William Winfrey Diggs, 78, husband of Penny Jean Diggs, passed away peacefully on September 17, 2025, at home surrounded by his loving family. Born on November 7, 1946, he was raised in the Messick area of Poquoson, and later was a long-time resident of Seaford, Virginia.

Winfrey was preceded in death by his parents James William “Futs” Diggs, Jr. and Sarah Virginia Diggs and a daughter Keresa Gayle Diggs. He is survived by his devoted wife of 32 years Penny Diggs, as well as his children Michelle Breeland, William Winfrey “Bill” Diggs, Jr. (Antonia), Kimberly Anne Sperling (Todd) and Sandy Findlay (Kevin); his grandchildren Robert Bellamy, Jessica Rafnson (Dylan), Daniel Bellamy (Tristan), Karen and Daniel Sperling, Alex, Mia and Sophia Diggs, Judiah, Rourke and Irelyn Strouse; and his great grandchildren Damien and Kairi Bellamy; Ella, Willow and Kaden Rafnson, Owen and Justice Bellamy, Jayden, Martin and Rosey Ortiz.  He is also survived by his siblings Hilda Spain (Bob), Elmer Diggs (Debbe), and Debra Bunting (Grayson) as well as many beloved extended family members and friends.

Winfrey attended Poquoson High School and took on the family tradition of working the water at age 12. He crabbed out of the Chesapeake Bay in a deadrise boat named for his daughter Kimberly Anne. Crabbing and fishing were the first of many careers Winfrey would pursue. He served as a Marine Patrol Officer of the Virginia Marine Resources Commission.  He earned an associate’s degree in criminal justice, leading to his role as a Deputy Sheriff for the York-Poquoson Sheriff’s Office where he achieved the rank of sergeant.  Winfrey enjoyed every kind of hunting and fishing with beloved friends and family members.

A celebration of life will be held at Tabernacle United Methodist Church led by Rev. Eric Vaudt, 831 Poquoson Avenue, Poquoson on September 23 at 10 a.m. followed by a reception. In lieu of flowers, memorial contributions may be made to the York-Poquoson Sheriff’s Office Community Fund (K-9 Unit), P.O. Box 99, Yorktown, VA 23690, or the charity of your choice.