Donald Trump’s relationship with journalism and American journalists’ reciprocal relationship with Trump were more like a battlefield. They provided an important, even exhilarating chapter in the history of political journalism of our times, which have certainly been fraught with problematic deviations. Writing from different places, Carla Baptista, a lecturer at Universidade Nova de Lisboa and a specialist in the history of the media and journalism, and Paulo Pena, a journalist from a multinational investigative journalism team (Investigate Europe) analyse and discuss these issues.