In 1981, Craig was a member of the team that represented John W. Hinckley, Jr., who attempted to assassinate Ronald Reagan; Hinckley was found not guilty by reason of insanity. Craig worked in the office of Senator Edward M. Kennedy as his chief defense, national security, and foreign policy aide from 1984 to 1988. Craig also defended Ted Kennedy's nephew William Kennedy Smith on charges of assault; William Kennedy Smith had earlier been acquitted on rape charges in 1991.