This painting was done by Heald in honor of the President of the Crow Wing County Historical Society, who passed away in 1934. Heald could have chosen to depict Hole-In-The-Day because he was a great leader, similar to Henry Cohen, or it may just be because Heald was fascinated by Hole-in-the-Day and early Crow Wing County History. In her short story "Waseya," she writes about Hole-in-the-Day and his many wives. In this artwork, she paints him in a fairly standard portrait, paying attention to his beadwork, his braided hair, and the feathers within it.