White House Correspondents’ Dinner: Donald Trump is no laughing matter

When I think about the difference between Donald Trump’s first term and Donald Trump’s second term, the image that stands out the most is the presidential bombing.

Not a country, in this case – a comedy routine.

It was this January’s keynote speech at the Alfalfa Club dinner, a huge Washington institution that exists only for the president to come in once a year and fire off a bunch of jokes prepared by his speechwriters.

Trump broke precedent and skipped it in his first term, but decided to give it a shot this time. On the surface, it may have seemed a subtle return to a kind of presidential normalcy — like his much-publicized first appearance at the most famous White House Correspondents’ Association dinner Saturday, a media gathering that traditionally also features a presidential standup set.

But when Trump stood up in his black tuxedo and addressed the Alfalfa Club’s ultra-elite membershipmade up mainly of longtime politicians and Fortune 500 CEOs, it did not go well. Here’s how the Washington Post describe the scene:

Some jokes landed with a thud, and the room fell silent repeatedly.

“I hate so many people in the room. Most of you like,” he said, according to an attendee. “Who in the hell thought this would happen?”

He said he might cut the speech short because he had to watch the invasion of Greenland, before admitting it was a joke.

“We’re not going to invade Greenland. We’re going to buy it,” he said. “It was never my intention to make Greenland the 51st state. I want to make Canada the 51st state. Greenland will be the 52nd state. Venezuela can be 53rd.”

Trump also pointed to Kevin Warsh, his nominee to be the next Fed chairman.

“If he doesn’t lower interest rates, I’m suing his ass,” Trump said. After a pause, he added, “I’m kidding.” After another beat I concluded, “Eh…”

It’s easy to see this as an anecdote about another snooty Washington establishment thumbing their nose at Trump, but that’s not really the story. The reason the jokes didn’t land wasn’t the audience, or the writing, or the delivery. It’s that they weren’t jokes – they were political.

When Trump spoke about his “hatred” to the audience, the current Trump Department of Justice worked his way through his enemies list. In fact, suing the Fed chairman to lower interest rates would actually make the lighter approach; in real life the sitting Fed chair (obviously a Lucerne member) just had publicly accused the White House of launching a special criminal research to achieve the same goal.

Trump made his foreign policy remarks just after he threatened to invade and annex Greenland, sparking a global crisis that only ended days earlier when the stock market started to melt. And statehood was no laughing matter in Canada, whose citizens resoundingly elected Prime Minister Mark Carney. “Never 51” platform after Trump threatened devastating tariffs if they did not join the US.

Trump’s first term featured many people who were on edge about his daily statements. But a great deal of abnormal rhetoric or reported behind-the-scenes behavior was also brushed aside as hot air, or exaggeration, or dark humor for fans who were in on the gag. It’s much more difficult this time, when they often have the might of government behind them, something that members of the media who attended Trump’s speech on Saturday understand only too well.

This is the difference between Trump I and Trump II: Nobody’s laughing this time.

First term, essay. Second quarter, punchline.

The deadly seriousness of Trump II vs. Trump I is a useful frame, in part because this new sense of unpredictability—and the fear that often accompanies it—crosses party lines. Both his critics and supporters have adjusted how they view and discuss him with this change in mind.

Let’s start with his supporters. During Trump’s first presidency, there was an entire intellectual scaffolding built around the idea that people needed to lighten up a little when it came to his more inflammatory or threatening or outlandish statements.

Columnist Salena Zito, who chronicled his 2016 voters on the spot, pointedly noted that they often took him seriously, but not literally; while the press took him literally, but not seriously. There was much discussion of his 1980s book The art of the deal and his endorsement of “true hyperbole,” which Trump described as “an innocent form of exaggeration.” Critics saw it as a manifesto for lying, and supporters cited it to reassure themselves that he was consciously adept at more outspokenness.

Democrats, of course, were never fans of Trump’s bullshit. But the first term was also filled with self-appointed strategists warning that Trump’s wilder provocations were merely “distractions” meant to distract his opponents from more serious and realistic concerns elsewhere.

Trump and his staff were happy maintain this idea yourself. When a statement or position caused an unusual amount of trouble, it was common to mock people for ever taking it at face value.

Did Trump say the Democrats committed treason during his State of the Union address? “He was clearly joking.” Did he say he would forgive people who carry out his orders illegally? a joke, of course! Bombing civilians? You took that stuff literally? Demanding Greenland? Haven’t you seen his hilarious Photoshop of Trump Tower in Nuuk?

Not so in Trump II: This time, his handpicked prosecutor actually tried to impeach elected Democrats after crying sedition (a grand jury was not amused), the Greenland talk really escalated into a military battleand just this month he apparently floated blanket waiver for staff.

Everyone is in on the “joke” now.

It is clear that many Trump statements that were dismissed as idle “trolling” in his first term were, in retrospect, more serious proposals held back by stronger political constraints or a less compliant cabinet. Now, in his second term, whether you agree with his decisions or not, these statements are no longer brushed off as easily as “means tweets” jerked up humorless scolding.

In his first term, Trump could get away with occasional sacrilegious talk about the “chosen” or the “second coming of God” by claims sarcasm. In his second term, when Trump posted a picture of himself play AI Jesusreligious conservatives were much less quick to reject it and forced him to take it down, even as the White House passed it off as a gag.

On the left, the “distraction” talk is also more muted. Then-Speaker Nancy Pelosi boasted in 2020 that she ignored Trump’s “bait” when he tweeted about sending the military into Minneapolis and shooting out-of-control protesters. No one in her party is say it in 2026.

In many ways, this kind of audience response is Trump’s dream. For decades he has been obsessed with the idea that the world “laughs” at America; an extension of his own lifelong grievance towards Manhattan snobs who mock his Louche Queens persona.

The legend even has it (denied by Trump) that he might never have been able to run for office if President Barack Obama hadn’t mocked him into a thunderous fight at the 2011. White House Correspondents’ Dinner. Now is finally his big chance to return to the same stage his hated predecessor occupied and deliver a barbecue of his own.

He probably won’t have to worry about excessive laughter this time.