Community Hero Diyawn Caldwell helps Alabamians navigate a failing prison system

Diyawn Caldwell, founder and president of Both Sides of the Wall and organizer of the Alabama Prison Strike, works on her computer at her home in Pensacola, Florida, on Jan. 8. Her husband is in an Alabama prison.
Diyawn Caldwell, founder and president of Both Sides of the Wall and organizer of the Alabama Prison Strike, works on her computer at her home in Pensacola, Florida, on Jan. 8. Her husband is in an Alabama prison.

You can’t have prisons without walls. And those walls naturally separate us into two groups: those inside them and those outside them.

But there’s a space between those two groups, too. That’s where Diyawn Caldwell does her work, helping folks on both sides of the prison wall.

‘You have to fight for those that you love’

Caldwell, 45, didn’t plan on being an advocate for Alabama prisoners. Although her family roots were in the Yellowhammer State, Caldwell was born into a military family and grew up on bases around the world. Her family settled in Alabama in 1992.

After graduating from Troy University, Caldwell entered corporate America, working in cybersecurity. In 2015, she met Cordarius Caldwell while he was incarcerated. After hearing firsthand about the reality of daily life in Alabama prisons — from his living conditions to the food he ate and the treatment he received — she knew she wanted to make a change.

“Seeing what's going on with someone that you truly love, I mean, it can only spark a fire under you,” Caldwell said. “It just didn't sit well with me.”

Diyawn Caldwell, founder and president of Both Sides of the Wall, and organizer of the Alabama Prison Strike, with a picture of her and her husband Cordarius Caldwell at her home in Pensacola Florida Sunday, January 8, 2023. Her husband is in an Alabama prison.
Diyawn Caldwell, founder and president of Both Sides of the Wall, and organizer of the Alabama Prison Strike, with a picture of her and her husband Cordarius Caldwell at her home in Pensacola Florida Sunday, January 8, 2023. Her husband is in an Alabama prison.

She cashed out her retirement in 2017, and she dove headfirst into advocacy, working with organizations and coalitions that were fighting for better treatment of prisoners. She also spoke before the Alabama Prison Study Commission about the toll that incarceration can have on their family members.

“Every time I hear of another stabbing, my heart sinks,” Caldwell told the commission, adding that the stress of worrying about her husband had caused her to have a heart attack.

In 2019, she decided to start a group of her own and began building Both Sides of the Wall. All the while, she’s had to push back against the notion that those in prison don’t deserve dignity because of the crimes that put them there.

“Committing a crime does not equate to a living death sentence or inhumane treatment,” Caldwell said. “You have to fight for those that you love. We do that [in the free world], so why would we sit down on our hands and allow our loved ones that are incarcerated to be treated unfairly and unconstitutionally?”

For her efforts advocating for Alabama prisoners and assisting their loved ones across the state through her organization, Both Sides of the Wall, Caldwell has been named the Montgomery Advertiser’s Community Hero for January. The honor is sponsored by South University.

Helping 'in any way possible'

Communication from one side of the prison wall to the other can be difficult, often leaving families guessing about their loved ones’ wellbeing. People across the state with incarcerated family or friends know that sometimes getting the most basic facts from the Alabama Department of Corrections — like whether their loved one is alive — feels nearly impossible.

“The biggest obstacle we face is the Department of Corrections unveiling the truth about anything that's going on within [the prisons],” she said.

That’s where Caldwell steps in. Because she’s gone through the same things, she knows who to get in touch with to get answers. She’s developed an extensive network of contacts throughout the prison system that can check on other prisoners and report back to her. And because she works at it full time, she can put more pressure on officials to provide those answers than people who don’t have that luxury.

But lack of access to reliable information is only one struggle that loved ones of the incarcerated face, she said. As a spouse of someone in prison, she knows the toll it can take, emotionally, financially and otherwise. Her organization provides funds for the incarcerated and their loved ones for food, hygiene products, phone calls, stamps and legal fees.

The group just assists residents from across the state “in any way possible.”

“Just to help these families navigate through this system that’s not designed to help us gives me joy. And I’m proud to do it, to help them, because I’ve been there when I didn’t have anyone, and I had to figure things out myself,” she said.

Christina Horvac, co-director of Both Sides of the Wall, estimates the organization gets 10 calls a day from people needing help. Horvac said Caldwell is the perfect person for the job, with the knowledge, outspokenness and loving heart needed to be successful.

“She is probably one of the sweetest people you’ll ever meet in your life, and she’d literally give anyone the shirt off of her back,” Horvac said.

‘We wanted to take a stand’

Last summer, as Caldwell was talking with other activists, prisoners and loved ones, they decided they needed to take some public action. It had been more than two years since the U.S. Department of Justice had sued Alabama over the conditions of its prisons — some of the most violent, overcrowded and understaffed in the country — and it seemed like nothing had really changed. To make matters worse, the Alabama Bureau of Pardons and Paroles was granting fewer paroles than ever before, causing more prisoners to sink into despair.

They planned a protest to be held outside ADOC’s Montgomery headquarters on Sept. 26. When they told some of the prisoners, they came back with another idea: a labor strike.

Alabama prisoners provide food, laundry and custodial services in the facilities, and many also work in manufacturing plants for pennies an hour. Those goods are sold to government offices and private consumers through Alabama Correctional Industries. The plan was simple: Don’t generate revenue for them until they listen to what they had to say.

Diyawn Caldwell, left, speaks during the Break Every Chain Rally on the Alabama Capitol steps in Montgomery on Oct. 14, 2022. The protestors were asking for prison and parole improvements.
Diyawn Caldwell, left, speaks during the Break Every Chain Rally on the Alabama Capitol steps in Montgomery on Oct. 14, 2022. The protestors were asking for prison and parole improvements.

Caldwell worked for weeks to organize the protest. When the day finally came, she walked into ADOC’s office and delivered a letter pleading for reforms to the parole board and state sentencing guidelines.

The labor strike made national headlines before ending about three weeks later.

Their demands weren’t met. But there were wins, like raising awareness of Alabama’s prison crisis and unifying loved ones of the incarcerated.

“Small wins turn into big wins, so we take what we can get and keep compounding on those,” she said.

Her organization held another rally in Montgomery in October, and Caldwell said she’s planning for more.

Community Heroes Montgomery

Community Heroes Montgomery, sponsored by South University, profiles one person each month.

The 12 categories the Montgomery Advertiser will focus on: educator, health, business leader, military, youth, law enforcement, fire/EMT, nonprofit/community service, religious leader, senior volunteer, entertainment (arts/music) and athletics (such as a coach).

Do you know a Community Hero?

To nominate someone for Community Heroes Montgomery, email communityheroes@gannett.com. Please specify which category you are nominating for and your contact information.

Evan Mealins is the justice reporter for the Montgomery Advertiser. Contact him at emealins@gannett.com or follow him on Twitter @EvanMealins.

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This article originally appeared on Montgomery Advertiser: Community Hero Diyawn Caldwell helps prisoners, their loved ones