The Alfred E. Smith Memorial Foundation dinner, an annual charity event that has long been a bastion of civility in an otherwise partisan political world, was disrupted by booing at the Waldorf-Astoria Thursday night as Donald Trump offered up a cruel roast of Hillary Clinton, drawing jeers from the otherwise genteel crowd.

It was an unusually awkward affair, by all accounts. It is a longstanding election-year tradition for both major party presidential candidates to be invited to attend the white-tie gala, where each takes the opportunity to give a lighthearted speech, gently ribbing themselves (and their opponents) in the spirit of former New York governor Al Smith, the first Catholic presidential nominee. “The purpose of the Al Smith Dinner is to show both our country and our Church at their best,” Cardinal Timothy Dolan, the archbishop of New York, wrote in a blog post in 2012 defending his decision to invite President Barack Obama, despite his support for abortion rights. “People of faith gathered in an evening of friendship, civility, and patriotism, to help those in need, not to endorse either candidate.”

Right out of the gate, however, Trump, misread the room. “They’ve had me to their homes, they’ve introduced me to their children, I’ve become their best friends in many instances,” he said, referring to the Who’s Who of Manhattan elite in the room before him. “They’ve asked for my endorsement and they always wanted my money. And even called me really a dear, dear friend. But then suddenly, decided when I ran for president as a Republican, that I’ve always been a no-good, rotten, disgusting scoundrel. And they totally forgot about me.” The response was notably silent.

Trump did land several jokes about his modesty (“In fact many people tell me that modesty is perhaps my best quality”), his “nasty woman” remark (“I don’t think so badly of Rosie O’Donnell anymore”), and the mainstream media attacking him unfairly. “You want the proof? Michelle Obama gives a speech and everyone loves it—it’s fantastic. They think she’s absolutely great. My wife, Melania, gives the exact same speech, and people get on her case.” For a moment, those following along on Twitter were ready to concede that the real-estate mogul had some decent comedic chops.

But Trump, continuing to be Trump, veered back into campaign mode soon afterwards. “Hillary is so corrupt, she got kicked off the Watergate Commission,” he said at one point, to an uncomfortable crowd. “How corrupt do you have to be to get kicked off the Watergate Commission? Pretty corrupt. Hillary is, and has been, in politics since the 70s. What’s her pitch? The economy is busted? The government’s corrupt? Washington is failing? ‘Vote for me. I’ve been working on these problems for 30 years. I can fix it’, she says.”

The hardest joke, however, nearly turned the crowd against him. “Hillary believes that it is vital to deceive the people by having one public policy and a totally different policy in private,” he said at one point, referring to her leaked speeches, drawing boos from the audience. “That’s O.K., I don’t know who they’re angry at, Hillary, you or I,” Trump continued. “For example, here she is tonight, in public, pretending not to hate Catholics.”

Clinton’s speech was more calibrated, mocking the embarrassing details about her life spilled by WikiLeaks (“it’s a treat for all of you too, because usually I charge a lot for speeches like this”), while still going after Trump. “You know, come to think of it, it’s amazing I’m up here after Donald. I didn’t think he’d be O.K. with a peaceful transition of power. And, Donald, after listening to your speech, I will also enjoy listening to Mike Pence deny that you ever gave it.”

She also joked, to Trump’s increasing discomfort, about his ties to Russia: “Donald really is as healthy as a horse, you know, the one Vladimir Putin rides around on”—and, of course, his widely panned appearances at the debates. “Donald wanted me drug-tested before last night’s debate. And look, I’ve got to tell you, I am so flattered that Donald thought I used some sort of performance enhancer. Now, actually, I did. It’s called preparation.”

rest at http://www.vanityfair.com/news/2016/10/donald-trump-al-smith-dinner?mbid=nl_CH_580a423cceb79a6c5ca4c601&CNDID=36886713&spMailingID=9736575&spUserID=MTMzMTgyOTM2MTc4S0&spJobID=1021698603&spReportId=MTAyMTY5ODYwMwS2

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