Bernicestine and Harold Bailey: Celebrating A Westport Couple’s Lifelong Commitment to Philanthropy

Harold and Bernicestine Bailey believe philanthropy is about more than giving money to support worthy causes. It’s also about using our knowledge, passion, and time to create a better, more equitable world.

For Harold, that mindset led him to participate in the 1968 student ‘walkout’ at Brown that prompted the Ivy League university to change its admission practices and improve the on-campus experience for Black students.

It has subsequently fueled decades dedicated to championing the inclusion, belonging and engagement of Black and other students of color and alumni at Brown — and a calendar that remains full with volunteer and board commitments even during his retirement.

For Bernicestine, this mindset has been the driving force behind a lifetime of volunteer work, which has also included groundbreaking work at Brown, as well as serving as Board Chair of the Mary and Eliza Center for History and Community and former trustee for the Westport Library and Fairfield County’s Community Foundation.

And it’s why, together, they have spent the past 20-plus years working to advance diversity, equity, and inclusion through Team Westport — an  official Committee of the town of Westport that has played an influential role in changing government policies and improving the community’s understanding of DEI.

Bernicestine and Harold Bailey recently joined Fairfield County’s Community Foundation, The Community Foundation for Greater New Haven, Hartford Foundation for Public Giving, and The Prosperity Foundation for a webinar during which they and other leading Black Connecticut philanthropists discussed their commitment to social action.

The webinar kicked off Black Philanthropy Month — a global celebration held each August to recognize and honor Black individuals and their contributions to philanthropy and social justice. Black Philanthropy Month aims to empower Black individuals to invest their time, talent, and money to create a better future for Black people everywhere.

“It’s important that we participate in the celebration of Black Philanthropy Month because it’s another opportunity for us to engage with the younger generation of Black philanthropists,” Harold said. “One of the messages we focused on during the webinar was the concept of paying it forward, and how it isn’t always about the size of the donation, but also about the work and wisdom that a person dedicates that makes the difference.”

Bernicestine and Harold are living examples of the power of Black philanthropy.

Even as they built successful careers and raised two children, the couple has always found the time and energy to contribute to their community and to advancing opportunities for people of color.

Together, through Brown’s alumni association, they helped launch the minority alumni committee that spawned generations of BIPOC alumni leaders. They also co-founded the Investment in Diversity scholarship fund – the first campus-wide Ivy League scholarship fund focused on Black students and other students of color  – which is valued at more than $6 million.

And while they have been widely celebrated for their work — including each receiving an honorary doctorate from their alma mater and serving as a trustee — their philanthropy has never been about personal recognition.

It has been about justice and improving opportunity.

“It sometimes feels strange that people see us as this power couple or icon,” Bernicestine said. “But it is an amazing feeling — and we are very honored that we can lead the next generation by setting a good example for them. For that, we are grateful.”

Watch the webinar: Celebrating Black Philanthropy — Intergenerational Approaches to Social Action