Holiday HOOPS & ARTS 25th Anniversary Year: Honoring Leadership During Black History Month

25 Years, 2000 Families, One Commitment

Holiday HOOPS & ARTS 25th Anniversary Black History Month marks a moment to reflect on leadership, service, and community impact.

From left to right, featuring founders Westley Holiday Sr. & Judy Holiday, Co-CEOs Faith Holiday & Westley Todd Holiday, board members Alisha Poitier & Shedrick Shields

Black History Month invites reflection on leadership that strengthens communities. As Holiday HOOPS & ARTS marks its 25th Anniversary year, we recognize a legacy built on service, discipline, and opportunity.

Founded in 2001 by Westley Holiday, Sr. and Judy Holiday, the organization was shaped by leaders who believed mentorship could change trajectories. A first-generation college athlete, Westley Sr. ranks number 22 on Bethune-Cookman University’s all-time men’s basketball scoring list and has spent more than 30 years as an educator and coach. Judy Holiday, a longtime social work leader and entrepreneur, has overseen multimillion-dollar Medicaid contracts while remaining deeply engaged in community service. Both were recently honored with the Bethune-Cookman University Vanguard Alumni Award in recognition of their lasting impact.

Over the past 25 years, that commitment has helped more than 2,000 youth and families pursue personal success.

Today, the mission continues through a broader leadership team committed to those same standards. Co-CEO Faith Holiday is a three-time Florida Regional Championship Coach and has led Holiday HOOPS teams in dozens of championship games across the country over the past 12 years. Faith emphasizes mentorship, discipline, and accountability both on and off the court. Co-CEO Westley Todd Holiday is a former Broadway artist/performer and a Columbia University graduate with a Master of Science in Nonprofit Management. He was named 2025 Strategic Advisor of the Year at the Fluxx Awards in Las Vegas for his leadership and strategic impact.

Holiday HOOPS & ARTS is further strengthened by leaders across its Board and Advisory council, including Board Members Alisha Poitier, an international online influencer who amplifies the organization’s voice and reach, and community health advocate and nurse practitioner Dr. Shedrick Shields, whose work reinforces the organization’s commitment to youth wellness. They are all but a sampling of the powerful Black and multicultural leadership within HH&A. More of our amazing roster of leaders can be found on our Governance Page here.

“Strategy matters, but people matter more. Every system we build only has value if it lifts someone up.”— Westley Todd Holiday, 2025 Fluxx Awards, Las Vegas

Black History Month is an opportunity to recognize leadership rooted in responsibility. For 25 years, Holiday HOOPS & ARTS has remained committed to helping young people obtain personal success, and that work continues.

As part of our 25th Anniversary year, we invite the community to join us at our Community Celebration on Saturday, March 21, 2026 from 10AM to 2PM.

Learn more and register here:https://www.holidayhoops.org/event-details/25th-anniversary-community-celebration