In this episode of Ask Dr. Sujay, part of the Sag Harbor Black History Series, Ambassador Sujay sits down with the late Bill Pickens — a six-generation pillar of Sag Harbor Hills — to reflect on the rich legacy of this historic African American beachfront community in the Village of Sag Harbor, Town of East Hampton.
Bill shares how his family’s journey began in 1908 with his Aunt Anna Holly, a teacher at Tuskegee University, founded by Booker T. Washington. He recounts the early days of Sag Harbor Hills, his father purchasing one of the original model homes in 1950, and the pride of receiving historic designation recognizing the community’s cultural and historical significance.
The conversation weaves together family photographs, childhood memories riding bikes with Colin Powell, professional accomplishments in global consulting, and reflections on the Sag Harbor Initiative — a moment that elevated the village onto the international intellectual stage.
More than history, this episode is about legacy, leadership, love, and stewardship. Bill speaks candidly about marriage, integrity, political hope, and the responsibility to protect one of the last remaining Black-owned beachfront communities in America.
This is a powerful remembrance of heritage, resilience, and the enduring spirit of Sag Harbor.
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