Billy Joe Gregory, Sr. Obituary

Billy Joe Gregory, Sr.

November 20, 1939 - April 2, 2026

Billy Joe Gregory, Sr. Obituary

Billy Joe Gregory Sr., age 86, of Wytheville, Virginia, and formerly of Harvard, Illinois, went home to be with his Savior on April 2, 2026. A man who believed the joy of the Lord was best shared through laughter, Joe was a natural at telling stories and jokes, ensuring that no one ever left his presence without a smile.


Joe lived a full and hardworking life. A graduate of Wauconda High School in Illinois, he spoke often of his years working for Hartwig Plumbing. A former coal miner, he also built his family a home with his own hands at the top of Windmill Gap, West Virginia. While residing there, he shared his faith and musical talents performing and writing songs with the Southern Gospel groups, "The Glorybound Singers" and "The Gregory Family.


Throughout his adulthood, Joe found happiness in cooking, gardening, camping, restoring vehicles, watching Westerns, attending car shows, and carpentry—often with his one-time best friend, Harley the boxer, by his side.


Before entering his final years of care, Joe was a beloved fixture of his neighborhood on

Freedom Lane in Wytheville. He was happiest sitting on his porch, greeting both friends and

strangers alike and talking for hours with the neighbors who became his dearest friends. He

cherished his trips to town to visit local restaurants, attend shows, and find the perfect produce at the farmers markets.


Joe loved Jesus and his family fiercely, but he spent many years looking forward to a very specific homecoming. We take great comfort in knowing that he is finally reunited with his beloved mother, Lena, whom the family so affectionately called "Gommy."


Joe is survived by his sisters: Rosella Rickert, Carol (Butch) Schade, and Pat Hensley. His legacy lives on through his children: Brenda Lee (Gary) Krabbe, Sandra Dee Olbrich, Tina Jo (Wallace) Williams, Billy Joe (Brandy) Gregory Jr., and Robert "Bob" (Heather) Gregory. He was the proud grandfather of David (Jessica) Krabbe, Keshia (JP Poroj) Krabbe, Jeremiah (Allison) Enberg, Jenny (Keith) Salas, Heather Gills, Evan (Amanda) Gills, Derek Williams, Brittany (Steve) Blackwell, Dylan (Taylor) Williams, Lexey Gregory, Leah Gregory, Dillon (Emily) Sennett, Dakota (Donnie Jones) Sennett, and Leland Gregory.


His spark continues in his great-grandchildren: Myah and Eliana Krabbe; Ezekiel and Uriah Poroj; Braxton Anderson; Isaac, Monroe, Bellamy, and Malia Salas; Jonah, Reece, and Anistyn Ayers; A.E. Gills; Courtney, Logan, and Kamree Williams; Samuel, Presley, Penelope, and Maggie Blackwell; Kenzy and Lainey Williams; Carson Sennett, and Oaklynn Jones; as well as his great-great-grandchild, Baylen Moses.


Joe was preceded in death by his father, Norman Gregory; his mother, Lena Gregory; an infant son, Baby Boy Gregory; brother, Robert Gregory; sister, Glena Faye Tudor; son-in-law, Tony Olbrich; and great-granddaughter, Lena Lee Krabbe.


The family wishes to extend a special thanks to the staff at Carrington Place in Wytheville for

their care over the last several years. Deepest gratitude is held for his long-term caretaker and

daughter-in-law, Heather Gregory, who devoted many years of compassion to being by his side; he loved her as if she were his own. The family also thanks Wythe Hospice for their support during his final days.


Per Joe’s wishes, he will be cremated by Grubb Funeral Home. There will be no formal funeral service; instead, the family will hold a celebration of life at a later date in Joe's honor.


Condolences may be sent to the family at: The Williams 745 Pinch Creek Rd Bland, VA 24315. Expressions of sympathy may be sent to the family at www.grubbfuneralhome.com

Grubb Funeral Home is in charge of the arrangements.

Billy Joe Gregory Sr., age 86, of Wytheville, Virginia, and formerly of Harvard, Illinois, went home to be with his Savior on April 2, 2026. A man who believed the joy of the Lord was best shared through laughter, Joe was a natural at telling stories and jokes, ensuring that no one ever left his presence without a smile.


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