The Dream Club’s Chief Dreamer

Colleen F. Sheehan

In 2011 and 2012, while more than 900 people were being murdered on the streets of Chicago, creative-writing students from DePaul University fanned out all over the city to interview people whose lives have been changed by the bloodshed. The result is How Long Will I Cry?: Voices of Youth Violence, an extraordinary and eye-opening work of oral history.

Told by real people in their own words, the book contains the extraordinary stories of 34 Chicagoans. This is one of them.

Judge Colleen F. Sheehan presides in the Cook County Juvenile Justice Division, one of the largest juvenile court systems in the nation. She is the daughter of Irish immigrants who taught her to work hard and pull herself “up by the bootstraps,” encouraging her to begin delivering papers at age 8 and to get her first real job— in a restaurant kitchen—at age 13. After graduating from John Marshall Law School in Chicago in 1987, she began her career as an assistant public defender for the Cook County Public Defender’s Office. In 1991, she went into private practice, representing clients in criminal and civil matters. She was elected as a Cook County Circuit Court judge in 2000.

Openly gay, Judge Sheehan believes that her sexual orientation often gives her empathy for young people from minority communities. “I am not saying that I know what it means to be an African-American 15-year-old or an African- American male,” she says. “But I can understand what it feels like to be hurt from discrimination.”

During the course of her career, Sheehan has become an advocate of “restorative justice,” an approach that stresses conflict-resolution over punitive incarceration, often through “peace circles” that bring together affected members of the community, including the victim and the offender. The focus of this approach is to help young offenders understand the real harm that resulted from their actions, to take responsibility for those crimes, and to commit to repairing the damage they’ve inflicted upon others. Restorative justice also encourages the community to be a part of the solution and the restorative efforts.

In conversation, Sheehan is confident and animated, taking on many characters, each with distinct accents and hand gestures. Drinking sparkling water and twirling a paper clip, she leans back in her chair as she speaks.

One day I was coming out of Whole Foods, and a man asked me if I would sign his petition to be a judge, and I said, “How do you do that?” He told me how to get the petitions downtown, and I thought, “I could do that.” I enjoyed being an attorney and did not want to abandon something that was so much a part of me. But I was searching for a different way to serve and needed to find the right path. I had secretly dreamed of being a judge one day, but didn’t dare believe that it could really happen. In that moment, the barrier of self-doubt suddenly lifted. I knew that I needed to do something about making my dream a reality. I ran for judge in 2000 and was successful.

In 2006, I was asked to come to Juvenile Court. It was a very sobering experience. During my first year or so in Juvenile Court, five kids I sentenced to probation were murdered. When a child is sentenced to probation, I have an ongoing relationship with that child, and I am very much invested in their well-being. I receive periodic reports from their probation officer as to their progress. The kids often come back to court and let me know how things are going with them. So to have a probation officer step up on a case and tell you a child has been murdered is gut-wrenching and surreal. Here we all are, living in this beautiful city of Chicago. But for some kids, it seems like they are living in a war zone.

When I first came to Juvenile Court, attorneys argued that science shows juvenile offenders’ brains are not as developed as adult brains and that’s why they were making bad decisions. The science was sound, but I thought it was being used to excuse bad behavior. I mean, even a 4-year-old knows that it’s wrong to break into somebody’s house and steal something. But after you work in Juvenile Court for a while, things aren’t so cut and dry. You see everything here. You have kids that are cognitively delayed. They were born that way. Maybe their parents didn’t have the correct nutrition. Maybe a child was born with drugs in his system. You get some kids that have been abandoned—and more than once. They’ve been abandoned by their parents, so their grandmother raises them for a while, and then their grandmother dies, and then a cousin starts to raise them. Now they’re 14 years old, and they’re getting in trouble, and the cousin says, “I can’t take it anymore.”

Then the state enters the picture. That may be necessary, but the state is not a decent substitute for a loving parent. These kids are in serious stress. There are real social, economic and race inequities stacked against these kids and their families. That is wrong. In America, the one thing everyone should have is a chance to succeed. I’m not saying that these children do not engage in bad or even criminal behavior, but it’s complicated.

