 Born in Cambridge, Massachusetts and raised in the Mayberry Village community of New Hartford, Connecticut, Flanagan graduated from Cornwall Academy after attending East Hartford High School for three years and earned a basketball scholarship to Hartwick College, but he dropped out after one year.Flanagan worked in Hartford before moving to Durango, Colorado to enroll at Fort Lewis College in 1967.Flanagan graduated from Fort Lewis in 1971 with a double major in elementary education and physical education.