Local government administrator. Born in Kilmarnock, Calderwood was the son of a mill worker and union official who had risen to become Provost of Darvel. He was educated at William Hulme's School in Manchester (England) and studied law the University of Manchester. He went on to serve successively as Town Clerk of Salford (1966-69), Bolton (1969-73) and Manchester (1973-79). He returned to Scotland as Chief Executive of Strathclyde Regional Council (1980-92), then the largest local authority in Britain responsible for providing services to half of Scotland's population. He went on to serve as Chairman of Greater Glasgow Health Board (1993-97). He was also a Governor of Glasgow Caledonian University and Deputy Chairman of Scottish Opera (1992-96).