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While working for several years as a freelance artist, Cummings was frequently published in the New York Times, The Canadian Forum, the Last Post, MacLean’s and the Toronto Star. In 1981, he was hired as the full-time editorial cartoonist for the Winnipeg Free Press. The fond is comprised of editorial cartoons, published in the Winnipeg Free Press, covering over two decades of political events. International leaders include Nelson Mandela.