Dr. Chertoff received his Bachelor of Science degree from Hunter College in New York. He received his medical degree from Rutgers Medical School in New Jersey. He did his medical training at Beth Israel Medical Center in New York, Hospital of Joint Disease Orthopaedic Institute in New York and Boston University School of Medicine in Massachusetts.
Dr. Chertoff also did fellowships at AO International Trauma in Malaga, Spain, Boston City Hospital – Trauma in Boston, Massachusetts and University of Louisville for hand surgery in Louisville, Kentucky.
In 1981, Dr. Chertoff joined the staff of the former Medical West Community Health Plan, now know as RiverBend Medical Center. In 1983, he started his private practice of orthopaedic and hand surgery.