Pilot was renowned for his poetic depictions of urban life and landscapes. Born in St. John’s, Newfoundland, he moved to Montréal with his widowed mother, who later married the artist Maurice Cullen. Under Cullen’s influence, Pilot began sketching outdoors and developed a sensitivity to light and atmosphere that would remain central to his art. After serving in the First World War, he studied at the Art Association of Montreal and in Paris at the Académie Julian and the École des Beaux-Arts, where he absorbed Impressionist and Post-Impressionist currents. His early works combined French artistic influences with distinctly Canadian subjects, especially views of Old Montréal, Québec villages, and winter streets.

By the 1930s and 1940s, Pilot had established himself as one of Canada’s most respected painters. He became a full member of the Royal Canadian Academy of Arts and exhibited internationally, including at the Royal Academy in London and the Paris Salon.  His paintings are now held in major institutions such as the National Gallery of Canada and the Montreal Museum of Fine Arts. Today, he is remembered as a master interpreter of Québec’s urban and rural character, and as a bridge between the generation of Canadian Impressionists and the emerging modernists.