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With self-deprecation on menu for presidents at correspondents’ dinner, it’s no wonder Trump is skipping it

Donald Trump attends the annual Alfred E. Smith Memorial Foundation Dinner at the Waldorf Astoria on Oct. 20, 2016, in New York. (Spencer Platt/Getty Images)

Suppose President Trump wasn’t skipping the White House correspondents’ dinner on Saturday. Suppose he showed up and, like other presidents before him, had to be funny, which at this particular dinner has traditionally meant being self-deprecating.

For example:

“I’m not doing so bad. I mean, at this point in his administration, William Henry Harrison had been dead for sixty-eight days!” (President Bill Clinton.)

Or, “It’s been quite a year … lots of ups, lots of downs. Except for my approval ratings, which have just gone down.” (President Barack Obama.)

“I always look forward to these dinners where I’m supposed to be funny — intentionally.” (President George W. Bush.)

Comedian Michelle Wolf will have the odd task of roasting an empty chair in President Trump's absence. (Video: Nicki DeMarco/The Washington Post)

Could Trump do it?

It’s a matter of speculation. But there’s already been one test case, the Al Smith dinner on Oct. 21, 2016, in the midst of the campaign. Though he opened to a few chuckles, his jokes, which went from funny to flat to offensive, soon drew silence, then gasps and finally loud, angry boos.

You can watch his full remarks below, but here are a few highlights:

  • “It’s great to be here with 1,000 wonderful people, or as I call it, a small intimate dinner with some friends. Or as Hillary calls it, her loudest crowd of the season.”
  • “Just before taking the dais, Hillary accidentally bumped into me and she very civilly said ‘Pardon me.’ And I very politely replied, ‘Let me talk to you about that after I get into office.’”
  • “Hillary is so corrupt, she got kicked off the Watergate commission.”
  • “We have learned so much from WikiLeaks. For example, Hillary Clinton believes it is vital to deceive the people by having one public policy and it is only different policy in private. That’s okay. I don’t know who they are angry at, Hillary or I. Here she is tonight in public, pretending not to hate Catholics.”
  • “Everyone knows, of course, Hillary has believed that it takes a village, which only makes sense, after all, in places like Haiti, where she has taken a number of them.”
  • “The media is even more biased this year than ever before.… You want the proof? Michelle Obama gives a speech and everyone loves it. … My wife, Melania, gives the exact same speech, and people get on her case.”
Watch Republican presidential nominee Donald Trump make jokes at the annual Alfred E. Smith Memorial Foundation dinner in New York, Oct. 20. (Video: The Washington Post)

Self-deprecating it wasn’t. Indeed, the jokes weren’t aimed at himself at all.

“The jokes he went to the stage with were completely consistent with his character,” said Jeff Shesol, a former speechwriter for President Bill Clinton.

It was a contrast even to Hillary Clinton, who isn’t famous for being funny. “This is such a special event that I took a break from my rigorous nap schedule. … It is a treat for all of you, too, because usually I charge a lot for speeches like this.”

Based on his performance at the Al Smith dinner, and Trump’s general attitude, Evan Davis, the founder of Headwriters who wrote jokes for Bush, thinks Trump couldn’t pull it off.

“Humor is human,” Davis said, adding that writing for Bush was easy because “he was always more than willing to shine a light on his own humility.”

Trump, on the other hand, seems like someone who cannot laugh at himself, said Davis.

Even Trump, at the Al Smith dinner, conceded that self-deprecation was not a strength.

“They say when you do this kind of event, you always start out with a self-deprecating joke,” Trump said. “Some people think this would be tough for me, but the truth is I’m actually a modest person. Very modest. In fact, many people tell me that modesty is perhaps my best quality. Even better than my temperament.”

Self-deprecation is useful, David Litt, a former speechwriter for Obama, told The Post. “It earns you some points with the crowd, and it gives the impression that president doesn’t take himself too seriously.”

