Cover photo for James Dennis 'Jimmy' Gregory's Obituary
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James Dennis 'Jimmy' Gregory

April 5, 1953 — February 19, 2017

James Dennis 'Jimmy' Gregory

Mr. James Dennis "Jimmy" Gregory, 63, of Shaw, MS, passed away Sunday, February 19, 2017, at his home. Visitation will be 1:00 to 2:00 p.m. Thursday, February 23, 2017, at Ray Funeral Home in Cleveland, MS. Celebration of Life services will immediately follow beginning at 2:00 p.m. Thursday, February 23, 2017, at Ray Funeral Home with Bro. Tommy Worthey officiating. Interment will be in Delta Heights Memorial Garden Cemetery.
Mr. Gregory was born to James O. Gregory and Amy Denise Sims Gregory on April 5, 1953, in Cleveland, MS. On November 9, 1987, he married Mary Dianne Harrison in Florence, AL. His entire life he had a passion for flight and began flying school in Merigold at the age of 18. Upon completion, he started working for Harold Tapley in Shaw then later went to work for Boyle Flying Services. His love for agricultural flight came full circle when he was able to purchase Harold Tapley's Flight Services in 1991.
During his time as a pilot he was a member of MAAA and recently received an Honorary Lifetime Membership Award in 2016. He often said to Dianne that he was so blessed to do what he loved for over 40 years, and in 2004 he retired to spend time with his family and his beloved recliner. He and Dianne turned into a regular "Fred and Daisy", and they loved every second of it.
They were together 24-7 after his retirement, and if two people were not meant to be, they could not live in harmony… but Jim and Dianne were meant to be. What they shared was an example of true love and dedication. Mr. Gregory was a loving husband, father, and brother, but his entire life revolved around his three grandchildren whom he described as the joy in his life and he always spoke highly of them. At a young age, Mr. Gregory's parents instilled old fashioned values and the love of the Lord in his heart and he passed this down to his family as well. You often could find him singing and playing hymns and enjoying music. He and his wife shared a strong love for horses. He was a gifted horse trainer, and he enjoyed training walking horses, as well as breaking, selling, and raising colts from their mares with his wife, Dianne. These horses took a huge part in the famous tomatoes that he was known for. He had a secret for growing the best around and he did it the old fashioned way with ingredients that came directly from their beloved horses and their barn. Well, his secret is out! Mr. Gregory was a true comedian by heart. He was naturally funny and entertaining, and he was known to give some outrageous nicknames to everybody he knew especially his grandchildren.
His first grandchild, Averie Claire, was given the pet name "Spark Plug" because her initials were AC which connected to AC Delco. His grandson, Wyatt, was given the pet name "Stymie" because if anything could get messed up, Wyatt could handle it. His last granddaughter, Parks, received the pet name "My Sweet, Pretty Girl". Most could describe him as one of a kind, and an outstanding character. In his spare time, he enjoyed western books and movies and probably held the largest collection in Bolivar County. Most importantly, he enjoyed life. He said often, "We've had a lot of heartache, Dianne, but we've had a real good life." He is preceded in death by his parents, James O. Gregory and Amy Denise Sims Gregory; and sons, James Matthew Gregory (11-18-1994) and Michael Allen Johnson (07-23-2007). Mr. Gregory is survived by his wife, Dianne Gregory of Shaw; daughter, Aimee Lori Gregory of Jackson; grandchildren, Parks Elizabeth Garrott of Jackson, Averie Claire Johnson of Ruleville and Matthew Wyatt Johnson of Ruleville; daughter-in-law, Casey Kent (Trapper) of Ruleville; siblings, Suellen Rogers (Keith) of Boyle, Denise Worthey (Tommy) of Cleveland, and Henry Gregory (Angie) of Cleveland; and a host of nieces, nephews, extended family members, and beloved friends. Pallbearers will be Lawrence Reginelli, Garth Tindle, Keith Rogers, Johnny Robinson, Jerry Harrison, and Johnny Sumrall. Flyover pilots will be Gene Jones, Ike Brunetti, John Horn, Fred Roark, and Brad Ouzts. In memory of Mr. Gregory, the family asks donations be made to St. Jude Children's Research Hospital.

Interment



3:00 am Thursday, February 23, 2017
Delta Heights Memorial Garden Cemetery Hwy 8 Cleveland, Mississippi, United States

Visitation



1:00 pm - 2:00 pm Thursday, February 23, 2017
Ray Funeral Home 206 Bishop Road Cleveland, Mississippi, United States

Celebration of Life



2:00 pm Thursday, February 23, 2017
Ray Funeral Home 206 Bishop Road Cleveland, Mississippi, United States
To order memorial trees or send flowers to the family in memory of James Dennis 'Jimmy' Gregory, please visit our flower store.

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