Photo Credit: Sterling Gilmore Photography
The three-day celebration of the 8th Annual WDB L.E.G.A.C.Y. Awards Weekend was about spotlighting Black business and making sure some prominent Chicagoland changemakers get their flowers. The event, created by Keeana Barber and hosted by WDB Marketing and its nonprofit arm, WDB Cares, mixed networking, recognition, and real support for business owners at every stage.
The weekend kicked off Friday with the L.E.G.A.C.Y. Talk Business Mixer. Entrepreneurs, panelists, and honorees gathered for food, conversation, and inspiration. Aisha “Pinky” Cole, founder of the fast-growing vegan chain The Slutty Vegan, delivered the keynote.
Saturday’s gala at 433 W Van Buren brought the heart of the weekend. Dressed to impress, guests honored standout leaders in the business community while tasting dishes from 15 Black-owned restaurants. The evening’s awards included:
- George Daniels – Leadership Award
- Trez Pugh – Community Award
- Myitii Sengstacke – Family L.E.G.A.C.Y. Award
- HRM Togbi Nyaho Tamakloe VI – Honoree, Visionary Leader from the Anlo Kingdom of Ghana
- Dr. Aleta “Englewood Barbie” Clark – Advocacy Award
- Tammera Holmes (posthumously) – Honored for her work with Aerostars, which introduced over 150 Black youth to aviation
Trez Pugh, owner of Sip & Savor, received a second nod for his community development work.
One of the night’s most anticipated moments was the announcement of the WDB Cares Young Entrepreneur of the Year Award, which came with $25,000 in cash and prizes.
The weekend wrapped with a Sunday brunch—a quieter moment to reflect, recharge, and share what’s next.
Barber, the force behind it all, continues to use the L.E.G.A.C.Y. platform to push Black entrepreneurship forward. Through WDB Cares, she’s also investing in the next generation with grants and business workshops focused on funding, marketing, and growth.
Here are some snapshots from the WDB L.E.G.A.C.Y. Awards Weekend, courtesy of WDB Marketing unless otherwise noted:
Photo Credit: Sterling Gilmore Photography
Photo Credit: Sterling Gilmore Photography
Photo Credit: Sterling Gilmore Photography
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