It's a little soon to say with any finality what exactly went wrong with the U.S. presidential election that someone like Donald Trump could so thoroughly break every conventionally-accepted rule of politics and still end up trouncing his eminently more-qualified opponent. Trump's strategy seems to have been one of donning helmet, elbow and knee pads and roller skates and simply plowing gracelessly through anything resembling opposition, while insulting and alienating anyone along the way who wasn't on side. In the roller derby rink that was this election, the track is littered with bruised competitors of both party stripes who never saw it coming.
Am I happy with the idea of Trump's boorishness being validated with what is arguably the most powerful job in the world? Hardly. But at least some of that disappointment is tempered by the prospect that Trump's victory represents something that eclipses either of the candidates, and that is the defeat (for now) of the establishment elites in both parties.
While it's a little late now to engage in the parlor game of pondering what could have been if Bernie Sanders had carried the populist torch for the Democrats, it remains a fact that the party's brass conspired against Sanders during the primaries, as revealed in leaked emails that saw Debbie Wasserman Shultz resign as chair of the DNC. From outward appearances, it appears the primaries were rigged, to use a Trumpian term. Sanders, like Trump, was able to look 'beyond the beltway', as it were, to the America that the elites would rather keep hidden, as it betrays any notion that globalist capitalism is working for anyone other than the investor class. Also, Sanders was getting by on donations from ordinary citizens, rather than engaging in the usual big ticket fundraising or depending on support from super pacs.
Perhaps this was the reason Sanders was shunted aside by whatever tactics the party's upper echelon could get away with. Meanwhile, the conventional wisdom being espoused was that the party needed Hillary Clinton, as she was much more 'electable' than Sanders.
On the other side of the aisle, Trump never seemed to have the full and unconditional support of his own party's establishment. While also being guilty of Sanders' sin - admitting that there really is an underclass being left behind by big business as usual - Trump was rude, crude and (supposedly) self-funded. In this way, he was Bernie Sanders' evil twin. Right down to the wire, Trump never did capture any sort of full-throated endorsement from House Speaker Paul Ryan.
So looking at the results through the above lens, Donald Trump captured the highest office in the land despite the tepid support of his own party's establishment, and Hillary Clinton failed in spite of what appears to have been an unethical leg-up from hers.
Furthermore, the positive lesson here is that if you acknowledge legitimate anger and give voice to those who are otherwise ignored, forgotten or taken for granted, very good things can happen. The downside of this Mobius Strip is that it took a campaign as malevolent as Trump's to finally make the point.