Born in Trenton, New Jersey, Ryan grew up in a house, "that revolved around going to games" and went to high school at the Lawrenceville School from 1960 to 1964. He graduated from Boston College as a history major in 1968. Ryan and his wife Elaine have a daughter Jessica, and a son Keith who died in 2008. They are grandparents of triplets. They have been married since 1969. Today, Ryan lives in Hingham, Massachusetts. The dedication page in Forty Eight Minutes, one of Ryan's books, says, "To Elaine Ryan: In the next life, maybe you'll get a nine-to-five man who makes seven figures." Ryan has also done humanitarian fundraisers for years to help inner-city teenagers with their educations.