Early Friday morning, February 19, 2021, Leonard L. Ashby Jr. peacefully entered into the Kingdom of Heaven. He was born on June 12, 1948, to the late Leonard Sr. and Emma Morning Ashby.

Leonard, attended the Williamsburg-James City County Schools.  He joined the United States Marine Corps, serving 7 years with tours in Vietnam and Okinawa.  Afterwards, he was employed by the US Government.   He accepted Christ as his personal savior and joined Mt. Gilead Baptist Church where he remained a member for over 30 years before recently joining Mount Pleasant Baptist Church.  Leonard was also a member of the Maceo Consolidate Lodge #124. 

On June 21 1969, he was united in holy matrimony to Paulette Cuffie.  They were blessed with three loving children and enjoyed 51 years of marriage.

Whether you called him Cutty Boo, GOAT, Lee, Dune, Uncle Leonard, or just friend, Leonard was loved, respected, and admired by many. He was skilled in so many areas.  A “Jack of All Trades”, Leonard was the “go to guy” for family and friends. If you needed a mechanic, locksmith, carpenter, electrician or just an ear to listen, you could go to Leonard for all that and more.  He loved his family dearly and was devoted to his grandchildren, attending as many of their events as his health allowed.  He was an avid golfer, loved bowling, fishing with his buddies and Pastor Ron Ellis, grilling, and playing cards with family and friends. Leonard loved coaching the “Topettes” softball team and played many years with different teams.  His presence was felt in the Williamsburg community and he will be greatly missed.   

He was preceded in death by his brother, Robert L. Ashby.  He leaves cherished memories with his loving and devoted wife, Paulette S. Ashby; son, Terrence Ashby (Linda); daughters, Shonda M. Ashby and Tamika L. Freeman (Steven); four grandchildren, Dante P. Ashby, Raven M. Freeman, Selina M. Ashby, and Brandon J. Freeman; three great-grandchildren,  Cayden and Christian Ashby and Skye Wooten; sisters, Brenda Jones (Quincy) and Jennifer Walton (Robert); aunt, Mary Wallace; uncle, Douglas Morning; sisters-in-law; Deanna C. Taylor, Aurelia C. Wallace; Debra C. Johnson, and Sarah C. Washington; brother-in-law, Willie J. Cuffie Jr.; special niece, Tracy Cuffie; a dear and devoted friend, John Moore; lifelong friend, Johnny Morman; special friends, Wilkco Carter and Leon Crump; and a host of nieces, nephews and other loving and caring relatives and friends.

A Homegoing service will be held 12:00 noon, Friday, February 26, 2021, at Mt Pleasant Baptist Church. Interment with military honors to follow in Williamsburg Memorial Park.  Due to the current health pandemic, only 50 people may be in attendance with facial coverings and social distancing requirements.  Facebook Livestream will be available at the start of the service.  A walk-thru viewing will be on Thursday from 4:00 p.m. to 6:00 p.m. in the funeral home. 

Professional services entrusted to the staff of Whiting’s Funeral Home, 7005 Pocahontas Trail, Williamsburg, Virginia 23185. 757-229-3011whitingsfuneralhome.com