Sometimes all I can do is to acknowledge how painful it must be for them. I tell them, “I see you’re in pain, and I’m so sorry. I’m sorry that all of us together—me, society, the system, your parents—have failed.” You see a young kid who’s so tough that they almost seem dead in the eyes. And then to see a single little tear just roll down their cheeks. Those are the kids that stick with me the most, when I make a profound connection to someone who is virtually a stranger to me, and connect with them on such a deep, human level.

In the past six years, thousands of people have come before me. And in only one case, the victim’s family seemed out for blood. In the remaining cases, I have been so amazed at the generosity of the victims who come to court and don’t want revenge or punishment for the minor. Time and time again I hear them say, “I want better for you.” These victims have suffered serious pain, whether it’s physical or emotional. I think it is the best in all of us that says, “If we can’t save a child, how can we have hope for any of us?” There’s just something about children that evokes empathy in people.

When I worked in the adult system, some defendants were as young as 17 years old. I’d ask them what they wanted out of life. What was their dream? The first time I asked a young man what his dream was, his face lit up. It was as if no one had ever asked them that question.

I was taken by the two responses I would get. Some young men and women turned into completely different people when they were asked about their dreams. They went from tough kids with an attitude to innocent and childlike. They opened up about what they wanted and how they were going to get it. Usually their dreams were unrealistic—playing in the NBA or the NFL—but they seemed happy dreaming big. The other response I would get was telling. Some kids didn’t have a clue what their dreams were. They had a flat affect, and I saw the deadening of the hope inside of them.

I remembered those young men and women when I was asked to have a CPS high-school student intern with me. That’s when I hatched the idea of Dream Club. Basically, the idea was that, if you had an adult who worked one-on-one with a kid every single day—if you could help them identify their dreams, formulate a plan and then help them execute that plan—then those kids could achieve anything.

I ran the idea by my sister, who is a social worker, and she said, “You really should make it a group of kids, so they can support each other’s dreams.” So I called the teacher in charge of the intern program back and said, “I’ll do it, but I want two or three kids.” She called me back and she asked if I would take four.

So these four kids were with me for nine months, two hours a day. We talked about goals and dreams: What’s a goal? What’s a dream? Why do you want that goal? Why do you want that dream? Why do you want 22-inch rims on your car? What’s the value of that? Maybe you want power. Maybe you want respect. Maybe you want notoriety. We discovered that what they wanted, even more than the rims, was what the rims represented.

Then we looked at how they could achieve those things in a way that was more meaningful and longer-lasting than owning 22-inch rims. I gave them movie cameras and sent them out to find out what other people’s dreams were. They interviewed attorneys, probation officers, judges and their peers. They were surprised at what people revealed. One of the attorneys they interviewed said, “I don’t want to be a lawyer. All I ever wanted to be was a writer. But I don’t know if I could ever make that change.” This shocked the kids. They looked at this young lawyer and thought he had it all. So they learned that what seemed to be an end-all and be-all wasn’t, and that the dream keeps evolving.

I took them out to “business lunches” at fancy restaurants. We visited college campuses. I tried to expose them to things they didn’t even know existed. On the day after the historic election of President Obama, we had a picnic in Millennium Park, in front of the Bean. Each of them declared their dream. At first, one girl said, “This is it. This is my dream. To be here, downtown, on this beautiful day, having a picnic in the park.” She had lived in Chicago her whole life and had never seen downtown.

Finally, each of them said that their dream was to go to college and find a way to pay for it. None of these kids had parents that went to college. And one young man never had anyone in his family make it past junior year in high school. We went to work. I helped them with the applications and, in one case, literally raced to Loyola with my intern, making the deadline by three minutes.

When we were making real headway, one of the kids came to me and said he wasn’t going to college because his father was giving him grief about being better than everyone else. In fact, he almost dropped out of high school. But in the end, they are all in college. Three of them are seniors now and they all still call and text me from time to time. My dream is to go to each of their graduations.

Once people found out about the Dream Club, they started asking me to share the experience. A probation officer asked me to speak to students. The topic was how to be successful on juvenile probation. So I went to this school, and I saw a bunch of kids who seemed fairly bored and not real thrilled to see a judge coming in to speak to them.

Then one young man asked me about a police shooting in New York City. “How did the police get away with that?”

A lot of people ask judges questions like that. But I couldn’t answer that question because I didn’t know all the specifics. I wasn’t in the courtroom. I left thinking, “I did a horrible job and I am never going back to a Chicago public high school again.”

