Randy Gregg is the owner of five Stanley Cup rings from his time with the Oilers, despite a string of retirements and medical-school commitments. Gregg, an Edmonton native, was a teenage hockey player of note, but he was also a genius. The University of Alberta had accepted him at age 16 and three years later, in 1975, he began the study of medicine. Currently, Dr. Gregg has a successful practice in the city of Edmonton.