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Robert Kakaygeesick Jr. was born in Warroad, Minnesota in 1948 and is a member of the Buffalo Point First Nation in southeastern Manitoba, where he lives with his wife Jackie. He holds dual Canadian and American citizenship.

Kakaygeesick is the great-grandson of John Kakaygeesick, a respected and influential medicine man of the Chippewas who lived to be 124 years old. This ancestral connection to traditional spiritual practices influences his artistic work.

Working primarily in watercolors, Kakaygeesick uses traditional symbols and stylized images in his paintings, aiming to bring the consciousness of the past into present-day conversation. His imagery is rooted in the values and spiritual beliefs of his Ojibwa heritage. The cycle and unity of life are central themes in his work, portrayed through circles and mists that frequently appear in his paintings, offerings of tobacco, and ascending images of both women and men as they metaphorically reach toward the mystery of life.

Kakaygeesick has developed a distinctive drawing style that depicts men, animals, and birds representing "Man and the spirits represented in him." While watercolors are his primary medium, he also works with acrylics, pastels, tempera, charcoal, and pen and ink.

His work has gained recognition across Canada, with one-man shows held in every major city from Vancouver to Toronto. Kakaygeesick's art is internationally recognized, with many of his pieces held in private and corporate collections. His paintings serve as a bridge between traditional Ojibwa spiritual concepts and contemporary artistic expression, making ancestral wisdom accessible to modern audiences.