Dr. Caldwell completed his undergraduate studies at Wake Forest University in Winston-Salem, North Carolina, and earned his Doctor of Medicine at the Medical College of Virginia in Richmond, Virginia. Following medical school, Dr. Caldwell completed an Orthopaedic Surgery Residency at the Medical College of Virginia, followed by a Sports Medicine Fellowship at the Mississippi Sports Medicine and Orthopaedic Center.

Dr. Caldwell has practiced at Tuckahoe Orthopaedics Associates Ltd. since 2005, and he is the President of Orthopaedic Research of Virginia. His areas of interest include injuries to the shoulder, elbow, and knee. He specializes in arthroscopic treatment of labral and rotator cuff injuries in the shoulder and the knee's meniscal, ligament, and cartilage injuries. Dr. Caldwell also serves as a master instructor at the Arthroscopy Association of North America courses in Chicago and the tournament physician for the ATP and WTA.