants at 24, observes, “Kevin, that guy that did a lot of years? He wants it, and you can see that. And that’s how I want to be, too. If I hear [of an opportunity] that’s going to be beneficial to me, I want to jump on it.”

Anthony came home about a year ago, after serving two and a half years for his role in a string of armed robberies when he was 20. He was sentenced to time served in federal court and expected to be transferred to state custody because of an outstanding bond in state court. To his surprise, he was released that day. “It was an insane feeling. I almost passed out when I heard I was going home.”

Once he got over the initial shock, his transition home was not as much of a jolt to Anthony’s system compared to some of the other men who served longer sentences. “I got on my feet very quick,” he remembers, and “my fingers were on fire” typing up job applications. He first got a job delivering pizzas, and later, with a small moving company, where he now works full time.

He originally signed up for Reentry Court because he wanted to get the year off his supervised release. “For the first three months in Reentry Court, [getting the year off my supervised release] was all I cared about.” But after a few months in the program, it wasn’t just about getting the year off anymore. He says he changed his thinking, which he attributes to discussions at Reentry Court sessions and especially to the Moral Reconation Therapy program. “In MRT, you learn to really put everything behind you, but to also accept what happened to you. I wouldn’t be here if I didn’t commit a crime. And I also wouldn’t have learned half the things I learned.”

Anthony recalls one of the Reentry Court’s recent guest speakers, who is the senior vice president of human resources at Yale-New Haven Hospital –– one of the largest employers in Connecticut. In New Haven and the surrounding area, jobs at Yale University and the Yale-New Haven Hospital are highly coveted. This speaker talked about the hospital’s commitment to hiring people with criminal records and offered advice to those interested in applying. During his presentation, he told a story about himself as a teenager, when a football teammate placed a gun in his hand during an emotionally charged moment. Though his reflex at the time was to hand the gun back, the speaker admitted he could have just as easily made a “bad decision” in that moment that would have prevented him from getting to where he is today. The story stuck with Anthony, who decided it needed tweaking. “He said if he’d made that bad decision, he wouldn’t be here today. But I think he could have made that bad decision and still been here. I took what he said and turned it, because I feel like, maybe he still could have,” Anthony insists, pointing to the success of his fellow Reentry Court participants, as well as the stories of many of our past guest speakers, who rebuilt their lives and went on to successful careers after committing crimes at a young age.

Steve says that Reentry Court has had a “humungous impact” on the way he thinks about courts and the criminal justice system, and other participants have echoed this sentiment. As Steve explains it, “you get to see a different side of people in Reentry Court. I was able to converse with prosecutors. You don’t get to know someone until you converse with them, see where their head is at. These are regular people. A lot of times we lose focus of the fact that [prosecutors and judges] are doing a job. I got to meet a good group of people from many walks of the judicial system. It showed me that they’re human beings; they have a heart.”

Leroy had a similar experience. The prosecutor who filed Leroy’s case is one of the team members who regularly attends Reentry Court. “During my time going back and forth to court, I hated the guy,” Leroy recalls. “I used to sit there in court and wonder, ‘Why does this prosecutor, who doesn’t even know me, want so badly to take me away from my family?’” When their paths crossed again in Reentry Court years later, Leroy’s feelings about the prosecutor had shifted. “When I saw him in there, I didn’t have no animosity — and that has a lot to do with the program and my growth.” The two shook hands, and even talked a little about Leroy’s case. Though Leroy still harbors some frustration about the way his case played out, he no longer holds on to any anger towards the prosecutor. “Whether I agree with everything he did or not, he was doing his job. He said it was nothing personal, it’s just that he has things to uphold. And I respected that, and that was it.”

The members are not the only ones whose relationships and views of “the system” are changed by this experience. Reentry Court gives judges, prosecutors, defense attorneys, and probation officers the opportunity to step outside of our usual roles, to work collaboratively toward a shared goal, and to relate differently to each other and our members in a way that is not possible in our day-to-day work.

Of course, Reentry Court is far from a magical cure-all. Many of the participants remain deeply frustrated about aspects of their own cases and about structural injustice as well. Kevin, for example, makes a passionate case against lengthy sentences for selling drugs and believes the criminal justice system is infected with racial bias. At the same time, he believes that Reentry Court “shows another side” of the system, and shows that “people [in the system] do have a heart; people do care.”

Much of the existing literature about reentry courts attempts to evaluate whether such programs reduce recidivism, often by measuring new arrests or convictions. Whether our Reentry Court ultimately reduces recidivism is not a question we can answer at this point. We have had too few participants to yield meaningful statistical results; moreover, our participants are not randomly selected because our program is voluntary. These features, combined with the fact that the program is still in its infancy, prevent us from reaching any empirical conclusions.

Anecdotally, we can say that the large majority of our 21 members to date have been successful. Most have found and retained jobs and housing, reunited with family, and avoided new criminal charges. A few of our members have occasionally failed drugs tests or been arrested on new, relatively minor charges. Four of our members have dropped out of the program, two by their own choice and two at our suggestion when it became apparent that they were was not able to commit to membership in the program. A single one of the members had to leave because of his arrest for a serious violent crime. One of our members tragically passed away from an overdose, despite having had no prior positive drug test results during his participation in the program.

We think the results of our program are encouraging, and we are encouraged as well by the unanticipated benefits. By changing the somewhat calcified way that members and their families view and relate to judges, lawyers, and probation officers, the Reentry Court increases public confidence and trust in the judicial system. And by changing the way judges, lawyers, and probation officers view and relate to people who have been convicted of crimes, Reentry Court challenges us to rethink how we do our jobs and how we understand and relate to the people who are most impacted by our criminal justice system.