Never achieving stardom as a player (excepting an F.A. Cup appearance for non-league Sutton United F.C against Leeds United F.C in 1970), Gradi embarked on an off-pitch career as a coach and manager. His first positions were at Chelsea F.C, followed by Derby County F.C, Wimbledon F.C, Crystal Palace F.C and Orient.
He eventually travelled to Crewe to become manager of Crewe Alexandra F.C in June 1983. He took the club from the bottom of the then Fourth Division to the First Division by the late 1990s, becoming the League's longest serving manager in the process.
His ability to spot talent in young players and to develop this is well-known. Graduates of the Gradi school include England internationals David Platt, Geoff Thomas, Danny Murphy and Seth Johnson, Welsh internationals Robbie Savage and David Vaughan and Northern Ireland internationals Neil Lennon and Steve Jones. A host of other players have achieved caps below 'full' international status - eg: schoolboy, under-18, under-21, etc.