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Canadian artist Phil Richards has said he considers portraiture to be “a collaboration between artist and subject.” Perhaps nowhere is that more clear than in a tiny last-minute change in his newly unveiled portrait of former prime minister Stephen Harper. The portrait includes many details and Easter eggs (more on that in a moment) but at the very top of the image is a collection of flags, one from New Brunswick, the ancestral home of Harper’s family. Barely visible (it’s a fraction of an inch across) is a red banner flying from the ship on the flag. Richards painted it flying the...