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Gregory H. Caldwell, 68, Columbia, KY (1953-2021)

Retired Master Sergeant Gregory H. Caldwell passed away on August 31, 2021 in Tyler, Texas. He was 68 years old.

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

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 fiancee Randy Helmberger, Joshua Martinez, Louis Martinez and Erica Newsom (Cole).
  • His mother Christine Rice
  • One brother, Joseph Caldwell (Kelly)
  • Three sisters, Cherita McFarland (Rick), Missy Roy (Jeff), and Janet Biggs
  • A special cousin Kathy Cox (Jimmie)
  • A daughter-in-law, Kim Soushek (Jim)
  • A sister-in-law, Judy Caldwell
  • Six grandchildren
  • 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.

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.

Grissom-Martin Funeral Home in charge of arrangements. Online condolences may be left at

This story was posted on 2021-09-09 20:18:07
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Grissom-Martin Funeral Home
Located one block off the Square at 200 Campbellsville Street in Columbia, KY.
To reach David and Cathy Martin, phone (270)-384-2149, or e-mail:
Large enough to serve comfortably; Small enough to serve personally.

G & G Monuments
Todd and Mandi Green and Jared Conover
1670 Liberty Road, Columbia, KY. email:, 270-634-0359
First Quality Marble and Granite

Stotts-Phelps-McQueary Funeral Home
Established 1922 | 210 Greensburg St., Columbia, KY 42728 | Jeff Jessie, Owner
270-384-2145,, email

Gregory H. Caldwell, 68, Columbia, KY (1953-2021)

2021-09-09 - Columbia, KY - Photo courtesy Grissom-Martin Funeral Home.
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