Donald Trump Again Fails to Mix in High Society

Donald Trump can’t even attend a charity event with elite Manhattan Catholics without gutting lustily booed for his classless, boorish behavior and bad jokes. He apparently thought it would get laughs to call Hillary Clinton a crook and say that she was only at the event to “pretend she doesn’t hate Catholics.”

To be clear, ripping on your opponent and prominent guests is expected at the Al Smith Dinner. Hillary Clinton made many jokes at Trump’s expense and didn’t spare Rudy Giuliani either. She said she wished Michael Bloomberg had agreed to speak because “she’d like to hear from a billionaire.” She complimented Kellyanne Conway but said that Trump probably wouldn’t pay her. She jabbed him repeatedly for not being willing to accept his pending defeat. And she said that immigrants look at the Statue of Liberty as a beacon of hope but that Trump sees her only as a “four.”

As for Guiliani, she cracked, “Many don’t know this but Rudy actually got his start as a prosecutor going after wealthy New Yorkers who avoided paying taxes. But as the saying goes, if you can’t beat them go on FOX News and call them a genius.”

As you might expect, Giuliani was a visibly poor sport about it.

In fairness to Trump, even the host laid into him.

The tone of the event was set before either candidate even spoke when [Al] Smith said “before the dinner started, Trump went to Hillary and asked ‘how are you?’ She said, ‘I’m fine — now get out of the ladies’ dressing room.’”

Trump has never been able to mix at these white tie events in Manhattan, which I suspect is a source of both his ostentatious striving and his bottomless resentment. But, personally, I think Jay Gatsby was a nicer guy, threw better parties, and did a better job disguising his mob connections.

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Martin Longman

Martin Longman is the web editor for the Washington Monthly. See all his writing at