Abstract: The election of Donald Trump has come as surprise to a lot of people. Perhaps rightly so, since this is man who tweets out mean insults to respected individuals in the middle of the night — thought temperamentally unfit to be President — and even rallied against by politicians from both sides of the aisle at some point or the other during the past year. Even surprising was the response of media outlets to his election, especially since, in their opinion, they had done what they could to stop Mr Trump. My intuition was that they were doing more harm than good — that their critiques were not strongly directed. If a news article voiced opposition to Donald Trump, it should have a negative sentiment. In case the opposition is not made blatantly clear, the overall sentiment of the article could indeed be positive. My approach is to create a corpus of articles about 2016 US Presidential Candidates. I intend to compare articles about the top 4 candidates for the 2016 US Presidential Election. A favorable outcome of this experiment would be an overall positive sentiment for all Trump articles, even though the author’s intent may be to mock him. If the sentiment was really positive, we could say that him being the media’s favorite legitimized his presidency.