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The collection consists of twenty-one illustrated letters written by Hank Hanft around 1919 to his approximately five-year-old brother Robbie, likely in or near Wisconsin. The letters were written using block letters, likely to assist a young child's ability to read them, and feature the use of pencil, crayon, and watercolors to produce drawings and paintings. The illustrations include scenes of fishing, farming, and hunting, and objects such as animals and plants, boats, and household and agricultural goods.
Hank also wrote moralizing stories, often about animals or children, with lessons such as, "Never Be Late," "Always Go to Sunday School," "When You Fight, Soak the Other Boy, But Don't Talk and Swear About It," among others. Two items relate to witches, one a watercolor painting of a Halloween scene with a witch flying on a broomstick and the other a short story about an old lady who refused to eat and turned into a witch. Only one letter is dated in the collection, written from Hank to his father on May 3, 1919, requesting financial support to cover housing costs, suggesting Hank may have been a young adult or attending school away from home.