He fought lengthy and legendary battles first with Chicago figures Samuel Insull, the utilities magnate, William Hale Thompson, the mayor, and Robert R. McCormick, the owner of The Chicago Tribune.
Han udkæmpede lange og legendariske slag først med Chicago personlighederne Samuel Insull, infrastruktur magnaten, William Hale Thompson, borgmesteren, og Robert R. McCormick, ejeren af The Chicago Tribune.