Why did Trump win? It'a actually pretty simple to explain:
My liberal critics rolled their eyes when I complained about  political  correctness. I hope they see things a little more clearly now.  The left  sorted everyone into identity groups and then told the people  in the  poorly-educated-white-male identity group that that's the only  bad one.  It mocked the members of this group mercilessly. It punished  them for  not being woke enough. It called them racists. It said their  video  games were sexist. It deployed Lena Dunham to tell them how  horrible  they were. Lena Dunham!
Trump Won Because Leftist Political Correctness Inspired a Terrifying Backlash
What every liberal who didn't see this coming needs to understand
reason.com
Robby Soave|Nov. 9, 2016 8:01 am
Many will say Trump won because he successfully capitalized on blue  collar workers' anxieties about immigration and globalization. Others  will say he won because America rejected a deeply unpopular alternative.  Still others will say the country is simply racist to its core. But there's another major piece of the puzzle, and it would be a  profound mistake to overlook it. Overlooking it was largely the problem,  in the first place.
 Trump won because of a cultural issue that flies under the radar and  remains stubbornly difficult to define, but is nevertheless hugely  important to a great number of Americans: political correctness.
                                                            
More specifically, Trump won because he convinced a great number of Americans that he would 
destroy political correctness.
 I have tried to call attention to this issue for years. I have warned that political correctness actually 
is  a problem on college campuses, where the far-left has gained  institutional power and used it to punish people for saying or thinking  the wrong thing. And ever since Donald Trump became a serious threat to  win the GOP presidential primaries, 
I have warned that a lot of people, both on campus and off it, were 
furious about political-correctness-run-amok—so furious that they would give power to any man who stood in opposition to it.
 I have watched this play out on campus after campus. I have watched  dissident student groups invite Milo Yiannopoulos to speak—not because  they particularly agree with his views, but because he denounces  censorship and undermines political correctness. I have watched students  cheer his theatrics, his insulting behavior, and his narcissism solely  because the enforcers of campus goodthink are outraged by it. It's not  about his ideas, or policies. It's not even about him. It's about  vengeance for social oppression.
 Trump has done to America what Yiannopoulos did to campus. This is a  view Yiannopoulos shares. When I spoke with him about Trump's success  months ago, he told me, "Nobody votes for Trump or likes Trump on the  basis of policy positions. That's a misunderstanding of what the Trump  phenomenon is."
 He described Trump as "an icon of irreverent resistance to political correctness." Correctly, I might add.
 What is political correctness? It's notoriously hard to define. I recently 
appeared on a panel with CNN's Sally Kohn,  who described political correctness as being polite and having good  manners. That's fine—it can mean different things to different people. I  like manners. I like being polite. That's not what I'm talking about.
 
The segment of the electorate who flocked to Trump because he  positioned himself as "an icon of irreverent resistance to political  correctness" think it means this: smug, entitled, elitist, privileged leftists jumping down the throats of ordinary folks who aren't up-to-date on the latest requirements of progressive society.
 Example: A lot of people think there are only two genders—boy and  girl. Maybe they're wrong. Maybe they should change that view. Maybe  it's insensitive to the trans community. Maybe it even flies in the face  of modern social psychology. But people think it. Political correctness  is the social force that holds them in contempt for that, or punishes  them outright.
 If you're a leftist reading this, you probably think that's stupid.  You probably can't understand why someone would get so bent out of shape  about being told their words are hurtful. You probably think it's not a  big deal and these people need to get over themselves. 
Who's the delicate snowflake now, huh?  you're probably thinking. I'm telling you: your failure to acknowledge  this miscalculation and adjust your approach has delivered the country  to Trump.
 There's a related problem: the boy-who-cried-wolf situation. I was happy to see a few liberals, like 
Bill Maher,  owning up to it. Maher admitted during a recent show that he was wrong  to treat George Bush, Mitt Romney, and John McCain like they were  apocalyptic threats to the nation: it robbed him of the ability to treat  Trump more seriously. The left said McCain was a racist supported by  racists, it said Romney was a racist supported by racists, but when an  actually racist Republican came along—and racists cheered him—it had  lost its ability to credibly make that accusation.
 This is akin to the political-correctness-run-amok problem: both are  examples of the left's horrible over-reach during the Obama years. The  leftist drive to enforce a progressive social vision was relentless, and  it happened too fast. I don't say this because I'm opposed to that  vision—like most members of the under-30 crowd, I have no problem with  gender neutral pronouns—I say this because it inspired a backlash that  gave us Trump.
 
My liberal critics rolled their eyes when I complained about  political correctness. I hope they see things a little more clearly now.  The left sorted everyone into identity groups and then told the people  in the poorly-educated-white-male identity group that that's the only  bad one. It mocked the members of this group mercilessly. It punished  them for not being woke enough. It called them racists. It said their  video games were sexist. It deployed Lena Dunham to tell them how  horrible they were. Lena Dunham!
 I warned that political-correctness-run-amok and liberal overreach  would lead to a counter-revolution if unchecked. That counter-revolution  just happened.
 There is a cost to depriving people of the freedom (in both the legal  and social senses) to speak their mind. The presidency just went to the  guy whose main qualification, according to his supporters, is that he  isn't afraid to speak his.