As a former US immigration attorney I can answer your question. The Entry/Exit system deals with people, not passports. It works with specific markers, such as first name, last name, date of birth, place of birth, height, weight, eye color, hair color, etc. So if that hypothetical person has different names in their passports (I have 3 passports with 2 different names as I changed my name when naturalizing in the United States), different birth dates, different birth places, and ideally different fingerprints to trick the reader of the biometric chip, then this will most likely work. Such a person would most likely be a spy for a foreign government though. Otherwise, not so much . . .