The president's top five jokes from the annual White House Correspondents' Dinner touched on television, the speaker of the House and - of course - He even brought a special guest for an assist at the end. (Video: Sarah Parnass/The Washington Post)

But given Trump’s contentious relationship with the press and the efforts he devotes to looking hostile to the “enemy of the American people,” maybe he doesn’t want those kind of points.

Plus, self-deprecation is not his strength.

Eric Schnure, a former White House speechwriter for Vice President Al Gore and co-founder of the Humor Cabinet, has written jokes for politicians on both sides of the aisle. He suggested another comedic approach Trump might have taken: playing an exaggerated version of himself, like Alec Baldwin.

That would have problems, too, suggested Schnure. It would be “really hard for Donald Trump because he’s already a caricature of himself,” Schnure said. “Can you make yuge any yuger?”

So the prospects were not promising to begin with. Perhaps that’s one reason Trump is skipping the dinner, a break with past presidents for which he has offered no explanation.

“He’s not going because he doesn’t want to be the subject of jokes,” Schnure suggested.

“Somewhere someone knows it was impossible to pull off,” said Mark Katz, the humorist who penned the William Henry Harrison joke for Clinton. “I think deep down he understands to stand in front of a room and ask people to laugh at your jokes is to submit yourself to their approval.”

“Instead he selected another audience on Saturday night,” Katz added, referring to the “BIG rally in Pennsylvania” the president tweeted about, which he will be holding instead of attending the dinner.

The speechwriters regard it as a missed opportunity, especially with relations between the press and the White House so stressed. He’s giving up the chance to use humor as other presidents have, to address things they otherwise couldn’t.

“It’s the one day the president can say out loud things that he and the White House denied for the rest of the year,” Katz said.

The jokes serve to humanize the presidents and earn them a moment of empathy while also giving them the chance to influence, if only slightly, the media narrative.

“Humor’s just a good way to address headaches and help steer the press away from taking those things too seriously,” Litt said. “If you can say this is a little absurd and everyone agrees this is absurd, you can help define what’s a political problem and what is not.”

At the 2014 dinner, for example, after the disastrous rollout of the website, Obama joked, “In 2008, my slogan was ‘Yes, we can.’ In 2013, my slogan was ‘control-alt-delete.’”

“Joking about the ACA and the rollout at the dinner was a way of saying, that’s in the past,” Litt said. “If it was truly as cataclysmic as our critics said it was, it wouldn’t be the kind of thing we’d joke about.”

Even the humorless President Richard Nixon, in the midst of the Watergate scandal, climbed on stage and said, “It is a privilege to be here at the White House correspondents’ dinner. I suppose I should say it is an executive privilege.” (A reference to his ultimately unsuccessful effort to keep his secret White House tapes out of the hands of a congressional committee.)

Trump is “walking away from a lot of upside, and I read the polls,” Katz said. “He could use the boost.”

Plus, he added, “there is a speech to be written that could be a home run,” in part because “the expectations would be very low for him walking into the room.”

On the other hand, Katz said, it could backfire and become a complete disaster.

“He has this kind of mean, Rat Pack sense of humor,” Katz said, comparing the president’s punchlines to clenched fists. “There’s a violence to them, an anger to them that’s unseemly.”

Take, for example, Trump’s tweet responding to a fan who asked “how much would it take for you to make out with Rosie O’Donnell?” Trump’s cruel punchline: “One trillion, at least!”

“Singe, don’t burn” is among the rules of political comedy, Schnure said.

On the other hand, “if a joke doesn’t burn, if it only singes, [Trump] doesn’t even think about it as funny,” Schnure said.

Comedy, of course, is far from a president’s main concern. But it has its uses.

“A president who is not funny just has fewer ways of engaging with the American public,” Litt said. “If you’re not willing to tell jokes, then humor is just one tool you don’t have that other presidents did.”

On the other hand, maybe Trump simply doesn’t want to be seen by his base hobnobbing at a glitzy dinner with reporters, who remain a foil for him (“enemy of the American people”) with his base.

As Ronald Reagan once said, “it’s hard when you’re up to your armpits in alligators to remember you came here to drain the swamp.”

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