Robert Anthony Gregory, Sr., age 70, affectionately known as “Tweety,” and “Greg,” to family and friends, was born on April 23, 1955, in Gloucester, VA. His parents were the late Nathaniel and Doris Berry. He departed his earthly life for eternal rest in peace with the Lord on August 17, 2025, in the Newport News Nursing and Rehabilitation Center, Newport News, VA.
Robert Sr. was previously married to the late Shirley Shabazz, with whom he had two children: Robert Gregory, Jr., and the late Tanika Gregory. He later married the late Flora Dandridge Gregory. This union blessed him with four daughters, Yvonne Coates, Tammy Ashby, Tina Ashby, and Sherry Shepperd. They enjoyed 33 years of marital bliss, and she was also his companion at the Newport News Nursing and Rehabilitation Center until her passing in 2021.
He was educated within the Gloucester County Public School System and subsequently pursued studies in Ministry. After establishing residence in Williamsburg, VA, he was employed by Sherwin-Williams Paint for several years before accepting a job at Eastern State Hospital (ESH), where he served as an Aide for 4 years, and then as an Inventory Specialist for 17 years. Due to health issues, he medically retired from ESH with 21 years of dedicated service.
From an early age, Robert Sr. displayed a warm spirit and a natural gift for making others feel at ease. His childhood was marked by moments of joy surrounded by parents who instilled the values of compassion, faith, and resilience. As he grew, his commitment to helping others became evident—whether it was lending a hand to neighbors, supporting friends in need, or simply sharing words of encouragement that brightened even the darkest days. His curiosity and a thirst for knowledge guided him toward many pursuits that would shape the man he became. Throughout his life, he was recognized for his engaging conversational skills, sharp wit, and distinctive laughter.
Robert Sr.’s dedication to service led him to work at various churches across VA, often accompanied by his wife, Flora. Both actively engaged in community outreach, traveling throughout the state to provide food for those in need and support for people experiencing homelessness, including those living under bridges. In addition to his professional and spiritual duties, Robert Sr. valued family time and frequently opened their home for gatherings. He was known for offering thoughtful advice, listening carefully, and providing steadfast encouragement. His impact extended beyond his immediate family, fostering lasting friendships built on kindness, resilience, and faith.
Robert Sr. enjoyed reading the Bible, watching westerns and Pittsburgh Steelers games, and listening to gospel music. At Newport News Nursing and Rehabilitation Center, he spent time in the breakroom with friends, joined social events, attended family gatherings, and joined in-house church services.
He treasured the consistent visits from his son, Robert Jr., who cut his hair and shaved him every few weeks. Having a personal barber was a routine aspect of his life. These occasions contributed to maintaining their special bond.
His cherished memories live on in the hearts of his son, four daughters, three sisters, four brothers, fourteen grandchildren, five great-grandchildren, nieces, nephews, in-laws, other relatives, and friends.
Robert Sr. will be truly missed but never forgotten. May he rest in peace.
