Claude and Britney, Two Donald Stewart Fellows, Reflect on How Their Commitment to Community Led Them to the African American Legacy Fund

Claude Robinson and Britney Robbins joined African American Legacy (AAL) from different paths—Claude as a staunch advocate for uplifting African American communities; Britney as CEO and founder of Grey Matter Experience, a nonprofit supporting youth entrepreneurship. Established in 2003 as an educational and philanthropic initiative of The Chicago Community Trust, AAL was created when leaders at the Trust and in Chicago’s African American community recognized the opportunity to expand reach and impact in African American neighborhoods. Each year, on behalf of The Chicago Community Trust, African American Legacy awards the Donald Stewart Fellowship to an individual who embodies leadership and service within their communities in Chicago. Donald Stewart was a distinguished educator and leader who, in addition to becoming the first African American CEO of The Chicago Community Trust, built a national reputation for championing education and equity. Both Claude and Britney received this honor and later became AAL board members, describing their journey as one shaped by recognition, relationship and responsibility.

In this conversation, Affinity Funds Specialist Carrie Goodale sits down with Claude and Britney as they share how the fellowship shaped their paths, what drew them to serve, and why they believe AAL’s collective philanthropy creates lasting impact for Chicago’s South and West side communities.

You both crossed paths in different ways before joining the board of AAL. How did the Donald Stewart Fellowship impact your lives and the work you were doing at the time?

Claude Robinson: For me, receiving the fellowship was incredibly fulfilling because it recognized the work I was deeply invested in at the time. I was at UCAN (Uhlich Children’s Advantage Network) leading community engagement efforts along with diversity, equity and inclusion initiatives, and supporting youth development in ways that felt both urgent and meaningful. The award created space for me to do even more of that work while also offering a platform to showcase the projects and impact already underway. It illuminated my leadership style, how I build relationships, get things done, and stay grounded in community. It sparked genuine excitement among my colleagues, board members and staff. Many of them hadn’t heard of the Donald Stewart Fellowship before, so the recognition not only affirmed my contributions but also introduced more people to Mr. Stewart’s legacy and the transformative work he championed.

Britney Robbins: I knew AAL primarily through my work as a grant recipient, so receiving the fellowship immediately sent me down a rabbit hole of learning everything I could about Donald Stewart—not only was he the first African American CEO at the Trust, he made tremendous contributions in diversity, equity and inclusion, in education, and in expanding opportunities for African American communities in Chicago. I felt extremely honored to be chosen to carry even a small part of his legacy. The award also helped me understand the full breadth of what AAL does—not just its grantmaking, but the intentional way it preserves Mr. Stewart’s vision and selects fellows who truly embody his values.

At the time, it was a pivotal moment for Grey Matter, and the $25,000 in unrestricted support made a real difference. We were focused on building internal capacity, and those funds allowed us to bring on additional staff so we could better serve our students. The fellowship strengthened us financially, but it also elevated our visibility and credibility in ways we hadn’t experienced before.

How did your fellowship experiences influence your decisions to join AAL?

CR: For me, joining AAL felt like a natural continuation of the work I’ve always done advocating for African American communities and the organizations serving them. Becoming a board member gave me a chance to stay connected, but from a different angle—helping guide decisions, spotlight organizations doing transformational work, and stay in community with people who share those values.

BR: After becoming a Fellow, I started attending more AAL events and connecting with board members, and I immediately felt a strong sense of belonging. It was one of the few rooms where I felt comfortable as my full self and affirmed in my leadership. I wanted to be intentional about serving on a board where I felt such alignment with the mission, vision and values.

You came into AAL from different starting points—one through a fellowship, one through grants. How do those paths compare in terms of impact?

CR: Recognition was the game‑changer for me. It affirmed the work I was already doing and allowed me to highlight people and projects that might otherwise get overlooked. It deepened my connection to AAL and strengthened my sense of purpose around lifting up community stories.

BR: For me, investment was the catalyst. AAL wasn’t just a one‑time funder; they supported Grey Matter for four years. That consistency brought credibility, and other funders took notice. It helped us build staff, networks, and the foundation that led us to our 10‑year milestone. That kind of long‑term belief in emerging leaders makes a huge difference.

Through your roles on the AAL board, how do you hope to contribute back to the community, and what impact do you see AAL’s grants having across Chicago?

CR: I want to keep bridging philanthropy and community by creating spaces where people can show up as themselves, and I want more people to know who Donald Stewart was. His legacy deserves to be protected and amplified. This ties directly to the impact—AAL helps elevate organizations that deserve more recognition. Their work becomes visible, supported and connected to a broader network. That ripple effect is powerful and needed.

BR: I want to help AAL grow into a long‑term anchor institution. I also bring the perspective of someone who’s been on the other side of the grant process. I hope to use that insight to shape our strategy, our RFPs and our planning in ways that truly meet community needs. When I think about impact, AAL’s grants don’t just strengthen organizations; they strengthen ecosystems. For us, unrestricted dollars meant more staff and more hands to support young people. AAL’s multi‑year grant helped us open doors, build trust and grow sustainability.

Looking ahead, how do you hope to stay connected to philanthropy and community beyond your AAL board service?

CR: I’ll always stay connected. Partnerships are the backbone of Chicago, and I want to keep being a connector across sectors. This work is part of who I am.

BR: For me, philanthropy is lifelong, whether I’m raising funds or helping direct them. Representation matters in these spaces, and I want to keep opening doors for young people who don’t yet know philanthropy can be a career path.