Donald Trump
The White House/Flickr

President Donald Trump's attempt at political comedy fell flat at one of Washington's most exclusive gatherings on Saturday night. Sources who attended the annual Alfalfa Club dinner at the Capital Hilton told The Washington Post that the president's material repeatedly failed to land, with the room falling silent on multiple occasions.

It was Trump's first address to the secretive organisation as president. Roughly 200 of America's most influential figures: political leaders, business executives, military officials, and diplomats, gathered for what is traditionally an evening of light-hearted political roasts. The laughter never came.

Enemies in the Audience

Trump opened by acknowledging the awkward guest list. He told the crowd he hated many of the people in the room, then quickly added that he liked most of them. He also asked who had thought this would ever happen, him addressing the club as president.

The audience included several figures at odds with his administration. JPMorgan Chase chief executive Jamie Dimon was there, and Trump is suing his bank. So was David Rubenstein, recently sacked as head of the Kennedy Center, and Federal Reserve Chairman Jerome Powell, whose role the administration has been investigating.

The president teased the crowd about his territorial ambitions, warning he might need to leave early to watch the invasion of Greenland. Then he revealed it was a joke. America would buy Greenland, not invade it. Canada would become the 51st state, Greenland the 52nd, Venezuela the 53rd, CNN reported.

Barbs That Missed Their Mark

Trump revived his 'Pocahontas' nickname for Senator Elizabeth Warren, referencing her past claims of Native American heritage. She was supposed to be at the dinner, he said, but could not find her reservation. It landed poorly, Mediaite disclosed.

Another barb targeted Joe Biden. Trump noted that Condoleezza Rice was in the audience and said he always assumed she would become the first female president. Then he suggested Biden had beaten her to it, implying Jill Biden had really been running things. That bombed too.

One bit backfired completely. Trump called on Mitt Romney to stand, apparently winding up for a joke at the former senator's expense. The crowd responded with warm applause for Romney instead. Trump abandoned the bit and conceded he could not poke fun at someone the room so clearly admired.

An Hour-Long Performance

The speech stretched past 60 minutes. Attendees described several quips that came across as mean-spirited rather than playful, and Trump did not always have the room on his side. He threatened to sue his newly nominated Federal Reserve chairman, Kevin Warsh, if interest rates do not come down, The Hill said. He also praised his wife, Melania, calling her a movie star after the release of her documentary.

Trump shrugged it off on Air Force One afterwards. It was a roast, he said. All comedy.

Washington's Most Secretive Gathering

The Alfalfa Club has brought together Washington's elite since 1913, when it was founded at the Willard Hotel. The name comes from the plant's deep roots and supposed willingness to do anything for a drink, a nod to the members' fondness for alcohol.

The dinner traditionally honours Confederate General Robert E. Lee's birthday, though it now functions mainly as a venue for bipartisan networking. The club did not admit Black members until 1974, or women until 1994.

Saturday's guest list included former President George W. Bush, Supreme Court Justices John Roberts and Elena Kagan, Senate Minority Leader Mitch McConnell, and Amazon founder Jeff Bezos. Trump left for Mar-a-Lago after the event to attend the wedding of his deputy chief of staff, Dan Scavino.