It doesn't matter how you perceive him. It's how a lot of people who voted for him perceive him, and many of them are people who had never voted before or haven't voted in a long time. He is not a career politician and for that reason, alone many people viewed him as an outsider, however valid that may or may not be. Then to exaggerate matters more his opposing candidate is someone who not only is a career politician, but under the public eye for decades with lots of people hating her, and her own husband was the president for 8 years. By all means, don't mistake me as one of those "I think Trump is better than Hillary" people. I'm explaining how voters perceive them to be, and that I propose a new strategy to beat Trump in 2020. Someone (preferably a female candidate, I agree it's time for a woman president) who doesn't have a direct relative who was a president and not part of such an established last name/family with a long history of baggage. Elizabeth Warren is technically a career politician, but there are a non-insignificant amount of people who would tolerate her more than Hillary for the reasoning I'm mentioning. Whether you think any of this is justified is beside the point, I'm talking about how lots of voters feel, and that's what decides elections.