James Winston

James R. Winston Jr., 61 of North Chesterfield, VA departed this life on March 31, 2025. He was affectionally known as “Jimmy Winston” to many who knew him, and Pop Pop Jimmy to his grandchildren.
He was born October 6, 1963 to the late James R. Winston Sr. and Hester B. Alston in Clifton Forge, VA. He was a member of the Healing Hearts Ministries in Chester, VA
Jimmy grew up in Covington, VA where he attended Covington High School. He played football and basketball. He was an avid sports fan. He also loved cars and always wanted to look good and have his clothes matching whenever he stepped out. He loved to travel, eating and spending time with family and friends.
Jimmy was a well rounded guy who never knew a stranger. He was a funny dude, full of life, jokester and friends to a lot of people whom he came in contact with.
Jimmy was an entrepreneur, CEO and owner of Winston’s Lawn Care Services and also worked as an independent truck driver for many years. He had big dreams and aspirations about what he wanted to do in life.
In addition to his parents he was preceded in death by his step father Harry “Pete” Alston Sr. Brother William “Billy” Brown and sister, Michelle McKnight.
He leaves to cherish his memory his devoted wife and friend Doritha Winston. His son Antwon R. Starkey, West Virginia, two bonus sons William Quarles, Phillip Foster Jr. (Richmond, VA) daughter Karita Winston (Ameilia VA). He has two brothers Artis “Ricky” Brown, Jermaine (Kimberly) Winston both of Clifton Forge, VA. Two step brothers Michael Alston, Donald Alston, one step sister Cynthia Alston all of Roanoke VA, He has 12 grandchildren. He has 3 sisters-in-law Deloris Quarles, Covington, VA, Deborah Spencer, Richmond, VA, Delethea Quarles Harrisonburg VA and brother-in-law Rudolph Quarles Jr. Washington DC and Llewellyn Spencer, Richmond, VA. He has several cousins, nieces and nephews and a ton of friends near and far. He had few cousins who held a special place in his heart Debbie and Jimmy Barber and Alphonso Calhoun but he loved all of his family.
A celebration of life and memorial service will be held on Friday April 11, 2025 at 12 noon at the Gospel Tabernacle Church of God in Christ, 415 S. Alleghany Ave, Covington, VA. A repass will follow immediately after service.
The family of Doritha Winston sincerely would like to thank each and everyone for the prayers, phone calls, text messages and all acts of kindness displayed to the entire family.