John W. Caldwell

John W. Caldwell

John W. Caldwell, a retired Air Force officer, combat veteran, command pilot, businessman, rancher, political operative, mentor to many and friend to all, passed away peacefully on April 28, 2021, in Santa Rosa Beach, Florida, with his family by his side. 

He was preceded in death by his younger brother, Perrin Lowrey Caldwell of Senatobia,  Mississippi. 

John leaves his loving wife of over 70 years, Pearl (Judy) Jank Caldwell; sons, John Williamson Caldwell IV and wife Marjorie McMeans Caldwell; James Perrin Caldwell and wife Jana Mason Caldwell;  grandsons, John “Will”  Williamson Caldwell V and Jackson McMeans Caldwell; many nieces and nephews and too many friends to list here. His impact on them was remarkable. 

Born March 14, 1925, John was the son of John W. Caldwell Jr. and Lady Grace Lowrey Caldwell of Helena, Arkansas. After the death of his father in 1934, he attended school in Florida and Mississippi. In 1943 he enlisted in the U.S. Army Air Corps and attended Concord College in West Virginia. He was selected for fighter pilot training at Craig field in Selma, Alabama and was commissioned as a 2nd lieutenant. He attended advanced fighter training in Texas at Harlingen and Randolph Field. He became a command pilot in both the P-47 and P-51 fighter aircraft, as well as rotary wing aircraft. 

In his 27-year military career, he completed five  tours of duty in the Pacific and flew over 25 different aircraft types including piston engine fighters, multi engine bombers and transports, fighter jets, and rotary wing. In 1947 John suffered severe injuries resulting from a plane crash in the Philippine Islands and was sent to San Antonio where he met his wife “Judy”, an Army 1st Lieutenant and registered nurse at Ft. Sam Houston. They were married on May 15, 1950, in Biloxi, Mississippi. After the transition from the Army Air Corps to the U.S. Airforce in 1948, he underwent flight training in rotary wing aircraft and became a helicopter pilot, volunteered for duty in Korea during that conflict, and completed 39 combat missions behind the lines in North Korea in 1953 in an Air-Sea rescue and infiltration role. After Korea John and Judy had two sons and were stationed in Washington DC, Florida, California, Hawaii and Texas. He retired from the Air Force in 1970. 

He is the author of the book “Bless Them All”, a collection of experiences in the Philippines as a pilot in the 44th fighter squadron, “The Guardians of the Pacific”. In 1970, he bought an underperforming business and turned it into a very profitable enterprise, providing his sons with the financial means to achieve their education and long-term security for his family. He retired to the family ranch in South Texas in 1985. 

John and Judy were active with the Goliad Presbyterian church, the Rotary club, local charities  and the Goliad nursing home. They raised Longhorn cattle, and John was actively involved in local politics (to both the delight and dismay of the local citizenry). John and Judy moved to Seagrove Beach, Florida in 2019 and were a common site in Seaside, where they frequently dined and chatted with friends in front of the Modica Market. He loved their ranch and Longhorns, beach fishing for pompano, and socializing with family and friends. 

He will be remembered for his kindness, outspokenness, incredible energy, outrageous practical jokes and his imagination. He shared his life experiences with his family and friends both to entertain, and to educate, and nothing pleased him more than to see a friend or loved one excel.

Our family wishes to thank his caregivers, Sue Knight, Angelia Lowrey, Paula Hughes, Amanita Robinson, Brooke Brighty, the Covenant Hospice nurses, Watercrest Senior Living and the Nurses at Sacred Heart Hospital Santa Rosa Beach for their incredible professionalism, compassion and kindness to John and his family. Also, to Charles and Carmel Modica, Melanie Scicluna and the staff at Modica Market in Seaside for making his last years so fun!

Services for John were held at Barrancas National Cemetery, located on Pensacola NAS, Wednesday, May 5, at 1 p.m. The funeral cortege lined up at 12:15 pm, Wednesday, May 5, at Olive Baptist Church Warrington Campus, 103 W. Winthrop Avenue, Pensacola, FL 32507, and departed at 12:30 p.m. sharp. In lieu of flowers, please consider a donation to the Gary Sinise Foundation.

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