Crickett Woloson: 2025 Colleen Willoughby Award Recipient

A Visionary in Trust-Based Philanthropy

Crickett Woloson, an avid runner, recently participated in a marathon where a participant’s tee shirt read “hard but difficult,” which resonated with her.  Still, as she added, things can be challenging, rewarding, and not executed perfectly, all at the same time.  These words describe how she navigated and ultimately became an impactful force in the philanthropic landscape of Baltimore through pioneering initiatives that integrate social justice, racial equity, and trust-based philanthropy (TBP) into the city’s funding ecosystem. As a leading visionary in the Baltimore Women’s Giving Circle (BWGC), she has co-chaired a team that has played a pivotal role in reshaping its values, streamlining grantmaking processes, and elevating its reputation within the greater Baltimore community.

Challenging the Status Quo in Philanthropy

Beyond her work with BWGC, Crickett and her husband founded the Elbow Fund, a donor-advised fund dedicated to supporting Baltimore’s Black-led nonprofits through trust-based principles. The Elbow Fund focuses on leadership development, mentoring, and strategic planning for social change organizations. The fund fosters grassroots leadership and increases investment in historically underfunded initiatives by prioritizing direct community engagement.

Her early advocacy for TBP placed her ahead of many in the philanthropic sector, positioning the BWGC and the Elbow Fund as trailblazers in equity-driven grantmaking. Her contributions were nationally recognized when she presented on TBP at the 2023 Philanos annual conference in Baltimore.

Extending Impact Beyond the Giving Circle

Since joining BWGC in 2009, Crickett has served in multiple leadership roles, including founding co-chair of the Racial Equity, Diversity, and Inclusion (REDI) Committee, established in response to the 2020 racial justice movement. She also co-chaired the Nominating and Leadership Committee and served on the Steering Committee, guiding the organization through challenging yet necessary conversations about equity in philanthropy.

Through her dedication, Crickett helped implement key initiatives such as revising the BWGC’s mission and values, developing equity-centered programming, and launching a Grants Learning Laboratory. These efforts reshaped BWGC’s approach to funding, increasing engagement with community-led organizations and adopting more equitable grantmaking practices.

Addressing Critical Needs in Baltimore

Baltimore’s Black-led nonprofits receive disproportionately low funding from traditional philanthropic sources. Recognizing this gap, Crickett has made it her mission to bridge the divide by fostering partnerships between funders and community leaders. As Director of the Elbow Fund, she identifies and uplifts emerging Black leaders, mentors them, and removes systemic barriers to funding and resources.

Her dedication extends beyond financial support. Crickett has facilitated educational programs and collaborative opportunities between grassroots organizations and institutional funders by leveraging relationships built over years of deep community engagement. This has strengthened the infrastructure of Black-led nonprofits and empowered them to drive sustainable change in their communities.

Philanthropic Collaboration and Leadership

Crickett’s commitment to collective giving is exemplified through her support of CLLCTIVLY, a Black-led organization that fosters collaboration and resource mobilization for social impact groups in Baltimore. Through the Elbow Fund, she has co-developed groundbreaking funding initiatives, including:

• Hand-in-Hand & Round of Applause Awards (2024) – Recognizing and funding ten organizations modeling deep collaboration and liberatory practices, with an additional $100,000 in community-directed grants distributed across 30 organizations.

• Solidarity Awards (2023) – Partnering with CLLCTIVLY for the annual CLLCTIVGIVE event, providing unrestricted funding to 15 organizations committed to racial justice and community empowerment.

Personal Journey in Philanthropy

Crickett’s philanthropic philosophy evolved through personal reflection and education. Her exposure to Baltimore’s systemic inequities led her to embrace community-driven solutions. Her participation in B’more Invested further reinforced her commitment to participatory grantmaking, where community representatives, rather than institutional donors, determine funding allocations. This model has redefined how philanthropy operates in Baltimore, ensuring that those closest to the challenges have the power to implement solutions.

Legacy of Impact: Crickett Woloson’s Transformative Philanthropy

Crickett Woloson’s work is a testament to the power of intentional, trust-based philanthropy. Baltimore’s nonprofit sector has leaned toward equity, collaboration, and community-driven decision-making through her leadership, creating a more inclusive and effective philanthropic ecosystem.

At the heart of her approach is Collective Giving, a model that fosters diverse perspectives, encourages shared decision-making, and sparks creativity. For Crickett, collective giving isn’t just about funding—it’s about bringing people together, inspiring social connection, and deepening their understanding of their communities. Centering the perspectives of both grantees and members ensures that philanthropy is a continuous learning process that builds trust and creates lasting impact.

Crickett has been incredibly passionate about the potential for giving circles, to offer more than just financial contributions—they create educational opportunities, collaboration, and empowerment opportunities. Women in giving circles gain insight into their communities' realities, form meaningful connections, and work collectively toward sustainable change.

Receiving this award reflects the collective effort behind the Giving Circle. “The work we’ve done took time, trust, and a commitment to listening,” Crickett shares. “It wasn’t a straight line, but we built something meaningful together.” She emphasizes that philanthropy thrives when decision-making is shared, voices are heard, and adaptability is embraced. Her leadership continues to inspire funders and changemakers, proving that philanthropy led by trust becomes a catalyst for lasting social impact.