Photo courtesy of Rudy-Rowland Funeral Home - Henderson
Feb 8, 1946 - Aug 26, 2025
Robbie was truly one of the most caring and genuine people I’ve ever known. He valued his friendships so much, that he didn’t hesitate to support and help in any way he could. I personally saw him in action in this regard. He was inspirational. We never discussed religion, but he demonstrated Christian values. I will miss you, Robbie.
EJ Logan Christopher
August 31, 2025 | Henderson, KY | Friend
I miss you,Dad.
Jansen Dilley
August 31, 2025 | Fulton, MO | Daughter
Affectionately known as “Rob”, “Robbie”, “Bob”, “Papa Rob”, and “Papaw”, he died Tuesday, August 26, 2025. Rob was born on February 8, 1946, in Henderson, KY, to James Herman Gregory and Allena Galloway. He was one of four children including Nancy, Larry “Mack”, and Michael “Mike”.
Rob graduated from Henderson County High School in 1964, and then from Murray State University in 1968, after which he enlisted in the Army and retired as a 1st Lt. from his duty and tour in Vietnam.
He married his first wife, Janet “Kay” Hart, on 6/8/1968 and together, they had daughter, Jansen in 1970. They were married until 1975. They remained friends and co-parents to Jansen until Rob’s passing.
He then married second wife, Deborah “Debbie” Brooks, in 1978, and she brought a son, Greg Walters, from a previous marriage. Rob loved Greg as his own. In 1980, Debbie and Rob had son, James “Jamie” Gregory. Rob and Debbie were married until her death on 2/22/1999.
Rob was the type of person who would do anything for you at the drop of a hat and cared deeply about all of his family and friends. Quoted by his sister, Nancy, “He was the best brother ever. He was so selfless, he always cared, and was always willing to help with whatever was needed.”
Rob had an outgoing personality, and he never met a stranger. He served and loved his country and respected anyone who did the same. He was a member of the Veteran’s Association, and his favorite pastimes were fishing with his son, Jamie, and collecting antiques.
Rob was a wonderful father, brother, uncle, grandfather, great-grandfather, and friend. He was loved and will be missed by all who had the pleasure of knowing him.
He was predeceased by his father James, his mother Allena, his brother Mack, and his second wife, Debbie.
Rob is survived by sister, Nancy Gregory Sommer and husband, John, and their daughter, Stacy, and son, Brad; Rob’s brother Michael “Mike” Gregory of Rockford, IL; Rob’s first wife, Kay Powers, of Springfield, MO, and their daughter, Jansen Dilley and husband, Michael, of Fulton, MO and their daughter, Lauren Fulton and husband, Ken and their two children, of Union, MO; daughter Lindsay Kuhel and husband, E.J., and their two daughters of Mabank, TX; Rob’s sons, James “Jamie” Gregory of Fulton, MO; son, Greg Walters and daughter, Adrianna Steiner and her husband Jake; and his special friend and classmate, Lois Harper of Henderson, KY; as well as two great- grandchildren.
Private family services will be held at a later date.
Please know that Rob Gregory loved each and every one of you and will always be with you. Rob will be greatly missed by everyone whose lives he touched.
Rudy-Rowland Funeral Home in Henderson, KY, is in charge of arrangements.
Online condolences may be made at www.rudyrowland.com.
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