Gregory H. Caldwell

July 31, 1953 ~ August 31, 2021 (age 68)

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Retired Master Sergeant, Gregory H. Caldwell, 68, departed this life on August 31, 2021 in Tyler, Texas. He was born in Taylor County, Kentucky on July 31, 1953.

Greg served proudly in the United States Air Force Special Operations for 20 years.  During his service he was awarded many medals, awards, and citations too numerous to mention.  After retiring from the Air Force, Greg earned his Bachelor of Science degree in both math and computer science from Texas A&M Commerce.  He also retired as the technology administrator from Cumby Independent School District in Cumby, Texas.

After his second retirement, he and his wife, Cindy, bought a home on the shores of Lake Bob Sandlin in Pittsburg, Texas.  They enjoyed spending time together fishing and going for evening rides on their pontoon.

Survivors include:

His beautiful bride of 24 years, Cynthia V. Caldwell

His children, Heather Sanders and fiancée Randy Helmberger, Joshua Martinez, Louis Martinez and Erica Newsom (Cole).

He is also survived by his mother Christine Rice, one brother Joseph Caldwell (Kelly). Three sisters, Cherita McFarland (Rick), Missy Roy (Jeff), and Janet Biggs and a special cousin Kathy Cox (Jimmie), a daughter-in-law, Kim Soushek (Jim) and a sister-in-law, Judy Caldwell.  Six grandchildren and many nieces and nephews.

Greg was preceded in death by a son, Josh Roche, his step-dad George Rice, his grandparents, Elmer and Beatrice Turner Caldwell, Twyman and Pearl Keltner Baker and by his brother Ricky Caldwell.  He was also preceded in death by a special aunt and uncle, Ruby and Phillip Keltner.

Cremation was chosen and a graveside service with full military honors will be held on November 6, 2021 at 1 PM CST at Bethany Baptist Church, 4560 Greensburg Rd, Columbia, KY.

In lieu of cards and flowers, the family request donations be made to Special Operations Warrior Foundation, 1137 Marbella Plaza Dr., Tampa, FL 33619, in Master Sergeant Gregory Caldwell’s name.


To send flowers to Gregory's family, please visit our floral store.


Memorial Service
November 6, 2021

1:00 PM
Bethany Baptist Church Cemetery
4560 Greensburg Rd
Columbia, KY 42728
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