President Donald Trump entered one of Washington’s most buttoned-up rooms Saturday night and delivered a speech full of playful jabs that should have left the audience in stitches but instead landed flat, greeted by long stretches of silence and more eye rolls than laughter.
Trump’s awkward comedy routine flopped inside a closed-door black-tie dinner for the Alfalfa Club — an elite, invitation-only gathering of Washington power brokers.
Trump’s jokes “landed with a thud, and the room fell silent repeatedly,” an outcome that appeared to catch the president off guard, according to The Washington Post, citing those in attendance. At one point, he warned the crowd that he might “cut the speech short,” a remark that underscored how poorly the room was responding.
The dinner, held at the Capital Hilton, marked Trump’s first appearance before the exclusive organization known for its dry humor, bipartisan mix and tradition of presidents poking fun at themselves. Roughly 200 members — CEOs, political figures and Washington insiders — attend each year. The evening is strictly off the record and closed to the media.
Trump opened by acknowledging the tension head-on.
“So many people in the room I hate. Most of you I like,” he said. “Who in the hell thought this was going to happen?”
The line did not loosen the room. Instead, it set the tone for a speech that leaned heavily on grievance and provocation, delivered to an audience that included several people Trump has publicly clashed with or targeted. Among them were JPMorgan Chase CEO Jamie Dimon, whose bank Trump is suing; David Rubenstein, whom Trump fired as head of the Kennedy Center; and Jerome Powell, the outgoing Federal Reserve chairman who is being investigated by the Justice Department.
Trump soon pivoted to foreign policy, suggesting he needed to wrap up quickly so he could watch “the invasion of Greenland,” before clarifying it was a joke.
“We’re not going to invade Greenland. We’re going to buy it,” he said. “It’s never been 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.”
According to attendees, the reaction was muted.
The remarks came at the end of a turbulent week in which Trump’s administration oversaw the arrest of journalist Don Lemon, seized ballots in Georgia after invoking fraud claims, and defended the shooting death of Alex Pretti in Minneapolis by federal immigration agents. During the same stretch, Trump attended a lavish screening of a documentary about first lady Melania Trump, complained publicly about not getting enough credit for his achievements, and fixated on his proposed White House ballroom.
At one point, Trump turned his attention to Kevin Warsh, his nominee to be the next Federal Reserve chairman.
“If he doesn’t lower interest rates, I’m suing his a– off,” Trump said. After a pause, he added, “I’m kidding.”
Asked later about the comment, Trump brushed it off.
“It’s a roast. It’s a comedy night,” he said, while still expressing hope that Warsh would cut rates. “I mean, if you watch him on television, you know, because I’ve watched interviews and statements, I hope he’s going to lower them. But he’s going to do what he wants to do.”
Trump also used the speech to needle political opponents. He revived his long-standing insult of Sen. Elizabeth Warren, referring to her as “Pocahontas” and saying she was supposed to attend the dinner, “but couldn’t find her reservation.” He noted that Condoleezza Rice was in the audience and said he once assumed she would become the first female president.
“Never in a million years would I have thought Joe Biden would beat her to it,” Trump added, implying that former first lady Jill Biden was the real power — another line that drew little response.
He teased but ultimately withheld a joke about Supreme Court Chief Justice John Roberts.
“I had the nastiest, most vicious joke about John Roberts,” Trump said. “If you think I’m going to tell that joke you can forget it.”
“I’m going to kiss his a– for a long time,” he added, referencing Roberts’ central role in cases involving his administration.
Reaction to his performance drew outright mockery online.
“He’s going to have that crowd arrested for not laughing at his amazing jokes.”
“Trump still doesn’t get it. People laugh at him… Not with him. Demented old fool.”
“Read the room Donny boy — no one fears you. They smell your incompetence.”
After the dinner, Trump boarded Air Force One and flew to Mar-a-Lago in Palm Beach, speaking extensively with reporters while still wearing his tuxedo.
“We had a good time at the Alfalfa dinner,” Trump said. “I think we did well, I hope we did well. But it was very good. Tremendous people.”
