Firstly, a good plan translates into exactly what was planned. No better, no worse, not early, not late, in exactly the expected format, etc. But, stuff happens and you never know in what form, from which direction nor whence it comes.
So, there was an election in the US. Someone had to win. Someone did. So what! who won? Unexpected outcome. So what? With that out of the way..
A democracy is election by the majority (OK, adjusted by the Electoral College in the US) most of whom happen not to be highbrow nor the most prosperous segment of the nation and are usually overrun by spiffy looking upper-class articulate intelligentsia. So what is the point?
In the 2016 US elections for POTUS, apart from Vladimir who Putin a good word, Donald Trump was clearly the smartest person in the election. He won by appealing to that section of the populace by speaking the "right" language, being down-to-earth, consistent and therefore trusted, and so on; irrespective of the vitriolic and his apparent idiotic utterances.
(He seems to have made a bet with someone, and won, that he could put out all his insults left, right and center, and get away with it. And, he has, and seems will continue to do so. And, probably sure likes it when a plan comes together.)
Apart from the people being transfixed by her past, Hillary Clinton didn't win simply because she was addressing the wrong people in a manner that was inappropriate such that it could not be inadvertently heard by the right people i.e. sufficient of those who could have swung the vote in her favour - those downtrodden forgottens but with equal voting rights.
Talk above people, and you tend to miss a lot of them. Hill, you Billy, you sure seem to have.
Even the current US President must have thought: "Barack! O bama, how did we get Trumped like this?"
Stuff happens, we have to deal with it.