Diary of a Times Square Thief documents a journey of discovery: the search for the writer of a mysterious diary that the filmmaker found on Ebay. This manuscript describes the adventures of a young man who, in the late eighties, left the Midwest of the United States to go to New York to realize his big dream: to become a writer. He fails, and the diary gives a frank and confronting account of the author's subsequent downfall. This is where the diary ends; its last pages have been cut out with a knife.