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Milton became involved with Air Canada in 1992, initially on a consulting basis. He was appointed executive vice-president and chief operating officer in 1996, and then became president and CEO in 1999. Shortly after he became CEO, American Airlines and Onex initiated a hostile takeover bid for Air Canada, which Milton helped to successfully defeat. Milton led Air Canada through significant restructuring. In 2004, he became chairman, president and CEO of ACE Aviation Holdings – a parent holding company under which the reorganized Air Canada and separate legal entities including Aeroplan, Air Canada Jazz, Air Canada Technical Services, Air Canada Cargo, Air Canada Groundhandling, Destina.ca and Touram (Air Canada Vacations) are held.