Community Hero Diyawn Caldwell helps prisoners, their loved ones


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.

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.





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