Still, I was really taken by their passion. As soon as that young man brought up the issue of the police and community relations, the whole room came alive. I was ignorant that this issue was a concern for kids. I thought, “With all the things that they have to worry about—violence, teen pregnancy, drug use, incarcerated parents and high unemployment—why do they care about the police-community relations?” They didn’t seem interested in talking to me about things that I thought had a more direct effect on their lives. Yet they were very interested in talking to me about the police and the community.

About a week later, the same probation officer asked me to speak at Fenger High School in front of about 100 kids. I thought, “Are you kidding me? Oh my God, this is nuts.” When I told friends that I was going to Fenger to speak, they said, “It’s a big a waste of time. Those kids aren’t going to listen. They’re going to act like wild animals. They’re going to completely disrespect you.” After all the stories I had heard, I was half expecting the principal to walk down the hallway with a gun in his hand and be like, “Okay, I gotcha covered, Judge!”

But Fenger was a beautiful school. It was clean, the floors were polished, and there was great woodwork all over the place. The teachers seemed energetic, and the students were in uniforms and seemed really well-behaved. I was really struck by that, because the principal told me earlier that day that a minor had been stabbed outside the school. So there was this contradiction that I was aware of as I walked the hallways.

The teacher introduced me: “All right, everybody, quiet down. Judge Sheehan is here, and she’s going to teach you about civics.” I was a bit shocked by that and said, “Thank you, but I am not going to teach you about civics. I came here today in spite of everyone telling me not to come.”

I continued, “I am not here to speak to you. I am here to listen.” You could have heard a pin drop.

I said, “I’m going to treat you with the respect that you deserve as young men and women. I expect the same—to be treated the same way—and if I’m not treated that way, I will leave. I will assume that you will behave like young men and women and that you and I can have a dialogue with each other.”

Well, I could see them sitting up straighter in their chairs. I could feel sort of the honor that was somehow bestowed in the room, the respect from them to me and me to them, and it changed the vibe of the room. I spoke for a while and then, just like before, a young man started aggressively questioning me about the police and his community and how they get away with what they get away with.

I could feel that I was losing them as they aligned with their classmate. I tried to convince him, the young man, that there were good and bad police, same as with any group. But he just said, “You ain’t out here. You don’t know.” And then he kept saying, “What are you gonna do about the problem? What are you going to do?”

And finally I looked him square in the eye and said, “What are you going to do about it?” And that stopped the room. I mean, the room was quiet.

And then he looked at me and said, “Well, what can I do about it?”

I said, “I don’t know. I guess you can do what you just did. Speak up when you see injustice. But it’s easier to be a victim and say what’s wrong than it is to be a part of a solution. It’s a whole lot harder, and it takes a lot more courage to be part of the solution.”

And at that moment, I had a sudden image of police and youth sitting together at a round table to talk about their conflict, a safe place to deal with this pain. Because I saw that most of this was born out of pain and crisis. So I asked, “Would you be interested in sitting in a circle not invested in blaming someone, but invested in a solution to this problem?”

He said he would. And, after my talk, about ten kids came up to me and asked, “Are you really gonna do that?”

I said, “I guess I have to now.” That is where the journey began.

I started talking about my idea to anyone that would listen. I was referred to a wonderful group called Community Justice for Youth Institute (CJYI). The group was very active in communities, using restorative-justice tools like peace circles. Since that day at Fenger High School, there have been many circles involving police and youth. Not long ago, I helped organize a daylong summit of 80 police and youth. They exchanged ideas, laughter and tears with each other. They lunched together and even participated in a “street yoga” session.

We created a video to share this success and to help cities from across the country find solutions to conflict. During a recent restorative-justice conference in Oakland, a Chicago team met with a member of the Oakland City Council, as well as the city attorney and chief of the school-district police, among others, to share the video. Later, officials in Oakland decided to show the video at a full city council meeting to demonstrate a way that all parties can address issues in a constructive way. I am not sure if the Chicago Police even know that they had that kind of positive effect on another city. Organizing peace circles is rewarding, but the time has come for these kinds of restorative practices to be institutionalized and become an integral part of the system. In order for real change to occur, there must be joint effort from communities, restorative-justice practitioners and individuals at the highest level of government. If we value peace, healing and cooperation, we all must give our time and treasure to it. Like Juvenile Court, it’s complicated and takes effort. But it’s worth it.