Ayanna Pressley’s Husband Spent 10 Years in Prison. Now He and Pressley Are Fighting for Re-Entry Reform

For U.S. Representative Ayanna Pressley of Massachusetts, the issue of prison re-entry is personal: Both her father and husband went through it themselves. Last week, her husband, Conan Harris, testified before the House Subcommittee on Crime, Terrorism, and Homeland Security on barriers to making a successful return from prison, drawing on his experience of reintegrating into his community after serving 10 years for drug trafficking.

When Pressley married Harris in 2014, he had already successfully reintegrated into the Boston community where he was raised. He had worked at Boston’s City Hall as a senior public safety adviser and would soon become executive director of My Brother’s Keeper Boston. And he had become an advocate for people like him who were struggling to restart their lives after a period of incarceration.

Harris and Pressley spoke with The Appeal about what the federal government’s role in re-entry should be, how Pressley is working to create pathways to success for incarcerated people, and how Harris was able to avoid the housing insecurity, unemployment, and other pitfalls that are common for people leaving prison. 

This interview has been edited for length and clarity.

In your congressional testimony, you said: “I am an ordinary person who has had extraordinary support.” What did that support look like when you left prison and were re-entering society, and can you pinpoint what part of that support made you succeed and get to where you are today?

Harris: Re-entry, as I talked about in the hearing, starts when you’re incarcerated. It is so crucial and important to do the work internally while you’re inside the institution before you come out. When I came home, I had to be prepared and ready for the resources that my family and other supports would be able to help me with. I think that one of the main things that was supportive was finding a safe place to sleep, rest my head, so I could collect my thoughts. All the other things that organizations can offer, like identification cards, are important, but it all starts with where you lay your head at night. And then employment was the second best thing. Being able to contribute to my household, being able to have money so I could be able to move from one place to another is so crucial, so important for one person to be entered back into society.

What are the major barriers you want to address when it comes to helping people re-entering society find a safe place to sleep at night?

Harris: It’s the political will to have transitional housing for people. I was very fortunate. I had a family who stood up and was ready for me to come home and offered me a room for some time to get back into society. I’ve seen through my work that everybody is not afforded the resources that I had. Everybody did not have an opportunity to come home and have a bed to sleep in at night. 

When we look at different cities and states, we see cranes up in the air, buildings being built, people being pushed out of their neighborhoods because rent is going up high. But we don’t see a political will to have transitional housing for folks coming home from incarceration. 

You also called for Congress to create a bipartisan advisory board of formerly incarcerated men and women. What would that board look like and what would its role be?

Harris: It’s so crucial and so important. A lot of times when people build stuff or think about how to help a population or a community, what they don’t think of enough is bringing people on board who have those experiences. I think one of the things that will make Congress more strong in their efforts to support returning citizens will be having people on the advisory board who can really give them some insight into what to do, how to do it, and the ability for it to be effective or not.

What do you see as the federal government’s role in reforming how re-entry works?

Harris: My wife and my congresswoman is doing great work around the People’s Justice Guarantee. But what I would say is it is really about laws and making it so the laws have the trickle-down effect to the state and to the city. 

Being able to bring back Pell Grants so folks can have a real shot at not just starting their education but earning their degree. That prepares them for when they come out and gives them skills to be able to compete in today’s workforce. Education was a lifesaver for myself. I never knew I could be smart as far as school is concerned until I got my first A in college. When I got my first A, it turned on a switch and it changed my life for the better because now I knew education was a possibility. Now I felt like I belonged, not just in school but everywhere else.  

Congresswoman, your father was also in and out of prison and you have always been close to someone with experience with the legal system. How have Conan’s experiences specifically shaped your views on criminal justice? 

Pressley: First I want to say I associate myself with all the comments Mr. Harris previously made. 

Secondly what Conan has helped me to realize is how many impacted persons there are when one person is incarcerated. I had my own lens and viewpoint as a child who was resentful and ashamed and living with very real societal and self-imposed shame and stigmatization because of my father’s incarceration. But I didn’t have the context to appreciate the things that I have appreciated through hearing Conan’s story about family members and the journey to go see him. He was one of the fortunate ones to have loved ones regularly visiting. When I go behind the wall with him now, it is heartbreaking. There are people there that haven’t had a visit from anyone in years. Conan did have people who were going and that really underscored for me that a big part of successful reintegration and re-entry is maintaining not only familiar bonds but relationships. Prison is cruel and it erases your humanity because there are so many demoralizing things that happen. You’re void, in solitary, of human touch. You’re void of dignified shelter. You’re void of quality food. And then on top of it, not only are there a number of unjust things happening, but they’re all very profitable. How much it costs to make a phone call or the challenges to put money on someone’s books. All these things have been privatized, monetized, and created a huge for-profit industry. 

When I talk to Conan, I get the experience of what it was like for his mother for many months to have an incarcerated son. The disproportionate burden borne by mothers whose partners are incarcerated. Just taking two and three buses to go do a visit. Conan sharing his own lived experiences has given me greater insight into what we need to do to make sure folks are coming out ready to make their greatest contribution. They’re eager to do that. It’s just about affording people the tools in advance of their release, queuing them up to be their most successful selves. 

People are leaving and they don’t have an ID and they’re leaving with less than—a Boston re-entry study found that returning citizens in Boston leave prison with less than $400. Thirty percent of incarcerated men and women are being released to homeless shelters. And then even though we have reform in Massachusetts, there’s still great employment discrimination. Conan’s family did not live in public housing, but there are many upon re-entry whose families live in public housing, and there are policies that don’t allow them to successfully reunite or that family risks eviction. 

So many of those who were making money illegitimately have a transferable skill set to make money legitimately and to make a very positive contribution, but that starts behind the wall, as Conan was saying, with Pell Grants, with workforce development training, with real jobs waiting for people when they get out. 

How can you release people to homeless shelters? They’re leaving with little money, they don’t have an ID, perhaps they’ve been away for 20 years and they don’t know how to use a phone or a computer. And now we’re saying, go make a contribution, go get a job, and if you don’t do that, you’re likely to recidivate and it’s simply because you want to be here. You’re just a born criminal. No. These are folks that want to make a positive contribution for their own self pride. 

How would the People’s Justice Guarantee address issues with re-entry?

Pressley: We have got to have re-entry programming, workforce development training, that begins behind the wall. Access to behavioral health, because … 95 percent of incarcerated people will be released from prison, returning to society—95 percent. It’s in our best interest to make sure that they are mentally whole, that they have the skill set to be productive, and that when we’re talking about training in trauma, that it is gender-specific and responsive. 

I have visited women behind the wall and the training they were getting was literally needlepoint. That’s not preparing any of them to be successful. It requires a formidable investment to guard against recidivism. It behooves everyone for us to make these investments. 

As many of the things that can be queued up behind the wall as possible, whether that’s registering to vote if you have those rights in your state, whether it’s getting an ID, whether it’s already having a job lined up. That was game-changing for Conan. When he came out, he had a job waiting for him. 

The People’s Justice Guarantee calls for the establishment of a federal agency with the sole responsibility of improving supports and services for returning citizens. It includes removing restrictions on occupational licenses, because even if you are doing training behind the wall for barbery or cosmetology, if folks are denied pursuing a license because they have a record, then that was in vain. We have to remove those barriers. This does disproportionately affect women trying to get into professions like nursing, teaching, cosmetology. 

I do think we can get to an 80 percent decrease in incarceration. There’s a lot of genius that is dying on the vine after people have reformed and rehabbed themselves and gone through a restorative justice process.