Named as one of the school’s athletic greats in Kim Beattie's Ridley: The Story of a School
, Crawford attended Ridley from 1947-56, serving as a Prefect in his final year. Crawford began his career at Wood Gundy in 1966 and, after four years, joined Burns Fry (now BMO Nesbitt Burns). During his 29 years with the firm, he became one of their top brokers, a Vice-President, Director, and a ten-year member of the Chairman’s Council. Additionally, he opened and established the company’s London and New York offices. In 1997, Crawford joined Gordon Private Client Corporation, which was acquired by HSBC. In 1999, he co-founded McFarlane Gordon Inc. now known as MGI Securities Inc.
He joined the Board of Governors of Ridley in 1977 and faithfully served the school in his role as Board member, Vice-President and then as Chairman from 2000 to 2004. It was Gordon who flew to England in 1995 to persuade Rupert Lane to become Ridley’s eighth Headmaster. Crawford and his wife, Eve generously sponsored and loyally supported the school's MGI - Gordon Distinguished Speakers' Series. He died on March 3, 2017 in Toronto.