His father was also named Hole-In-The-Day, and the younger succeeded him as chief of the community.
He is oftentimes described as a handsome man with polished manners, and he mingled easily in white society during his many trips to Washington, D.C., and St. Paul.
He dressed in fashionable European-style clothes, but he always kept his hair long and continued to wear a blanket draped across one shoulder. Euro-American fashion was simplistic in the 1800s, and individuals like Hole-In-The-Day made it visually more exciting with the inclusion of Ojibwe accessories and items of adornment. He also continued to wear Ojibwe-style moccasins.
He was popular with both men and women, and he was a accomplished public speaker. Reverend Claude H. Beaulieu says of him:
"Hole-in-the-Day was a man of distinguished appearance and native courtliness of manner. His voice was musical and magnetic, and with these qualities he had a subtle brain, a logical mind, and quite a remarkable gift of oratory. In speech he was not impassioned, but clear and convincing, and held fast the attention of his hearers."
Soon white men in both the nation's capital and the territorial capital began to look upon him as a spokesman for all his people.
