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April 30, 2011, turned out to be one of Washington's weirder nights.
The president of the United States had just secretly ordered the raid that would take out Sept. 11 attack mastermind Osama bin Laden and he was about to deliver jokes at the White House Correspondents' Association dinner.
But it was the barbs that President Barack Obama and headliner Seth Meyers hurled at real estate mogul-turned-reality TV star Donald Trump that created a political narrative that lives on: jokes = presidential revenge campaign. (For the record, Trump has said he had a good time. He told The Post's Karen Tumulty he didn't decide to run for president until the night after Mitt Romney lost in 2012.)
Let's rewind 15 years: He was sitting in the ballroom, the roasting was intense, and everyone in the packed ballroom saw it. This was when we still had a monoculture, when people all sort of watched the same things, so much of America also saw it. We also all knew the same celebrities, and a swarm had descended upon Washington for the weekend, invited by news organizations to sit at their tables. We're talking Scarlett Johansson, Sean Penn, Mila Kunis, half the cast of "Glee," if you remember what that was.
Trump was at a Washington Post table, at the invitation of Lally Weymouth, whose family owned The Post. At the time, Trump was mostly known as host of NBC's "The Apprentice" - and for peddling the theory that Obama had not been born in the U.S. "The Donald" was a source of both public cultural fascination and derision.
Trump had attended this dinner before, in 1993 at the invitation of Vanity Fair editor Graydon Carter. In 2011, he sat at Table 98 near Carter, Republican House Speaker John A. Boehner, and The Post's then-executive editor Marcus Brauchli.
Outside the newsroom, some media critics wondered why in the world The Post extended the invite. Inside the newsroom, "many reporters and editors felt that ... hosting Donald Trump at a Post table appeared to endorse the birther conspiracies in a way," recalled Roxanne Roberts, then The Post's chief chronicler of the Washington social scene. She was seated directly behind Trump.
"It would be safe to say the newsroom was always kind of conflicted on these kinds of invitations," Brauchli said. "On the one hand, they didn't always love the nonjournalistic invitations but they also enjoyed them. …Looking back on it, he was certainly a newsworthy person."
"He was jovial and gregarious on the way in - as he met people, he was trying to impress them and talk to them."
After dinner, Obama took to the dais to deliver his set.
Obama, known for strong comedic timing, spent several minutes focused squarely on Trump. In the lead-up to the dinner, the Obama White House communications team pulled in comedy writer and director Judd Apatow to offer feedback on Obama's drafted set. "I think you're a little light on your Trump jokes," Apatow recalled saying, in a 2020 podcast with former Obama speechwriter Jon Lovett.
"This was the beginning of birtherism," Apatow said. "And I explained how much I disliked the man and I think you should go hard on him." They talked about how it'd be "funny for the president to describe, in insane detail, an entire episode of 'The Apprentice,' and then make a flippant remark about how qualified Donald Trump was."
Lovett wasn't sure Obama would go for it, Apatow said, "because it was kind of a conceptual bit, it wasn't a one-liner." But he did. From Obama's set:
Donald Trump is here tonight! Now, I know that he's taken some flak lately, but no one is happier, no one is prouder to put this birth certificate matter to rest than the Donald. And that's because he can finally get back to focusing on the issues that matter – like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac? But all kidding aside, obviously, we all know about your credentials and breadth of experience. For example – no, seriously, just recently, in an episode of Celebrity Apprentice at the steakhouse, the men's cooking team cooking did not impress the judges from Omaha Steaks. And there was a lot of blame to go around. But you, Mr. Trump, recognized that the real problem was a lack of leadership. And so ultimately, you didn't blame Lil' Jon or Meatloaf. You fired Gary Busey. And these are the kind of decisions that would keep me up at night. Well handled, sir. Well handled.
The camera kept still on Trump, who held a steady gaze on Obama, with pursed lips and a slight hint of a smile. The room erupted with laughter. Brauchli recalled the mood shifted then.
Former Republican House speaker Newt Gingrich was there with wife, Callista. He does not remember laughing at Obama's Trump jokes. What he does remember is "Obama had all the advantages of being president, and went after Trump, who'd gone after Obama," he recalled to The Post. "I certainly didn't think of Trump as a presidential candidate at that stage. And of course, he had a lot of free publicity out of it."
Then came the headliner. Meyers "stood up and really went to town on Trump," Carter recalled in 2016.
Meyers had a team of comedy writers - John Mulaney, Neal Brennan - pitch him jokes before the dinner. Former "Tonight Show" writer Jon Rineman, recounting the writing session during a 2024 podcast interview, said his pitches fell flat, except for his last joke: "Donald Trump has been saying he's going to run for president as a Republican, which is surprising because I thought he was running as a prank."
Meyers asked "is there a better word than 'prank'?" Rineman suggested "joke." Brennan said "Yes, that's the word, right there."
Cut to the night of the dinner, and Meyers started his Trump material with that Rineman's bit - with the "joke" edit. The room erupted with laughter, applause and "oooohs."
The camera showed Trump - furrowed brows, unmoving face.
Meyers then launched into several minutes of Trump jokes. "Gary Busey said recently that Donald Trump would make an excellent president. Of course, he said the same thing about an old, rusty bird cage he found," he joked. "Donald Trump often appears on Fox, which is ironic because a fox often appears on Donald Trump's head."
Trump's demeanor, and the room's laughter, stayed constant.
Former Obama speechwriter David Litt, who had joined the White House just weeks before, could see most of the ballroom and Trump from his seat in the back of the room.
"I could see him turn like a very intense shade of purple. I think the cliché is beet red, but I actually, it was like I'd never seen a human turn that color," Litt recalled. "What I remember most clearly about that night: it was the people laughing the loudest were not Democrats or journalists, it was Republicans. Because they all felt like, hey, this guy is dragging down our party. He's taking up all of our oxygen and he's making us look stupid."
Trump didn't stick around after the speeches ended. He wasn't spotted at any after party, Roberts said.
"He basically - he exited immediately," Brauchli said. "He rose from the table, took [his wife] Melania by the arm, and made a beeline for the exit. He didn't say goodnight, he shot out of the room. It wasn't just that Obama ripped him, Seth Meyers lacerated him, too. It was humiliating."
Reflecting on the dinner in 2020, Meyers told The Post "I don't think that anything I did was out of line. Lest anyone forget, [Trump] wasn't just an ordinary citizen who just happened to have a seat at that dinner. He was a birther, just basically banging the drum on the idea that the president wasn't from this country, which is as racist today as it was then."
Trump always has insisted he had a good time that night. He was flattered, he said, to have Obama shine so much attention on him.
Roberts, who interviewed Trump for a 2016 piece about the night, "said he was very honored that the president made jokes about him." During a 2017 interview with "Fox & Friends," Trump called the narrative that he hated the 2011 dinner one of the "great misconceptions." He noted that Obama ribbed him, joking that he'd rename the White House after Trump. "I loved that evening. I had the greatest time."
But Roberts said Trump didn't find Meyers funny, having told her the comic was "too nasty, out of order."
In any event, the 2011 barbs weren't enough to turn him off from the dinner. Trump returned to the scene of the crime four years later, this time as the guest of Fox News. He was jovial. He even gave then-national security adviser Susan Rice a hug before they all sat down, telling the Hill "she's a good woman."
"I don't know what's going to happen," Trump said before the 2015 program began, but he pointed to his seat, front and center of the room. "They certainly have me in the right location."
Indeed, Obama lobbed one joke his way: "And Donald Trump is here. Still. Anyway."
The cameras panned to Trump. Seated beside his wife, Trump laughed and flashed a big smile.
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