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These photocopied set of letters from Orr to the Chicago Tribune-or more specifically Mr. J.M. Patterson- shows the back and forth negotiation and job offer to become a cartoonist for the newspaper. The letters are not all complete, or always clear, but these papers ultimately do give insight into Orr's character and relationship with Tribune overall. Also of note, several of the letters show the letterhead of Orr's 1917 employer Nashville Tennessean Newspaper that again highlights his career as a politlical cartoonist.