WASHINGTON >> Donald Trump decided to mingle with members of the mainstream media he loves to lash out against, and his presidential debut at Washington’s annual Gridiron dinner was certain to invite close watch to see how he handled the expected ribbing.
The white-tie gala is the kind of establishment event that Trump has shunned since taking office. But what was supposed to be a good-natured bread-breaking between the president and press could become a flashpoint if Trump, who has labeled reporters “fake news” and the “enemy of the American people,” proves unable to poke fun at himself or take a lashing from the press.
“I think he is in a potentially strange spot where he either attacks the press in a way that works really well at a rally but just gets crickets in that room, or he has spent the past two years calling reporters ‘fake news’ and then suddenly admits it’s just the act,” said David Litt, a former speechwriter for President Barack Obama who helped write many of Obama’s comedy speeches.
At the dinner, journalists in costume perform song parodies before politicians from both parties give their speeches. The Gridiron’s motto — “singe, don’t burn” — suggests speakers should feel free to poke and prod, but gingerly. Every president since Grover Cleveland has been subjected at least once.
Trump skipped the event last year and sent Vice President Mike Pence instead. Trump also passed up the White House Correspondents’ Association dinner. It’s not known whether he will attend that dinner on April 28; his Gridiron reception could serve as a test.
Despite Trump’s reputation for being notoriously thin-skinned, Trump has subjected himself to roasts in the past.
At New York City’s Friar’s Club in 2004, Regis Philbin and others skewered the New York City real estate developer for his sexual escapades and business failures. Video of the event shows Trump laughing heartily and delivering a rebuttal that was classic Trump.
In addition to thanking his wife and mocking Philbin’s height, Trump bragged about his success in developing casinos in Atlantic City, New Jersey, and claimed he’d drawn the “biggest crowd they’ve ever had.”
Seven years later, Trump agreed to be pilloried at a 2011 Comedy Central roast that included Snoop Dogg, Seth MacFarlane and Mike “The Situation” Sorrentino. Trump scowled through most of the event, said Ray James, who served as lead writer.
James said Trump was difficult to work with, handcuffing writers, constantly asking whether things were funny and changing jokes to inflate his wealth.
“He didn’t get it, he didn’t think the jokes were funny,” said James, adding that Trump also made clear to writers that certain topics were off-limits.
“Donald Trump’s rule was, ‘Don’t say I have less money than I say I do,’” roaster Anthony Jeselnik told Joan Rivers in 2013. “He was like, ‘Make fun of my kids, do whatever you want. Just don’t say I don’t have that much money.’”
The closest Trump has come in recent years to the Gridiron dynamic was New York’s Al Smith dinner during the 2016 campaign, also attended by Trump’s Democratic presidential rival, Hillary Clinton.
Trump began innocently enough. He joked that Senate Minority Leader Chuck Schumer, D-N.Y., used to love Trump when he was a Democrat. He poked fun at a plagiarism incident involving his wife.
But Trump’s remarks soon devolved into bitterness and insults, with the soon-to-be-president earning boos as he accused Clinton of corruption and hating Catholics.
Jeff Nussbaum, a partner at the speechwriting firm West Wing Writers who has worked with numerous politicians to craft speeches for the event, said Trump’s “insult comic” style isn’t one that’s typically been well-received at these kinds of gatherings.
“Humor is an incredibly powerful weapon. But to wield it on others, you need to demonstrate that you can turn it on yourself first. And that’s something President Trump has never demonstrated,” said Nussbaum.
Robert Lehrman, a former speechwriter for Al Gore and professor at American University who has written about the use of comedy in politics, pointed to Sarah Palin’s 2009 self-deprecating speech at the Gridiron, which included a joke about being able to see the Russian Embassy from her hotel room, as a potential model for Trump.
Lehrman warned of the potential ramifications of a joke gone bad.
In a Washington Press Club Foundation dinner in 2004, then-Sen. Jon Corzine, D-N.J., compared sharing a media market with Schumer to “sharing a banana with a monkey … take a little bite of it and he will throw his own feces at you.” The joke infuriated Schumer, souring their relationship.
“There are consequences that Chris Rock doesn’t have,” Lehrman said.