James was born on December 1, 1943, in Rubottom, the son of James Jackson and Mildred Marcella (Miller) Caldwell. He was raised in Leon where he also attended schools and graduated with the Class of 1962. Following graduation, he moved to Andrews, TX where he worked in the oil field until he was drafted into the military. James served in the United States Army from March 9, 1965, until he was honorably discharged on February 15, 1967. During his service, he earned the rank of Specialist E-4 and was awarded the Expert Rifle, Good Conduct, and National Defense Service Medals. James was stationed in Frankfurt, Germany where he was a radio telecommunications operator and specialized in teletype during the Viet Nam War.

When James returned from the service, he made his home in Marietta where he worked at Marietta Sportswear. A few months later he met and fell in love with Carol Wheeler. They married on February 2, 1968. Together, they made their home in Kingston.

James began taking classes at Murray State College in August of 1968. He graduated there with his associate degree in 1970. He then attended to Southeastern Oklahoma State University in Durant, OK where he earned his bachelor's degree in education focusing on biological sciences in May of 1972. James began teaching biology and chemistry at Kingston High School in August of 1972. He immediately started working on his master's degree in education administration at SOSU. James earned that degree in 1974. That same year, he accepted the middle school/high school principal position at Springer, OK Public School. After one year there, he returned to Kingston to serve as high school principal for three years. During his principal tenure, James attended classes at the University of Oklahoma, Oklahoma State University, and completed his superintendent's certification at Central State University in Edmond, OK. He accepted the superintendent position at Kingston in 1978 where he served for the next 13 years. In June of 1991 James accepted the superintendent position in Barnsdall, OK and served there until June of 1994. He then served as superintendent in Antlers, OK, until his retirement in 1998. In August of 1998, James and Carol returned to their home in Kingston. James spent the next 25 years in his yard and garden and spent countless hours with his children, grandchildren, and great-grandchildren. He was always proud of the vegetables he grew, his yard, his wife, and the accomplishments of his children and grandchildren.

James is preceded in death by his parents, Jack and Mildred; two brothers, Jackie Ray Caldwell and BG Caldwell; and three sisters, Janice Graham, Rhonda Navarro, and Mary Buckaloo.

Those left to cherish his memory are his wife, Carol of the home; son, Jason Caldwell and wife Melissa of Kingston; daughter, Jamie Schrunk and husband Jordan of Kingston; six grandchildren, Jessica Bumpass and husband Bryce of Kingston, Jaime Furister and wife Hannah of Healdton, OK, Daniel Furister of Kingston, Hunter Caldwell of Katy, TX, Christopher Salas and wife Mallori of Prague, OK, and Phoenix Salas of Kingston; eight great-grandchildren, Parker Young, Hadley Bumpass, Remington Furister, Konner Furister, Banks Bumpass, Avalon Salas, Haven Caldwell, and Bowen Furister; sisters, Callie McGill and husband Vance of Thackerville, OK, Carmen Cox of Marietta, and Marcy Bartee and husband Tony of Marietta; and brothers, Mike Caldwell and wife Connie of Sanger, TX, Robert Caldwell and wife Connie of Ardmore, and Bill Caldwell and fiancée Deanne of Marietta.