People were amazed. How could Trump do so poorly at a dinner known for a bit of self-deprecating humor and political/media elites congratulating themselves on their success?

No one should be surprised. And the "why not" provides a deep insight into who Trump is and what drove him into this presidential race in the first place.

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Remember that Trump has always viewed himself as someone on the outside looking in. His father was a big deal in Queens as a real estate developer, but never risked taking his business into Manhattan. Trump, even when he became extremely wealthy, was never accepted by the old-money elite of New York City, who viewed him as too brash, too in-your-face for their taste.

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And remember, too, that the clearest motivation for Trump to run for president in 2016 reportedly came in 2011 when he was absolutely roasted by President Obama and comedian Seth Meyers at the White House Correspondents' Association dinner. That was Trump, yet again, as the guy on the outside looking in — this time at the Washington elite, all of whom were laughing at him.

Trump, in short, has never liked or felt comfortable around the sort of people who go to the Alfred Smith dinner or the White House correspondents' dinner. He's always believed that those people sneer at him, that they judge him as unworthy of their attention and their respect. That they view him as less than them.

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And so, it's no surprise that Trump (a) didn't feel comfortable in the room last night and (b) didn't get a very warm reception from the crowd. It was, quite literally, not his people. For all of the ostentatious wealth and the braggadocio, Trump knows that these people don't like him and have never accepted him.

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My guess is that Trump's reaction on the campaign trail in the wake of the Al Smith dinner will be even more aggressive and anti-elite than it was going into last night. Trump is an able reader of crowds; he will know that they were laughing/booing at him. And, if it's anything like what happened in the wake of the 2011 White House correspondents' dinner, he will use his own resentment to drive him in the final 18 days of this race.