Seventh Annual Donald Stewart Fellowship Awarded to Richard Wallace

Each year, African American Legacy, an initiative of The Chicago Community Trust, awards the Donald Stewart Fellowship to an individual who embodies leadership and service within African American communities in Chicago. Donald Stewart was a distinguished educator and leader who built a national reputation for championing education and equity and became the first African American CEO of the Trust.

This year’s awardee is Richard Wallace, founder and director of Equity and Transformation (EAT). Founded by and for formerly incarcerated individuals, EAT works with Chicagoans in the informal economy to elevate their voices, strengthen workers’ rights, and support pathways to stable income. The informal economy includes people who earn income outside of traditional jobs, such as street vending, home‑based businesses, cash‑paid work, and other forms of work that are not regulated, taxed, or protected by the state. Richard sat down with the Trust to reflect on his journey and what receiving the Donald Stewart Fellowship means for his life’s work.

Take us back to when this work first felt like yours to do. What was happening in your life then, and how did that experience lead you to the work you’re doing today?

This work first felt like mine when I was a kid. My mother worked in prison ministry and took me with her to facilities across Illinois. Inside those prisons, I met some of the most brilliant people I’ve ever known, and even then, I couldn’t understand why so much wisdom lived behind bars instead of in our communities. That question stayed with me, especially after I later became system impacted, having been directly affected by the courts and incarceration system. It helped me believe that transformation was possible.

For a time, that sense of purpose showed up through music and poetry, using rap to talk about economic exclusion and the challenges Black men face. When I became a father and needed stability, I studied sociology at Roosevelt University and applied for an organizing job at the Chicago Workers Collaborative. Organizing Black and Brown temp workers helped me see people realize their own power, and that experience showed me this was the work I was meant to do.

Much of what I do today also traces back to 2016, when I was selected as part of the inaugural Atlantic Fellows for Racial Equity which is a global fellowship for leaders committed to advancing racial equity. For the first time, people invested in me financially, emotionally and intellectually, and that support made Equity and Transformation possible. We officially founded EAT in 2018 as I grappled with how to shine a light on informal and survival economies that are often dismissed or criminalized. That understanding shaped our work from the beginning, whether knocking on doors in neighborhoods like Englewood, Austin, and across the West Side or publishing the Survival Economies Report. Today, EAT has 11 staff members, and my role as executive director focuses on fundraising and supporting the team. We’ve endured major challenges because of the strength of our system impacted leadership team and our commitment to centering healing.

What was your first reaction when you learned you were receiving the Donald Stewart Fellowship?

When I learned I was receiving the award, my mind went straight back to a younger version of myself at Illinois Youth Center in St. Charles, being constantly told I would not amount to anything while still quietly believing that anything was possible. What stayed with me most, though, was thinking about the young people who are still there. I want them to know this story and understand that no matter what people around them are saying, they matter, their ideas matter, and their lives have value. I believe their experiences, no matter how difficult, can shape a vision for a world where this kind of suffering no longer exists. Making that connection in that moment took my breath away and reminded me how far I have come and why this work matters so deeply.

Before Equity and Transformation existed, what gaps did you see that led you to found this organization? Was there a specific person or situation that stayed with you and grounds the work you lead?

Before Equity and Transformation existed, I kept running into the same problem. While organizing in the temp labor sector, I met a young man on the West Side near Madison and Pulaski. We worked hard to get him placed in a job, and he did everything right; showed up every day, worked hard, never missed a shift. Around 90 days, when he was eligible to be hired full time, the company ran a background check and fired him. Months later, I saw him back on the block. When I asked what happened, he said, “I’m just trying to eat.” That moment exposed a core contradiction: we demand people work to survive, deny them access to stable jobs, and then punish them for poverty. I also saw system impacted people’s stories used to shape policy without including us in leadership. Those gaps led to Equity and Transformation. Today, we address them by supporting people holistically, through healing, economic stability, organizing, and research grounded in lived experience, in communities like Austin, Englewood, West Garfield Park, Joliet, and Peoria.

Donald Stewart believed in developing leaders and institutions that serve communities over the long term. Is there someone you’ve worked with in your organization that exemplifies the leadership you seek to cultivate? What did you see in them and what did it feel like watching them step into their own power.

For me, the person who really exemplifies the leadership we try to cultivate at Equity and Transformation is Alonzo Waheed. He joined us in 2019 during our second year and immediately showed deep commitment to the work. He started as an intern, moved into organizing, and eventually stepped into policy work. Today, he is our policy director. What has meant the most is witnessing the very human milestones along that journey like getting his driver’s license back, building credit, securing stable housing, and choosing where he wanted to live. Those changes did not just improve his financial situation; they transformed his emotional and psychological well-being. I have lived that kind of transformation myself, but seeing it unfold in Alonzo’s life has been one of the greatest joys of this work. Watching him grow into not just a leader, but a partner helping move this mission forward, reflects the kind of long-term leadership development Donald Stewart believed in and what we are committed to building.

Looking ahead, how do you build on Donald Stewart’s legacy through this award, and what impact do you want your work to have on Chicago’s communities in the years to come?

Looking ahead, I hope people take one clear thing from my story: investing in system impacted leadership is essential to equity. We have to trust people with lived experience to lead, even when that challenges how society is used to seeing us. Equity is not possible without that trust.

I also hope my story encourages other system impacted people to believe in themselves and step into their own power. That path doesn’t have to look like mine. I chose nonprofit work, but I want the next generation to step into law, healthcare, technology, or whatever they imagine, believing their lives are full of possibility.

For me, this award is about amplification. I hope it opens space for people who feel unseen to take their next step, while being honest that this work takes time, education, and sustained effort. Building on Donald Stewart’s legacy means committing to the long view, developing leaders, trusting impacted voices, and creating institutions that last. If people walk away believing in themselves a little more, then I’ve done my part.