Keith R. Gregory

Keith Ravone Gregory, 33, of Virginia Beach, Virginia, passed away on October 12, 2025, just a few days shy of celebrating his 34th birthday. He was born on October 17, 1991, in Virginia Beach to Sandra Hayes & Harry Winstead.

Keith was a proud graduate of Landstown High School and a devoted member of New Hope Baptist Church. Known for his humble spirit and unwavering faith, Keith loved God with his whole heart. He brought joy and laughter to everyone around him and was deeply loved by his family and friends.

A man of many talents, Keith enjoyed singing, drawing, grocery shopping, and watching football especially when cheering for his favorite team, the Dallas Cowboys. He had a passion for gaming and could often be found playing on his PlayStation, challenging friends to friendly competitions.

Keith also shared his vibrant personality and opinions through his own Facebook talk show, “Red & Blue Pill Show,” where he discussed life, perspective, and what it meant to be an “alpha male.” His creativity, humor, and authenticity made him unforgettable.

Keith will be deeply missed by all who knew him, but his laughter, love, and light will continue to live on in our hearts. And as he would say, “Man, order me some Grubhub  I ain’t waiting on these doctors.”

Keith leaves to cherish his memories his parents, Sandra Hayes & Harry Winstead; stepfather, Winchaus Hayes; siblings, AnJanai Gregory, Shaquierra Gregory, Dominique Gregory; grandmother, Gloria Smith; uncles, Lawrence Gregory (Sylvia); Luculus Gregory, Ronnell Muhammad, Gary Ward; other family, Phyllis & Mattie, Jamar Andrews, Ameshia Gregory; aunt, Arlene Gregory; and a host of other relatives and friends.