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After work as an architect’s draftsman, Steele became a staff artist at Harper’s, working under the artist and art editor Edward Penfield. Seeing growing demand for illustrations at Harper’s and other popular magazines, he became a freelance artist in 1897. His work accompanied stories by Mark Twain, Rudyard Kipling, and many other writers.

Steele’s drawings featured in Scribner’s, Harper’s, Century, The Metropolitan Magazine, Hearst’s International, Liberty, McClure’s, and many other books and magazines.