James Alexander Miles, Sr.

James Alexander Miles Sr. affectionately known to many as “T-Bird”, 80 of Shipman, VA earned his heavenly wings on October 6, 2026, at Hillsdale Health & Rehab in Charlottesville, VA. He passed away with his beloved wife and her faithful son by his side.

He was born in Charlottesville, VA on February 17, 1946, to the late Charles E. Miles, Sr. and Frances L. Miles.

James grew up in Nelson County, where he attended local schools through the tenth grade. At the young age of 16, his uncle, Clifford Allen, taught him how to drive tractor-trailers, igniting a lifelong passion for the open road for generations to come. After gaining years of valuable experience driving for several different transportation companies, James turned his expertise into entrepreneurship by organizing his own independent operations out of Shipman, Virginia, including M&M Trucking LLC and B & M Trucking. Known across the region for his strong work ethic and exceptional skill, “T-Bird” was highly respected by fellow drivers on and off the road.

Beyond his work, James truly loved life’s simple pleasures and spending time with his family. He had a deep, special bond with his grand and great grandchildren. James was famous for his sense of humor; if he knew you, he had created a nickname just for you. He spent hours talking on the phone with his truck-driving buddies and family, often jokingly teasing them by saying, “I thought you had moved to China,” even if they had just spoken a day or two before. In quieter moments, he found peace just sitting around, watching the vehicles roll by on the road.

James was preceded in death by his first wife, Rev. Betty Miles; his two sons, James A. Miles Jr. and Walter O. Miles; his daughter-in-love Samantha Miles; his parents, Charles E. Miles, Sr. and Frances L. Miles; brother Charles E Miles II; his grandson Jerel Q.O. Harris; his nephew, John Bego, Jr.; his niece, Kiera L. Miles; his aunts Claire Allen & Shirley Woodson; his brothers-in-law Walter Allen Jr., Ralph Allen, & George Allen.

His love and legacy will be cherished and carried on by his surviving family: his Devoted wife of 25 years Maxine Miles; Son, Kevin Miles Sr. (Kelly); Stepdaughter; Poochie Bartee (Edward) Sisters, Gloria Miles and Jacqueline Bouknight (David, Sr.); Brothers-in-law, Alfred Rose (Laufan), Warren Allen, Melvin Allen (Robin), Herbert Allen (Ann), and James Allen; Aunts, Gladys Fleming & Alice Jeffries; Uncle, Clifford Allen; 22 grandchildren and 28 great grandchildren as well as a host of nieces, nephews, cousins, and friends.

A funeral service will be conducted at 1:00 p.m. on Saturday, October 17, 2026 at Pleasant Grove Baptist Church with Pastor Anton Thompson officiating.

The family will receive friends one hour prior to the service.

Interment will follow in the Miles Family Cemetery in Shipman.

Arrangements by Wells/Sheffield Funeral Chapel, Lovingston (434-263-4097).