There is a book entitled "Sin in the Second City" by Karen Abbott which paints an astonishing picture of Chicago in the days when John Day Sr. moved his family there soon after the San Francisco earthquake. It is centered on the Everleigh sisters who ran the most elegant bordello in the city and the ubiquitous corruption of the police and city officials and the play "Front Page," which became a movie, gives one an idea of the newspaper game as it was practiced in John Day's time. One of the authors was Ben Hecht, whom Dorothy knew. It was not uncommon for the editors of the city's newspapers to call one of the hundreds of bordellos to locate a reporter when some story was breaking and he could not be found at his desk. John Day, I'm told, was no stranger to either bars or bordellos and money was scarce in the Day household when he was on a "tear," He seems to have thought it not a bad idea to introduce his sons to this world as part of their education, but it was an altogether different story with his daughters. They were to be brought up as proper young ladies, so when Dorothy defied him and set out to become a newspaper woman he disowned her. In the old man's defense it is only just to say that he knew what kind of world she was entering. The men she met at the radical publications she favored were certainly a cut above the average but it was inevitable that she meet the other kind as well and she did in the person of Lionel Moise. He was a tough guy, rough on his women and much admired by Ernest Hemingway. I have a vague memory of Dorothy making a disparaging remark about Hemingway but I don't know if she had known him. The liaison with Moise was almost the end of her as it led to abortions and attempted suicide.
It is interesting to note that when her mother was dying she asked Dorothy "Do you really believe we will see those we have known in life--your father, for instance? When Dorothy said yes, her mother responded "I don't know whether I want to see your father again."