I think the reason Trump won is the same reason the Tea Party was so successful in winning. Independents and Conservatives wanted to try something new. They were fed up with the same thing happening year after year with promises being made by both Democrats and Republicans, with neither side following through.
The problem is the media painted the Tea Party as a racist group that hated Obama—and liberals still think that. I remember many Tea Party leaders saying, “You don’t have to vote for our candidate, just don’t re-elect the the incumbent.” Liberals say they want change and they want to work together, but when they actually had the chance to get new blood into DC they chose not to. All they heard was the word “racist + Tea Party”, then they repeated it, and they ignored everything else.
Trump’s victory was partly because of how bad Hillary was as a candidate, partly because how upset the majority of America was about Obama’s policies—dispite how likable he is as a person, and I think mostly about trying a businessman (something new) in the White House.
Trump voters didn’t buy the media’s portrayal of him as a racist because the media has cried wolf so many times before we wouldn’t believe them even if it were true. But again, Liberals heard “racist + Trump”, they repeated it, and ignored everything else. They didn’t even realize that they were helping him to win, and they still don’t realize that with every ridiculous statement they make, they are actually helping him. They are setting the bar so low, that he just has to be an OK president to get elected again; and this could be a bad thing.