John Whitecross was born in Winnipeg on February 12, 1919. Whitecross attended Robert H. Smith School and St. John's Cathedral Boys School, prior to serving in the Second World War. During the war Whitecross was a member of the Royal Canadian Navy who say duty in eastern and western commands and in Newfoundland. This period was followed by studies at the University of Manitoba, culminating in a bachelor’s degree in Architecture completed in 1949. After his studies, Whitecross was employed by the City of Winnipeg, working as a designer and planner; he registered with the Manitoba Association of Architects in 1951. Many of his works are defined by a modernist approach to design. Beyond his work, Whitecross was known as an avid outdoorsman.