Dr. Fleming, upon completion of his secondary education at Philips Academy, Andover, Massachusetts, attended Princeton University, graduating with a degree in Biochemistry. He received his medical degree from Columbia University College of Physicians and Surgeons in 1972. His surgical internship and residencies were completed at the Roosevelt Hospital in New York and his orthopaedic residency at the New York Orthopaedic Hospital of the Columbia Presbyterian Medical Center. He served as an orthopaedic surgeon at the Naval Regional Medical Center while on active duty in Charleston, South Carolina.