Jack Charlton (Author) Jack Charlton, OBE, Freeman of the City of Dublin and Honorary Irish citizen, was an authentic footballing hero. Big Jack, The Boss, 'The Rainmaker' - Charlton was one of English football's most popular characters, enjoying success as a player and a manager, most notably as part of the England team that won the 1966 World Cup and later as manager of the Republic of Ireland national team from 1986 to 1996.