Jerry O'Connor has been a college instructor, journalist, historian, tour guide, and lecturer. A passion for realism and authenticity has characterized O'Connor's journalism career, beginning with a four-page centerfold feature for the Chicago Sunday Tribune Magazine in 1965.

He's also written for Chicago Tribune section one; Chicago Tribune Perspective and Flashback sections; Finest Hour, British Heritage, Proceedings (U.S. Naval Institute), Naval History (U.S. Naval Institute, multiple, lead,) and World War II (multiple, lead). He's been instructor, Harper College, Palatine, IL (8 years), Oakton College, Skokie, IL (12 years), lecturer, Cunard Queen Mary 2 (four trans-Atlantic voyages, 16 lectures, averaging 325 passengers per lecture). He's been on the NBC Today Show, and he was named Author of the Year by the U.S. Naval Institute in 2000 for his body of work.

Jerry began writing about World War II in 1978 by disclosing the intact but unknown existence of Winston Churchill's mythic war headquarters in central London. The four-page feature directly contributed to opening the site to the public in 1985.