For forty-eight years, Roy Greenaway was a top investigative journalist for the Toronto Star, where he broke such news stories as the discovery of insulin. He also interviewed Al Capone in Chicago, who provided the quotable quote “I don’t even know what street Canada is on.” For his remaining two decades at the newspaper, Greenaway was a member of the Press Gallery at Queen’s Park. In 1966, the year of his retirement, he published an autobiographical book entitled The News Game.

Greenaway was also a self-taught painter, who exhibited with the Royal Canadian Academy of Arts in the 1940s and had his first solo show in 1958. “On his way home from work,” as Colin S. MacDonald writes, “he sketched scenes of old buildings and streets now demolished.” The title of this painting refers to Chestnut and Elm Streets in Toronto, now no longer recognizable as a neighbourhood, but then part of the adjacent Italian district.